Flavonoids from Camptosorus sibiricus Rupr

Three new flavonol glycosides, kaempferol-3-O-(6-trans-caffeoyl)-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranoside (1), kaempferol-3-O-(6-trans-caffeoyl)-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranoside-7-O-beta-D-glucopyranoside (2), and kaempferol-3-O-(6-trans-p-coumaroyl)-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranoside-7-O-beta-D-glucopyranoside (3), were isolated from the aerial part of Camptosorus sibiricus. Their structures were elucidated by spectroscopic methods, including 2D NMR spectral techniques.     

New flavonol glycosides from leaves of Symplocarpus renifolius.

A study was carried out to evaluate flavonol glycosides in leaves of Symplocarpus renifolius (Araceae). From the water fraction of the MeOH extract, three new flavonol glycosides were isolated along with three known compounds, kaempferol-3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-7-O-b eta-D-glucopyranoside,quercetin-3-O-beta-D-glucopyranosyl-(1-->2)-beta-D -glucopyranoside, and caffeic acid. The structures of the new flavonol glycosides were elucidated by chemical and spectral analyses as quercetin-3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-7-O-be ta-D-glucopyranoside, isorhamnetin-3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyra nos yl-7-O-beta-D-glucopyranoside, and quercetin-3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-7-O-(6 '-trans-caffeoyl)-beta-D-glucopyranoside.     

火绒草黄酮类成分的分离与鉴定(Ⅱ)

目的对火绒草的化学成分进行研究,为进一步开发利用该植物资源提供依据。方法采用反复正相硅胶、反相ODS、Sephadex LH-20等柱色谱以及高效液相色谱法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。结果从火绒草体积分数为70%的乙醇溶液提取物中又分离鉴定了7个黄酮类化合物,分别为芹菜素(apigenin,1)、山柰酚-3-O-(6″-O-乙酰基)-β-D-吡喃葡萄糖苷[kaempferol-3-O-(6″-O-acetyl)-β-D-glucopyranoside,2]、山柰酚-3-O-(6″-O-反式对香豆酰基)-β-D-吡喃葡萄糖苷[kaempferol-3-O-(6″-O-trans-p-coumaroyl)-β-D-glucopyranoside,3]、山柰酚-3-O-(6″-O-顺式对香豆酰基)-β-D-吡喃葡萄糖苷[kaempferol-3-O-(6″-O-cis-p-coumaroyl)-β-D-glucopyranoside,4]、槲皮素-7-O-β-D-吡喃葡萄糖苷(quercetin-7-O-β-D-glucopyranoside,5)、槲皮素-3-甲氧基-7-O-β-D-吡喃葡萄糖苷(quercetin-3-me-thoxy-7-O-β-D-glucopyranoside,6)、槲皮万寿菊素-7-O-β-D-吡喃葡萄糖苷(quercetagetin-7-O-β-D-glucopyranoside,7)。结论化合物1为首次从火绒草植物中分离得到,化合物2～7为首次从火绒草属植物中分离得到。     

Chemical constituents of Saxifraga stolonifera (L.) Meeb

To study the chemical constituents of Saxifraga stolonifera (L.) Meeb., chromatographic techniques were applied to separate and purify the compounds, and their structures were confirmed on the basis of physicochemical properties and spectral data. Ten compounds were isolated and identified as 5-O-methylnorbergenin (1), 3, 4-dihydroxyallylbenzene-4-O-beta-D-glucopyranoside (2), (7R, 8S)-4, 9, 9'-trihydroxyl-3-methoxyl-7, 8-dihydrobenzofuran-1'-propylneolignan-3'-O-beta-D-glucopyranoside (3), quercetin-3-O-beta-D-xylopyranosyl-(1 --> 2)-beta-D-galactopyranoside (4), kaempferol-3-O-alpha-L-rhamnopyranoside (5), (3S, 5R, 6R, 7E, 9R)-3, 5, 6, 9-tetrahydroxy-7-megastigmane (6), benzyl-O-alpha-L-rhamnopyranosyl-(1 --> 6)-beta-D-glucopyranoside (7), p-hydroxyacetophenone (8), pyrogallic acid (9) and p-hydroxyphenol (10). Compound 1 is a new compound. Compounds 2-10 were isolated from this plant for the first time.     

Flavonoids from flowers of Malva crispa L. (Malvaceae)

The following flavonoids were isolated and identified from the flowers of Malva crispa L.: kaempferol 3-O-beta-glucopyranoside, 3-O-(6"-tran-p-coumaroyl)-beta-D-glucopyranoside, 7-O-beta-D-glucopyranoside, 3-O-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranoside and 3,7-O-diglucoside as well as quercetin 3-O-beta-D-glucopyranoside, 3-O-alpha-L-rhamnopyranosyl (1-->6) -beta-D-glucopyranoside and apigenin 7-O-beta-D-glucopyranoside. Their structures were established by chemical analysis, UV, 1H and 13C NMR spectrometry.     

Antioxidative flavonoids from leaves of Carthamus tinctorius

A total of eight flavonoids (1-8), including a novel quercetin-7-O-(6'-O-acetyl)-beta-D-glucopyranoside (6) and seven known flavonoids, luteolin (1), quercetin (2), luteolin 7-O-beta-D-glucopyranoside (3), luteolin-7-O-(6'-O-acetyl)-beta-D-glucopyranoside (4) quercetin 7-O-beta-D-glucopyranoside (5), acacetin 7-O-beta-D-glucuronide (7) and apigenin-6-C-beta-D-glucopyrano syl-8-C-beta-D-glucopyranoside (8), have been isolated from the leaves of the safflower (Carthamus tinctorius L.) and identified on the basis of spectroscopic and chemical studies. The antioxidative activity of these flavonoids was evaluated against 2-deoxyribose degradation and rat liver microsomal lipid peroxidation induced by hydroxyl radicals generated via a Fenton-type reaction. Among these flavonoids, luteolin-acetyl-glucoside (4) and quercetin-acetyl-glucoside (6) showed potent antioxidative activities against 2-deoxyribose degradation and lipid peroxidation in rat liver microsomes. Luteolin (1), quercetin (2), and their corresponding glycosides (3 & 5) also exhibited strong antioxidative activity, while acacetin glucuronide (7) and apigenin-6,8-di-C-glucoside (8) were relatively less active.     

Four new glycosides from Pleurospermum franchetianum

Four new glycosides, pleurofranosides I-IV, together with eight known compounds were isolated from the whole plants of Pleurospermum franchetianum Hemsl. Based on the spectral data and chemical evidence, the structures of pleurofranosides 1, II, III and IV were elucidated to be 16beta, 21beta, 23, 28-tetrahydroxyolean-12-ene-3beta-yl-O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranoside, 13beta, 28-epoxy-16beta, 23-dihydroxyolean-11-ene-3beta-yl-O-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-beta-D-fucopyranoside, 13beta, 28-epoxy-16beta, 23-dihydroxyolean-11-ene-3beta-yl-O-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-fucopyranosyl-(1 --> 2)]-beta-D-glucopyranoside and 12beta, 28-epoxy-16beta, 23-dihydroxyolean-11-ene-3beta-yl-O-beta-D-glucopyranosyl-(1 --> 3)-[beta-D-glucopyranosyl-(1 --> 2)]-beta-D-glucopyranoside. The known compounds identified were octadecyl caprate, beta-sitosterol, (22E, 20S, 24R)-5alpha, 8alpha-epidioxy-ergosta-6, 22-dien-3-beta-ol, daucosterol, alpha-spinasterol-3-O-beta-D-glucopyranoside, quercetin-3, 7-di-O-beta-D-glucopyranoside, kaempferol-3, 7-di-O-alpha-L-rhamnopyranoside and kaempferol-3-O-beta-D-glucopyranosyl-7-O-alpha-L-rhamnopyranoside, respectively.     

红芽大戟化学成分研究

目的研究茜草科植物红芽大戟(Knoxia corymbosa Willd．)的化学成分。方法利用硅胶、聚酰胺等色谱技术分离纯化,根据化合物的理化性质和光谱数据进行鉴定。结果从红芽大戟的正丁醇萃取部分分离得到4个黄酮醇苷成分,分别鉴定为:槲皮素-7-O-α-L-阿拉伯糖-3-O-β-D-6″-乙酰基吡喃葡糖苷(quercetin-7- O-α-L-arabinosyl-3-O-β-D-6″-acetylglucopyranoside,1);山奈酚-7-O-α-L-阿拉伯糖-3-O-β-D-吡喃葡糖苷(kaempferol-7-O-α-L-arabinosyl-3-O-β-D-glucopyranoside,2);槲皮素-3-O-β-D-吡喃葡糖苷(quercetin-3-O-β-D-glucopyranoside,3); 槲皮素-3-O-β-D-6″-乙酰基吡喃葡糖苷(quercetin-3-O-β-D-6″-acetylglucopyranoside,4)。结论化合物1为新化合物,其余均为首次从该种植物分到。     

Iridoids from Phlomis aurea Decne growing in Egypt

A new iridoid gentiobioside (4, assigned the name phlomiside) was isolated from the leaves of Phlomis aurea growing in Egypt, in addition to auroside (1), lamiide (2), 8-epi-loganin (3), forsythoside B (5), quercetin-3-O-beta-D-glucopyranoside (6) and kaempferol-3-O-beta-D-glucopyranosyl-(1-6)-beta-D-glucopyranoside (7). Structures of these compounds were elucidated by conventional methods of analysis as well as by different spectroscopic techniques.     

Acylphloroglucinol glycosides from the fruits of Pyracantha fortuneana

Three new acylphloroglucinol glycosides, namely pyrafortunosides A (1), B (2) and C (3), together with three known glycosides (4-6), were isolated from the fruits of Pyracantha fortuneana (Maxim.) Li. Their structures were established to be 2,4,6-trihydroxy-acetophenone-6-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (1), 2,4,6-trihydroxy-benzophenone-6-O-alpha-L-rhamno-pyranosyl-(1-->6)-beta-D-glucopyranoside (2), 2,4,6-trihydroxy-benzophenone-6-O-beta-D-apiofuranosyl-(1-->6)-beta-D-gluco-pyranoside (3), garcimangosone D (4), 2,4,6-trihydroxy-acetophenone-6-O-beta-D-glucopyranoside (5), and 2,4,6-trihydroxy-acetophenone-4-O-beta-D-glucopyranoside (6) by spectral analysis. The three known glycosides (4-6) were obtained from this genus for the first time.     

南葶苈子化学成分的分离与结构鉴定南葶苈子化学成分的分离与结构鉴定

目的研究南葶苈子的化学成分。方法用硅胶、聚酰胺-6、反相硅胶C₁₈和Sephadex LH 20柱色谱进行分离纯化。用MS,¹HNMR,13CNMR,HSQC,HMBC,TOCSY等波谱学方法,结合化学定性和薄层酸水解确定化合物结构。结果从南葶苈子中分离得到15个化合物,鉴定了12个化合物的结构,分别为:槲皮素-3-O-β-D-吡喃葡糖基-7-O-β-龙胆双糖苷(I);山萘酚-3-O-β-D-吡喃葡糖基-7-O-β-龙胆双糖苷(II);异鼠李素-3-O-β-D-吡喃葡糖基-7-O-β-龙胆双糖苷(III);槲皮素-7-O-β-龙胆双糖苷(IV);山萘酚-7-O-β-龙胆双糖苷(V);异鼠李素-7-O-β-龙胆双糖苷(VI);槲皮素-3,7-二-O-β-D-吡喃葡糖苷(VII);山萘酚-3,7-二-O-β-D-吡喃葡糖苷(VIII);异鼠李素-3,7-二-O-β-D-吡喃葡糖苷(IX);山萘酚-3-O-β-D-吡喃葡糖基-7-O-β-D-［2-芥子酰基-β-D-吡喃葡糖基(1→6)］-吡喃葡糖苷(X);芥子酸乙酯(XI);4-甲氧基芥子酸(XII)。结论X和VI是新化合物,IV,V,VII,VIII,IX均为首次自十字花科植物中分离得到,I,II,III均为首次自播娘蒿属中分离得到,XI和XII为首次自该植物中分离得到。     

素馨花中黄酮苷类化学成分研究

目的:研究素馨花药材70%乙醇提取物中具有抗乙型肝炎病毒(hepatitis B virus,HBV)活性的化学成分。方法:通过硅胶柱色谱、聚酰胺柱色谱、Sephadex LH-20柱色谱及HPLC、重结晶等方法进行分离纯化,根据化合物的理化性质和波谱数据(1H-NMR,13C-NMR,UV,MS)鉴定化学结构。结果:从素馨花干燥花蕾70%乙醇提取物的抗HBV活性部位中,分离得到6个黄酮苷类化合物,分别鉴定为山柰酚-3,7-O-双-β-D-吡喃葡萄糖苷(1)、山柰酚-3-O-(6″-O-乙酰基)-β-D-吡喃葡萄糖苷(2)、槲皮素-3-O-桑布二糖苷(3)、硫磺菊苷(4)、紫铆黄素-7-O-β-D-吡喃葡萄糖苷(5)、合金欢素-7-O-(α-D-芹菜呋喃糖)(1→6)-β-D-吡喃葡萄糖苷(6)。结论:化合物1～6均为首次从该植物中分离得到。     

<Emphasis Type="Italic">In vivo</Emphasis> anti-inflammatory effect of a new steroidal saponin,mannioside A,and its derivatives isolated from <Emphasis Type="Italic">Dracaena mannii</Emphasis>

A new steroidal saponin, mannioside A (1), was isolated from the stem bark of Dracaena mannii, together with the known pennogenin (2), pennogenin-3-O-beta-D-glucopyranoside (3) and pennogenin-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->3)]-beta-D-glucopyranoside (4). Their structures were determined using 1D-and 2D-NMR spectroscopy and mass spectrometry. Compounds 1 and 3 significantly inhibited carrageenan-induced paw edema in the rat; compound 4 was moderately active whereas 2 showed very weak activity.     

Antioxidant constituents and a new triterpenoid glycoside from<Emphasis Type="Italic">Flos Lonicerae</Emphasis>

As a component of our continuing investigations into herb-derived antioxidant agents, we have evaluated the antioxidant effects of Flos Lonicerae (Lonicera japonica flowers), via 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, total reactive oxygen species (ROS), hydroxyl radical (*OH), and peroxynitrite (ONOO-) assays. Among the methanolic extract and the dichloromethane, ethyl acetate, n-butanol, and water fractions, the EtOAc fraction of Flos Lonicerae exhibited marked scavenging/inhibitory activities, as follows: IC50 values of 4.37, 27.58 +/- 0.71, 0.47 +/- 0.05, and 12.13 +/- 0.79 microg/mL in the DPPH, total ROS, ONOO-, and *OH assays, respectively. Via a bioactivity-guided fractionation approach, a new triterpenoid glycoside, oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-xylopyranosyl(1-->6)]-beta-D-glucopyranosyl ester (12), along with eleven known compounds, including chrysoeriol (1), luteolin (2), 5-hydroxymethyl-2-furfural (3), caffeic acid (4), protocatechuic acid (5), chrysoeriol 7-O-beta-D-glucopyranoside (6), isorhamnetin 3-O-beta-D-glucopyranoside (7), kaempferol 3-O-beta-D-glucopyranoside (8), quercetin 3-O-beta-D-glucopyranoside (9), hederagenin 3-O-alpha-L-arabinopyranoside (10), and luteolin 7-O-beta-D-glucopyranoside (11), were isolated from the EtOAc fraction. The structures of isolated compounds 1-12 were elucidated via spectroscopic analyses. Compound 12 was isolated from a natural source for the first time. Compounds 2, 4, 5, 7, 9, and 11 evidenced marked scavenging activities, with IC50 values of 2.08-11.76 microM for DPPH radicals, and 1.47-6.98 microM for ONOO-.     

油茶叶的化学成分

目的研究油茶叶中的化学成分。方法运用多种色谱法进行分离纯化,通过理化性质和波谱数据分析以及和对照品对照进行结构鉴定。结果从油茶叶分离并鉴定了10个化合物,分别鉴定为:羽扇豆烷醇(1)、1-(3′,5′-二甲氧基)苯基-2-(4″-羟基)苯基乙烷(2)、齐墩果酸(3)、胡萝卜苷(4)、山柰酚(5)、山柰酚-3-O-(2″,6″-二-O-反式-对-羟基桂皮酰基)-β-D-葡萄糖苷(6)、槲皮素(7)、槲皮素-3-O-β-D-葡萄糖苷(8)、槲皮素-3-O-β-D-半乳糖苷(9)、槲皮素-3-O-α-L-鼠李糖苷(10)。结论化合物1-6、8、9均为首次从油茶叶中分离得到,其中化合物2为首次从山茶属中分离得到。     

Isolation and identification of antioxidants from Sophora japonica

A new flavonol triglycoside, kaempferol 3-O-alpha-L-rhamnopyranosyl-(1 --> 6)-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranoside (1), as well as two known kaempferol 3-O-[alpha-L-rhamnopyranosyl-(1 --> 6)]-[beta-D-glucopyranosyl-(1 --> 2)]-beta-D-glucopyranoside (2) and kaempferol 3-O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranoside-7-O-alpha-L-rhamnopyranoside (3), were isolated from the n-BuOH extract of the pericarps of Sophora japonica by bioassay-guided fractionation. The structure of compound 1 was established by UV, IR, MS, and one- and two-dimensional NMR spectroscopy, including DEPT, NOESY, DQF-COSY, TOCSY, HMQC, and HMBC experiments. Compounds 1-3 showed antioxidative activity in DPPH and cytochrome-c assay using HL-60 cell system.     

Studies on the constituents of trichosanthes root. II. Constituents of roots of Trichosanthes cucumeroides Maxim

From the fresh roots of Trichosanthes cucumeroides Maxim., three new triterpenoid glycosides with a bitter taste were obtained together with methyl palmitate, palmitic acid, alpha-spinasterol, stigmast-7-en-3 beta-ol, alpha-spinasterol 3-O-beta-D-glucopyranoside, stigmast-7-en-3 beta-ol 3-O-beta-D-glucopyranoside and vanillic acid. On the basis of the results of spectral and chemical investigations, these glycosides were characterized as 25-O-beta-D-glucopyranosyl-11-oxocucurbit-5-ene-3 beta,24(R), 25-triol 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranosyl-(1----2)-beta -D- glucopyranoside, 25-O-beta-D-(6-O-acetyl)-glucopyranosyl-11-oxocucurbit-5-ene-3 beta,24(R), 25-triol 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranosyl(1----2)- beta-D-glucopyranoside and 11-oxocucurbit-5-ene-3 beta,24(R), 25-triol 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranosyl-(1----2)- beta-D-glucopyranoside.     

多刺绿绒蒿的化学成分

从多刺绿绒蒿Meconopsis horridula Hook.f.et Thoms的全草中分离鉴定了13个化合物,分别为:木犀草素-7-O-β-D-葡萄糖苷(1)、山奈酚-3-O-β-D-葡萄糖( 1→2)-β-D-葡萄糖苷(2)、槲皮素-3-O-β-D-半乳糖(1→6)-β-D-葡萄糖苷(3)、小麦黄素-7-O-β-D-葡萄糖苷(4)、山奈酚-3-O-β-D-葡萄糖(5)、桂皮酰胺(6)、对羟基桂皮酰胺对羟基苯乙胺(7)、小麦黄素(8)、木犀草素(9)、槲皮素(10)、芹菜素(11)、山奈酚-4'-甲醚(12)、山奈酚(13).其中化合物1、5、6、7、12、13为首次从该属中分离得到,化合物2、3、4为首次从该植物中分离得到.     

Cucurbitane and hexanorcucurbitane glycosides from the fruits of Cucurbita pepo cv dayangua

Phytochemical investigation of the fruits of Cucurbita pepo cv dayangua has led to the isolation of two cucurbitane glycosides: cucurbitacin L 2-O-beta-D-glucopyranoside (1), cucurbitacin K 2-O-beta-D-glucopyranoside (2) and two hexanorcucurbitane glycosides: 2,16-dihydroxy-22,23,24,25,26,27-hexanorcucurbit-5-en-11,20-dione 2-O-beta-D-glucopyranoside (3) and 16-hydroxy-22,23,24,25,26,27-hexanorcucurbit-5-en-11,20-dione 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranoside (4). Compounds 1, 2 and 3 were isolated from Cucurbita genus for the first time, while compound 4 is a new one. Their structures were determined on the basis of chemical and spectroscopic evidence.     

板栗花的化学成分

目的对板栗花的化学成分进行分离和结构鉴定。方法采用硅胶柱色谱、凝胶柱色谱和重结晶等分离方法对板栗花体积分数为90%的乙醇溶液提取物进行化学分离;通过谱学分析方法结合化合物理化性质对化合物结构进行鉴定。结果分离得到11个化合物,分别鉴定为2α,3β,23-三羟基齐墩果烷-12-烯-28-酸(2α,3β,23-trihydroxyolean-12-en-28-acid,1)、4-喹啉酮-2-羧酸-正丁基酯(4-quinolinone-carboxylic-2-acidn-butyl ester,2)、槲皮素-3-O-β-D-半乳糖苷(quercetin-3-O-β-D-ga-lactopyranoside,3)、山柰酚(kaempferol,4)、槲皮素(quercetin,5)、山柰酚-3-O[6″-O-反式-对-香豆酰基]-β-D-吡喃葡萄糖苷(kaempferol-3-O-[6″-O-(E)-p-coumaroyl]-β-D-glucopyranoside,6)、山柰酚-3-O-[2″,6″-O-双-反式-对-香豆酰基]-β-D-吡喃葡萄糖苷(kaempferol-3-O-[2″,6″-di-O-(E)-p-coumaroyl]-β-D-glucopyranoside,7)、没食子酸(gallic acid,8)、原儿茶酸(protocatechuic acid,9)、5-羟甲基糠醛(5-hydroxymethylfurfuraldehyde,10)、槲皮素3-O-β-D-葡萄糖醛酸甲酯(quercetin-3-O-β-D-glucuronide6″-methyl ester,11)。结论化合物1,2,11为从栗属植物中首次分离得到,化合物3为从该植物中首次分离得到。