The chemical structures, plant origins, ethnobotany and biological activities of homoisoflavanones

Abstract

This work reviews the four basic structural types of homoisoflavanones. The relationships between the various structures of homoisoflavanones and their plant origins, ethnobotany and biological activities are put into perspective.

The first synthesis of the antiangiogenic homoisoflavanone, cremastranone

“…These compounds are categorized into four types: 3-benzyl-4-chromanones, 3-benzylidene-4-chromanones, 3-benzyl-3-hydroxy-4-chromanones and scillascillins. 6 In general, these compounds are reported to show anti-inflammatory, anti-oxidative, anti-bacterial, anti-cancer, anti-histaminic, anti-viral, and anti-phosphodiesterase activities. Cremastranone ( 1 ), 5,7-dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-6-methoxychroman-4-one, is a 3-benzyl-4-chromanone that has been isolated from the plants Muscari armeniacum , 7 Chionodoxa luciliae , 8 Scilla natalensis , 9 Merwilla plumbea , 10 and Cremastra appendiculata (D. Don) 11 ( 1 ; Fig.…”

The cytotoxic effects of Scilla nervosa (Burch.) Jessop (Hyacinthaceae) aqueous extract on cultured HepG2 cells

“…Previous studies have revealed that the bulbs contain homoisoflavanones and stilbenoids (Bangani et al, 1999;Silayo et al, 1999). The chemical structures, plant origins, ethnobotany and biological activities of homoisoflavanones have been reviewed by Du Toit et al (2010). Studies by Bangani et al (1999) demonstrated 5 homoisoflavanones and 2 stilbenoids, while Silayo et al (1999) demonstrated 13 homoisoflavanones and 3 stilbenoids.…”

Synthesis of Natural Homoisoflavonoids Having Either 5,7-Dihydroxy-6-methoxy or 7-Hydroxy-5,6-dimethoxy Groups

“…Its naturally occurring congeners ( 2–10 ), which contain either 5,7-dihydroxy-6-methoxy or 7-hydroxy-5,6-dimethoxy groups, have been reported already as shown in Figure 1 and most of them lack common names other than eucomnalin ( 9 ; autumnalin) and 3,9-dihydroeucomnalin ( 4 ; 3,9-dihydroautumnalin). Two review articles deal with the natural origins and structures of most homoisoflavonoids [7,8], and thereafter various studies of the homoisoflavonoids have been published [9–11]. Nevertheless, there have not been synthetic efforts towards such homoisoflavonoids since the synthesis of 4 and 9 was reported in 1971 [12].…”