Neoflavonoid

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

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

  • Neoflavones[1] are derived from the 4-phenylcoumarin (or 4-aryl-coumarin) backbone (C15H12O2).[2] The first neoflavone isolated from natural sources was calophyllolide from Calophyllum inophyllum seeds (1951).[3] It is also found in the bark and timber of the plant Mesua thwaitesii, endemic to Sri Lanka.[4]
  • Neoflavenes possess the 4-phenylchromen backbone (C15H10O2). Dalbergichromene, extracted from the stem-bark and heartwood of Dalbergia sissoo, is an example of such compounds[5]

Other examples
  • Coutareagenin (5-hydroxy-7-methoxy-4-(3,4-dihydroxyphenyl)-2H-benzo-1-pyran-2-on) found in Hintonia latiflora[6]
  • Dalbergin
  • Nivetin isolated from Echinops niveus[7]

References
  1. Ollis, W. D. (1966). "The neoflavanoids, a new class of natural products". Experientia. 22 (12): 777–783. doi:10.1007/BF01897407. PMID 5973205.
  2. Nishimura, S.; Taki, M.; Takaishi, S.; Iijima, Y.; Akiyama, T. (2000). "Structures of 4-aryl-coumarin (neoflavone) dimers isolated from Pistacia chinensis BUNGE and their estrogen-like activity" (PDF). Chemical & Pharmaceutical Bulletin. 48 (4): 505–8. doi:10.1248/cpb.48.505. PMID 10783069.
  3. Garazd, M. M.; Garazd, Ya. L.; Khilya, V. P. (2003). "Neoflavones. 1. Natural Distribution and Spectral and Biological Properties". Chemistry of Natural Compounds. 39: 54–121. doi:10.1023/A:1024140915526.
  4. Bandaranayake, Wickramasinghe M. (1975). "Xanthones and 4-phenylcoumarins of Mesua thwaitesii". Phytochemistry. 14: 265–269. doi:10.1016/0031-9422(75)85052-7.
  5. Mukerjee, S.K. (1971). "Dalbergichromene". Tetrahedron. 27 (4): 799–803. doi:10.1016/S0040-4020(01)92474-3.
  6. Korec, R.; Heinz Sensch, K.; Zoukas, T. (2000). "Effects of the neoflavonoid coutareagenin, one of the antidiabetic active substances of Hintonia latiflora, on streptozotocin-induced diabetes mellitus in rats". Arzneimittel-Forschung. 50 (2): 122–8. PMID 10719614.
  7. Singh, R.P.; Pandey, V.B. (1990). "Nivetin, a neoflavonoid from Echinops niveus". Phytochemistry. 29 (2): 680–681. doi:10.1016/0031-9422(90)85148-9.


The dictionary definition of neoflavonoid at Wiktionary

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