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

• Coutareagenin (5-hydroxy-7-methoxy-4-(3,4-dihydroxyphenyl)-2H-benzo-1-pyran-2-on) found in Hintonia latiflora^[7]
• Dalbergin
• Nivetin isolated from Echinops niveus^[8]

References

1. The neoflavanoids, a new class of natural products. Cellular and Molecular Life Sciences, Volume 22, Number 12 / december 1966
2. Revised structure of neoflavone in Coutarea hexandra. Munekazu Iinuma, Toshiyuki Tanaka, Koji Hamada, Mizuo Mizuno, Fujio Asai, Gesa Reher and Ljubomir Kraus, Phytochemistry, Volume 26, Issue 11, 1987, Pages 3096-3097.
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. Xanthones and 4-phenylcoumarins of Mesua thwaitesii from bark, timber and seeds.
6. Dalbergichromene : A new neoflavonoid from stem-bark and heartwood of Dalbergia sissoo. Mukerjee S. K., Saroja T. and SeshadriT. R., Tetrahedron, Volume 27, Issue 4, 1971, Pages 799-803
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. Nivetin, a neoflavonoid from Echinops niveus. Singh P. and Pandey V.B., Phytochemistry, Volume 29, Issue 2, 1990, Pages 680-681

External links