187:
144:
97:-docosapentaenoic acid). They are also commonly termed n-6 DPA and n-3 DPA, respectively; these designations describe the position of the double bond being 6 or 3 carbons closest to the (omega) carbon at the methyl end of the molecule and is based on the biologically important difference that n-6 and n-3 PUFA are separate PUFA classes, i.e. the
571:
206:) and docosahexaenoic acid (DHA 4,7,10,13,16,19-22:6n-3 or cervonic acid) in the metabolic pathway of DHA in eucaryotes. Eicosapentaenoic acid is elongated to clupanodonic acid, which in turn is converted by Δ4-desaturase to docosahexaenoic acid 22:6n-3 (see
105:, respectively. Mammals, including humans, can not interconvert these two classes and therefore must obtain dietary essential PUFA fatty acids from both classes in order to maintain normal health (see
246:
333:, along with its metabolite DHA and other long chain omega-3 fatty acids, is under study to determine properties of omega-3 fats in humans, such as in
230:
266:
124:
The two isomers osbond acid and clupanodonic acid have the same number of double bonds, but on different positions along the chain, so they are
217:
class of PUFA metabolites. These metabolites include four resolvins of T series and three of D series (RvT1, RvT2, RvT3, RvT4, RvD1
118:
214:
584:
294:
469:"Beneficial Outcomes of Omega-6 and Omega-3 Polyunsaturated Fatty Acids on Human Health: An Update for 2021"
213:
Mammalian cells, including human cells, metabolize DPAn-3 to an array of products that are members of the
346:
207:
30:
645:
585:"Elucidation of novel 13-series resolvins that increase with atorvastatin and clear infections"
282:
202:. It is an intermediate compound between eicosapentaenoic acid (EPA 5,8,11,14,17-20:5n-3 or
640:
106:
311:
Salmon, red (sockeye), filets with skin, smoked (Alaska Native) 0.335 g in 1 filet (108 g)
8:
612:
549:
522:
495:
468:
444:
417:
393:
366:
330:
156:
102:
98:
617:
554:
500:
449:
398:
167:, AA). Arachidonic acid is elongated to docosatetraenoic acid (7,10,13,16-22:4n-6 or
539:
247:
Specialized proresolving mediators § n-3 DPA-derived protectins/neuroprotectins
607:
599:
544:
534:
490:
480:
439:
429:
388:
378:
317:
Beef, variety meats and by-products, brain, cooked, simmered 0.326 g in 3 oz (85 g)
164:
572:"DPA Nutrient List." National Nutrient Database for Standard Reference Release 27.
174:
281:
Docosapentaenoic acid (DPA) is an n-3 fatty acid that is structurally similar to
203:
194:
showing physiological numbering (red) and chemical numbering (blue) conventions.
151:
showing physiological numbering (red) and chemical numbering (blue) conventions.
250:
523:"A review of the biologic and pharmacologic role of docosapentaenoic acid n-3"
634:
285:(EPA) with the same number of double bonds, but two more carbon chain units.
163:. It is formed in two steps from eicosatetraenoic acid (5,8,11,14-20:4n-6 or
621:
558:
504:
453:
402:
334:
168:
131:
383:
125:
34:
434:
485:
302:
27:
603:
171:, AdA), which in turn is converted by Δ4-desaturase to osbond acid.
234:
231:
Specialized proresolving mediators § n-3 DPA-derived resolvins
267:
Specialized proresolving mediators § n-3 DPA-derived maresins
270:
229:(do not confuse with D series resolvins derived from DHA); see
186:
38:
143:
293:
These are the top five sources for DPA according to the USDA
314:
Fish, salmon, Atlantic, farmed, raw 0.334 g in 3 oz (85 g)
182:-7,10,13,16,19-docosapentaenoic acid (clupanodonic acid)
119:
Essential fatty acid § Nomenclature and terminology
364:
198:n-3 DPA is an n-3 fatty acid with the trivial name
582:
321:Seal meat and human breast milk are rich in DPA.
139:-4,7,10,13,16-docosapentaenoic acid (osbond acid)
632:
466:
367:"Omega-3 Fatty Acids and PPARgamma in Cancer"
308:Fish oil, salmon 0.407 g in 1 tbsp. (13.6 g)
77:-7,10,13,16,19-docosapentaenoic acid (i.e. 7
583:Dalli, J; Chiang, N; Serhan, C. N. (2015).
409:
358:
49:-4,7,10,13,16-docosapentaenoic acid (i.e. 4
415:
611:
548:
538:
494:
484:
443:
433:
392:
382:
37:. DPA is primarily used to designate two
208:Docosahexaenoic acid § Biosynthesis
185:
142:
516:
514:
460:
33:(PUFA) which contains 22 carbons and 5
633:
520:
511:
418:"Discovery of essential fatty acids"
467:Djuricic I, Calder PC (July 2021).
13:
365:Edwards IJ, O'Flaherty JT (2008).
215:specialized proresolving mediators
14:
657:
301:Fish oil, menhaden 0.668 g in 1
540:10.12688/f1000research.2-256.v2
576:
565:
1:
352:
295:Agricultural Research Service
324:
276:
69:-docosapentaenoic acid) and
7:
416:Spector AA, Kim HY (2015).
347:List of omega-3 fatty acids
340:
253:), and three maresins (MaR1
16:Group of isomeric compounds
10:
662:
190:The chemical structure of
147:The chemical structure of
116:
112:
31:polyunsaturated fatty acid
26:) designates any straight
422:Journal of Lipid Research
521:Yazdi, PG (Nov 2013).
329:Clupanodonic acid, an
237:), two protectins (PD1
195:
159:with the trivial name
152:
117:For nomenclature, see
283:eicosapentaenoic acid
189:
146:
107:essential fatty acids
20:Docosapentaenoic acid
435:10.1194/jlr.R055095
384:10.1155/2008/358052
103:omega-3 fatty acids
99:omega-6 fatty acids
486:10.3390/nu13072421
331:omega-3 fatty acid
196:
153:
200:clupanodonic acid
192:clupanodonic acid
653:
626:
625:
615:
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165:arachidonic acid
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631:
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604:10.1038/nm.3911
592:Nature Medicine
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519:
512:
479:(7). Figure 3.
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355:
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289:Dietary sources
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264:
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244:
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228:
224:
220:
204:timnodonic acid
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141:
122:
115:
17:
12:
11:
5:
659:
649:
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646:Alkenoic acids
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628:
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575:
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510:
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408:
356:
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339:
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306:
278:
275:
262:
258:
254:
251:Neuroprotectin
242:
238:
226:
222:
218:
183:
173:
157:ω-6 fatty acid
155:n-6 DPA is an
140:
130:
114:
111:
15:
9:
6:
4:
3:
2:
658:
647:
644:
642:
639:
638:
636:
623:
619:
614:
609:
605:
601:
598:(9): 1071–5.
597:
593:
586:
579:
573:
568:
560:
556:
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546:
541:
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532:
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371:PPAR Research
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68:
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36:
32:
29:
25:
21:
595:
591:
578:
567:
530:
526:
476:
472:
462:
428:(1): 11–21.
425:
421:
411:
374:
370:
360:
337:mechanisms.
335:inflammation
328:
320:
292:
288:
287:
280:
212:
199:
197:
191:
179:
175:
169:adrenic acid
160:
154:
148:
136:
132:
126:regioisomers
123:
94:
90:
86:
82:
78:
74:
70:
66:
62:
58:
54:
50:
46:
42:
35:double bonds
23:
19:
18:
641:Fatty acids
161:osbond acid
149:osbond acid
635:Categories
377:: 358052.
353:References
261:, and MaR3
225:, and RvD5
28:open chain
473:Nutrients
325:Functions
277:Nutrition
622:26236990
559:25232466
527:F1000Res
505:34371930
454:25339684
403:18769551
341:See also
305:(13.6 g)
235:Resolvin
613:4560998
550:4162505
533:: 256.
496:8308533
445:4274059
394:2526161
271:Maresin
241:and PD2
113:Isomers
39:isomers
620:
610:
557:
547:
503:
493:
452:
442:
401:
391:
265:; see
257:, MaR2
245:; see
221:, RvD2
588:(PDF)
303:tbsp.
618:PMID
555:PMID
501:PMID
450:PMID
399:PMID
375:2008
269:and
249:and
233:and
101:and
608:PMC
600:doi
545:PMC
535:doi
491:PMC
481:doi
440:PMC
430:doi
389:PMC
379:doi
273:).
263:n-3
259:n-3
255:n-3
243:n-3
239:n-3
227:n-3
223:n-3
219:n-3
210:).
180:cis
176:all
137:cis
133:all
109:).
93:,19
89:,16
85:,13
81:,10
75:cis
71:all
65:,16
61:,13
57:,10
47:cis
43:all
24:DPA
637::
616:.
606:.
596:21
594:.
590:.
553:.
543:.
529:.
525:.
513:^
499:.
489:.
477:13
475:.
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426:56
424:.
420:.
397:.
387:.
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297::
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624:.
602::
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507:.
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456:.
432::
405:.
381::
178:-
135:-
121:.
95:Z
91:Z
87:Z
83:Z
79:Z
73:-
67:Z
63:Z
59:Z
55:Z
51:Z
45:-
22:(
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