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.
- Neoflavones1 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 compounds5
Other examples
- Coutareagenin (5-hydroxy-7-methoxy-4-(3,4-dihydroxyphenyl)-2H-benzo-1-pyran-2-on) found in Hintonia latiflora6
- Dalbergin
- Nivetin isolated from Echinops niveus7
References
References
- Ollis, W. D. (1966). "The neoflavanoids, a new class of natural products". Experientia. 22 (12): 777–783. doi:10.1007/BF01897407. PMID 5973205.
- 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.
- Garazd, M. M.; Garazd, Ya. L.; Khilya, V. P. (2003). "Neoflavones. 1. Natural Distribution and Spectral and Biological Properties". Chemistry of Natural Compounds. 39 (1): 54–121. Bibcode:2003CNatC..39...54G. doi:10.1023/A:1024140915526.
- Bandaranayake, Wickramasinghe M. (1975). "Xanthones and 4-phenylcoumarins of Mesua thwaitesii". Phytochemistry. 14 (1): 265–269. Bibcode:1975PChem..14..265B. doi:10.1016/0031-9422(75)85052-7.
- Mukerjee, S.K. (1971). "Dalbergichromene". Tetrahedron. 27 (4): 799–803. doi:10.1016/S0040-4020(01)92474-3.
- 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.
- Singh, R.P.; Pandey, V.B. (1990). "Nivetin, a neoflavonoid from Echinops niveus". Phytochemistry. 29 (2): 680–681. Bibcode:1990PChem..29..680S. doi:10.1016/0031-9422(90)85148-9.