A new acylated flavonoid glycoside from the flowers of Camellia nitidissima and its effect on the induction of apoptosis in human lymphoma U937 cells

From the EtOH extract of the flowers of Camellia nitidissima Chi, a new acylated flavonoid glycoside, quercetin 7-O-(6″-O-E-caffeoyl)-β-d-glucopyranoside (1), has been isolated, together with three known flavonoids: quercetin (2), quercetin 3-O-β-d-glucopyranoside (3), and quercetin 7-O-β-d-glucopyranoside (4). Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 was shown to inhibit proliferation and to induce apoptosis of human lymphoma U937 cells.     

Two new isoflavone triglycosides from the small branches of Sophora japonica

Two new isoflavone triglycosides, genistein 4′-O-(6″-O-α-l-rhamnopyranosyl)-β-sophoroside (1), and genistein 4′-O-(6?-O-α-l-rhamnopyranosyl)-β-sophoroside (2), together with five known compounds, namely, sophorabioside, genistin, rutin, quercetin 3-O-β-d-glucopyranoside, and kaempferol 3-O-β-d-glucopyranoside, were isolated from the small branches of Sophora japonica L. Their structures were elucidated on the basis of spectroscopic analyses and chemical evidence.     

A new isoflavone from Blepharis ciliaris of an Egyptian origin

A phytochemical study of the aerial parts of Blepharis ciliaris (L.) B.L. Burtt. led to the isolation of one new isoflavone glycoside caffeic acid ester: genistein-7-O-(6″-O-E-caffeoyl-β-d-glucopyranoside) (4), along with seven known compounds: methyl veratrate (1), methyl vanillate (2), protocatechuic acid (3), naringenin-7-O-(3″-acetyl-6″-E-p-coumaroyl-β-d-glucopyranoside) (5), naringenin-7-O-(6″-E-p-coumaroyl-β-d-glucopyranoside) (6), apigenin-7-O-(6″-E-p-coumaroyl-β-d-glucopyranoside) (7), and acteoside (8). Their structures were established on the basis of detailed analyses of physical, chemical, and spectral data. Compounds 1, 2, 3, 6, and 8 were isolated for the first time from this plant. The antioxidant activity of the different extracts as well as for some of the isolated compounds was evaluated.     

(<Emphasis Type="Italic">Z</Emphasis>)-3-Hexenyl diglycosides from <Emphasis Type="Italic">Spermacoce laevis</Emphasis> Roxb.

A new (Z)-3-hexenyl O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside was isolated from the aerial part of Spermacoce laevis, along with 17 known compounds: (6S,9R)-roseoside, (Z)-3-hexenyl O-β-d-glucopyranoside, (Z)-3-hexenyl O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside, (Z)-3-hexenyl O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside, phenyethyl O-β-d-glucopyranoside, phenyethyl O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside, phenyethyl O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside, benzyl O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside, benzyl O-β-d-xylopyranosyl-(1→6)-β-d-glucopyranoside, asperuloside, 6α-hydroxyadoxoside, asperulosidic acid, kaempferol 3-O-β-d-glucopyranoside, kaempferol 3-O-rutinoside, quercetin 3-O-β-d-galactopyranoside, quercetin 3-O-α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside, and rutin. The structure determinations were based on physical data and spectroscopic evidence.     

猫眼草的抗氧化活性成分的分离鉴定与活性测定

目的研究猫眼草(Euphorbia lunulataBge.)全草抗氧化活性成分。方法以抗氧化活性为指标,运用多种柱色谱等现代分离手段对体积分数60%乙醇提取物进行活性追踪分离;根据理化性质和谱学技术分析确定化合物的化学结构;采用DPPH自由基清除法对提取物、各流份及分离得到的化合物进行体外抗氧化活性评价。结果从猫眼草体积分数60%乙醇提取物的乙酸乙酯萃取层(活性部位)中分离得到8个化合物。分别鉴定为东莨菪素(scopoletin,1)、异嗪皮啶(isofraxi-din,2)、金丝桃苷(hyperin,3)、柚皮素-7-O-β-D-葡萄糖苷(naringenin-7-O-β-D-glucopyranoside,4)、quercetin-3-O-(6″-galloyl)-β-D-galactopyranoside(5)、quercetin-3-O-(2″-galloyl)-β-D-galactopyrano-side(6)、槲皮素(quercetin,7)、芹菜素-7-O-β-D-葡萄糖苷(apigenin-7-O-β-D-glucopyranoside,8)。结论化合物1~5首次从猫眼草中分离得到;化合物8首次从大戟属植物中分离得到。化合物3、5、6、7具有较强的抗氧化活性。     

沙生蜡菊花中黄酮类成分的分离与鉴定

目的研究沙生蜡菊(Helichrysum arenarium(L.)Moench)花的化学成分。方法采用硅胶柱色谱?ODS柱色谱和HPLC柱色谱分离纯化,依据理化性质、波谱数据分析进行结构鉴定。结果从沙生蜡菊花的甲醇提取物中分离得到8个黄酮类化合物,分别鉴定为山奈酚3-O-β-D-吡喃葡萄糖苷(kaempferol 3-O-β-D-glucopyranoside,1)、木犀草素3′-O-β-D-吡喃葡萄糖苷(luteolin3′-O-β-D-glucopyranoside,2)、木犀草素7-O-β-D-吡喃葡萄糖苷(luteolin7-O-β-D-glucopyranoside,3)、木犀草素6-羟基-7-O-β-D-吡喃葡萄糖苷(luteolin6-hydroxy-7-O-β-D-glucopyranoside,4)、木犀草素3′-甲氧基-6-羟基-7-O-β-D-吡喃葡萄糖苷(luteolin3′-methoxyl-6-hydroxy-7-O-β-D-glucopyranoside,5)、黄芩素7-O-β-D-吡喃葡萄糖苷(scutellarein7-O-β-D-glucopyranoside,6)、山柰酚3-O-β-D-龙胆二糖苷(kaempferol3-gentiobioside,7)、山柰酚3-O-(3-β-D-吡喃葡萄糖基)-β-D-吡喃葡萄糖苷(kaempferol3-O-(3-β-D-glucopyranosyl)-β-D-glucopyranoside,8)。结论化合物2、4~8为首次从蜡菊属植物中分离得到。     

西南山茶化学成分的分离与鉴定

目的研究西南山茶叶的化学成分。方法采用硅胶柱色谱、Sephadex LH-20柱色谱等方法进行分离纯化,根据波谱学数据和理化性质进行结构鉴定。结果从西南山茶叶体积分数95%乙醇提取物的乙酸乙酯萃取物中分离并鉴定了11个化合物,分别为槲皮素(quercetin,1)、芦丁(rutin,2)、槲皮素-3-O-α-D-阿拉伯糖苷(quercetin-3-O-α-D-arabinofuranoside,3)、槲皮素-3-O-β-D-半乳糖苷(quercetin-3-O-β-D-galactopyranoside,4)、槲皮素-3-O-β-D-鼠李糖苷(quercetin-3-O-β-D-rhamno-side,5)、山柰酚(kaempferol,6)、山柰酚-3-O-(2″,6″-二反式-对香豆酰基)-β-D-葡萄糖苷(kaempfer-ol-3-O-[2″,6″-di-(E)-p-coumaroyl]-β-D-glucopyranoside,7)、羽扇豆醇(lupeol,8)、齐墩果酸(olean-olic acid,9)、原儿茶酸(3,4-dihydroxybenzoic acid,10)和没食子酸乙酯(ethyl gallate,11)。结论化合物1~11均首次从西南山茶中分离得到,其中化合物7为首次从山茶属植物中分离得到。     

制首乌中两个新化合物

目的：研究制首乌(Radix Polygoni multiflori Preparata)化学成分。方法：应用硅胶、Sephadex、反相硅胶柱色谱对制首乌正丁醇萃取部分中化学成分进行分离纯化,应用理化常数测定和光谱(IR,MS,¹HNMR,¹³CNMR,2D-NMR)分析技术鉴定结构。结果：分离并鉴定了5个单体化合物：大黄素甲醚-8-O-β-D-葡糖苷(Ⅰ)、大黄素-8-O-β-D-葡糖苷(Ⅱ)、决明蒽酮-8-O-β-D-葡糖苷(Ⅲ)、6-甲氧基-2-乙酰基-3-甲基-1,4-萘醌-8-O-β-D-葡糖苷(Ⅳ)、2,3,5,4′-四羟基二苯乙烯-2-O-(2″-O-乙酰基)-β-D-葡糖苷(Ⅴ)。结论：Ⅳ和Ⅴ为新化合物。     

中药黄蜀葵花化学成分的分离与鉴定(Ⅱ)

目的研究中药黄蜀葵(Abelmoschus manihot(L.)Medic.)花的化学成分,为进一步开发利用该植物资源提供依据。方法采用正相硅胶、反相ODS、Sephadex LH-20等柱色谱以及高效液相色谱等手段进行分离纯化,并通过理化性质与光谱分析鉴定化合物的结构。结果从黄蜀葵花体积分数为95%的乙醇提取物的大孔吸附树脂洗脱物中分离鉴定了9个以槲皮素为母核的黄酮类化合物,分别为槲皮素(quercetin,1)、金丝桃苷(hyperoside,2)、槲皮素-3-O-β-D-葡萄糖苷(quercetin-3-O-β-D-glucopyranoside,3)、槲皮素-3-O-β-D-6″-乙酰葡萄糖苷(quercetin-3-O-β-D-6″-acetylglucopyr-anoside,4)、槲皮素-3-O-刺槐糖苷(quercetin-3-O-robinoside,5)、槲皮素-3-O-芸香糖苷(quercetin-3-O-rutinoside,6)、槲皮素-3-O-β-D-木糖基-(1→2)-β-D-半乳糖苷(quercetin-3-O-β-D-xylopyranosyl(1→2)-β-D-galactopyranoside,7)、槲皮素-3′-O-β-D-葡萄糖苷(quercetin-3′-O-β-D-glucopyranoside,8)以及槲皮素-7-O-β-D-葡萄糖苷(quercetin-7-O-β-D-glucopyranoside,9)。结论化合物4、5、7和9为首次从秋葵属植物中分离得到。     

New benzophenone and quercetin galloyl glycosides from <Emphasis Type="Italic">Psidium guajava</Emphasis> L.

New benzophenone and flavonol galloyl glycosides were isolated from an 80% MeOH extract of Psidium guajava L. (Myrtaceae) together with five known quercetin glycosides. The structures of the novel glycosides were elucidated to be 2,4,6-trihydroxybenzophenone 4-O-(6″-O-galloyl)-β-d-glucopyranoside (1, guavinoside A), 2,4,6-trihydroxy-3,5-dimethylbenzophenone 4-O-(6″-O-galloyl)-β-d-glucopyranoside (2, guavinoside B), and quercetin 3-O-(5″-O-galloyl)-α-l-arabinofuranoside (3, guavinoside C) by NMR, MS, UV, and IR spectroscopies. Isolated phenolic glycosides showed significant inhibitory activities against histamine release from rat peritoneal mast cells, and nitric oxide production from a murine macrophage-like cell line, RAW 264.7.     

Two new compounds from Comastoma pedunlulatum

Two new compounds, a xanthonoid and a flavonoid C-glycoside, were isolated from the ethyl acetate extract of the dried herb of Comastoma pedunlulatum. The structures of the new compounds were elucidated, respectively, as 1,8-dihydroxy-3,5-dimethoxyxanthone 1-O-[2-(4′-hydroxy-3′,5′-dimethoxy-E-cinnamoyl)]-β-d-xylopyranosyl-(1-6)-β-d-glucopyranoside (1) and 6″-O-acetylisoorientin (2) on the basis of their spectroscopic and physicochemical properties.     

New flavonol glycosides and new xanthone from Polygala japonica

Three new flavonol glycosides and a new xanthone were isolated from Polygala japonica HOUTT. with eight known compounds. Their structures were identified as 1,7-dihydroxy-3,4-dimethoxy-xanthone (1), kaempferol-7,4′-dimethyl ether (2), physcion (3), guazijinxanthone (4), rhamnetin (5), polygalin A (6), 3,5,7-trihydroxy-4′-methoxy-flavone-3-O-β-d-galactopyranoside (7), 3,5,3′-trihydoxy-7,4′-dimethoxy-flavone-3-O-β-d-galactopyranoside (8), 3,5,3′,4′-tetrahydroxy-7-methoxy-flavone-3-O-β-d-galactopyranoside (9), 3,5,3′,4′-tetrahydroxy-7-methoxy-flavone-3-O-β-d-glucopyranoside (10), polygalin B (11), polygalin C (12). Among them, compound 4 is a new xanthone, and 6, 11 and 12 are new flavonol glycosides. Compounds 1, 4, 7 and 8 were tested for cytotoxic activity with MTT assays on five human tumor cell lines, K562, A549, PC-3M, HCT-8 and SHG-44. Compound 4 showed cytotoxic activity against all the five cell lines.     

Two new acetylated flavonoid glycosides from Centaurium spicatum L

Two new acetylated flavonol glycosides, quercetin 3-O-[(2,4-diacetyl-α-l-rhamnopyranosyl)-(1→6)]-2,4-diacetyl-β-d-galactopyranoside (1) and quercetin 3-O-[(2,4-diacetyl-α-l-rhamnopyranosyl)-(1→6)]-3,4-diacetyl-β-d-galactopyranoside (2), in addition to two known acetylated quercetin glycosides quercetin 3-O-[(2,3,4-triacetyl-α-l-rhamnopyranosyl)-(1→6)-β-d-galactopyranoside (3) and quercetin 3-O-[(2,3,4-triacetyl-α-l-rhamnopyranosyl)-(1→6)-3-acetyl-β-d-galactopyranoside (4), were isolated from the aerial part of Centaurium spicatum (L.) Fritsch (Gentianaceae). Structure elucidation, especially the localization of the acetyl groups, and complete ¹H and ¹³C NMR assignments of these biologically active compounds were carried out using one- and two-dimensional NMR measurements, including ¹H- and ¹³C-NMR, DEPT-135, H–H COSY, HMQC and HMBC, in addition to HR-FAB/MS experiments.     

Raddeanalin,a new flavonoid glycoside from the leaves of Salix raddeana Laksh.

A new flavonoid glycoside, diosmetin 7-O-β-D-xylopyranosyl(1–6)-β-d-glucopyranoside, named raddeanalin (1), was isolated from the ethanolic extract of the leaves of Salix raddeana Laksh. together with three known compounds, kaempferol 3-O-glucoside (2), quercetin 3-O-glucoside (3) and quercetin 3-O-rutinoside (4). The structure of new compound was established by the spectral data and chemical properties.     

Two new anthraquinone glycosides from the roots of Rheum palmatum

Two new anthraquinone glycosides, named 1-methyl-8-hydroxyl-9,10-anthraquinone-3-O-β-d-(6′-O-cinnamoyl)glucopyranoside (1) and rhein-8-O-β-d-[6′-O-(3″-methoxyl malonyl)]glucopyranoside (2), have been isolated from the roots of Rheum palmatum, together with seven known compounds, rhein-8-O-β-d-glucopyranoside (3), physcion-8-O-β-d-glucopyranoside (4), chrysophanol-8-O-β-d-glucopyranoside (5), aleo-emodin-8-O-β-d-glucopyranoside (6), emodin-8-O-β-d-glucopyranoside (7), aleo-emodin-ω-O-β-d-glucopyranoside (8), and emodin-1-O-β-d-glucopyranoside (9). Their structures were elucidated on the basis of chemical and spectral analysis.     

Antiulcerogenic Activity of Alhagi maurorum.

Abstract

Six main flavonoid glycosides were isolated, for the first time, from the ethanol extract of Alhagi maurorum Boiss (Leguminosae).. They were identified as kaempferol, chrysoeriol, isorhamnetin, chrysoeriol-7-O.-xylosoid, kaempferol-3-galactorhamnoside, and isorhamnetin 3-O.-β-D-apio-furanosyl (1-2) β-D-galactopyranoside. Their identities were established by m.p., UV, EI-mass, Fab-mass, 600 MHz ¹H and ¹³C NMR. The total extract (300 and 400 mg/kg) and two of the isolated compounds (chrysoeriol 7-O.-xylosoid and kaempferol-3-galactorhamnoside, 100 mg/kg each) showed a very promising antiulcerogenic activity with curative ratios 66.31%, 69.57%, 75.49%, and 77.93%, respectively.     

Five new glycosides from <Emphasis Type="Italic">Hypericum erectum</Emphasis> Thunb.

Five new glycosides, quercetin 3′-O-β-d-galactopyranoside (1), quercetin 3-O-(2″-acetyl)-β-d-glucopyranoside (2), 4,6-dihydroxy-2-methoxyphenyl 1-O-β-d-glucopyranoside (3), 4-hydroxy-2,6-dimethoxyphenyl 1-O-α-l-rhamnopyranosyl (1 → 6)-β-d-glucopyranoside (4) and 3-methyl-but-2-en-1-yl β-d-glucopyranosyl (1 → 6)-β-d-glucopyranoside (5), were isolated from Hypericum erectum Thunb. Their structures were established on the basis of spectral and chemical data.     

Pregnane glycosides from Dracaena cochinchinensis

Two new pregnane glycosides, named dracaenoside C and D, were isolated from the fresh stems of Dracaena cochinchinensis. Their structures were established as 3β,14α-dihydroxypregna-5,16(17)-diene-20-one?3-O-α-L-rhamnopyranosyl(1→2)[α-L-rhamnopyranosyl(1→4)]-β-D-glucopyranoside (1) and 3β,14α-dihydroxypregna-5,16(17)-diene-20-one?3-O-α-L-rhamnopyranosyl(1→2)[β-D-glucopyranosyl(1→3)]-β-D-glucopyranoside (2) by means of 2D NMR spectral and chemical methods.     

A new flavonol glycoside from glandless cotton seeds

A new flavonol glycoside, namely quercetin 3-O-[α-d-apiofuranosyl(1–5)-β-d-apiofuranosyl(1–2)]-α-l-rhamnopyranosyl(1–6)-β-d-glucopyranoside (1), was isolated from glandless cotton seeds together with the known compounds quercetin 3-O-α-l-rhamnopyranosyl(1–2)-[α-l-rhamnopyranosyl(1–6)]-β-d-glucopyranoside (manghaslin, 2), kaempferol 3-O-β-d-apiofruranosyl(1–2)-β-d-glucopyranoside (3) and kaempferol 3-O-α-l-rhamnopyranosyl(1–6)-β-d-glucopyranoside (4). It is interesting that the tetrasaccharide fragment of 1 contained both a β-apiosyl and an unusual α-apiosyl group.     

Two new glycosides from Leonurus japonicus

Two new glycosides, 1,6-di-O-syringoyl-β-d-glucopyranose (1) and quercetin 3-O-[(3-O-syringoyl-α-l-rhamnopyranosyl)-(1 → 6)-β-d-glucopyranoside] (2), along with seven known compounds were isolated from the MeOH extract of Leonurus japonicus. The structures of these compounds were elucidated by spectral analysis.