Bioactive Constituents of Chinese Natural Medicines. III. Absolute Stereostructures of New Dihydroflavonols, Hovenitins I, II, and III, Isolated from Hoveniae Semen Seu Fructus, the Seed and Fruit of Hovenia dulcis THUNB. (Rhamnaceae) : Inhibitory Effect on Alcohol-Induced Muscular Relaxation and Hepatoprotective Activity

Yoshikawa, Masayuki; Murakami, Toshiyuki; Ueda, Tomohiko; Yoshizumi, Satoshi; Ninomiya, Kiyofumi; Murakami, Nobutoshi; Matsuda, Hisashi; Saito, Masayuki; Fujii, Wataru; Tanaka, Takaharu; Yamahara, Johji

doi:10.1248/yakushi1947.117.2_108

Cited by 68 publications

(33 citation statements)

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“…The fruit contains protein, fat, glucose, potassium nitrate, and potassium malate [7]. The fruit stalk and rachis contains glucose, fructose and sucrose [8][9][10].…”

Section: Chemical Constituentsmentioning

confidence: 99%

Hovenia dulcis Thunb. 枳椇子 (Zhijuzi, Oriental Raisin Tree Seed)

Liu

Hua

Wang

2015

Dietary Chinese Herbs

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“…The fruit contains protein, fat, glucose, potassium nitrate, and potassium malate [7]. The fruit stalk and rachis contains glucose, fructose and sucrose [8][9][10].…”

Section: Chemical Constituentsmentioning

confidence: 99%

Hovenia dulcis Thunb. 枳椇子 (Zhijuzi, Oriental Raisin Tree Seed)

Liu

Hua

Wang

2015

Dietary Chinese Herbs

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“…Hepatoprotective Effects of Flavonol Oligoglycosides In the course of our studies on hepatoprotective constituents from natural medicines, we have characterized new diarylheptanoid glycosides from Betula platyphylla, 13) dihydroflavonols from Hovenia dulcis, 14) sesquiterpenes from Curcuma zedoaria, 15) and triterpene oligoglycosides from Bupleurum scorzonerifolium 16) as the active principles. Since we have found that some flavonol oligoglycosides from Tilia argentea showed potent in vitro and in vivo hepatoprotective effects, 17) flavonol oligoglycosides (3, 4, 6-9) were examined by monitoring the inhibition of cytotoxicity induced by 1006 Vol.…”

Section: O-(6-o-trans-p-coumaroyl)-b -D-glucopyranosyl(1→2)-b -Dglucomentioning

confidence: 99%

Medicinal Foodstuffs. XXV. Hepatoprotective Principle and Structures of Ionone Glucoside, Phenethyl Glycoside, and Flavonol Oligoglycosides from Young Seedpods of Garden Peas, Pisum sativum L.

et al. 2001

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As a part of our characterization studies on the chemical constituents of medicinal foodstuffs, 1,2) we have characterized bioactive steroid and triterpenoid saponins and diterpene oligoglycosides from Leguminous edible beans [e.g., fenugreek (Trigonella foenum-graecum), 3) kidney bean (Phaseolus vulgaris), 4) hyacinth bean (Dolichos lablab), 5) and sword bean (Canavalia gladiata) 6) ]. We previously reported the isolation and structure elucidation of two oleanane-type triterpene oligoglycosides, pisumsaponins I and II, and two kaurane-type diterpene oligoglycosides, pisumosides A and B, from green peas, the immature seeds of Pisum (P.) sativum L. (garden peas), together with several bioactive saponins: soyasaponin I, bersimoside I, and dehydrosoyasaponin I.7) This plant has been widely cultivated from ancient times and consumed as a vegetable. The agricultural species of P. sativum are known to be classified into two groups differing in the edible part as immature seed or young seedpod. In a continuing study on P. sativum, we have isolated an ionone glucoside, pisumionoside (1), a phenethyl glycoside, sayaendoside (2), and two flavonol oligoglycosides, pisumflavonosides I (3) and II (4), from the young seedpods of P. sativum. Furthermore, we examined protective effects of the flavonol glycoside constituents on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. The in vitro active component was found to show protective effects on liver injury induced by D-galactosamine and lipopolysaccharide and by carbon tetrachloride in mice. This paper deals with the isolation and structure elucidation of these glycosides as well as the hepatoprotective effect of flavonol oligoglycosides.Structures of Pisumionoside (1), Sayaendoside (2), and Pisumflavonosides I (3) and II (4) from the Young Seedpods of P. sativum The constituents of the young seedpods of P. sativum were separated by the procedures shown in Chart 1. Namely, the aqueous methanolic extract from the young seedpods was partitioned into an ethyl-acetate and water mixture to furnish the ethyl-acetate soluble portion and water phase. The water phase was subjected to reversedphase and normal-phase silica gel column chromatography and finally HPLC to give pisumionoside (1, 0.0001%), sayaendoside (2, 0.0001%), and pisumflavonosides I (3, 0.0013%) and II (4, 0.0005%) together with quercetin 3-kaempferol 3-sophorotrioside (9, 0.0016%), 9) and L-tryptophan (0.0048%). However, diterpene and triterpene oligoglycosides from the immature seeds of this plant 7) were not isolated from the young seedpods.Pisumionoside (1) was obtained as a white powder with negative optical rotation ([a ] D 26 Ϫ3.4°). The IR spectrum of 1 showed absorption bands due to hydroxyl and olefin functions at 3432, 1671, and 1076 cm Ϫ1 . In the negative-ion and positive-ion FAB-MS of 1, quasimolecular ion peaks were observed at m/z 807 (2MϪH) Ϫ and m/z 427 (MϩNa) ϩ and the molecular formula C 19 H 32 O 9 of 1 was determined by high-resolution MS measurement. Acid hydrolysis of ...

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“…Estudos recentes da química e farmacologia de H. dulcis têm revelado promissor potencial bioativo para a espécie. De seus pseudofrutos, foram isoladas saponinas triterpênicas que exercem atividade inibitória na liberação de histamina em exsudato de células peritoniais de ratos e alguns flavonóides com atividade i n i b i d o r a d o r e l a x a m e n t o m u s c u l a r e a t i v i d a d e hepatoprotetora 20,21,22 . Nas folhas, constatou-se a presença de saponinas triterpênicas e alguns glicosídeos com atividade inibidora da percepção do sabor adocicado 8,9,16,18,19 .…”

Section: Introductionunclassified

Atividade antineoplásica e tripanocida de Hovenia dulcis Thunb. cultivada in vivo e in vitro

Castro¹,

Pelliccione²,

Figueiredo³

et al. 2002

Rev. bras. farmacogn.

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Cited by 68 publications

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Hovenia dulcis Thunb. 枳椇子 (Zhijuzi, Oriental Raisin Tree Seed)

Hovenia dulcis Thunb. 枳椇子 (Zhijuzi, Oriental Raisin Tree Seed)

Medicinal Foodstuffs. XXV. Hepatoprotective Principle and Structures of Ionone Glucoside, Phenethyl Glycoside, and Flavonol Oligoglycosides from Young Seedpods of Garden Peas, Pisum sativum L.

Atividade antineoplásica e tripanocida de Hovenia dulcis Thunb. cultivada in vivo e in vitro

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