Flavonol Glycosides from Croton menthodorus Reduce in vitro Morphine Withdrawal

We currently report the effects of quercetin-3- O -(2- O -ß-apiofuranosyl)-rutinoside (Q), rutin (R), kaempferol-3- O -rutinoside (K) and kaempferol-3- O -(6- O -trans- p -coumaroyl)-ß-D-glucopyranoside (K1) isolated from Croton menthodorus on in vitro morphine withdrawal. The results indicated that all flavonol glycosides tested (1 × 10 -7, 1 × 10 -6, and 1 × 10 -5 M) dose-dependently reduced morphine withdrawal in vitro. These data suggest that flavonol glycosides from Croton menthodorus may play an important role in morphine withdrawal control.     

Note Polyphenols of Ocimum sanctum from Suriname

Apigenin, luteolin, apigenin-7- O -ß-D-rutinopyranoside, luteolin-7- O -ß-D-glucopyranoside, vicenin-2, vitexin, isovitexin, orientin, isoorientin, aesculetin, aesculin, chlorogenic acid and caffeic acid have been isolated from the aerial parts of O. sanctum L.     

珠子参的化学成分

目的对珠子参[PanaxjaponicusC.A.Mey.var.major(Buck.)C.Y.Wu et K.M.Feng]根茎的化学成分进行研究。方法采用硅胶柱色谱进行分离纯化,根据理化性质和波谱数据进行结构鉴定。结果分离得到8个化合物,分别鉴定为苯甲酸(benzoin acid,1)、豆甾醇(stigmasterol,2)、齐墩果酸(oleanolic acid,3)、胡萝卜苷(daucosterol,4)、齐墩果酸-28-O-β-D-吡喃葡萄糖苷(oleanolicacid-28-O-β-D-glucopyranoside,5)、齐墩果酸-3-O-β-D-吡喃葡萄糖基(1→2)-β-D-(6′-丁酯)吡喃葡萄糖醛酸苷(oleanolic acid-3-O-β-D-glucopyranoside(1→2)-β-D-glucorunopyranosy-6′-O-butylester,6)、竹节参皂苷IVa(chikusetsusaponinⅣa,7)、人参皂苷Ro(ginsenoside,8)。结论化合物6为新化合物,化合物1、2为首次从该种植物中分离得到。     

黄腊果果皮化学成分的分离与鉴定

目的研究黄腊果果皮的化学成分。方法采用反复硅胶柱色谱法、Sephadex LH-20柱色谱法、重结晶和HPLC等方法进行分离纯化,并通过NMR技术鉴定其化学结构。结果从黄腊果中分离得到8个化合物,分别鉴定为:3-羟基-2-甲基-4-吡喃酮(3-hydroxy-2-methyl-4-pyrone,1)、芥子醛(sinapaldehyde,2)、2-甲基-4-吡喃酮-3-O-β-D-吡喃葡萄糖苷(2-methyl-4-pyrone-3-O-β-D-glucopyr-anoside,3)、3,5-二甲氧基-4-羟基苯甲酸-7-O-β-D-葡萄糖苷(3,5-dimethoxyl-4-hydroxybenzoic acid-7-O-β-D-glucopyranoside,4)、胡萝卜苷(daucosterol,5)、β-谷甾醇(sitosterol,6)、3-O-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖-30-降甲基齐墩果-12,20(29)-二烯-28-羧酸(3-O-α-Lrhamnopyrano-syl-(1→2)-α-L-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid,7)、3-O-β-D-吡喃葡萄糖-(1→3)-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖-30-降甲基齐墩果-12,20(29)-二烯-28-羧酸(3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-D-glucopyranosyl-(1→3)-α-L-arabi-nopyranosyl-30-norolean-12,20(29)-dien-28-oic acid,8)。结论化合物1-4为首次从木通科植物中分离得到,化合物6-8为首次从黄腊果中分离得到。     

Kaempferol 3-O-(2-O-ß-D-Glucopyranosyl-6-O-a-L-Rhamnopyranosyl-ß-D-Glucopyranoside) from the African Plant Erythrina abyssinica

The flavonol, 3- O -(2- O-ß -D-glucopyranosyl-6- O-a -L-rhamnopyranosyl- ß -D-glucopyranoside), was isolated from Erythrina abyssinica Lamarck, an African plant widely used as folk remedies against malaria and syphilis. The structure was established on the basis of homo- and heteronuclear two-dimensional nuclear magnetic resonance techniques.     

Two New Saponins from the Root Bark of Aralia Elata

In addition to three known saponins, araloside A, stipuleanosides R 1 and R 2, two new saponins, named durupcosides A and B, have been isolated from the root bark of Aralia elata as their methylesters. Their structures have been established as 3-O-ß-D-glucopyranosyl (1?2)-[a-L-arabinofuranosyl (1?4)]-ß-D-glucuronopyranosyl oleanolic acid and 3-O-a-L-arabinopyranosyl (1?2)-[ß-D-glucopyranosyl (1?3)]-ß-D-glucuronopyranosyl oleanolic acid, respectively, on the basis of spectroscopic data and chemical reactions.     

Triterpenoid saponins from Vaccaria segetalis

A new triterpenoid saponin, named segetoside C (1), and two known saponins, vaccaroid A (vaccaroside A) (2) and dianoside G (3), have been isolated from the seeds of Vaccaria segetalis. On the basis of chemical reaction and spectral data, the structure of segetoside C (1) has been established as: gypsogenic acid-28-O-[β-D-glucopyranosyl-(1 → 3)]-[6-O-acetyl-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranoside.     

骨碎补中的苯丙素类成分及其对UMR 106细胞增殖作用的影响

目的研究骨碎补(Drynaria fortunei)中的苯丙素类成分,并讨论它们对大鼠类成骨细胞UMR 106增殖的影响。方法采用硅胶、Sephadex LH-20、ODS柱色谱分离骨碎补根茎的活性成分,应用理化方法及1D-NMR、2D-NMR方法确定化学结构,并检测对UMR 106细胞增殖的影响。结果从骨碎补体积分数为60%乙醇提取物中的大孔吸附树脂柱色谱的体积分数为30%乙醇洗脱部分,分离得到7个苯丙素类化合物和2个苯甲酸类化合物,分别鉴定为:(E)-4-O-β-D-吡喃葡萄糖基反式咖啡酸(1)、(E)-p-松针酸β-D-吡喃葡萄糖苷(2)、阿魏酸β-D-吡喃葡萄糖苷(3)、反式咖啡酸(4)、p-香豆酸4-O-β-D-吡喃葡萄糖苷(5)、二氢异阿魏酸(6)、二氢咖啡酸(7)、香草酸4-O-β-D-吡喃葡萄糖苷(8)、原儿茶酸(9)。并检测了化合物1~9对UMR 106细胞增殖的影响。结论化合物1首次从该种植物中分离得到,化合物2~8首次从该属植物中分离得到。化合物1~4显示了对UMR 106细胞的促增殖作用,而其他化合物则没有显示活性。     

过山蕨中有机酸类化学成分

目的研究过山蕨(Camptosorus sibiricusRupr.)中有机酸类化学成分。方法采用反复硅胶柱层析分离纯化,通过理化常数测定和光谱分析鉴定其化学结构。结果从过山蕨中分离得到了11个有机酸类化合物,即咖啡酸(caffeic acid,1)、香豆酸(courmaric acid,2)、原儿茶酸(protocate-chuic acid,3)、对羟基苯甲酸(4 hydroxybenzoic acid,4)、异香草酸(isovanillic acid,5)、2,4二羟基苯甲酸(2,4 dihydroxybenzoic acid,6)、肉桂酸(cinnamic acid,7)、丁二酸(succinic acid,8)、棕榈酸(palmitic acid,9)、香豆酸4OβD吡喃葡萄糖苷(transpcoumaric acid 4OβDglucopyranoside,10)、咖啡酸4OβD吡喃葡萄糖苷(caffeic acid 4OβDglucopyranoside,11)。结论化合物2~11,均为首次从该属植物中分离得到。     

黄腊果叶中化学成分的分离与鉴定(Ⅰ)

目的研究黄腊果(Stauntonia brachyanthera Hand.-Mazz.)叶中的化学成分。方法采用反复硅胶柱色谱法、Sephadex LH-20柱色谱法、制备薄层色谱法和重结晶等方法进行分离纯化,通过理化性质与波谱分析方法鉴定化合物的结构。结果从黄腊果叶体积分数70%乙醇溶液提取物中分离鉴定6个化合物,分别为3β,20α,24-trihydroxy-29-norolean-12-en-28-oic acid 24-O-β-D-glucopyrano-side(1)、牡荆素(vitexin,2)、山奈酚(kaempferol,3)、apigenin-7-O-β-D-neospheroside(4)、3,23-di-hydroxy-akebonic acid(5)、3-O-β-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid(6)。结论化合物1～4为首次从野木瓜属植物中分离得到,化合物5为首次从黄腊果中分离得到。     

黄连水提液化学成分的分离与鉴定

目的对黄连(Coptis chinensis Franch.)的化学成分进行研究。方法采用不同柱色谱技术进行分离,通过波谱手段确定化合物结构。结果分离鉴定了22个化合物,其中9个生物碱类化合物,分别为小檗碱(berberine,1)、巴马亭(palmatine,2)、黄连碱(coptisine,3)、表小檗碱(epiberber-ine,4)、药根碱(jatrorrhizine,5)、非洲防己碱(columbamine,6)、groenlandicine(7)、木兰花碱(mag-noflorine,8)、8-氧化黄连碱(8-oxocoptisine,9);9个有机酸类化合物,分别为5-阿魏酰奎宁酸(5-O-feruloyl-D-quinic acid,10)、4-阿魏酰奎宁酸(4-O-feruloyl-D-quinic acid,11)、3-甲氧基-4-羟基苯甲酸(3-methoxy-4-hydroxybenzoic acid,12)、阿魏酸(ferulic acid,13)、香草酸-4-O-β-D-葡萄糖苷(va-nillic acid-4-O-β-D-glucopyranoside,14)、3-(3',4'-二羟基苯基)-(2R)-乳酸-4'-O-β-D-吡喃葡萄糖苷(3-(3',4'-dihydroxyphenyl)-(2R)-lactic acid-4'-O-β-D-glucopyranoside,15)、3-(4'-羟基苯基)-(2R)-乳酸(3-(4'-hydroxyphenyl)-(2R)-lactic acid,16)、3-(3',4'-二羟基苯基)-(2R)-乳酸(3-(3',4'-dihydroxyphenyl)-(2R)-lactic acid,17)、3-(3',4'-二羟基苯基)-(2R)-乳酸甲酯(3-(3',4'-di-hydroxyphenyl)-(2R)-lactic acid methyl ester,18);4个木脂素类化合物,分别为异落叶松树脂素-9-O-β-D-吡喃葡萄糖苷(isolarisiresinol-9-O-β-D-glucopyranoside,19)、(+)-松脂醇-4,4'-O-β-D-吡喃葡萄糖苷((+)-pinoresinol-4,4'-O-β-D-diglucopyranoside,20)、7S,8R,8'R-(+)-落叶松脂素-4,4'-O-β-D-吡喃葡萄糖苷(7S,8R,8'R-(+)-larisiresnol-4,4'-O-β-D-diglucopyranoside,21)、7S,8R,8'R-(+)-落叶松脂素-4-O-β-D-吡喃葡萄糖苷(7S,8R,8'R-(+)-larisiresinol-4-O-β-D-glucopyranoside,22)。结论化合物15、16、18-22为首次从黄连植物中分离得到,化合物16、18、19首次从黄连属植物中分离得到。     

太白楤木根皮的齐墩果酸皂甙

从太白楤木(Aralia taibaiensis Z.Z.Wang et H.C.Zheng)根皮中首次分离到5个齐墩果酸皂甙,根据理化性质和光谱数据,分别鉴定为木皂甙A(1),3-O-[α-L-呋喃阿拉伯糖(1→4)-β-D-吡喃葡萄糖醛酸丁酯]-齐墩果酸-28-O-β-D-吡喃葡萄糖甙(2),3-O-[α-L-呋喃阿拉伯糖(1→4)-β-D-吡喃葡萄糖醛酸乙酯]-齐墩果酸-28-O-β-D-吡喃葡萄糖甙(3),屏边三七甙R₂(4)和3-O-｛β-D-吡喃葡萄糖(1→3)[α-L-呋喃阿拉伯糖(1→4)]-β-D-吡喃葡萄糖醛酸乙酯｝-齐墩果酸-28-O-β-D-吡喃葡萄糖甙(5)。2,3和5为新化合物,分别命名为太白楤木皂甙I(taibaienoside I)、太白楤木皂甙II(taibaienoside II)和太白楤木皂甙III(taibaienoside III)。     

New glycosides from <Emphasis Type="Italic">Dracocephalum tanguticum</Emphasis> maxim

Four new glycosides, luteolin-7-methoxy-3′-O-(3″-O-acetyl)-β-D-gluco pyranuronic acid-6″-methyl ester (1), benzyl-6-[(2E)-2-butenoate]-β-D-glucopyranoside (2), 2-methoxy-4-(2-propen-1-yl)penyl-6-acetate-β-D-glucopyranoside (3), and 2-methoxy-4-(2-propen-1-yl)penyl-6-[(2E)-2-butenoate]-β-D-glucopyranoside (4), along with benzyl-β-D-glucopyranoside (5), 2-methoxy-4-(2-propen-1-yl)penyl-β-D-glucopyranoside (6), and pectolarigenin (7), were isolated from the whole plant of Dracocephalum tanguticum Maxim. The structures of 1-4 were elucidated by detailed spectroscopic analyses, including HR-ESI-MS and 2D NMR spectroscopic data. The inhibitory effects against nitric oxide production in LPS-stimulated RAW264.7 cells of all seven compounds were also evaluated.     

空心莲子草中三萜皂苷类化学成分的研究

为了研究苋科植物空心莲子草[Alternanthera philoxeroides(Mart.)Griseb]抗病毒活性的物质基础,对其化学成分进行了研究。本文主要报道从空心莲子草正丁醇部位分离得到的5个三萜皂苷类化合物,经图谱分析,结构分别鉴定为:3-O-β-D-吡喃葡萄糖(1→3)-O-[β-D-吡喃葡萄糖]-齐墩果酸-28-O-β-D-葡萄糖醛酸苷(1)、齐墩果酸-3-O-β-D-吡喃葡萄糖醛酸苷(2)、齐墩果酸-3-O-β-D-吡喃葡萄糖醛酸-28-O-β-D-吡喃葡萄糖苷(竹节参苷Ⅳa,3)、3-O-β-D-吡喃葡萄糖醛酸丁酯-齐墩果酸-28-O-β-D-吡喃葡萄糖苷(4)和3-O-β-D-吡喃葡萄糖醛酸-常春藤皂苷K(尼泊尔常春藤皂苷K,5),其中化合物1为新化合物,化合物4和5为首次从该植物中分离得到。     

Three new saponins from the leaves of Ilex hylonoma

Three new triterpenoid saponins, hylonosides III-V (1-3) have been isolated, along with three known oleanolic acid saponins (4-6), from the methanol extract of leaves of Ilex hylonoma. The structures were elucidated using a combination of homo- and hetero-nuclear 2D NMR techniques (COSY, TOCSY, NOESY, HMQC and HMBC) and negative FAB-MS. The new compounds were characterized as 3-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-glucuronopyranosyl siaresinolic acid-28-O-beta-D-glucopyranosyl ester (1), 3-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucuronopyranosyl siaresinolic acid-28-O-beta-D-glucopyranosyl ester (2), 3-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucuronopyranosyl oleanolic acid-28-O-beta-D-glucopyranosyl ester (3).     

中药黄蜀葵花化学成分的分离与鉴定（III）

目的 研究中药黄蜀葵（Abelmoschus manihot (L.）Medic)花的化学成分。方法 采用正相硅胶、反相ODS、Sephadex LH-20等柱色谱以及HPLC等手段进行分离纯化,并通过理化性质与光谱分析方法鉴定了化合物的结构。结果 从黄蜀葵花体积分数为95%的乙醇提取物中分离鉴定了9个化合物,分别为棉皮素 8-O-β-D-葡萄糖醛酸苷（gossypetin 8-O-β-D-glucuronide,1）、棉皮素 3-O-β-葡萄糖-8-O-β-葡萄糖醛酸（gossypetin 3-O-β-glucopyranoside-8-O-β-glucuronopyranoside,2）、棉皮素 3'-O-β-D-葡萄糖苷（gossypetin 3'-O-β-D-glucopyranoside,3）、tiliroside（4）、山奈酚3-O-[(3"-O-乙酰基-6"-O-(E)-对羟基桂皮酰基)]-β-D-葡萄糖苷（kaempferol 3-O-[3"-O-acetyl -6"-O-(E)-p-coumaroyl)]-β-D-glucopyranoside,5）、槲皮素 3-O-[β-D-木糖基(1→2)-a-L-鼠李糖基(1→6)]-β-D-半乳糖苷（quercetin 3-O-[β-D-xylopyranosyl(1→2)-a-L-rhamnopyranosyl(1→6)-β-D-galactopyranoside,6）、4-羟基苯甲酸 β-D-葡萄糖酯（4-hydroxybenzoic acid β-D-glucose ester,7）、原儿茶酸（protocatechuic acid,8）、原儿茶酸 3-O-β-D-葡萄糖苷（protocatecheuic acid 3-O-β-D-glucoside,9)。结论 其中化合物2、4-9为首次从秋葵属中分离得到,并首次报道了化合物5、6、9在DMSO-d₆中的光谱数据。     

Biotransformation of oleanolic acid by Alternaria longipes and Penicillium adametzi

Microbial transformation of oleanolic acid (1) was carried out. Six transformed products (2-7) from 1 by Alternaria longipes and three transformed products (8-10) from 1 by Penicillium adametzi were isolated. Their structures were elucidated as 2α,3α,19α-trihydroxy-ursolic acid-28-O-β-d-glucopyranoside (2), 2α,3β,19α-trihydroxy-ursolic acid-28-O-β-d-glucopyranoside (3), oleanolic acid 28-O-β-d-glucopyranosyl ester (4), oleanolic acid-3-O-β-d-glucopyranoside (5), 3-O-(β-d-glucopyranosyl)-oleanolic acid-28-O-β-d-glucopyranoside (6), 2α,3β,19a-trihydroxy-oleanolic acid-28-O-β-d-glucopyranoside (7), 21β-hydroxyl oleanolic acid-28-O-β-d-glucopyranoside (8), 21β-hydroxyl oleanolic acid (9), and 7α,21β-dihydroxyl oleanolic acid (10) based on the extensive NMR studies. Among them, 10 was a new compound and compounds 5 and 8-10 had stronger cytotoxic activities against Hela cell lines than the substrate. At the same time, it was reported for the first time in this paper that the skeletons of compounds 2 and 3 were changed from oleanane to uranane and seven glycosidation products were obtained by biotransformation.     

中药墨旱莲中的三萜皂苷

从中药墨旱莲Eclipta prostrataL．中分离得到5个三萜皂苷,根据理化性质和光谱数据,分别鉴定为eclalbasaponins Ⅱ(1),Ⅰ(2),Ⅲ(3),3-O[β-D-吡喃葡糖(1→2)-β-D-吡喃葡糖]-16R-乙氧基-齐墩果酸-28-O-β-D-吡喃葡糖苷(4)和3-O[β-D-吡喃葡糖(1→2)-β-D-吡喃葡糖]-刺囊酸-28-Oβ-D-吡喃葡糖苷(5)。化合物4和5为新化合物,分别命名为eclalbasaponins XI和eclalbasaponins XII。化合物1和5具有诱导稻瘟霉菌丝变形活性。     

番石榴叶中一个新的没食子酰苷类成分

为了研究番石榴叶Psidium guajava L.的化学成分, 用各种柱色谱方法从其乙醇水提取物中分离得到5个具有没食子酰结构的酚酸类化合物, 并采用光谱、质谱及文献对照等方法鉴定其结构, 分别为1-O-(6-O-没食子酰基-β-D-葡萄糖)-1,2-丙二醇 (1)、没食子酸 (2)、鞣花酸 (3)、鞣花酸-4-O-β-D-葡萄糖 (4)、槲皮素-3-O-(6"-没食子酰基) β-D-半乳糖 (5)。化合物4与5为首次在该植物中分离得到, 化合物1为一新的酚酸类化合物。     

Chemical constituents from the leaves of Cistus parviflorus

A phytochemical investigation on the leaves of Cistus parviflorus led to the isolation of 18 compounds. The structures of the isolated compounds were elucidated as kaempferol 3-O-(3′′,6′′-di-O-E-p-coumaroyl)-β-D-glucopyranoside (1), scopoletin (2),kaempferol 3-O-(3′′-O-E-p-coumaroyl)-β-D-glucopyranoside (3), kaempferol 3-O-(6′′-O-E-p-coumaroyl)-β-D-glucopyranoside (4), kaempferol 3-O-β-D-glucopyranoside (5), kaempferol 3-O-α-L-rhamnopyranosyl-(1→2)-(6′′-O-E-p-coumaroyl)-β-D-glucopyranoside (6), methyl flavogallonate(7), quercetin 3-O-β-D-glucopyranoside (8), quercetin 3-O-β-D-galactopyranoside (9), hydroquinone (10), arbutin (11), methyl β-glucopyranoside (12), shikimic acid (13), (S)-1,2-propandiol-1-O-β-D-glucopyranoside (14), benzyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (15), 2-phenethyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (16), corchoionoside C (17), kaempferol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (18) by the analysis of the MS and NMR spectroscopic data and comparison with the literature. Compounds 1–2, 6–7, 10–12, and 14–16 were isolated from Cistus genus for the first time.