Rotenoids and 7,2,'4',5'-Tetramethoxyisoflavone in Amorpha fruticosa L. Fruits

Abstract

From the petrol-ether extract of ripe Amorpha fruticosa fruits two rotenoids and one isoflavone have been isolated. The ripe fruits of Amorpha fruticosa L. (Papilionaceae) contain glycerides and essential oil [I], the rotenoid glycoside amor~hine [2] and its analogous [3], as well as small amounts of 7,8-dehydroamorphygenine, amorphygenine, amorphygenol [3], 22,23-dihydroamorphygenine [4] and 6a,l2a-dehydro-a-toxycarol[5]. According to [5] this last compound is responsible for the insecticidal activity of the fruit extracts. Recently the fruits have used in Bulgaria for the production of an aromatic extract (absolute) which has been well accepted in the perfumery industry. This extract was the subject of our investigation.After long storage at +So the absolute deposed fine needle-like crystals (ca. 0.06 %) with IR absorbtion of y-pyrones (1650, 1580, 1515, 1110 cm"), giving on TLC (silica-gel) two spots with similar Rf-values, further separated on a silica-gel column. The less polar compound was identified (m.p., UV, IR, 'H-NMR, MS) as 6a,l2a-dehydro-a-toxycarol, recently isolated from the same plant [5], and the more polar -as 6a,l2a-dehydrodeguelin, found in other members of the Papilionaceae [61.

Antibacterial and Cytotoxic Phenolic Metabolites from the Fruits ofAmorpha fruticosa

“…The remaining known compounds were identified as 2-[( E )-styryl]-5-geranylresorcin-1-carboxylic acid ( 16 ), amorfrutin B ( 17 ), 2-carboxy-3,5-dihydroxy-4-geranylbibenzyl ( 18 ), 2-geranyl-5-[( Z )-styryl]­resorcin ( 19 ), amorphastilbol ( 20 ), 2-geranyl-5-(2-phenylethyl)­resorcin ( 21 ), amorfrutin A ( 22 ), xanthoangelol ( 23 ), sermundone ( 24 ), rot-2′-enonic acid ( 25 ), deguelin ( 26 ), α-toxicarol ( 27 ), 6a,12a-dehydrodeguelin ( 28 ), dalpanol ( 29 ), rotenone ( 30 ), dalbinol ( 31 ), hydroxy­amorphispironone ( 32 ), 6′- O -β- d -glucopyranosyl­dalpanol ( 33 ), daidzein, 5,7-dihydroxy-4′-methoxyisoflavone, 5-hydroxy-7,4′-dimethoxyisoflavone, afrormorsin, 7-hydroxy-2′,4′,5′-trimethoxy­isoflavone, 7,2′,4′,5′-tetramethoxy­isoflavone, munduserone, cis -12a-hydroxy­munduserone, 6-deoxyclitoriacetal, cis -12a-hydroxyrot-2′-enonic acid, sumatrolic acid, tephrosin, 11-hydroxytephrosin, 12a-hydroxydalpanol, rotenolone, 11-hydroxyrotenone, amorphigenin, amorphispironone, 11-licoagroside F, kaempferol 3- O -α- l -rhamnopyranosyl-(1→2)-β- d -glucopyranoside-7- O -α- l -rhamnopyranoside ( 13a ), and 6′- O -β- d -glucopyranosyl-12a-hydroxydalpanol ( 33a ) by comparison with the literature data.…”

New Rotenoids inAmorpha fruticosaFruits

“…The species B could As a starting material which contains components with lower polarity, an industrial sample of "Absolute of Amorpha" (Pharmachim, Bulgaria) was used, produced by extraction of the ripe fruits with petrol. It was separated on a silica column with mixtures of chloroformether (1). For polar components, the ground fruits (2 kg) were extracted with chloroform-methanol 1: 1(3 x 1 000 ml).…”

“…Ginseng, the roots of Panax ginseng C. A. Meyer (Araliaceae), has been used in traditional Chinese medicine for treatment of various disorders for thousands of years (1,2). Recent studies showed the major active ingredients of ginseng to be a group of ginsenosides, and they are named ginsenoside R (x = a, b1, b2, c, d, e, g1 .…”

Antitumor Agents, 138. Rotenoids and Isoflavones as Cytotoxic Constituents from Amorpha fruticosa

“…Another known rotenoid, 12aß-hydroxyamorphigenin [6], was first shown to exhibit extremely potent cytotoxicity (ED50 <0.001 µ-g/ml) in six neoplastic cell lines. In addition to these compounds, three isoflavones (afrormosin [1], 7,2',4',5'-tetramethoxyisoflavone [2], 8methylretusin [3]) and five rotenoids (amorphispironone [4], amorphigenin [5], dalpanol [7], 12aß-hyd oxydalpanol [8], and tephrosin [9]) were isolated. Compound 8 was isolated for the first time as a natural product from this plant.…”