Prenylated and Benzylated Flavonoids from the Fruits of Cudrania tricuspidata

Abstract

Three new prenylated isoflavones, 5,7-dihydroxy-6-(2''-hydroxy-3''-methylbut-3''-enyl)-4'-methoxylisoflavone (1), 5,4'-dihydroxy-6-(3''-methylbut-2''-enyl)-2'''-(4'''-hydroxy-4'''-methylethyl)-3'''-methoxydihydrofurano-[4''',5''';7,8]isoflavone (2), and 5,4'-dihydroxy-8-(3''-methylbut-2''-enyl)-2'''-(4'''-hydroxy-4'''-methylethyl)furano-[4''',5''';6,7]isoflavone (3), a benzylated dihydroflavonol, 5,7,4'-trihydroxy-8-p-hydroxybenzyldihydroflavonol (4), and eight known flavonoids (5-12) were isolated from the fruits of Cudrania tricuspidata. The structures of these compounds were determined on the basis of MS and (1)H and (13)C NMR spectroscopic data, including 2D NMR experiments. Compounds 2, 3, 6, 7, 8, 10, 11, and 12 inhibited LPS-induced nitric oxide production, with IC(50) values of 11.8-41.8 microM.

Chemical Composition and Antioxidant Activity of Steam-Distilled Essential Oil and Glycosidically Bound Volatiles from Maclura Tricuspidata Fruit

“…Several beneficial effects of M. tricuspidata extracts have been reported including anticancer [13,14], anti-inflammatory [15], antioxidant [16,17], and antidiabetes effects [18]. Various bioactive compounds such as prenylated xanthones, phenolic acids and flavonoids have already been identified from its leaves, root, stem and fruit [19][20][21].…”

Topical Application of Cudrania tricuspidata Stem Extract Inhibits Atopic Dermatitis-Like Skin Lesions in an NC/Nga Mouse Model: An Experimental Animal Study

“…Extracts of the fruit, leaves, root-bark and stems of C. tricuspidata have been traditionally used for hepato-protection [8]- [10], and as anti-hypertension [11], anti-diabetes [12] [13], anti-allergy [14] and antioxidation [15]- [17] treatments in Korea. Well-known physiologically active compounds of C. tricuspidata are isoflavones and flavonoids from the fruits [18], gerontoxanthone, cudraflavone B, gericudranin, cudraxanthones, isocudraxanthones, some flavanones and macluraxanthone from the roots [9] [19], kaempferol and kaempferol-D-glucopyranoside from the leaves [20], and kaempferide-D-glucopyranoside and naringenin-D-glucopyranoside from the stems [21]. However, the anti-AD effects of C. tricuspidata have not been studied except for a recent report using fruit extract [22].…”

Isoflavones with neuroprotective activities from fruits of Cudrania tricuspidata

“…Repeated column chromatography and preparative HPLC of the EtOAc soluble extract resulted in the isolation of ten new isoflavones, cudraisoflavones B-K (1-10), as well as 27 known isoflavones, 5,7,3 0 ,4 0 -tetrahydroxy-6,8-diprenylisoflavone (11), warangalone, auriculasin (Nkengfack et al, 1989), erythrinin B (12) (Jain and Sharma, 1974), gancaonin B (13), gancaonin A (Fukai et al, 1990), osajin, euchrenone b 8 , euchrenone b 9 (Mizuno et al, 1990), alpinumisoflavone, 4 0 -O-methyl-alpinumisoflavone (Olivares et al, 1982), 5,7,4 0 -trihydroxy-6,8- E (Sekine et al, 1999), anagyroidisoflavone A (Sato et al, 1995), euchrenone b 10 , senegalensin (Tanaka et al, 2001), eryvarin B (Tanaka et al, 2000), 5,7-dihydroxy-6-(2 00 -hydroxy-3 00 -methylbut-3 00 -enyl)-4 0 -methoxylisoflavone (Han et al, 2009), 3 0 ,5-dihydroxy-4 0 -methoxyl-2 00 ,2 00 -dimethylpyrano[6 00 ,5 00 -h]isoflavone, derrone (Tsukayama et al, 1992), 4 0 -O-methyl-2 00 -hydroxydihydroalpinumisoflavone (Abdel-Kader et al, 2006), isoerysenegalensein E (ElMasry et al, 2002), biochanin A (Klier et al, 2012), lupiwighteone (Tahara et al, 1991), 5,3 0 ,4 0 -trihydroxy-6 00 ,6 00 -dimethylpyrano-[2 00 ,3 00 ;7,6]isoflavone (Jain et al, 1978), erythrinin C (Tahara et al, 1985), and flemiphilippinin G (Fu et al, 2012), respectively (see Fig. 1).…”