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Diarylheptanoid

From Wikipedia, the free encyclopedia
Class of chemicals found in plants
Curcumin, a linear diarylheptanoid

Thediarylheptanoids (also known asdiphenylheptanoids) are a class of plantsecondary metabolites. Diarylheptanoids consist of two aromatic rings (aryl groups) joined by a seven carbons chain (heptane) and having various substituents.[1] They can be classified into linear (curcuminoids) and cyclic diarylheptanoids. The best known member iscurcumin, which is isolated fromturmeric (Curcuma longa) and is known as food coloring E100. Some otherCurcuma species, such asCurcuma comosa also produce diarylheptanoids.

They have been reported from plants in 10 different families, e.g.Betulaceae andZingiberaceae.

A diarylheptanoid is an intermediate in the biosynthesis ofphenylphenalenones inAnigozanthos preissii[2] orWachendorfia thyrsiflora (Haemodoraceae).[3]

Cyclic diarylheptanoids

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Myricanone, a cyclic diarylheptanoid

Cyclic diarylheptanoids formed frommyricanone can be isolated from the bark ofMyrica rubra (Myricaceae).[4] Two cyclic diarylheptanoids, namedostryopsitrienol andostryopsitriol, can be isolated from the stems of endemic Chinese medicinal plantOstryopsis nobilis (Betulaceae).[5]Acerogenin M can be found inAcer nikoense (Sapindaceae).[6]Jugcathayenoside and (+)-galeon can be found in the root bark ofJuglans cathayensis (Juglandaceae).[7]

Health effects

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The antioxidant activity of diarylheptanoids isolated from rhizomes ofEtlingera elatior (Zingiberaceae) is greater than that ofα-tocopherol.[8]

References

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  1. ^Brahmachari, Goutam (2013-02-20).Chemistry and Pharmacology of Naturally Occurring Bioactive Compounds. CRC Press. pp. 285–.ISBN 9781439891674. Retrieved5 July 2013.
  2. ^Hölscher, Dirk; Schneider, Bernd (1995). "A diarylheptanoid intermediate in the biosynthesis of phenylphenalenones in Anigozanthos preissii".Journal of the Chemical Society, Chemical Communications (5):525–526.doi:10.1039/C39950000525.
  3. ^Brand, S; Hölscher, D; Schierhorn, A; Svatos, A; Schröder, J; Schneider, B (2006). "A type III polyketide synthase from Wachendorfia thyrsiflora and its role in diarylheptanoid and phenylphenalenone biosynthesis".Planta.224 (2):413–428.doi:10.1007/s00425-006-0228-x.PMID 16496097.S2CID 38508249.
  4. ^Akazawa, H; Fujita, Y; Banno, N; Watanabe, K; Kimura, Y; Manosroi, A; Manosroi, J; Akihisa, T (2010)."Three new cyclic diarylheptanoids and other phenolic compounds from the bark of Myrica rubra and their melanogenesis inhibitory and radical scavenging activities".Journal of Oleo Science.59 (4):213–221.doi:10.5650/jos.59.213.PMID 20299768.
  5. ^Zhang, Yan-Xia; Xia, Bing; Zhou, Yan; Ding, Li-Sheng; Peng, Shu-Lin (2013)."Two new cyclic diarylheptanoids from the stems of Ostryopsis nobilis".Chinese Chemical Letters.24 (6):512–514.doi:10.1016/j.cclet.2013.03.035.S2CID 95251161. Archived fromthe original on 2020-05-29. Retrieved2018-10-27.
  6. ^Akihisa, T; Taguchi, Y; Yasukawa, K; Tokuda, H; Akazawa, H; Suzuki, T; Kimura, Y (2006)."Acerogenin M, a cyclic diarylheptanoid, and other phenolic compounds from Acer nikoense and their anti-inflammatory and anti-tumor-promoting effects".Chemical & Pharmaceutical Bulletin.54 (5):735–739.doi:10.1248/cpb.54.735.PMID 16651781.
  7. ^Li, Juan; Sun, Jia-Xiang; Yu, Heng-Yi; Chen, Zu-Yu; Zhao, Xiao-Ya; Ruan, Han-Li (2013). "Diarylheptanoids from the root bark of Juglans cathayensis".Chinese Chemical Letters.24 (6):521–523.doi:10.1016/j.cclet.2013.03.050.
  8. ^Mohamad, Habsah; Lajis, Nordin H.; Abas, Faridah; Ali, Abdul Manaf; Sukari, Mohamad Aspollah; Kikuzaki, Hiroe; Nakatani, Nobuji (2005). "Antioxidative constituents ofEtlingera elatior".Journal of Natural Products.68 (2):285–288.doi:10.1021/np040098l.PMID 15730265.

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