759:: (i) Foods containing at least 1.7 g per serving of plant stanol esters, eaten twice a day with meals for a total daily intake of at least 3.4 g, as part of a diet low in saturated fat and cholesterol, may reduce the risk of heart disease. A serving of supplies ___grams of plant stanol esters. Reviewing clinical trials involving phytosterol supplementation, the FDA concluded that when consumed in the range of 1 to 3 grams in enriched foods, phytosterols resulted in statistically significant (5-15%) reductions in blood LDL cholesterol levels relative to placebo. The FDA also concluded that a daily dietary intake of 2 grams a day of phytosterols (expressed as non-esterified phytosterols) is required to demonstrate a relationship between phytosterol consumption and cholesterol lowering for reduced CVD risk.
840:, a rare genetic disorder which results in a 50- to 100-fold increase in blood plant sterol levels and is associated with rapid development of coronary atherosclerosis. Phytosterolaemia has been linked to mutations in the ABCG5/G8 proteins which pump plant sterols out of enterocytes and hepatocytes into the lumen and bile ducts, respectively. Plant sterol levels in the blood have been shown to be positively, negatively or not associated with CVD risk, depending on the study population investigated.
184:
20:
254:
89:
268:
226:
212:
198:
287:
240:
301:
814:. Phytosterols reduce cholesterol levels by competing with cholesterol absorption in the gut via one or several possible mechanisms, an effect that complements statins. Phytosterols further reduce cholesterol levels by about 9% to 17% in statin users. The type or dose of statin does not appear to affect the cholesterol-lowering efficacy of phytosterols.
776:
material: "Plant sterols help reduce cholesterol." This statement when used, shall be shown in letters up to twice the size and prominence as those of the primary statement. "High cholesterol is a risk factor for heart disease." This statement when used, shall be shown in letters up to the same size and prominence as those of the primary statement.
860:
of 0.6 to 2.5 g/day showed no difference between the two forms on total cholesterol, LDL cholesterol, HDL cholesterol, or triglyceride levels. Trials looking at high doses (> 4 g/day) of plant sterols or stanols are very limited, and none have yet to be completed comparing the same high dose of plant sterol to plant stanol.
799:(CVD) and overall mortality under well-defined circumstances, the evidence has been inconsistent for phytosterol-enriched foods or supplements to lower risk of CVD, with two reviews indicating no or marginal effect, and another review showing evidence for use of dietary phytosterols to attain a cholesterol-lowering effect.
755:: (i) Foods containing at least 0.65 g per serving of plant sterol esters, eaten twice a day with meals for a daily total intake of at least 1.3 g, as part of a diet low in saturated fat and cholesterol, may reduce the risk of heart disease. A serving of supplies ___grams of vegetable oil sterol esters.
2250:
Assmann, Gerd; Cullen, Paul; Erbey, John; Ramey, Dena R.; Kannenberg, Frank; Schulte, Helmut (2006). "Plasma sitosterol elevations are associated with an increased incidence of coronary events in men: Results of a nested case-control analysis of the
Prospective Cardiovascular Münster (PROCAM) study".
770:
reviewed the evidence of 84 randomized controlled trials published between 1994 and 2007 involving phytosterol supplementation. An average 8.8% reduction in LDL-cholesterol was observed at a mean intake of 2 grams per day. Health Canada concluded that sufficient scientific evidence exists to support
1744:
Gylling, H; Plat, J; Turley, S; Ginsberg, H. N; Ellegård, L; Jessup, W; Jones, P. J; Lütjohann, D; Maerz, W; Masana, L; Silbernagel, G; Staels, B; Borén, J; Catapano, A. L; De Backer, G; Deanfield, J; Descamps, O. S; Kovanen, P. T; Riccardi, G; Tokgözoglu, L; Chapman, M. J; European
Atherosclerosis
859:
to lower cholesterol continues to be a hotly debated topic. Plant sterols and stanols, when compared head-to-head in clinical trials, have been shown to equally reduce cholesterol levels. A meta-analysis of 14 randomized, controlled trials comparing plant sterols to plant stanols directly at doses
731:
can be reduced on average by 7 to 10.5% if a person consumes 1.5 to 2.4 grams of plant sterols and stanols per day, an effect usually established within 2–3 weeks. Longer-term studies extending up to 85 weeks showed that the cholesterol-lowering effect could be sustained. Based on this and other
888:
predominate. Sitosterol regulates membrane fluidity and permeability in a similar manner to cholesterol in mammalian cell membranes. Plant sterols can also modulate the activity of membrane-bound enzymes. Phytosterols are also linked to plant adaptation to temperature and plant immunity against
775:
individuals: Primary statement: " of provides X% of the daily amount* of plant sterols shown to help reduce/lower cholesterol in adults." Two additional statements that could be used in combination or alone, adjacent to the primary statement, without any intervening printed, written or graphic
863:
The debate regarding sterol vs. stanol safety is centered on their differing intestinal absorption and resulting plasma concentrations. Phytostanols have a lower estimated intestinal absorption rate (0.02 - 0.3%) than phytosterols (0.4 - 5%) and consequently blood phytostanol concentration is
349:
The intake of naturally occurring phytosterols ranges between ~200–300 mg/day depending on eating habits. Specially designed vegetarian experimental diets have been produced yielding upwards of 700 mg/day. The most commonly occurring phytosterols in the human diet are β-sitosterol,
1377:
Andersson, S W; Skinner, J; Ellegård, L; Welch, A A; Bingham, S; Mulligan, A; Andersson, H; Khaw, K-T (2004). "Intake of dietary plant sterols is inversely related to serum cholesterol concentration in men and women in the EPIC Norfolk population: A cross-sectional study".
2179:
Fassbender, Klaus; Lütjohann, Dieter; Dik, Miranda G.; Bremmer, Marijke; König, Jochem; Walter, Silke; Liu, Yang; Letièmbre, Maryse; Von
Bergmann, Klaus (2008). "Moderately elevated plant sterol levels are associated with reduced cardiovascular risk—The LASA study".
908:
Moreau, Robert A.; Nyström, Laura; Whitaker, Bruce D.; Winkler-Moser, Jill K.; Baer, David J.; Gebauer, Sarah K.; Hicks, Kevin B. (2018). "Phytosterols and their derivatives: Structural diversity, distribution, metabolism, analysis, and health-promoting uses".
1472:"Plant Sterols and Blood Cholesterol - Scientific substantiation of a health claim related to plant sterols and lower/reduced blood cholesterol and reduced risk of (coronary) heart disease pursuant to Article 14 of Regulation (EC) No 1924/2006[1]"
1501:
2487:
Talati, Ripple; Sobieraj, Diana M.; Makanji, Sagar S.; Phung, Olivia J.; Coleman, Craig I. (2010). "The
Comparative Efficacy of Plant Sterols and Stanols on Serum Lipids: A Systematic Review and Meta-Analysis".
345:
products highlighting phytosterol content. Cereal products, vegetables, fruit and berries, which are not as rich in phytosterols, may also be significant sources of phytosterols due to their higher intakes.
1827:
Trautwein, Elke A.; Duchateau, Guus S. M. J. E.; Lin, Yuguang; Mel'nikov, Sergey M.; Molhuizen, Henry O.F.; Ntanios, Fady Y. (2003). "Proposed mechanisms of cholesterol-lowering action of plant sterols".
802:
Coadministration of statins with phytosterol-enriched foods increases the cholesterol-lowering effect of phytosterols, again without any proof of clinical benefit and with anecdotal evidence of potential
161:(ergosta-5,7,22-trien-3β-ol). Important: Ergosterol is not a plant sterol. Ergosterol is a component of fungal cell membranes, serving the same function in fungi that cholesterol serves in animal cells.
2144:
Strandberg, Timo E.; Gylling, Helena; Tilvis, Reijo S.; Miettinen, Tatu A. (2010). "Serum plant and other noncholesterol sterols, cholesterol metabolism and 22-year mortality among middle-aged men".
2215:
Rajaratnam, Radhakrishnan A; Gylling, Helena; Miettinen, Tatu A (2000). "Independent association of serum squalene and noncholesterol sterols with coronary artery disease in postmenopausal women".
732:
efficacy data, the EFSA scientific panel provided the following health advisory: "Plant sterols have been shown to lower/reduce blood cholesterol. Blood cholesterol lowering may reduce the risk of
100:(saturation). They are divided into 4,4-dimethyl phytosterols, 4-monomethyl phytosterols, and 4-desmethyl phytosterols based on the location of methyl groups at the carbon-4 position. Stanols are
788:
levels was first demonstrated in humans in 1953. From 1954 to 1982, phytosterols were subsequently marketed as a pharmaceutical under the name
Cytellin as a treatment for elevated cholesterol.
1890:
Scholle, JM; Baker, WL; Talati, R; Coleman, CI (2009). "The effect of adding plant sterols or stanols to statin therapy in hypercholesterolemic patients: Systematic review and meta-analysis".
1058:"Effects of Phytosterols supplementation on blood glucose, glycosylated hemoglobin (HbA1c) and insulin levels in humans: a systematic review and meta-analysis of randomized controlled trials"
2411:
O'Neill, F.H.; Brynes, A.; Mandeno, R.; Rendell, N.; Taylor, G.; Seed, M.; Thompson, G.R. (2004). "Comparison of the effects of dietary plant sterol and stanol esters on lipid metabolism".
2364:"Comparison of the effects of plant sterol ester and plant stanol ester-enriched margarines in lowering serum cholesterol concentrations in hypercholesterolaemic subjects on a low-fat diet"
1505:
771:
a relationship between phytosterol consumption and blood cholesterol lowering. Based on this evidence, Health Canada approved the following statements for qualifying foods intended for
53:. More than 250 sterols and related compounds have been identified. Free phytosterols extracted from oils are insoluble in water, relatively insoluble in oil, and soluble in alcohols.
825:
Phytosterols have a long history of safe use, dating back to
Cytellin, the pharmaceutical preparation of phytosterols marketed in the US from 1954 to 1982. Phytosterol esters have
5976:
1007:
Genser, B.; Silbernagel, G.; De Backer, G.; Bruckert, E.; Carmena, R.; Chapman, M. J.; Deanfield, J.; Descamps, O. S.; Rietzschel, E. R.; Dias, K. C.; März, W. (2012).
6314:
6265:
4296:
2553:
De Smet, E; Mensink, R. P; Plat, J (2012). "Effects of plant sterols and stanols on intestinal cholesterol metabolism: Suggested mechanisms from past to present".
2321:
Pinedo, S.; Vissers, M. N.; Bergmann, K. v.; Elharchaoui, K.; Lutjohann, D.; Luben, R.; Wareham, N. J.; Kastelein, J. J. P.; Khaw, K.-T.; Boekholdt, S. M. (2006).
6260:
1855:
De Smet, E; Mensink, RP; Plat, J (2012). "Effects of plant sterols and stanols on intestinal cholesterol metabolism: suggested mechanisms from past to present".
6190:
1545:
5903:
5969:
6474:
5933:
318:
The richest naturally occurring sources of phytosterols are vegetable oils and products made from them. Sterols can be present in the free form and as
5928:
1422:
6404:
6200:
5943:
5872:
4117:
6195:
5962:
5923:
2286:
Sudhop, Thomas; Gottwald, Britta M.; Von
Bergmann, Klaus (2002). "Serum plant sterols as a potential risk factor for coronary heart disease".
6270:
2015:
Lea, L.J.; Hepburn, P.A. (2006). "Safety evaluation of phytosterol-esters. Part 9: Results of a
European post-launch monitoring programme".
6287:
5862:
3838:
952:
Akhisa, T.; Kokke, W. (1991). "Naturally occurring sterols and related compounds from plants". In
Patterson, G. W.; Nes, W. D. (eds.).
1056:
Salehi-Sahlabadi A, Varkaneh HK, Shahdadian F, Ghaedi E, Nouri M, Singh A, Farhadnejad H, Găman MA, Hekmatdoost A, Mirmiran P (2020).
833:
were subject to postlaunch monitoring after being introduced to the EU market in 2000, and no unpredicted side effects were reported.
5014:
2741:
1975:
843:
The link between plant sterols and CVD or CHD risk is complicated because phytosterol levels reflect cholesterol absorption. (See
6185:
1160:
Moreau RA, Hicks KB (2004). "The in vitro hydrolysis of phytosterol conjugates in food matrices by mammalian digestive enzymes".
5823:
334:
and fats, without, however, changing their relative composition. Sterols are therefore a useful tool in checking authenticity.
979:
3925:
350:
campesterol and stigmasterol, which account for about 65%, 30% and 3% of diet contents, respectively. The most common plant
6028:
3971:
2787:
2448:"Unesterified plant sterols and stanols lower LDL-cholesterol concentrations equivalently in hypercholesterolemic persons"
2052:
Silbernagel, G.; Fauler, G.; Renner, W.; Landl, E. M.; Hoffmann, M. M.; Winkelmann, B. R.; Boehm, B. O.; Marz, W. (2008).
1976:"The New Low-Cholesterol Diet: Plant Sterols and Stanols: What are sterols and stanols, and does anyone like to eat them?"
6033:
5250:
3766:
2323:"Plasma levels of plant sterols and the risk of coronary artery disease: The prospective EPIC-Norfolk Population Study"
1440:
817:
Because of their cholesterol reducing properties, some manufacturers are using sterols or stanols as a food additive.
2646:
1933:
Katan, M. B.; Grundy, S. M.; Jones, P.; Law, M.; Miettinen, T.; Paoletti, R.; Stresa
Workshop, Participants (2003).
6180:
4593:
3831:
2054:"The relationships of cholesterol metabolism and plasma plant sterols with the severity of coronary artery disease"
1486:
5081:
2590:"Connecting growth and defense: The emerging roles of brassinosteroids and gibberellins in plant innate immunity"
2095:"The associations of cholesterol metabolism and plasma plant sterols with all-cause and cardiovascular mortality"
6362:
1746:
1457:"Blood cholesterol reduction health claims on phytosterols can now be judged against EFSA new scientific advice"
1205:"Estimation of plant sterol and cholesterol intake in Finland: Quality of new values and their effect on intake"
6175:
5792:
5197:
4408:
2093:
Silbernagel, G.; Fauler, G.; Hoffmann, M. M.; Lutjohann, D.; Winkelmann, B. R.; Boehm, B. O.; Marz, W. (2010).
1295:"Divergent changes in serum sterols during a strict uncooked vegan diet in patients with rheumatoid arthritis"
64:-lowering effects from long-term consumption of phytosterols, there is insufficient evidence for an effect on
6519:
1747:"Plant sterols and plant stanols in the management of dyslipidaemia and prevention of cardiovascular disease"
1203:
Valsta, L. M.; Lemström, A.; Ovaskainen, M.-L.; Lampi, A.-M.; Toivo, J.; Korhonen, T.; Piironen, V. (2007).
169:
Esterification of the hydroxyl group at carbon 3 with fatty/organic acids or carbohydrates results in plant
6126:
5007:
3243:
2734:
2017:
826:
745:
354:
in the human diet are sitostanol and campestanol, which combined make up about 5% of dietary phytosterol.
150:
Removing carbon 24 and hydrogens from carbons 22 and 23, and inverting the stereochemistry at C-24 yields
6210:
6105:
6077:
3824:
3793:
2765:
880:
cells, which contain only one major sterol, plant cells synthesize an array of sterol mixtures in which
96:
They have a fused polycyclic structure and vary in carbon side chains and / or presence or absence of a
5816:
4733:
1998:
331:
6439:
6372:
6205:
6100:
6095:
5119:
5114:
5109:
5103:
3918:
3787:
2589:
6066:
5574:
5549:
5496:
4696:
3964:
2780:
5954:
6524:
6514:
6144:
5040:
5000:
2727:
796:
733:
1935:"Efficacy and Safety of Plant Stanols and Sterols in the Management of Blood Cholesterol Levels"
6353:
6233:
6163:
5992:
5154:
4860:
4458:
4418:
4413:
3198:
65:
6414:
1107:"Health benefits of 4,4-dimethyl phytosterols: an exploration beyond 4-desmethyl phytosterols"
6509:
6121:
6090:
5809:
5124:
5095:
5060:
5055:
4796:
3045:
2639:
1528:"Food Labeling; Health Claim; Phytosterols and Risk of Coronary Heart Disease; Proposed Rule"
183:
6424:
6319:
6297:
5564:
5491:
5242:
4829:
4728:
4723:
4586:
4503:
4273:
3911:
3071:
772:
2193:
2157:
1763:
8:
5338:
5305:
5144:
4611:
3957:
2773:
73:
69:
2624:
1527:
253:
6000:
4185:
3856:
2693:
2393:
2121:
2094:
1915:
1721:
1696:
1587:
1403:
1359:
1270:
1245:
1185:
1142:
1082:
1057:
1033:
1008:
57:
2536:
2424:
2228:
1697:"Controversial role of plant sterol esters in the management of hypercholesterolaemia"
1347:
1105:
Zhang, Tao; Liu, Ruijie; Chang, Ming; Jin, Qingzhe; Zhang, Hui; Wang, Xingguo (2020).
6243:
5544:
5530:
5134:
4893:
4878:
4870:
4691:
4668:
4367:
3848:
3810:
2611:
2570:
2505:
2469:
2428:
2385:
2344:
2303:
2268:
2232:
2197:
2161:
2126:
2075:
2034:
1956:
1907:
1872:
1809:
1768:
1726:
1672:
1628:
1579:
1436:
1395:
1351:
1316:
1275:
1226:
1177:
1146:
1134:
1126:
1087:
1038:
934:
926:
808:
807:. Statins work by reducing cholesterol synthesis via inhibition of the rate-limiting
728:
327:
2397:
2362:
Hallikainen, M A; Sarkkinen, E S; Gylling, H; Erkkilä, A T; Uusitupa, M I J (2000).
1919:
1502:"Health claims: plant sterol/stanol esters and risk of coronary heart disease (CHD)"
1487:"Health claims: plant sterol/stanol esters and risk of coronary heart disease (CHD)"
1456:
1407:
1363:
267:
225:
211:
6061:
5270:
4791:
4761:
4718:
4710:
4197:
4088:
3385:
3161:
3101:
2632:
2601:
2562:
2532:
2497:
2459:
2420:
2375:
2334:
2295:
2260:
2224:
2189:
2153:
2116:
2106:
2065:
2026:
1946:
1903:
1899:
1864:
1837:
1799:
1758:
1716:
1708:
1662:
1618:
1591:
1571:
1471:
1428:
1387:
1343:
1306:
1265:
1257:
1216:
1189:
1169:
1118:
1077:
1069:
1028:
1020:
918:
319:
922:
286:
239:
197:
6023:
5898:
5466:
5406:
5275:
5139:
4943:
4915:
4839:
4766:
4579:
4433:
4428:
4423:
4378:
3504:
3419:
3377:
2885:
2679:
2264:
1009:"Plant sterols and cardiovascular disease: A systematic review and meta-analysis"
836:
A potential safety concern regarding phytosterol consumption is in patients with
830:
804:
561:
143:
By hydrogenating the double bond between carbons 5 and 6 and removing carbon 24,
61:
385:
300:
189:
108:
23:
6484:
6469:
6451:
6085:
5867:
5846:
5734:
5717:
5679:
5481:
5456:
5370:
5357:
5295:
5065:
4937:
4921:
4865:
4438:
4308:
4264:
3770:
3724:
3637:
3632:
3622:
3599:
3561:
3551:
3132:
2683:
2659:
2501:
2339:
2322:
2070:
2053:
1712:
1073:
1024:
837:
471:
370:
259:
151:
77:
3816:
2030:
1334:
Weihrauch, JL; Gardner, JM (1978). "Sterol content of foods of plant origin".
1173:
6503:
6419:
6048:
5893:
5699:
5694:
5689:
5674:
5636:
5611:
5515:
5471:
5447:
5313:
5280:
5265:
5260:
5202:
5177:
5172:
5167:
5129:
5031:
5023:
4988:
4888:
4844:
4816:
4533:
4470:
4193:
4145:
3715:
3681:
3676:
3627:
2857:
2751:
2523:
Hartmann, Marie-Andrée (1998). "Plant sterols and the membrane environment".
2464:
2447:
1804:
1787:
1667:
1650:
1432:
1261:
1130:
930:
767:
685:
396:
338:
157:
Further removal of hydrogens from carbons 7 and 8 from brassicasterol yields
101:
2380:
2363:
2299:
1391:
1293:Ågren, J. J.; Tvrzicka, E.; Nenonen, M. T.; Helve, T.; Hänninen, O. (2007).
6409:
6399:
5938:
5918:
5709:
5646:
5616:
5486:
5430:
5290:
5255:
5228:
4883:
4801:
4781:
4748:
4620:
4498:
4304:
4249:
4080:
3998:
3869:
3729:
3647:
3566:
3556:
3499:
3482:
3467:
3436:
3396:
3366:
3292:
2971:
2951:
2698:
2615:
2574:
2566:
2509:
2473:
2432:
2389:
2348:
2307:
2272:
2236:
2201:
2165:
2130:
2079:
2038:
1960:
1911:
1876:
1868:
1841:
1813:
1772:
1730:
1676:
1623:
1606:
1583:
1575:
1399:
1320:
1279:
1230:
1181:
1138:
1091:
1042:
938:
885:
751:
623:
402:
380:
273:
231:
217:
170:
130:
50:
34:
2795:
2719:
1632:
358:
Sterol composition in crude oils (as percentage of total sterol fraction)
6340:
6329:
6324:
6302:
6292:
6225:
5985:
5913:
5888:
5851:
5739:
5669:
5662:
5657:
5628:
5606:
5525:
5508:
5375:
5192:
5187:
5182:
4959:
4932:
4776:
4683:
4673:
4648:
4628:
4553:
4538:
4528:
4508:
4285:
4226:
4156:
4127:
4053:
3864:
3701:
3691:
3667:
3652:
3494:
3459:
3343:
3338:
3206:
3170:
3147:
3086:
3035:
3025:
2975:
2895:
2688:
1355:
785:
654:
409:
391:
375:
365:
323:
292:
245:
203:
144:
123:
116:
97:
38:
2606:
2111:
1221:
1204:
1055:
844:
6479:
6459:
6429:
6391:
6309:
6282:
6275:
6255:
6248:
6136:
6018:
5908:
5856:
5684:
5594:
5380:
5318:
5207:
4976:
4949:
4926:
4638:
4633:
4543:
4518:
4443:
4336:
4331:
4236:
4221:
4216:
4174:
4042:
3935:
3899:
3889:
3686:
3604:
3530:
3489:
3477:
3472:
3358:
3348:
3142:
3137:
3090:
2703:
2655:
1311:
1294:
1122:
1106:
881:
592:
306:
158:
137:
19:
6464:
5396:
5333:
5323:
4811:
4663:
4658:
4653:
4476:
4386:
4346:
4244:
4208:
4065:
4038:
4030:
3989:
3981:
3943:
3884:
3313:
3222:
3175:
3106:
2946:
2801:
2759:
2674:
1951:
1934:
873:
502:
342:
330:. Some of the sterols are removed during the deodorization step of
88:
6238:
6149:
5984:
5749:
5586:
5569:
5461:
5401:
5328:
5285:
5223:
5162:
4955:
4806:
4738:
4643:
4559:
4355:
4281:
4170:
4161:
4141:
4132:
4061:
4015:
3879:
3657:
3642:
3614:
3543:
3509:
3308:
3180:
3081:
3055:
3040:
2991:
2981:
2941:
2866:
2805:
531:
440:
2361:
2092:
1826:
1607:"Serum plant sterols and their relation to cholesterol absorption"
1006:
956:. Champaign, IL: American Oil Chemists' Society. pp. 172–228.
907:
326:. The bound form is usually hydrolyzed in the small intestines by
92:
Nomenclature of the structure of a tetracyclic damarane triterpene
6345:
6056:
6038:
6010:
5989:
5756:
5727:
5599:
5554:
5520:
5503:
5365:
4786:
4771:
4323:
4019:
4007:
3535:
3525:
3446:
3267:
3262:
3190:
3185:
3127:
3122:
3076:
3050:
2986:
2925:
2920:
2846:
2837:
2797:
2445:
41:, that serve as structural components of biological membranes of
2320:
2143:
5801:
5773:
5768:
5761:
5744:
5722:
5559:
5539:
5425:
5343:
4603:
4567:
4484:
4363:
4102:
4069:
3874:
3696:
3238:
3096:
3030:
2996:
2967:
2880:
2663:
2446:
Vanstone, CA; Raeini-Sarjaz, M; Parsons, WE; Jones, PJ (2002).
2410:
877:
856:
811:
795:, where cholesterol lowering has been proven to reduce risk of
792:
46:
2587:
1469:
1454:
104:
sterols, having no double bonds in the sterol ring structure.
4756:
2178:
1376:
1202:
855:
The equivalent ability and safety of plant sterols and plant
42:
5793:
List of phytochemicals and foods in which they are prominent
2051:
1562:
Pollak, OJ (1953). "Reduction of blood cholesterol in man".
136:
By hydrogenating the double bond between carbons 5 and 6, β-
2486:
2285:
2214:
727:
The European Foods Safety Authority (EFSA) concluded that
2654:
1889:
1743:
1292:
1788:"The Cholesterol-Lowering Action of Plant Stanol Esters"
1651:"Ingestion of phytosterols is not potentially hazardous"
985:. Agriculture and Agri-Food Canada, Government of Canada
60:
have been marketed for decades. Despite well-documented
5039:
2249:
1246:"Food Ingredients That Inhibit Cholesterol Absorption"
3765:
Terpene synthase enzymes (many), having in common a
2588:
De Bruyne, L; Höfte, M; De Vleesschauwer, D (2014).
1694:
1690:
1688:
1686:
748:has approved the following claim for phytosterols:
1932:
845:
Phytosterols as a marker for cholesterol absorption
2552:
1854:
129:Removing a hydrogen from carbons 22 and 23 yields
2413:Nutrition, Metabolism and Cardiovascular Diseases
2253:Nutrition, Metabolism and Cardiovascular Diseases
1683:
281:Structures of some common sterols, for comparison
6501:
1830:European Journal of Lipid Science and Technology
1745:Society Consensus Panel on Phytosterols (2014).
1333:
1104:
864:generally lower than phytosterol concentration.
829:(GRAS) status in the US. Phytosterol-containing
173:, i.e. oleates, ferulates and (acyl) glycosides.
3846:
2045:
1604:
2843:Iridoid glycosides (iridoids bound to a sugar)
2208:
1546:"Plant Sterols and Blood Cholesterol Lowering"
1424:Ullmann's Encyclopedia of Industrial Chemistry
5970:
5817:
5008:
4587:
3965:
3919:
3832:
2781:
2735:
2640:
2217:Journal of the American College of Cardiology
1695:Weingartner, O.; Bohm, M.; Laufs, U. (2008).
1470:European Food Safety Authority (2008-08-21).
1455:European Food Safety Authority (2009-07-31).
1421:Alfred Thomas (2007), "Fats and Fatty Oils",
1420:
1002:
1000:
977:
4601:
2490:Journal of the American Dietetic Association
1892:Journal of the American College of Nutrition
1644:
1642:
1336:Journal of the American Dietetic Association
2749:
2243:
1159:
951:
5977:
5963:
5824:
5810:
5015:
5001:
4594:
4580:
3972:
3958:
3926:
3912:
3839:
3825:
2788:
2774:
2742:
2728:
2647:
2633:
2452:The American Journal of Clinical Nutrition
2279:
2014:
1611:The American Journal of Clinical Nutrition
997:
111:. The nomenclature is shown on the right.
2605:
2463:
2379:
2338:
2120:
2110:
2069:
1950:
1926:
1803:
1762:
1720:
1666:
1639:
1622:
1543:
1310:
1269:
1243:
1220:
1081:
1032:
3933:
2522:
980:"Phytosterols and stanols: Topic 10075E"
903:
901:
87:
18:
3979:
2555:Molecular Nutrition & Food Research
2548:
2546:
1973:
1857:Molecular Nutrition & Food Research
779:
313:
6502:
2368:European Journal of Clinical Nutrition
1785:
1779:
1561:
1380:European Journal of Clinical Nutrition
973:
971:
969:
967:
965:
963:
954:Physiology and Biochemistry of Sterols
867:
784:The ability of phytosterols to reduce
178:Structures of some common phytosterols
5958:
5805:
4996:
4575:
3953:
3907:
3820:
2769:
2723:
2628:
2194:10.1016/j.atherosclerosis.2006.10.032
2158:10.1016/j.atherosclerosis.2009.11.007
1764:10.1016/j.atherosclerosis.2013.11.043
1648:
898:
16:Class of steroids derived from plants
2543:
107:The molecule in the article lead is
1484:
1478:
960:
850:
337:As common sources of phytosterols,
13:
5022:
3767:terpene synthase N terminal domain
1999:"GRAS Notice 000181: Phytosterols"
1605:Tilvis, RS; Miettinen, TA (1986).
1427:(7th ed.), Wiley, p. 9,
14:
6536:
5831:
762:
717:
299:
285:
266:
252:
238:
224:
210:
196:
182:
5082:p-Hydroxybenzoic acid glucoside
2581:
2516:
2480:
2439:
2404:
2355:
2314:
2172:
2137:
2086:
2008:
1996:
1990:
1967:
1883:
1848:
1820:
1737:
1661:(11): 2485, author reply 2486.
1598:
1555:
1537:
1525:
1519:
1499:
1493:
1463:
1448:
1414:
1370:
1327:
1286:
122:By removing carbons 24 and 24,
56:Phytosterol-enriched foods and
5251:α-Cyano-4-hydroxycinnamic acid
5198:Phloroglucinol carboxylic acid
4409:List of phytochemicals in food
1904:10.1080/07315724.2009.10719784
1237:
1196:
1153:
1098:
1049:
945:
872:Sterols are essential for all
1:
2537:10.1016/S1360-1385(98)01233-3
2425:10.1016/S0939-4753(04)80033-4
2327:The Journal of Lipid Research
2229:10.1016/S0735-1097(00)00527-1
2099:The Journal of Lipid Research
2058:The Journal of Lipid Research
1348:10.1016/S0002-8223(21)05668-6
923:10.1016/j.plipres.2018.04.001
892:
6127:Geranylgeranyl pyrophosphate
3244:Geranylgeranyl pyrophosphate
2265:10.1016/j.numecd.2005.04.001
2018:Food and Chemical Toxicology
1299:British Journal of Nutrition
1209:British Journal of Nutrition
876:. In contrast to animal and
827:generally recognized as safe
133:(stigmasta-5,22-dien-3β-ol).
83:
26:, a prototypical phytosterol
7:
6106:Dimethylallyl pyrophosphate
4734:Pyrocatecollic type tannins
3794:Dimethylallyl pyrophosphate
1974:Griffin, RM (Feb 2, 2009).
978:Patterson, CA (July 2006).
140:(Stigmastanol) is obtained.
10:
6541:
2502:10.1016/j.jada.2010.02.011
2340:10.1194/jlr.M600371-JLR200
2071:10.1194/jlr.P800013-JLR200
1244:Jesch ED, Carr TP (2017).
1074:10.1007/s40200-020-00526-z
911:Progress in Lipid Research
154:(ergosta-5,22-dien-3β-ol).
6449:
6389:
6382:
6338:
6223:
6171:
6162:
6135:
6114:
6101:Isopentenyl pyrophosphate
6096:5-Diphosphomevalonic acid
6075:
6047:
6008:
5999:
5881:
5839:
5784:
5708:
5645:
5627:
5585:
5446:
5415:
5389:
5356:
5304:
5241:
5216:
5153:
5120:3,5-Dihydroxybenzoic acid
5115:2,6-Dihydroxybenzoic acid
5110:2,4-Dihydroxybenzoic acid
5104:2,3-Dihydroxybenzoic acid
5094:
5074:
5048:
5030:
4987:
4968:
4908:
4853:
4828:
4747:
4709:
4682:
4619:
4610:
4566:
4552:
4517:
4483:
4469:
4456:
4399:
4377:
4354:
4345:
4322:
4295:
4272:
4263:
4235:
4207:
4184:
4155:
4126:
4110:
4101:
4079:
4052:
4029:
4006:
3997:
3988:
3942:
3898:
3855:
3809:
3788:Isopentenyl pyrophosphate
3780:
3758:
3742:Norisoprenoids (modified)
3741:
3714:
3666:
3613:
3598:
3581:
3518:
3445:
3435:
3418:
3357:
3331:
3301:
3276:
3255:
3231:
3221:
3160:
3115:
3064:
3018:
3009:
2960:
2934:
2913:
2894:
2856:
2813:
2758:
2670:
2031:10.1016/j.fct.2006.01.017
1174:10.1007/s11745-004-1294-3
820:
5575:Syn-propanethial-S-oxide
5497:Phenethyl Isothiocyanate
5041:Monohydroxybenzoic acids
4697:1,3,6-Trigalloyl glucose
3781:Activated isoprene forms
3582:Sesquarterpenes/oids (7)
2831:Monocyclic (single ring)
1792:The Journal of Nutrition
1713:10.1093/eurheartj/ehn580
1655:The Journal of Nutrition
1485:FDA (8 September 2000).
1433:10.1002/14356007.a10_173
1262:10.3746/pnf.2017.22.2.67
1025:10.1093/eurheartj/ehr441
6315:Cholesta-7,24-dien-3-ol
6266:4alpha-Methylzymosterol
6145:Prephytoene diphosphate
5993:metabolic intermediates
5654:Saturated cyclic acids
5155:Trihydroxybenzoic acids
4419:O-methylated flavonoids
4414:C-methylated flavonoids
3404:Secodehydroabietic acid
2525:Trends in Plant Science
2381:10.1038/sj.ejcn.1601083
2300:10.1053/meta.2002.36298
1939:Mayo Clinic Proceedings
1392:10.1038/sj.ejcn.1601980
1062:J Diabetes Metab Disord
797:cardiovascular diseases
757:For plant stanol esters
722:
341:have been developed as
115:By removing carbon 24,
66:cardiovascular diseases
45:. They encompass plant
6234:Farnesyl pyrophosphate
6164:Non-mevalonate pathway
5096:Dihydroxybenzoic acids
4459:Flavonoid biosynthesis
4297:3-hydroxyanthocyanidin
3199:Farnesyl pyrophosphate
2567:10.1002/mnfr.201100722
2465:10.1093/ajcn/76.6.1272
1869:10.1002/mnfr.201100722
1842:10.1002/ejlt.200390033
1805:10.1093/jn/129.12.2109
1786:Nguyen, Tu T. (1999).
1701:European Heart Journal
1668:10.1093/jn/137.11.2485
1576:10.1161/01.CIR.7.5.702
1013:European Heart Journal
739:
734:coronary heart disease
93:
27:
6367:-Dihydroxycholesterol
6261:14-demethyllanosterol
6122:Geranyl pyrophosphate
6091:Phosphomevalonic acid
6067:β-Hydroxybutyric acid
5550:3,3'-Diindolylmethane
5478:Aglycone derivatives
5243:Hydroxycinnamic acids
5125:Ethyl protocatechuate
5061:4-Hydroxybenzoic acid
5056:3-Hydroxybenzoic acid
4830:Flavono-ellagitannins
4821:Phlorofucofuroeckol B
4797:Phlorofucofuroeckol A
4729:Catechol-type tannins
4724:Polyflavonoid tannins
4274:3-deoxyanthocyanidins
3401:Sandaracopimaric acid
3046:Geranyl pyrophosphate
91:
22:
6520:Hypolipidemic agents
6425:24-Methylenelophenol
6320:7-Dehydrodesmosterol
6298:7-Dehydrocholesterol
5565:Allyl isothiocyanate
5492:Allyl isothiocyanate
5306:Aromatic amino acids
5217:Other phenolic acids
4612:Hydrolysable tannins
4504:Secoisolariciresinol
3591:Tetraprenylcurcumene
3072:Grapefruit mercaptan
1624:10.1093/ajcn/43.1.92
780:Cholesterol lowering
773:hypercholesterolemic
314:Dietary phytosterols
6415:4α-methylfecosterol
6358:-Hydroxycholesterol
5339:5-hydroxytryptophan
5145:Protocatechuic acid
4854:Other Miscellaneous
3857:Natural monophenols
3374:Dehydroabietic acid
2840:(cyclopentane ring)
2112:10.1194/jlr.P002899
1222:10.1079/BJN20041234
1111:Food & Function
868:Functions in plants
359:
74:glycated hemoglobin
70:fasting blood sugar
58:dietary supplements
6001:Mevalonate pathway
5426:Phenolic compounds
4669:Tellimagrandin IIs
3849:phenolic compounds
3811:Phenolic compounds
2834:Bicyclic (2 rings)
2694:Dihydrotachysterol
1649:Jones, PJ (2007).
1312:10.1079/BJN2000234
1250:Prev Nutr Food Sci
1123:10.1039/C9FO01205B
357:
328:pancreatic enzymes
94:
28:
6497:
6496:
6493:
6492:
6244:2,3-Oxidosqualene
6219:
6218:
6158:
6157:
5952:
5951:
5799:
5798:
5545:Indole-3-carbinol
5531:Diallyl disulfide
5440:
5439:
5352:
5351:
5237:
5236:
5135:Homogentisic acid
5106:(Hypogallic acid)
5090:
5089:
4983:
4982:
4904:
4903:
4871:Synthetic tannins
4833:(complex tannins)
4719:Proanthocyanidins
4711:Condensed tannins
4705:
4704:
4692:Digalloyl glucose
4602:Types of natural
4465:
4464:
4452:
4451:
4395:
4394:
4368:Isoliquiritigenin
4318:
4317:
4259:
4258:
4097:
4096:
3803:
3802:
3751:7,8-dihydroionone
3710:
3709:
3577:
3576:
3414:
3413:
3382:Lambertianic acid
3156:
3155:
3005:
3004:
2820:Acyclic (linear,
2717:
2716:
2607:10.1093/mp/ssu050
1798:(12): 2109–2112.
809:HMG-CoA reductase
729:blood cholesterol
715:
714:
320:fatty acid esters
6532:
6475:Ergostatetraenol
6387:
6386:
6346:Steroid hormones
6169:
6168:
6062:Acetoacetic acid
6006:
6005:
5979:
5972:
5965:
5956:
5955:
5934:Stigmastadienone
5904:δ-7-stigmasterol
5826:
5819:
5812:
5803:
5802:
5407:Alkylresorcinols
5271:Chlorogenic acid
5046:
5045:
5037:
5036:
5017:
5010:
5003:
4994:
4993:
4944:Phenylpropanoids
4916:Diarylheptanoids
4792:Fucophlorethol A
4617:
4616:
4596:
4589:
4582:
4573:
4572:
4434:Prenylflavonoids
4429:Pyranoflavonoids
4424:Furanoflavonoids
4352:
4351:
4270:
4269:
4198:Leucodelphinidin
4186:Flavan-3,4-diols
4108:
4107:
4089:Dalbergichromene
4004:
4003:
3995:
3994:
3974:
3967:
3960:
3951:
3950:
3928:
3921:
3914:
3905:
3904:
3841:
3834:
3827:
3818:
3817:
3611:
3610:
3443:
3442:
3420:Sesterterpenoids
3386:Levopimaric acid
3248:Geranyl-linalool
3229:
3228:
3162:Sesquiterpenoids
3102:Perillyl alcohol
3016:
3015:
2911:
2910:
2790:
2783:
2776:
2767:
2766:
2744:
2737:
2730:
2721:
2720:
2649:
2642:
2635:
2626:
2625:
2620:
2619:
2609:
2585:
2579:
2578:
2550:
2541:
2540:
2520:
2514:
2513:
2484:
2478:
2477:
2467:
2443:
2437:
2436:
2408:
2402:
2401:
2383:
2359:
2353:
2352:
2342:
2318:
2312:
2311:
2283:
2277:
2276:
2247:
2241:
2240:
2212:
2206:
2205:
2176:
2170:
2169:
2141:
2135:
2134:
2124:
2114:
2090:
2084:
2083:
2073:
2049:
2043:
2042:
2012:
2006:
2005:
2003:
1994:
1988:
1987:
1985:
1983:
1971:
1965:
1964:
1954:
1952:10.4065/78.8.965
1930:
1924:
1923:
1887:
1881:
1880:
1852:
1846:
1845:
1836:(3–4): 171–185.
1824:
1818:
1817:
1807:
1783:
1777:
1776:
1766:
1741:
1735:
1734:
1724:
1692:
1681:
1680:
1670:
1646:
1637:
1636:
1626:
1602:
1596:
1595:
1559:
1553:
1552:
1550:
1541:
1535:
1534:
1532:
1523:
1517:
1516:
1514:
1513:
1504:. Archived from
1497:
1491:
1490:
1482:
1476:
1475:
1467:
1461:
1460:
1452:
1446:
1445:
1418:
1412:
1411:
1374:
1368:
1367:
1331:
1325:
1324:
1314:
1290:
1284:
1283:
1273:
1241:
1235:
1234:
1224:
1200:
1194:
1193:
1157:
1151:
1150:
1102:
1096:
1095:
1085:
1053:
1047:
1046:
1036:
1004:
995:
994:
992:
990:
984:
975:
958:
957:
949:
943:
942:
905:
851:Sterol vs stanol
838:phytosterolaemia
831:functional foods
360:
356:
303:
289:
270:
256:
242:
228:
214:
200:
186:
6540:
6539:
6535:
6534:
6533:
6531:
6530:
6529:
6500:
6499:
6498:
6489:
6445:
6378:
6343:
6334:
6215:
6154:
6131:
6110:
6071:
6043:
6024:Acetoacetyl-CoA
5995:
5983:
5953:
5948:
5929:Stigmastadienol
5894:δ-5-avenasterol
5889:δ-7-avenasterol
5877:
5835:
5830:
5800:
5795:
5780:
5735:Polysaccharides
5718:Monosaccharides
5704:
5641:
5623:
5581:
5482:Isothiocyanates
5467:Gluconasturtiin
5457:isothiocyanates
5442:
5441:
5436:
5411:
5385:
5358:Phenylethanoids
5348:
5300:
5276:Diferulic acids
5233:
5212:
5149:
5140:Orsellinic acid
5086:
5070:
5026:
5021:
4979:
4964:
4938:Naphthoquinones
4900:
4849:
4840:Epicutissimin A
4832:
4824:
4743:
4701:
4678:
4606:
4600:
4562:
4548:
4521:
4513:
4491:
4487:
4479:
4461:
4448:
4391:
4379:Dihydrochalcone
4373:
4341:
4314:
4291:
4255:
4231:
4203:
4180:
4159:
4151:
4130:
4122:
4093:
4075:
4048:
4025:
3984:
3978:
3946:
3938:
3932:
3894:
3851:
3845:
3805:
3804:
3799:
3776:
3754:
3737:
3706:
3662:
3602:
3600:Tetraterpenoids
3594:
3573:
3514:
3505:Cholecalciferol
3431:
3428:Geranylfarnesol
3410:
3393:Neoabietic acid
3378:Isopimaric acid
3353:
3327:
3297:
3272:
3251:
3217:
3152:
3111:
3060:
3011:
3010:Monoterpenoids
3001:
2956:
2930:
2906:
2902:
2898:
2890:
2886:Isovaleric acid
2876:
2872:
2852:
2809:
2794:
2754:
2748:
2718:
2713:
2684:Ergocalciferols
2680:Cholecalciferol
2666:
2660:membrane lipids
2653:
2623:
2594:Molecular Plant
2586:
2582:
2551:
2544:
2521:
2517:
2485:
2481:
2444:
2440:
2409:
2405:
2360:
2356:
2319:
2315:
2294:(12): 1519–21.
2284:
2280:
2248:
2244:
2213:
2209:
2182:Atherosclerosis
2177:
2173:
2146:Atherosclerosis
2142:
2138:
2091:
2087:
2050:
2046:
2013:
2009:
2001:
1995:
1991:
1981:
1979:
1972:
1968:
1931:
1927:
1888:
1884:
1853:
1849:
1825:
1821:
1784:
1780:
1751:Atherosclerosis
1742:
1738:
1693:
1684:
1647:
1640:
1603:
1599:
1560:
1556:
1548:
1544:Health Canada.
1542:
1538:
1530:
1524:
1520:
1511:
1509:
1498:
1494:
1483:
1479:
1468:
1464:
1453:
1449:
1443:
1419:
1415:
1386:(10): 1378–85.
1375:
1371:
1332:
1328:
1291:
1287:
1242:
1238:
1201:
1197:
1158:
1154:
1103:
1099:
1054:
1050:
1005:
998:
988:
986:
982:
976:
961:
950:
946:
906:
899:
895:
870:
853:
823:
805:adverse effects
782:
765:
742:
725:
720:
562:Palm kernel oil
316:
309:
304:
295:
290:
276:
271:
262:
257:
248:
243:
234:
229:
220:
215:
206:
201:
192:
187:
86:
62:LDL cholesterol
17:
12:
11:
5:
6538:
6528:
6527:
6525:Phytochemicals
6522:
6517:
6515:Food additives
6512:
6495:
6494:
6491:
6490:
6488:
6487:
6485:Ergocalciferol
6482:
6477:
6472:
6470:Ergostatrienol
6467:
6462:
6456:
6454:
6452:Ergocalciferol
6447:
6446:
6444:
6443:
6432:
6427:
6422:
6417:
6412:
6407:
6405:Cycloeucalenol
6402:
6396:
6394:
6384:
6380:
6379:
6377:
6376:
6369:
6360:
6350:
6348:
6336:
6335:
6333:
6332:
6327:
6322:
6317:
6312:
6306:
6305:
6300:
6295:
6290:
6285:
6279:
6278:
6273:
6268:
6263:
6258:
6252:
6251:
6246:
6241:
6236:
6230:
6228:
6221:
6220:
6217:
6216:
6214:
6213:
6208:
6203:
6198:
6193:
6188:
6183:
6178:
6172:
6166:
6160:
6159:
6156:
6155:
6153:
6152:
6147:
6141:
6139:
6133:
6132:
6130:
6129:
6124:
6118:
6116:
6112:
6111:
6109:
6108:
6103:
6098:
6093:
6088:
6086:Mevalonic acid
6082:
6080:
6073:
6072:
6070:
6069:
6064:
6059:
6053:
6051:
6045:
6044:
6042:
6041:
6036:
6031:
6026:
6021:
6015:
6013:
6003:
5997:
5996:
5982:
5981:
5974:
5967:
5959:
5950:
5949:
5947:
5946:
5941:
5936:
5931:
5926:
5921:
5916:
5911:
5906:
5901:
5896:
5891:
5885:
5883:
5879:
5878:
5876:
5875:
5870:
5868:Ergostatrienol
5865:
5860:
5854:
5849:
5847:Brassicasterol
5843:
5841:
5837:
5836:
5829:
5828:
5821:
5814:
5806:
5797:
5796:
5791:
5789:
5782:
5781:
5779:
5778:
5777:
5776:
5771:
5766:
5765:
5764:
5754:
5753:
5752:
5747:
5732:
5731:
5730:
5725:
5714:
5712:
5706:
5705:
5703:
5702:
5697:
5692:
5687:
5682:
5680:Anacardic acid
5677:
5672:
5667:
5666:
5665:
5660:
5651:
5649:
5643:
5642:
5640:
5639:
5633:
5631:
5625:
5624:
5622:
5621:
5620:
5619:
5614:
5604:
5603:
5602:
5591:
5589:
5583:
5582:
5580:
5579:
5578:
5577:
5572:
5567:
5562:
5557:
5552:
5547:
5537:
5536:
5535:
5534:
5533:
5523:
5516:Organosulfides
5513:
5512:
5511:
5506:
5501:
5500:
5499:
5494:
5489:
5476:
5475:
5474:
5469:
5464:
5452:
5450:
5448:Glucosinolates
5444:
5443:
5438:
5437:
5435:
5434:
5428:
5422:
5420:
5413:
5412:
5410:
5409:
5404:
5399:
5393:
5391:
5387:
5386:
5384:
5383:
5378:
5373:
5371:Hydroxytyrosol
5368:
5362:
5360:
5354:
5353:
5350:
5349:
5347:
5346:
5341:
5336:
5331:
5326:
5321:
5316:
5310:
5308:
5302:
5301:
5299:
5298:
5296:Sinapinic acid
5293:
5288:
5283:
5278:
5273:
5268:
5263:
5258:
5253:
5247:
5245:
5239:
5238:
5235:
5234:
5232:
5231:
5226:
5220:
5218:
5214:
5213:
5211:
5210:
5205:
5200:
5195:
5190:
5185:
5180:
5175:
5170:
5165:
5159:
5157:
5151:
5150:
5148:
5147:
5142:
5137:
5132:
5127:
5122:
5117:
5112:
5107:
5100:
5098:
5092:
5091:
5088:
5087:
5085:
5084:
5078:
5076:
5072:
5071:
5069:
5068:
5066:Salicylic acid
5063:
5058:
5052:
5050:
5043:
5034:
5032:Phenolic acids
5028:
5027:
5024:Aromatic acids
5020:
5019:
5012:
5005:
4997:
4991:
4989:Aromatic acids
4985:
4984:
4981:
4980:
4975:
4973:
4966:
4965:
4963:
4962:
4953:
4947:
4941:
4935:
4930:
4924:
4922:Anthraquinones
4919:
4912:
4910:
4906:
4905:
4902:
4901:
4899:
4898:
4897:
4896:
4891:
4886:
4881:
4873:
4868:
4866:Pseudo tannins
4863:
4861:Tannin sources
4857:
4855:
4851:
4850:
4848:
4847:
4842:
4836:
4834:
4826:
4825:
4823:
4822:
4819:
4814:
4809:
4804:
4799:
4794:
4789:
4784:
4779:
4774:
4769:
4764:
4759:
4753:
4751:
4745:
4744:
4742:
4741:
4736:
4731:
4726:
4721:
4715:
4713:
4707:
4706:
4703:
4702:
4700:
4699:
4694:
4688:
4686:
4680:
4679:
4677:
4676:
4671:
4666:
4661:
4656:
4651:
4646:
4641:
4636:
4631:
4625:
4623:
4614:
4608:
4607:
4599:
4598:
4591:
4584:
4576:
4570:
4564:
4563:
4558:
4556:
4550:
4549:
4547:
4546:
4541:
4536:
4531:
4525:
4523:
4515:
4514:
4512:
4511:
4506:
4501:
4495:
4493:
4489:
4481:
4480:
4475:
4473:
4471:Flavonolignans
4467:
4466:
4463:
4462:
4457:
4454:
4453:
4450:
4449:
4447:
4446:
4441:
4439:Methylenedioxy
4436:
4431:
4426:
4421:
4416:
4411:
4405:
4403:
4397:
4396:
4393:
4392:
4390:
4389:
4383:
4381:
4375:
4374:
4372:
4371:
4360:
4358:
4349:
4343:
4342:
4340:
4339:
4334:
4328:
4326:
4320:
4319:
4316:
4315:
4313:
4312:
4309:Guibourtinidin
4301:
4299:
4293:
4292:
4290:
4289:
4278:
4276:
4267:
4265:Anthocyanidins
4261:
4260:
4257:
4256:
4254:
4253:
4247:
4241:
4239:
4233:
4232:
4230:
4229:
4224:
4219:
4213:
4211:
4205:
4204:
4202:
4201:
4190:
4188:
4182:
4181:
4179:
4178:
4167:
4165:
4153:
4152:
4150:
4149:
4138:
4136:
4124:
4123:
4121:
4120:
4114:
4112:
4105:
4099:
4098:
4095:
4094:
4092:
4091:
4085:
4083:
4077:
4076:
4074:
4073:
4058:
4056:
4050:
4049:
4047:
4046:
4035:
4033:
4027:
4026:
4024:
4023:
4012:
4010:
4001:
3992:
3986:
3985:
3977:
3976:
3969:
3962:
3954:
3948:
3940:
3939:
3931:
3930:
3923:
3916:
3908:
3902:
3896:
3895:
3893:
3892:
3887:
3882:
3877:
3872:
3867:
3861:
3859:
3853:
3852:
3844:
3843:
3836:
3829:
3821:
3815:
3813:
3807:
3806:
3801:
3800:
3798:
3797:
3791:
3784:
3782:
3778:
3777:
3775:
3774:
3771:protein domain
3762:
3760:
3756:
3755:
3753:
3752:
3749:
3745:
3743:
3739:
3738:
3736:
3735:
3732:
3727:
3725:Natural rubber
3721:
3719:
3716:Polyterpenoids
3712:
3711:
3708:
3707:
3705:
3704:
3699:
3694:
3689:
3684:
3679:
3673:
3671:
3664:
3663:
3661:
3660:
3655:
3650:
3645:
3640:
3638:Delta-Carotene
3635:
3633:Gamma-Carotene
3630:
3625:
3623:Alpha-Carotene
3619:
3617:
3608:
3596:
3595:
3593:
3592:
3589:
3585:
3583:
3579:
3578:
3575:
3574:
3572:
3571:
3570:
3569:
3564:
3562:Betulinic acid
3559:
3554:
3552:Oleanolic acid
3546:
3541:
3538:
3533:
3528:
3522:
3520:
3516:
3515:
3513:
3512:
3507:
3502:
3497:
3492:
3487:
3486:
3485:
3480:
3475:
3470:
3465:
3464:Citrostadienol
3462:
3451:
3449:
3440:
3433:
3432:
3430:
3429:
3425:
3423:
3416:
3415:
3412:
3411:
3409:
3408:
3407:Palustric acid
3405:
3402:
3399:
3394:
3391:
3388:
3383:
3380:
3375:
3372:
3369:
3363:
3361:
3355:
3354:
3352:
3351:
3346:
3341:
3335:
3333:
3329:
3328:
3326:
3325:
3322:
3319:
3316:
3311:
3305:
3303:
3299:
3298:
3296:
3295:
3290:
3287:
3280:
3278:
3274:
3273:
3271:
3270:
3265:
3259:
3257:
3253:
3252:
3250:
3249:
3246:
3241:
3235:
3233:
3226:
3219:
3218:
3216:
3215:
3212:
3209:
3204:
3201:
3196:
3193:
3188:
3183:
3178:
3173:
3167:
3165:
3158:
3157:
3154:
3153:
3151:
3150:
3145:
3140:
3135:
3133:Bornyl acetate
3130:
3125:
3119:
3117:
3113:
3112:
3110:
3109:
3104:
3099:
3094:
3084:
3079:
3074:
3068:
3066:
3062:
3061:
3059:
3058:
3053:
3048:
3043:
3038:
3033:
3028:
3022:
3020:
3013:
3007:
3006:
3003:
3002:
3000:
2999:
2994:
2989:
2984:
2979:
2964:
2962:
2958:
2957:
2955:
2954:
2949:
2944:
2938:
2936:
2932:
2931:
2929:
2928:
2923:
2917:
2915:
2908:
2904:
2900:
2892:
2891:
2889:
2888:
2883:
2878:
2874:
2870:
2863:
2861:
2858:Hemiterpenoids
2854:
2853:
2851:
2850:
2844:
2841:
2835:
2832:
2829:
2817:
2815:
2811:
2810:
2793:
2792:
2785:
2778:
2770:
2764:
2762:
2756:
2755:
2752:phytochemicals
2747:
2746:
2739:
2732:
2724:
2715:
2714:
2712:
2711:
2706:
2701:
2696:
2691:
2686:
2677:
2671:
2668:
2667:
2652:
2651:
2644:
2637:
2629:
2622:
2621:
2580:
2561:(7): 1058–72.
2542:
2531:(5): 170–175.
2515:
2479:
2438:
2403:
2354:
2313:
2278:
2242:
2223:(5): 1185–91.
2207:
2171:
2136:
2105:(8): 2384–93.
2085:
2044:
2025:(8): 1213–22.
2007:
1989:
1966:
1925:
1882:
1863:(7): 1058–72.
1847:
1819:
1778:
1736:
1682:
1638:
1597:
1554:
1536:
1518:
1492:
1477:
1462:
1447:
1442:978-3527306732
1441:
1413:
1369:
1326:
1285:
1236:
1195:
1152:
1097:
1068:(1): 625–632.
1048:
1019:(4): 444–451.
996:
959:
944:
896:
894:
891:
869:
866:
852:
849:
822:
819:
781:
778:
764:
761:
741:
738:
724:
721:
719:
716:
713:
712:
709:
706:
703:
700:
697:
694:
691:
688:
682:
681:
678:
675:
672:
669:
666:
663:
660:
657:
651:
650:
647:
644:
641:
638:
635:
632:
629:
626:
620:
619:
616:
613:
610:
607:
604:
601:
598:
595:
589:
588:
585:
582:
579:
576:
573:
570:
567:
564:
558:
557:
554:
551:
548:
545:
542:
539:
537:
534:
528:
527:
524:
522:
519:
516:
513:
510:
508:
505:
499:
498:
495:
492:
489:
486:
483:
480:
477:
474:
472:Cottonseed oil
468:
467:
464:
461:
458:
455:
452:
449:
446:
443:
437:
436:
433:
430:
427:
424:
421:
418:
415:
412:
406:
405:
399:
397:∆7-Avenasterol
394:
388:
383:
378:
373:
371:Brassicasterol
368:
363:
339:vegetable oils
315:
312:
311:
310:
305:
298:
296:
291:
284:
282:
278:
277:
272:
265:
263:
260:Brassicasterol
258:
251:
249:
244:
237:
235:
230:
223:
221:
216:
209:
207:
202:
195:
193:
188:
181:
179:
175:
174:
163:
162:
155:
152:brassicasterol
148:
141:
134:
127:
120:
85:
82:
78:mortality rate
15:
9:
6:
4:
3:
2:
6537:
6526:
6523:
6521:
6518:
6516:
6513:
6511:
6508:
6507:
6505:
6486:
6483:
6481:
6478:
6476:
6473:
6471:
6468:
6466:
6463:
6461:
6458:
6457:
6455:
6453:
6448:
6441:
6437:
6433:
6431:
6428:
6426:
6423:
6421:
6420:Isofucosterol
6418:
6416:
6413:
6411:
6408:
6406:
6403:
6401:
6398:
6397:
6395:
6393:
6388:
6385:
6381:
6374:
6370:
6368:
6366:
6361:
6359:
6357:
6352:
6351:
6349:
6347:
6342:
6337:
6331:
6328:
6326:
6323:
6321:
6318:
6316:
6313:
6311:
6308:
6307:
6304:
6301:
6299:
6296:
6294:
6291:
6289:
6286:
6284:
6281:
6280:
6277:
6274:
6272:
6269:
6267:
6264:
6262:
6259:
6257:
6254:
6253:
6250:
6247:
6245:
6242:
6240:
6237:
6235:
6232:
6231:
6229:
6227:
6222:
6212:
6209:
6207:
6204:
6202:
6199:
6197:
6194:
6192:
6189:
6187:
6184:
6182:
6179:
6177:
6174:
6173:
6170:
6167:
6165:
6161:
6151:
6148:
6146:
6143:
6142:
6140:
6138:
6134:
6128:
6125:
6123:
6120:
6119:
6117:
6113:
6107:
6104:
6102:
6099:
6097:
6094:
6092:
6089:
6087:
6084:
6083:
6081:
6079:
6074:
6068:
6065:
6063:
6060:
6058:
6055:
6054:
6052:
6050:
6049:Ketone bodies
6046:
6040:
6037:
6035:
6032:
6030:
6027:
6025:
6022:
6020:
6017:
6016:
6014:
6012:
6007:
6004:
6002:
5998:
5994:
5991:
5987:
5980:
5975:
5973:
5968:
5966:
5961:
5960:
5957:
5945:
5944:Stigmastenone
5942:
5940:
5937:
5935:
5932:
5930:
5927:
5925:
5922:
5920:
5917:
5915:
5912:
5910:
5907:
5905:
5902:
5900:
5897:
5895:
5892:
5890:
5887:
5886:
5884:
5880:
5874:
5873:Ergostadienol
5871:
5869:
5866:
5864:
5861:
5858:
5855:
5853:
5850:
5848:
5845:
5844:
5842:
5838:
5834:
5827:
5822:
5820:
5815:
5813:
5808:
5807:
5804:
5794:
5790:
5787:
5783:
5775:
5772:
5770:
5767:
5763:
5760:
5759:
5758:
5755:
5751:
5748:
5746:
5743:
5742:
5741:
5738:
5737:
5736:
5733:
5729:
5726:
5724:
5721:
5720:
5719:
5716:
5715:
5713:
5711:
5710:Carbohydrates
5707:
5701:
5700:Fertaric acid
5698:
5696:
5695:Coutaric acid
5693:
5691:
5690:Caftaric acid
5688:
5686:
5683:
5681:
5678:
5676:
5675:Tartaric acid
5673:
5671:
5668:
5664:
5661:
5659:
5656:
5655:
5653:
5652:
5650:
5648:
5647:Organic acids
5644:
5638:
5637:Chlorophyllin
5635:
5634:
5632:
5630:
5626:
5618:
5615:
5613:
5612:Indicaxanthin
5610:
5609:
5608:
5605:
5601:
5598:
5597:
5596:
5593:
5592:
5590:
5588:
5584:
5576:
5573:
5571:
5568:
5566:
5563:
5561:
5558:
5556:
5553:
5551:
5548:
5546:
5543:
5542:
5541:
5538:
5532:
5529:
5528:
5527:
5524:
5522:
5519:
5518:
5517:
5514:
5510:
5507:
5505:
5502:
5498:
5495:
5493:
5490:
5488:
5485:
5484:
5483:
5480:
5479:
5477:
5473:
5472:Glucoraphanin
5470:
5468:
5465:
5463:
5460:
5459:
5458:
5455:Precursor to
5454:
5453:
5451:
5449:
5445:
5432:
5431:Phlorotannins
5429:
5427:
5424:
5423:
5421:
5418:
5414:
5408:
5405:
5403:
5400:
5398:
5395:
5394:
5392:
5388:
5382:
5379:
5377:
5374:
5372:
5369:
5367:
5364:
5363:
5361:
5359:
5355:
5345:
5342:
5340:
5337:
5335:
5332:
5330:
5327:
5325:
5322:
5320:
5317:
5315:
5314:phenylalanine
5312:
5311:
5309:
5307:
5303:
5297:
5294:
5292:
5289:
5287:
5284:
5282:
5281:Coumaric acid
5279:
5277:
5274:
5272:
5269:
5267:
5266:Cinnamic acid
5264:
5262:
5261:Chicoric acid
5259:
5257:
5254:
5252:
5249:
5248:
5246:
5244:
5240:
5230:
5227:
5225:
5222:
5221:
5219:
5215:
5209:
5206:
5204:
5203:Syringic acid
5201:
5199:
5196:
5194:
5191:
5189:
5186:
5184:
5181:
5179:
5178:Eudesmic acid
5176:
5174:
5173:Ethyl gallate
5171:
5169:
5168:Chebulic acid
5166:
5164:
5161:
5160:
5158:
5156:
5152:
5146:
5143:
5141:
5138:
5136:
5133:
5131:
5130:Gentisic acid
5128:
5126:
5123:
5121:
5118:
5116:
5113:
5111:
5108:
5105:
5102:
5101:
5099:
5097:
5093:
5083:
5080:
5079:
5077:
5073:
5067:
5064:
5062:
5059:
5057:
5054:
5053:
5051:
5047:
5044:
5042:
5038:
5035:
5033:
5029:
5025:
5018:
5013:
5011:
5006:
5004:
4999:
4998:
4995:
4992:
4990:
4986:
4978:
4974:
4971:
4967:
4961:
4957:
4954:
4951:
4948:
4945:
4942:
4939:
4936:
4934:
4931:
4928:
4925:
4923:
4920:
4917:
4914:
4913:
4911:
4907:
4895:
4892:
4890:
4887:
4885:
4882:
4880:
4877:
4876:
4874:
4872:
4869:
4867:
4864:
4862:
4859:
4858:
4856:
4852:
4846:
4845:Acutissimin A
4843:
4841:
4838:
4837:
4835:
4831:
4827:
4820:
4818:
4817:7-Phloroeckol
4815:
4813:
4810:
4808:
4805:
4803:
4800:
4798:
4795:
4793:
4790:
4788:
4785:
4783:
4780:
4778:
4775:
4773:
4770:
4768:
4765:
4763:
4760:
4758:
4755:
4754:
4752:
4750:
4749:Phlorotannins
4746:
4740:
4737:
4735:
4732:
4730:
4727:
4725:
4722:
4720:
4717:
4716:
4714:
4712:
4708:
4698:
4695:
4693:
4690:
4689:
4687:
4685:
4681:
4675:
4672:
4670:
4667:
4665:
4662:
4660:
4657:
4655:
4652:
4650:
4647:
4645:
4642:
4640:
4637:
4635:
4632:
4630:
4627:
4626:
4624:
4622:
4621:Ellagitannins
4618:
4615:
4613:
4609:
4605:
4597:
4592:
4590:
4585:
4583:
4578:
4577:
4574:
4571:
4569:
4565:
4561:
4557:
4555:
4551:
4545:
4542:
4540:
4537:
4535:
4534:Pterostilbene
4532:
4530:
4527:
4526:
4524:
4520:
4516:
4510:
4507:
4505:
4502:
4500:
4497:
4496:
4494:
4486:
4482:
4478:
4474:
4472:
4468:
4460:
4455:
4445:
4442:
4440:
4437:
4435:
4432:
4430:
4427:
4425:
4422:
4420:
4417:
4415:
4412:
4410:
4407:
4406:
4404:
4402:
4401:Miscellaneous
4398:
4388:
4385:
4384:
4382:
4380:
4376:
4369:
4365:
4362:
4361:
4359:
4357:
4353:
4350:
4348:
4344:
4338:
4335:
4333:
4330:
4329:
4327:
4325:
4321:
4310:
4306:
4303:
4302:
4300:
4298:
4294:
4287:
4283:
4280:
4279:
4277:
4275:
4271:
4268:
4266:
4262:
4251:
4248:
4246:
4243:
4242:
4240:
4238:
4234:
4228:
4225:
4223:
4220:
4218:
4215:
4214:
4212:
4210:
4206:
4199:
4195:
4194:Leucocyanidin
4192:
4191:
4189:
4187:
4183:
4176:
4172:
4169:
4168:
4166:
4163:
4158:
4154:
4147:
4146:Gallocatechol
4143:
4140:
4139:
4137:
4134:
4129:
4125:
4119:
4118:Luteoliflavan
4116:
4115:
4113:
4109:
4106:
4104:
4100:
4090:
4087:
4086:
4084:
4082:
4081:Neoflavonoids
4078:
4071:
4067:
4063:
4060:
4059:
4057:
4055:
4051:
4044:
4040:
4037:
4036:
4034:
4032:
4028:
4021:
4017:
4014:
4013:
4011:
4009:
4005:
4002:
4000:
3999:Anthoxanthins
3996:
3993:
3991:
3987:
3983:
3975:
3970:
3968:
3963:
3961:
3956:
3955:
3952:
3949:
3945:
3941:
3937:
3929:
3924:
3922:
3917:
3915:
3910:
3909:
3906:
3903:
3901:
3897:
3891:
3888:
3886:
3883:
3881:
3878:
3876:
3873:
3871:
3870:Benzenetriols
3868:
3866:
3863:
3862:
3860:
3858:
3854:
3850:
3842:
3837:
3835:
3830:
3828:
3823:
3822:
3819:
3814:
3812:
3808:
3795:
3792:
3789:
3786:
3785:
3783:
3779:
3772:
3768:
3764:
3763:
3761:
3757:
3750:
3748:3-oxo-α-ionol
3747:
3746:
3744:
3740:
3733:
3731:
3728:
3726:
3723:
3722:
3720:
3717:
3713:
3703:
3700:
3698:
3695:
3693:
3690:
3688:
3685:
3683:
3682:Cryptoxanthin
3680:
3678:
3677:Canthaxanthin
3675:
3674:
3672:
3669:
3665:
3659:
3656:
3654:
3651:
3649:
3646:
3644:
3641:
3639:
3636:
3634:
3631:
3629:
3628:Beta-Carotene
3626:
3624:
3621:
3620:
3618:
3616:
3612:
3609:
3606:
3601:
3597:
3590:
3588:Ferrugicadiol
3587:
3586:
3584:
3580:
3568:
3565:
3563:
3560:
3558:
3555:
3553:
3550:
3549:
3547:
3545:
3542:
3540:Serratenediol
3539:
3537:
3534:
3532:
3529:
3527:
3524:
3523:
3521:
3517:
3511:
3508:
3506:
3503:
3501:
3498:
3496:
3493:
3491:
3488:
3484:
3481:
3479:
3476:
3474:
3471:
3469:
3466:
3463:
3461:
3458:
3457:
3456:
3453:
3452:
3450:
3448:
3444:
3441:
3438:
3437:Triterpenoids
3434:
3427:
3426:
3424:
3421:
3417:
3406:
3403:
3400:
3398:
3395:
3392:
3390:Mercusic acid
3389:
3387:
3384:
3381:
3379:
3376:
3373:
3371:Communic acid
3370:
3368:
3365:
3364:
3362:
3360:
3356:
3350:
3347:
3345:
3342:
3340:
3337:
3336:
3334:
3330:
3323:
3320:
3317:
3315:
3312:
3310:
3307:
3306:
3304:
3300:
3294:
3291:
3288:
3285:
3282:
3281:
3279:
3275:
3269:
3266:
3264:
3261:
3260:
3258:
3254:
3247:
3245:
3242:
3240:
3237:
3236:
3234:
3230:
3227:
3224:
3220:
3213:
3210:
3208:
3205:
3202:
3200:
3197:
3194:
3192:
3189:
3187:
3184:
3182:
3179:
3177:
3174:
3172:
3169:
3168:
3166:
3163:
3159:
3149:
3146:
3144:
3141:
3139:
3136:
3134:
3131:
3129:
3126:
3124:
3121:
3120:
3118:
3114:
3108:
3105:
3103:
3100:
3098:
3095:
3092:
3088:
3085:
3083:
3080:
3078:
3075:
3073:
3070:
3069:
3067:
3063:
3057:
3054:
3052:
3049:
3047:
3044:
3042:
3039:
3037:
3034:
3032:
3029:
3027:
3024:
3023:
3021:
3017:
3014:
3008:
2998:
2995:
2993:
2990:
2988:
2985:
2983:
2980:
2977:
2973:
2969:
2966:
2965:
2963:
2959:
2953:
2950:
2948:
2945:
2943:
2940:
2939:
2937:
2933:
2927:
2924:
2922:
2919:
2918:
2916:
2912:
2909:
2897:
2893:
2887:
2884:
2882:
2879:
2868:
2865:
2864:
2862:
2859:
2855:
2848:
2845:
2842:
2839:
2836:
2833:
2830:
2827:
2823:
2819:
2818:
2816:
2812:
2807:
2803:
2799:
2791:
2786:
2784:
2779:
2777:
2772:
2771:
2768:
2763:
2761:
2757:
2753:
2745:
2740:
2738:
2733:
2731:
2726:
2725:
2722:
2710:
2707:
2705:
2702:
2700:
2697:
2695:
2692:
2690:
2687:
2685:
2681:
2678:
2676:
2673:
2672:
2669:
2665:
2661:
2657:
2650:
2645:
2643:
2638:
2636:
2631:
2630:
2627:
2617:
2613:
2608:
2603:
2600:(6): 943–59.
2599:
2595:
2591:
2584:
2576:
2572:
2568:
2564:
2560:
2556:
2549:
2547:
2538:
2534:
2530:
2526:
2519:
2511:
2507:
2503:
2499:
2496:(5): 719–26.
2495:
2491:
2483:
2475:
2471:
2466:
2461:
2458:(6): 1272–8.
2457:
2453:
2449:
2442:
2434:
2430:
2426:
2422:
2419:(3): 133–42.
2418:
2414:
2407:
2399:
2395:
2391:
2387:
2382:
2377:
2374:(9): 715–25.
2373:
2369:
2365:
2358:
2350:
2346:
2341:
2336:
2333:(1): 139–44.
2332:
2328:
2324:
2317:
2309:
2305:
2301:
2297:
2293:
2289:
2282:
2274:
2270:
2266:
2262:
2258:
2254:
2246:
2238:
2234:
2230:
2226:
2222:
2218:
2211:
2203:
2199:
2195:
2191:
2187:
2183:
2175:
2167:
2163:
2159:
2155:
2151:
2147:
2140:
2132:
2128:
2123:
2118:
2113:
2108:
2104:
2100:
2096:
2089:
2081:
2077:
2072:
2067:
2064:(2): 334–41.
2063:
2059:
2055:
2048:
2040:
2036:
2032:
2028:
2024:
2020:
2019:
2011:
2000:
1993:
1977:
1970:
1962:
1958:
1953:
1948:
1945:(8): 965–78.
1944:
1940:
1936:
1929:
1921:
1917:
1913:
1909:
1905:
1901:
1898:(5): 517–24.
1897:
1893:
1886:
1878:
1874:
1870:
1866:
1862:
1858:
1851:
1843:
1839:
1835:
1831:
1823:
1815:
1811:
1806:
1801:
1797:
1793:
1789:
1782:
1774:
1770:
1765:
1760:
1757:(2): 346–60.
1756:
1752:
1748:
1740:
1732:
1728:
1723:
1718:
1714:
1710:
1706:
1702:
1698:
1691:
1689:
1687:
1678:
1674:
1669:
1664:
1660:
1656:
1652:
1645:
1643:
1634:
1630:
1625:
1620:
1616:
1612:
1608:
1601:
1593:
1589:
1585:
1581:
1577:
1573:
1569:
1565:
1558:
1547:
1540:
1529:
1522:
1508:on 2012-10-09
1507:
1503:
1496:
1488:
1481:
1473:
1466:
1458:
1451:
1444:
1438:
1434:
1430:
1426:
1425:
1417:
1409:
1405:
1401:
1397:
1393:
1389:
1385:
1381:
1373:
1365:
1361:
1357:
1353:
1349:
1345:
1341:
1337:
1330:
1322:
1318:
1313:
1308:
1304:
1300:
1296:
1289:
1281:
1277:
1272:
1267:
1263:
1259:
1255:
1251:
1247:
1240:
1232:
1228:
1223:
1218:
1214:
1210:
1206:
1199:
1191:
1187:
1183:
1179:
1175:
1171:
1168:(8): 769–76.
1167:
1163:
1156:
1148:
1144:
1140:
1136:
1132:
1128:
1124:
1120:
1117:(1): 93–110.
1116:
1112:
1108:
1101:
1093:
1089:
1084:
1079:
1075:
1071:
1067:
1063:
1059:
1052:
1044:
1040:
1035:
1030:
1026:
1022:
1018:
1014:
1010:
1003:
1001:
981:
974:
972:
970:
968:
966:
964:
955:
948:
940:
936:
932:
928:
924:
920:
916:
912:
904:
902:
897:
890:
887:
883:
879:
875:
865:
861:
858:
848:
846:
841:
839:
834:
832:
828:
818:
815:
813:
810:
806:
800:
798:
794:
789:
787:
777:
774:
769:
768:Health Canada
763:Health Canada
760:
758:
754:
753:
752:sterol esters
747:
737:
735:
730:
718:Health claims
710:
707:
704:
701:
698:
695:
692:
689:
687:
686:Sunflower oil
684:
683:
679:
676:
673:
670:
667:
664:
661:
658:
656:
653:
652:
648:
645:
642:
639:
636:
633:
630:
627:
625:
622:
621:
617:
614:
611:
608:
605:
602:
599:
596:
594:
591:
590:
586:
583:
580:
577:
574:
571:
568:
565:
563:
560:
559:
555:
552:
549:
546:
543:
540:
538:
535:
533:
530:
529:
525:
523:
520:
517:
514:
511:
509:
506:
504:
501:
500:
496:
493:
490:
487:
484:
481:
478:
475:
473:
470:
469:
465:
462:
459:
456:
453:
450:
447:
444:
442:
439:
438:
434:
431:
428:
425:
422:
419:
416:
413:
411:
408:
407:
404:
400:
398:
395:
393:
389:
387:
384:
382:
379:
377:
374:
372:
369:
367:
364:
362:
361:
355:
353:
347:
344:
340:
335:
333:
332:refining oils
329:
325:
321:
308:
302:
297:
294:
288:
283:
280:
279:
275:
269:
264:
261:
255:
250:
247:
241:
236:
233:
227:
222:
219:
213:
208:
205:
199:
194:
191:
185:
180:
177:
176:
172:
171:sterol esters
168:
167:
166:
165:In addition:
160:
156:
153:
149:
146:
142:
139:
135:
132:
128:
125:
121:
118:
114:
113:
112:
110:
105:
103:
99:
90:
81:
79:
76:, or overall
75:
71:
67:
63:
59:
54:
52:
48:
44:
40:
37:, similar to
36:
35:phytosteroids
32:
25:
21:
6510:Phytosterols
6436:Phytosterols
6435:
6410:Obtusifoliol
6400:Cycloartenol
6364:
6355:
5939:Stigmasterol
5924:Stigmastenol
5919:Stigmastanol
5899:β-Sitosterol
5859:(Vitamin D2)
5833:Phytosterols
5832:
5785:
5629:Chlorophylls
5617:Vulgaxanthin
5607:Betaxanthins
5526:Polysulfides
5509:Thiocyanates
5487:Sulforaphane
5416:
5291:Ferulic acid
5256:Caffeic acid
5229:Ellagic acid
4969:
4960:isocoumarins
4933:Kavalactones
4875:Tannin uses
4802:Tetrafucol A
4782:Diphlorethol
4767:6,6'-Bieckol
4762:8,8′-Bieckol
4684:Gallotannins
4649:Casuarictins
4629:Punicalagins
4554:Curcuminoids
4499:Matairesinol
4400:
4305:Apigeninidin
4250:Aromadendrin
4157:Flavan-4-ols
4128:Flavan-3-ols
3865:Benzenediols
3734:Gutta-balatá
3730:Gutta percha
3668:Xanthophylls
3648:Neurosporene
3567:Moronic acid
3557:Ursolic acid
3500:Testosterone
3483:Stigmasterol
3468:Cycloartenol
3455:Phytosterols
3454:
3397:Pimaric acid
3367:Abietic acid
3318:Manoyl oxide
3293:Salvinorin A
3283:
3223:Diterpenoids
3087:Thujaplicins
3012:(2,modified)
2952:Phellandrene
2896:Monoterpenes
2825:
2821:
2814:Basic forms:
2709:Phytosterols
2708:
2699:Fusidic acid
2597:
2593:
2583:
2558:
2554:
2528:
2524:
2518:
2493:
2489:
2482:
2455:
2451:
2441:
2416:
2412:
2406:
2371:
2367:
2357:
2330:
2326:
2316:
2291:
2287:
2281:
2259:(1): 13–21.
2256:
2252:
2245:
2220:
2216:
2210:
2188:(1): 283–8.
2185:
2181:
2174:
2152:(1): 282–7.
2149:
2145:
2139:
2102:
2098:
2088:
2061:
2057:
2047:
2022:
2016:
2010:
1992:
1980:. Retrieved
1969:
1942:
1938:
1928:
1895:
1891:
1885:
1860:
1856:
1850:
1833:
1829:
1822:
1795:
1791:
1781:
1754:
1750:
1739:
1707:(4): 404–9.
1704:
1700:
1658:
1654:
1614:
1610:
1600:
1570:(5): 702–6.
1567:
1563:
1557:
1539:
1521:
1510:. Retrieved
1506:the original
1495:
1480:
1465:
1450:
1423:
1416:
1383:
1379:
1372:
1342:(1): 39–47.
1339:
1335:
1329:
1305:(2): 137–9.
1302:
1298:
1288:
1256:(2): 67–80.
1253:
1249:
1239:
1215:(4): 671–8.
1212:
1208:
1198:
1165:
1161:
1155:
1114:
1110:
1100:
1065:
1061:
1051:
1016:
1012:
987:. Retrieved
953:
947:
914:
910:
886:stigmasterol
871:
862:
854:
842:
835:
824:
816:
801:
790:
783:
766:
756:
749:
743:
726:
624:Rapeseed oil
578:62.6 – 70.4
575:12.3 – 16.1
547:50.2 – 62.1
541:18.7 – 29.1
403:Stigmasterol
386:β-Sitosterol
381:Stigmasterol
351:
348:
336:
317:
274:Cycloartenol
232:Stigmastanol
218:Stigmasterol
190:β-sitosterol
164:
147:is obtained.
131:stigmasterol
126:is obtained.
119:is obtained.
109:β-sitosterol
106:
95:
55:
31:Phytosterols
30:
29:
24:β-sitosterol
6341:Cholesterol
6330:Cholesterol
6325:Desmosterol
6303:Cholesterol
6293:Lathosterol
6271:Zymosterone
6226:Cholesterol
5986:Cholesterol
5914:Spinasterol
5852:Campesterol
5740:Beta-glucan
5670:Oxalic acid
5663:Quinic acid
5658:Phytic acid
5595:Betacyanins
5376:Oleocanthal
5193:Norbergenin
5188:Tannic acid
5183:Gallic acid
4977:Polyphenols
4950:Xanthonoids
4927:Chalconoids
4777:Eckstolonol
4674:Terflavin B
4639:Vescalagins
4634:Castalagins
4539:Piceatannol
4529:Resveratrol
4519:Stilbenoids
4509:Pinoresinol
4444:Castavinols
4286:Delphinidin
4237:Flavanonols
4227:Eriodictyol
4054:Isoflavones
3936:polyphenols
3900:Polyphenols
3702:Rubixanthin
3692:Astaxanthin
3653:Phytofluene
3605:Carotenoids
3495:Cholesterol
3490:Tocopherols
3460:Campesterol
3359:Resin acids
3344:Gibberellin
3339:Aphidicolin
3332:Tetracyclic
3207:Longifolene
3171:Artemisinin
3148:Umbellulone
3036:Citronellol
3026:Citronellal
2689:Cholesterol
2656:Cholestanes
1617:(1): 92–7.
1564:Circulation
889:pathogens.
791:Unlike the
786:cholesterol
655:Soybean oil
572:8.4 – 12.7
544:8.9 – 13.9
410:Coconut oil
392:Avenasterol
376:Campesterol
366:Cholesterol
324:glycolipids
293:Cholesterol
246:Campestanol
204:Campesterol
145:campestanol
124:cholesterol
117:campesterol
98:double bond
39:cholesterol
6504:Categories
6480:Ergosterol
6460:Fecosterol
6430:Sitosterol
6392:Sitosterol
6310:Zymosterol
6288:Zymostenol
6283:Zymosterol
6276:Zymosterol
6256:Lanosterol
6249:Lanosterol
6137:Carotenoid
6019:Acetyl-CoA
5909:Momordenol
5863:Ergostenol
5857:Ergosterol
5685:Malic acid
5381:Oleuropein
5319:tryptophan
5208:Theogallin
5075:Glycosides
4952:(C6-C1-C6)
4929:(C6-C3-C6)
4918:(C6-C7-C6)
4879:Enological
4659:Punicalins
4654:Grandinins
4544:Pinosylvin
4522:(C6-C2-C6)
4337:Leptosidin
4332:Aureusidin
4222:Naringenin
4217:Hesperidin
4209:Flavanones
4175:Luteoforol
4043:Kaempferol
3990:Flavonoids
3982:flavonoids
3947:(C6-C3-C6)
3944:Flavonoids
3890:Dillapiole
3687:Zeaxanthin
3531:Lanosterol
3478:Sitosterol
3473:Sitostanol
3349:Paclitaxel
3256:Monocyclic
3143:Ascaridole
3138:Eucalyptol
3091:Hinokitiol
3065:Monocyclic
2935:Monocyclic
2802:terpenoids
2760:Terpenoids
2704:Lanosterol
2288:Metabolism
1512:2011-09-06
989:7 November
893:References
882:sitosterol
874:eukaryotes
750:For plant
690:0.2 – 1.3
659:0.6 – 1.4
597:0.6 – 3.8
593:Peanut oil
556:0.2 – 2.4
536:2.2 – 6.7
518:75.6 – 90
512:2.3 – 3.6
497:0.7 – 1.4
494:1.4 – 3.3
491:1.9 – 3.8
485:1.2 – 1.8
482:7.2 – 8.4
479:0.1 – 0.9
476:0.7 – 2.3
445:0.2 – 0.6
307:Ergosterol
159:ergosterol
138:sitostanol
6465:Episterol
5587:Betalains
5397:Capsaicin
5334:thyroxine
5324:histidine
5049:Aglycones
4956:Coumarins
4812:Bifuhalol
4739:Flavolans
4664:Roburin A
4644:Castalins
4477:Silymarin
4387:Phloretin
4356:Chalcones
4347:Chalcones
4245:Taxifolin
4162:flavanols
4133:flavanols
4066:Genistein
4039:Quercetin
4031:Flavonols
3980:Types of
3934:Types of
3885:Carvacrol
3847:Types of
3759:Synthesis
3615:Carotenes
3510:Ecdysones
3314:Forskolin
3302:Tricyclic
3289:Epimanool
3214:Nootkatin
3211:Muurolene
3203:Juniperol
3195:Chanootin
3176:Bisabolol
3107:Carvacrol
2947:Terpinene
2849:(4 rings)
2796:Types of
2750:Types of
2675:Adosterol
1147:208646899
1131:2042-6496
931:1873-2194
917:: 35–61.
521:3.1 – 14
503:Olive oil
343:margarine
102:saturated
84:Structure
6442:instead.
6383:Nonhuman
6375:instead.
6239:Squalene
6150:Phytoene
6115:Geranyl-
5750:Lentinan
5728:Pentoses
5570:Piperine
5521:Sulfides
5504:Nitriles
5462:Sinigrin
5402:Gingerol
5329:tyrosine
5286:Coumarin
5224:Vanillin
5163:Bergenin
4884:Drilling
4807:Trifucol
4560:Curcumin
4488:((C6-C3)
4282:Cyanidin
4171:Apiforol
4142:Catechin
4062:Daidzein
4016:Apigenin
4008:Flavones
3880:Carnosol
3658:Phytoene
3643:Lycopene
3544:Squalane
3536:Saponins
3447:Steroids
3309:Cembrene
3286:-Abienol
3277:Bicyclic
3181:Cadinene
3116:Bicyclic
3082:p-Cymene
3056:Linalool
3041:Geraniol
2992:Sabinene
2982:Camphene
2961:Bicyclic
2942:Limonene
2926:Myrcenes
2867:Isoprene
2847:Steroids
2838:Iridoids
2806:isoprene
2798:terpenes
2616:24777987
2575:22623436
2510:20430133
2474:12450893
2433:15330272
2398:19548242
2390:11002384
2349:17074925
2308:12489060
2273:16399487
2237:10758959
2202:17137582
2166:19962145
2131:20228406
2080:18769018
2039:16542769
1961:12911045
1920:41438503
1912:20439548
1877:22623436
1814:10573535
1773:24468148
1731:19158117
1677:17951490
1584:13042924
1408:19049641
1400:15054420
1364:43470157
1321:11242480
1280:28702423
1231:15522137
1182:15638245
1139:31804642
1092:32550215
1043:22334625
939:29627611
702:56 – 63
693:0 – 0.2
680:1.5 – 5
677:1 – 4.5
671:52 – 58
668:16 – 19
665:16 – 24
662:0 – 0.3
646:0 – 0.8
643:0 – 6.6
640:45 – 58
637:0 – 0.7
634:18 – 39
628:0.4 – 2
609:48 – 65
603:12 – 20
600:0 – 0.2
587:0 – 2.1
584:0 – 1.4
569:0 – 0.3
566:1 – 3.7
553:0 – 5.1
550:0 – 2.8
532:Palm oil
515:0.6 – 2
507:0 – 0.5
488:80 – 90
457:55 – 67
451:18 – 24
448:0 – 0.2
441:Corn oil
432:0.6 – 2
426:50 – 70
423:12 – 18
417:0 – 0.9
414:0.6 – 2
6191:CDP-MEP
6057:Acetone
6039:HMG-CoA
6034:HMB-CoA
6011:HMG-CoA
5990:steroid
5762:Inulins
5757:Fructan
5723:Hexoses
5600:Betanin
5555:Allicin
5540:Indoles
5366:Tyrosol
4946:(C6-C3)
4940:(C6-C4)
4894:Tanning
4787:Difucol
4772:Dieckol
4604:tannins
4568:Tannins
4485:Lignans
4370:, et.c.
4324:Aurones
4311:, et.c.
4288:, et.c.
4252:, et.c.
4200:, et.c.
4177:, et.c.
4148:, et.c.
4103:Flavans
4045:, et.c.
4022:, et.c.
4020:Chrysin
3796:(DMAPP)
3526:Betulin
3324:Pimarol
3321:Pimaral
3268:Retinal
3263:Retinol
3232:Acyclic
3191:Cedrene
3186:Cadinol
3128:Borneol
3123:Camphor
3077:Menthol
3051:Halomon
3019:Acyclic
2987:Thujene
2921:Ocimene
2914:Acyclic
2664:sterols
2122:2903788
1978:. WebMD
1722:2642922
1633:3942097
1592:3165910
1271:5503415
1190:4043005
1083:7270433
1034:3279314
857:stanols
793:statins
708:7 – 13
699:8 – 11
696:7 – 13
631:5 – 13
606:5 – 13
429:5 – 16
420:7 – 10
352:stanols
51:stanols
47:sterols
6363:20α,22
6201:HMB-PP
6186:CDP-ME
5774:Pectin
5769:Lignin
5745:Chitin
5560:Alliin
5390:Others
5344:L-DOPA
4909:Others
4364:Butein
4111:Flavan
4070:Orobol
3875:Apiole
3718:(many)
3697:Lutein
3548:Acids
3239:Phytol
3097:Thymol
3031:Citral
2997:Carene
2968:Pinene
2881:Prenol
2828:forms)
2808:units)
2804:(# of
2614:
2573:
2508:
2472:
2431:
2396:
2388:
2347:
2306:
2271:
2235:
2200:
2164:
2129:
2119:
2078:
2037:
1982:6 July
1959:
1918:
1910:
1875:
1812:
1771:
1729:
1719:
1675:
1631:
1590:
1582:
1439:
1406:
1398:
1362:
1356:659760
1354:
1319:
1278:
1268:
1229:
1188:
1180:
1162:Lipids
1145:
1137:
1129:
1090:
1080:
1041:
1031:
937:
929:
878:fungal
821:Safety
812:enzyme
711:3 – 6
705:2 – 7
674:2 – 4
649:0 – 5
618:0 – 5
615:0 – 5
612:7 – 9
581:4 – 9
526:0 – 4
466:1 – 4
463:1 – 3
460:4 – 8
454:4 – 8
435:2 – 8
43:plants
6434:More
6339:From
6211:DMAPP
6196:MEcPP
6078:DMAPP
4757:Eckol
4072:et.c.
3790:(IPP)
3607:) (8)
3519:Other
2826:trans
2394:S2CID
2002:(PDF)
1997:FDA.
1916:S2CID
1588:S2CID
1549:(PDF)
1531:(PDF)
1526:FDA.
1500:FDA.
1404:S2CID
1360:S2CID
1186:S2CID
1143:S2CID
983:(PDF)
6440:here
6438:see
6373:here
6371:See
6176:DOXP
5988:and
5786:Misc
5417:Misc
4970:Misc
4958:and
2974:and
2907:)(2)
2824:and
2800:and
2612:PMID
2571:PMID
2506:PMID
2470:PMID
2429:PMID
2386:PMID
2345:PMID
2304:PMID
2269:PMID
2233:PMID
2198:PMID
2162:PMID
2127:PMID
2076:PMID
2035:PMID
1984:2013
1957:PMID
1908:PMID
1873:PMID
1810:PMID
1769:PMID
1727:PMID
1673:PMID
1629:PMID
1580:PMID
1437:ISBN
1396:PMID
1352:PMID
1317:PMID
1276:PMID
1227:PMID
1178:PMID
1135:PMID
1127:ISSN
1088:PMID
1039:PMID
991:2017
935:PMID
927:ISSN
884:and
744:The
723:EFSA
322:and
49:and
33:are
6450:To
6390:To
6344:to
6224:To
6206:IPP
6181:MEP
6076:to
6029:HMB
6009:to
5882:C29
5840:C28
4889:Ink
3439:(6)
3422:(5)
3284:cis
3225:(4)
3164:(3)
2860:(1)
2822:cis
2602:doi
2563:doi
2533:doi
2498:doi
2494:110
2460:doi
2421:doi
2376:doi
2335:doi
2296:doi
2261:doi
2225:doi
2190:doi
2186:196
2154:doi
2150:210
2117:PMC
2107:doi
2066:doi
2027:doi
1947:doi
1900:doi
1865:doi
1838:doi
1834:105
1800:doi
1796:129
1759:doi
1755:232
1717:PMC
1709:doi
1663:doi
1659:137
1619:doi
1572:doi
1429:doi
1388:doi
1344:doi
1307:doi
1266:PMC
1258:doi
1217:doi
1170:doi
1119:doi
1078:PMC
1070:doi
1029:PMC
1021:doi
919:doi
847:).
746:FDA
740:FDA
736:".
401:∆7-
390:∆5-
6506::
6354:22
4366:,
4307:,
4284:,
4196:,
4173:,
4144:,
4068:,
4064:,
4041:,
4018:,
2905:16
2901:10
2899:(C
2869:(C
2662::
2658:,
2610:.
2596:.
2592:.
2569:.
2559:56
2557:.
2545:^
2527:.
2504:.
2492:.
2468:.
2456:76
2454:.
2450:.
2427:.
2417:14
2415:.
2392:.
2384:.
2372:54
2370:.
2366:.
2343:.
2331:48
2329:.
2325:.
2302:.
2292:51
2290:.
2267:.
2257:16
2255:.
2231:.
2221:35
2219:.
2196:.
2184:.
2160:.
2148:.
2125:.
2115:.
2103:51
2101:.
2097:.
2074:.
2062:50
2060:.
2056:.
2033:.
2023:44
2021:.
1955:.
1943:78
1941:.
1937:.
1914:.
1906:.
1896:28
1894:.
1871:.
1861:56
1859:.
1832:.
1808:.
1794:.
1790:.
1767:.
1753:.
1749:.
1725:.
1715:.
1705:30
1703:.
1699:.
1685:^
1671:.
1657:.
1653:.
1641:^
1627:.
1615:43
1613:.
1609:.
1586:.
1578:.
1566:.
1435:,
1402:.
1394:.
1384:58
1382:.
1358:.
1350:.
1340:73
1338:.
1315:.
1303:85
1301:.
1297:.
1274:.
1264:.
1254:22
1252:.
1248:.
1225:.
1213:92
1211:.
1207:.
1184:.
1176:.
1166:39
1164:.
1141:.
1133:.
1125:.
1115:11
1113:.
1109:.
1086:.
1076:.
1066:19
1064:.
1060:.
1037:.
1027:.
1017:33
1015:.
1011:.
999:^
962:^
933:.
925:.
915:70
913:.
900:^
80:.
72:,
68:,
6365:R
6356:R
5978:e
5971:t
5964:v
5825:e
5818:t
5811:v
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5433:)
5419::
5016:e
5009:t
5002:v
4972::
4595:e
4588:t
4581:v
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4490:2
4164:)
4160:(
4135:)
4131:(
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3966:t
3959:v
3927:e
3920:t
3913:v
3840:e
3833:t
3826:v
3773:)
3769:(
3670::
3603:(
3093:)
3089:(
2978:)
2976:β
2972:α
2970:(
2903:H
2877:)
2875:8
2873:H
2871:5
2789:e
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2775:v
2743:e
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2598:7
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