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Review | Special issue | Vol 47, No. 2, 1998, pp.1179-1205
Published online, 1st January, 1970
DOI: 10.3987/REV-97-SR(N)9
Isoprenoid-substituted Flavonoids from Artocarpus Plants (Moraceae)

Taro Nomura,* Yoshio Hano, and Miwa Aida

*Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan

Abstract

Many phenolic compounds including flavonoids have been isolated from the plants of Morus and Artocarpus species (Moraceae). Most of Morus and Artocarpus flavonoids are characterized by the structure bearing an isoprenoid side chain at the C-3 position of flavone skeleton and 2’,4’-dioxygenated (e.g. morusin, 4) or 2’,4’,5’-trioxygenated (e.g. artonin E, 51) pattern in the B ring. Particularly, some of Artocarpus flavonoids have a unique structure having the C-C linkage between an isoprenoid side chain at the C-3 position and the 6’-carbon of the B ring. These flavones considered to be biogenetically derived from the C-3 isoprenoid-substituted flavones. Some of the Artocarpus flavonoids, such as artonin I (31), have been regarded as optically active Diels-Alder type adducts. The structure of artonin I (31) was established utilizing the enzyme system of Morus alba cell cultures which specifically produced the natural Diels-Alder type adducts. Some of the isoprenylated flavonoids from the moraceous plants showed the interesting biological activity. Artonin E (51) was a potent inhibitor of arachidonate 5-lipoxygenase and inhibited the release of the TNF-α from BALB/3T3 cells by treatment of okadaic acid, stronger than morusin (4) did. This article reviews the chemistry and biological activities of isoprenoid-substituted flavonoids isolated from the root barks and/or barks of Artocarpus species.