Neoflavonoid

Structure of the neoflavonoids backbone (neoflavan represented)

Neoflavonoids are a class of polyphenolic compounds.[1] While flavonoids (in the narrow sense) have the 2-phenylchromen-4-one backbone, neoflavonoids have the 4-phenylchromen backbone with no hydroxyl group substitution at position 2.

Types

Chemical structure of 4-phenylcoumarin (neoflavone backbone).

Neoflavonoids include 4-arylcoumarins (neoflavones), 4-arylchromanes, dalbergiones and dalbergiquinols.

  • Neoflavones[2] are derived from the 4-phenylcoumarin (or 4-Aryl-coumarin) backbone (C15H12O2, molar mass : 224.25g/mol, exact mass : 224.083729).[3] The first neoflavone isolated from natural sources was calophyllolide from Calophyllum inophyllum seeds (1951).[4] It is also known to found in bark and timber of Sri Lankan endemic plant Mesua thwaitesii.[5]
  • Neoflavenes possess the 4-phenylchromen backbone (chemical formula : C15H10O2, exact mass : 222.0680792). Dalbergichromene, extracted from the stem-bark and heartwood of Dalbergia sissoo, is an example of such compounds[6]

Other examples

References

  1. ↑ The neoflavanoids, a new class of natural products. Cellular and Molecular Life Sciences, Volume 22, Number 12 / december 1966
  2. ↑ Iinuma, Munekazu; Tanaka, Toshiyuki; Hamada, Koji; Mizuno, Mizuo; Asai, Fujio; Reher, Gesa; Kraus, Ljubomir (1987). "Revised structure of neoflavone in Coutarea hexandra". Phytochemistry. 26: 3096–3097. doi:10.1016/S0031-9422(00)84609-9.
  3. ↑ Structures of 4-Aryl-coumarin (Neoflavone) Dimers Isolated from Pistacia chinensis BUNGE and Their Estrogen-like Activity. Satoshi NISHIMURA, Motohiko TAKI, Sachiko TAKAISHI, Yasuteru IIJIMA and Toshiyuki AKIYAMA, Chem. Pharm. Bull. 48(4) 505—508 (2000)
  4. ↑ Neoflavones. 1. Natural Distribution and Spectral and Biological Properties. M. M. Garazd, Ya. L. Garazd and V. P. Khilya, Chemistry of Natural Compounds, Volume 39, Number 1 / janvier 2003.
  5. ↑ Bandaranayake, Wickramasinghe M. (1975). "Xanthones and 4-phenylcoumarins of Mesua thwaitesii". Phytochemistry. 14: 265–269. doi:10.1016/0031-9422(75)85052-7.
  6. ↑ Mukerjee, S.K. (1971). "Dalbergichromene". Tetrahedron. 27: 799–803. doi:10.1016/S0040-4020(01)92474-3.
  7. ↑ Effects of the neoflavonoid coutareagenin, one of the antidiabetic active substances of Hintonia latiflora, on streptozotocin-induced diabetes mellitus in rats. Korec R., Sensch K. H., Zoukas T., Symposium der Paul-Martini-Stiftung in Verbindung mit der Akademie der Wissenschaften und der Literatur, Mainz, Germany (12/11/1999) 2000, vol. 50, no 2, pp. 189-224 (33 ref.), pp. 122-128
  8. ↑ Singh, R.P.; Pandey, V.B. (1990). "Nivetin, a neoflavonoid from Echinops niveus". Phytochemistry. 29: 680–681. doi:10.1016/0031-9422(90)85148-9.



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