维药斯亚旦化学成分研究

目的研究维药斯亚旦的化学成分。方法采用正相硅胶、ODS、Sephadex LH-20等柱色谱以及高效制备液相等手段进行分离纯化,并用化学方法和光谱方法鉴定了化合物的结构。结果从斯亚旦中分离鉴定了10个化合物,分别为:五加苷K(1)、常春藤皂苷元-3-O-α-L-鼠李糖基(1→2)-α-L-吡喃阿拉伯糖苷(2)、常春藤皂苷元-3-O-β-D-吡喃木糖基(1→3)-α-L-鼠李糖基(1→2)-α-L-吡喃阿拉伯糖苷(3)、quercetin-3-[6-ferulyl-β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-β-D-glucopyrano-side](4)、quercetin-3-sophorotriosides(5)、quercetin-3-glucosyl(1→2)-galactosyl(1→2)-glucoside(6)、quercetin-3-(6-feruloylglu-cosyl)(1→2)-galactosyl(1→2)-glucoside(7)、3-O-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖常春藤皂苷元-28-O-α-L-吡喃鼠李糖基(1→4)-β-D-吡喃葡萄糖基(1→6)-β-D-吡喃葡萄糖(8)、3-O-β-D-吡喃葡萄糖基(1→6)-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖常春藤皂苷元-28-O-α-L-吡喃鼠李糖基(1→4)-β-D-吡喃葡萄糖基(1→6)-β-D-吡喃葡萄糖苷(9)和芦丁(10)。结论化合物1,4,5为首次从黑种草属中分离得到,化合物6为首次从该种中分离得到。     

Saponins from the roots ofPulsatilla koreana

From the roots ofPulsatilla koreana, three monodesmosides(pulsatilla saponins A, B and D) and two bisdesmosides(pulsatilla saponins F and H) were isolated. The structure of these saponins have been determined as hederagenin 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranoside(A), hederagenin 3-O-β-D-glucopyranosyl(1→4)-α-L-arabinopyranoside(B), hederagenin 3-O-α-L-rhamnopyranosyl (1→2)-[β-D-glucopyranosyl(1→4)]-α-L-arabinopyranoside(D), 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester (F) and 3-O-α-L-rhamnopyranosyl(1→2)-[β-D-glucopyranosyl(1→4)]-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester(H) on the basis of chemical and spectral studies. Pulsatilla saponin B is the first report of its presence in plants but saponins A, D, F, and H have recently been isolated from the same genusP. cernua.     

黑种草子化学成分研究

从民族药黑种草子(Semen nigellae)中分离得到七个化合物,其中两个为新化合物,分别命名为黑种草甙(nigeglanoside)和黑种草糖(nigelancae)。经理化常数测定和光谱解析确定其结构分别为山萘酚-3-O-β-D-吡喃半乳糖基(1→3)-β-D-吡喃葡萄糖基(1→3)-β-D-吡喃葡萄糖甙和2-O-α-D-吡喃半乳糖基(1→4)-β-D-吡喃葡萄糖基-β-D-呋喃果糖甙。另外五个已知化合物分别为附子碱的氯化物(fuzitinechloride)、常春藤皂甙、蔗糖(sucrose)、β-谷甾醇(β-sitosterol)和环劳顿醇(cyclolandenol)。     

Two new triterpenoid saponins from the leaves of Ilex kudingcha

Two new triterpene saponins, ilekudinchosides F (1) and G (2), along with three known saponins were isolated from the leaves of Ilex kudingcha C. J. Tseng. The new compounds were characterized as 3β,19α-dihydroxy-12α-ethoxy-urs-13(18)-ene-28,20β-lactone-3-O-[β-D-glucopyranosyl(1 → 3)]-[α-L-rhamnopyranosyl(1 → 2)]-α-L-arabinopyranoside (1) and 3β,19α-dihydroxy-12α-methoxy-urs-13(18)-ene-28,20β-lactone-3-O-[α-L-rhamnopyranosyl(1 → 2)]-α-L-arabinopyranoside (2). The new structures were elucidated by spectroscopic methods including 1D and 2D NMR, HR-TOF-MS, and CD spectrometry, and the known compounds were identified by the comparison of their NMR and HR-TOF-MS data with those reported in the literature.     

Saponins from the stem bark ofKalopanax pictum var.magnificum (I)

Three triterpenoid saponins were isolated from the methanol extract of the stem bark ofKalopanax pictum Nakai var.magnificum (Araliaceae). The structures of these saponins were identified as hederagenin 3-O-α-L-arabinopyranoside, hederagenin-3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranoside and 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester.     

薯蓣属植物化学成分的研究——Ⅱ.叉蕊薯蓣中甾体皂甙的分离和鉴定

从叉蕊薯蓣(D.collettii HooK.f.)根茎的乙醇提取物分离到四个甾体皂甙,根据理化性质、光谱数据,推定化学结构为3-O-(β-D-葡萄吡喃糖)-约莫皂甙元(3-O-(β-D-glucopyranosyl)-yamogenin)[Ⅰ];3-O-[α-L-鼠李吡喃糖(1→4)-β-D-葡萄吡喃糖]-约莫皂甙元(3-O-[α-L-rahmnopyranosyl(1→4)-β-D-glucopyranosyl]-yamogenin)[Ⅱ];3-O-{α-L-鼠李吡喃糖(1→4)-[α-L-鼠李吡喃糖(1→2)]-β-D-葡萄吡喃糖}-约莫皂甙元(3-O-{α-L-rhamnopyranosyl(1→4)-[α-L-rhamnopyranosyl(1→2)]-β-D-glucopranosyl}-yamogenin)[Ⅲ];3-O-{β-D-葡萄吡喃糖(1→3)-[α-L-鼠李吡喃糖(1→2)3-β-D-葡萄吡喃糖}-约莫皂甙元(3-O-{β-D-glucopyranosyl(1→3)-[α-L-rhamnopyranosyl(1→2)]-β-D-glucopyranosyl}-yamogenin)[Ⅳ]。其中Ⅰ为已知物,Ⅱ、Ⅲ、Ⅳ为首次从植物界得到的新甾体皂甙。     

Three triterpenoid saponins acylated with monoterpenic acid from Gymnocladus chinensis

A new triterpenoid saponin acylated with monoterpenic acid, together with two known triterpenoid saponins, has been isolated from the fruit of Gymnocladus chinensis Baill. Their structures were elucidated as 2β,23-dihydroxy-3-O-α-L-rhamnopyranosyl-21-O-{(6S)-2-trans-2,6-dimethyl-6-O-[3-O-(β-D-glucopyranosyl)-4-O-((6S)-2-trans-2,6-dimethyl-6-hydroxy-2,7-octadienoyl)-β-L-arabinopyranosyl]-2,7-octadienoyl}-acacic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 6)]-β-D-glucopyranosyl ester (1), gymnocladus saponin E (2), and gymnocladus saponin F(2) (3).     

New spirostanol glycosides from Solanum nigrum and S. jasminoides

A new characteristic steroidal glycoside possessing a hydroxyl group at C-23, inunigroside A (1), was isolated from the withered berries of Solanum nigrum L. On the basis of spectroscopic analysis, the structure of 1 was characterized as (5α,22S,23S,25R)-3β,23-dihydroxyspirostane 3-O-β-lycotetraoside. Next, a major steroidal sapogenol, (22R, 25S)-3β,15α-dihydroxy-spirost-5-ene (3), was obtained from the acid hydrolysate of the methanolic extract of the aerial parts of Solanum jasminoides L. A new bisdesmoside, 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl (22R,25S)-3β,15α-dihydroxyspirost-5-ene 15-O-α-L-rhamnopyranoside (4), named jasminoside A, was isolated from the methanolic extract of S. jasminoides.     

瘤果黑种草子的化学成分

目的研究中药瘤果黑种草子的化学成分。方法运用多种色谱方法分离化学成分;依据这些化学成分的理化性质和波谱(NMR、EI-MS)数据分析鉴定化合物的结构。结果从瘤果黑种草子中初步分离得到5个化合物,分别鉴定为胡萝卜苷(1)、常春藤皂苷元-3-O-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖苷(2)、常春藤皂苷元-3-O-β-D-吡喃木糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖苷(3)、3-O-β-D-吡喃木糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖常春藤皂苷元-28-O-β-D-吡喃葡萄糖酯苷(4)、山奈酚-3-O-β-D-吡喃葡萄糖基-(1→2)-β-D-吡喃半乳糖基-(1→2)-β-D-吡喃葡萄糖苷(5)。结论化合物4为首次从黑种草属植物中分离得到,化合物5为首次从该种植物中分离得到。     

玄参根中的一个新三萜四糖苷(英文)

在中药玄参提取分离的过程中,分离得到1个新三萜四糖苷3β-O-(β-D-xylopyranosyl-(1→2)-[β-D-glucopyranosyl(1→4)-β-D-glucopyranosyl-(1→3)]-β-D-fucopyranosyl-11,13(18)diene-olean-23α,28 dio1(1)和3个已知的苯乙醇苷(2～4),化合物2、3均为首次从该属植物中分离得到。通过1D,2D NMR和HR-ESI-MS等光谱数据阐明了化合物1的结构。     

藏药独一味根化学成分的研究

继前报从藏药独一味(Lamiophlomisrotatakudo)根的正丁醇提取物中分离得到两个甙类成分。经化学和光谱分析,两个化合物的结构分别鉴定为3-羟基-4-甲氧基苯乙基-O-[α-L-吡喃鼠李糖(1→3)]-O-[β-D-呋喃芹菜糖(1→6)]-4-O-阿魏酰基-β-D-吡喃葡萄糖甙(1)和3-甲氧基-4-羟基苯乙基-O-[α-L-吡喃鼠李糖(1→3)]-O-[β-D-呋喃芹菜糖(1→6)]-4-O-阿魏酰基-β-D-吡喃葡萄糖甙(2),后者为一新化合物,命名为独一味甙A(lamiophlomiosideA)。     

海燕化学成分的分离与鉴定

目的研究海洋生物海燕(Asterina pectinifera)的化学成分。方法采用大孔树脂柱色谱、硅胶柱色谱、凝胶柱色谱、制备薄层色谱、高效液相色谱等手段分离纯化,根据理化性质、波谱分析和文献对照的方法对所分离的化合物进行结构鉴定。结果从海燕体内分离并鉴定了9个化合物,分别为:3-十八烷氧基-1,2-丙二醇[3-(octadecyloxy)-1,2-propanediol,1]、正二十碳酸(arachidic acid,2)、胆甾-7-烯-3β-醇(cholesta-7-ene-3β-ol,3)、尿嘧啶(uracil,4)、5α-胆甾烷-3β,4β,6α,7α,8,15β,16β,26-八醇(5α-cholestane-3β,4β,6α,7α,8,15β,16β,26-octol,5)、5α-胆甾烷-3β,6α,8,15α,24-五醇(5α-cholestane-3β,6α,8,15β,24-pentaol,6)、色氨酸(tryptophan,7)、3,4-二羟基苯甲酸(3,4-dihydroxybenzoic acid,8)、pectinioside B([(5α,20R,22R,23S,24S)-22,23-epoxy-3β,6α,20-trihydroxyergost-(9)11-ene 6-O-{β-D-galactopyranosyl-(1→4)-[β-D-quinovopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-[β-D-quinovopyranosyl-(1→2)]-β-D-xylopyranosyl-(1→3)-β-D-quinovopyranoside}-3-O-sodium sulfate],9)。结论化合物2、8为首次从海燕中分离得到,化合物9为首次从中国海域的海星纲中分离得到。首次采用二维核磁技术确定化合物9的结构,并首次对其1H-NMR数据及二维谱数据进行归属。     

Triterpenoidal saponins from the leaves ofKalopanax pictum var.chinense

One new triterpenoidal bisdesmoside, saponin C (3) were isolated from the leaves ofKalopanax pictum var.chinense along with two known saponins, saponin B (2, sapindoside C) and saponin A (1, sapindoside B). On the basis of chemical and spectral evidences, the structure of a new triterpenoidal saponin has been elucidated to be 3-O-β-D-glucopyranosyl(1→4)-β-D-xylopyranosyl(1→3)-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl-23-hydroxyolean-12-en-28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester.     

Two new phenolic glycosides from the rhizome of Gastrodia elata

Two new phenolic glycosides, named parishins F-G (1-2), together with known parishin E, were isolated from the rhizome of Gastrodia elata. The new structures were established as 1,3-di-[4-O-(β-D-glucopyranosyl) benzyl]-2-{4-O-[β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl] benzyl} citrate (1) and 2-[4-O-(β-D-glucopyranosyl)benzyl] citrate (2), by means of MS, 1D, and 2D NMR spectral analyses, as well as chemical methods.     

Two new steroidal saponins from the tubers ofLiriope spicata

Two novel steroidal saponins designated as spicatosidesA(1) andB(2) were isolated from the tubers ofLiriope spicata and their structures were clucidated as 25(S)-ruscogenin-1-O-β-D-glucopyranosyl (1→2)-[β-D-xylopyranosyl (1→3)]-β-D-fucopyranoside (1) and 26-O-β-D-glucopyranosyl 25(S)-22-O-methyl-furost-5-en-1β, 3β, 26-triol 1-O-β-D-glucopyranosyl (1→2)-[β-D-xylopyranosyl (1→3)]-β-D-fucopyranoside (2), respectively.     

Clematomandshurica saponin E, a new triterpenoid saponin from Clematis mandshurica

A new triterpenoid saponin, clematomandshurica saponin E, together with four known saponins were isolated and characterized from the roots and rhizomes of Clematis mandshurica (Ranunculaceae), a commonly used traditional Chinese medicine with anti-inflammatory and antirheumatoid activities. On the basis of spectroscopic analysis, including HR-ESI-MS, IR, 1D, and 2D NMR spectral data and hydrolysis followed by chromatographic analysis, the structure of the new triterpenoid saponin was elucidated as 3-O-α-L-rhamnopyranosyl-(1 → 6)-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 4)-β-D-ribopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside.     

Three New Triterpenoid Saponins from the Seeds of Vaccaria segetalis

Abstract

Three new triterpenoid saponins, named segetoside G (1), H (2) and I (3), have been isolated from the seeds of Vaccaria segetails. On the basis of chemical reaction and spectral data, their structures have been established as: 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-arabinofuranosyl (1 → 3)]-β-D-(4-O-acetyl)-fucopyranosyl-gypsogenin-3-O-β-D-gal-actopyranosyl-(1 → 2)-β-D-(6-O-butyl ester)-glucuronopyranoside (1), 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-(5-O-acetyl)-arabinofuranosyl-(1 → 3)]-β-D-(4-O-acetyl)-fucopyranosyl-gypsogenin-3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranoside (2) and 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-(5-O-acetyl)-arabinofuranosyl-(1 → 3)]-β-D-(4-O-acetyl)-fucopyranosyl-quillaic acid-3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranoside (3).     

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.     

Metabolite profiling of the leaves of the Brazilian folk medicine Sideroxylon obtusifolium

Sideroxylon obtusifolium (Roem. & Schult.) T. D. Penn. (family Sapotaceae) is a tree native to Central and South America. Infusions of the bark and the leaves are used in Brazilian folk medicine as an anti-inflammatory remedy. However, information on the constituents of S. obtusifolium remains scarce, and only common pentacyclic triterpenoids have been previously reported. HPLC-DAD/MS analyses revealed that saponins and flavonoids were the main constituents of the leaves. From the butanol-soluble fraction of an ethanolic extract, a total of four saponins and ten flavonol glycosides were isolated by a combination of chromatographic methods including Sephadex LH-20, MPLC, and HPLC. Their structures were established by acid hydrolysis and spectroscopic methods, mainly MS (n), 1D and 2D NMR experiments. The compounds include the new triterpene glycoside 3-O-( β-D-glucopyranosyl)-protobassic acid 28-O- β-D-apiofuranosyl-(1 → 3)-O-[O- β-D-apiofuranosyl-(1 → 3)- β-D-xylopyranosyl-(1 → 4)]-O- α-L-rhamnopyranosyl-(1 → 2)- α-L-arabinopyranosyl ester ( 1), as well as the new flavonol glycosides, quercetin-3-O-(O- α-L-rhamnopyranosyl-(1→ 2)-O-[ β-D-glucopyranosyl-(1 → 3)]- β-D-galactopyranoside) ( 6) and kaempferol-3-O-(O- α-L-rhamnopyranosyl-(1 → 2)-O-[ β-D-glucopyranosyl-(1 → 3)]- β-D-galactopyranoside) ( 8). In addition, catechin and a glycerogalactolipid, gingerglycolipid A, were obtained from the ethyl acetate-soluble fraction. The isolated compounds could be used in the future as chemical markers for quality control of this herbal drug.     

A Pair of 24-hydroperoxyl Epimeric Dammarane Saponins from Flower-buds of Panax Ginseng

Abstract

Further investigation on the saponins of the flower-buds of Panax ginseng C. A. Meyer has resulted in the isolation and structural elucidation of a pair of new 24-epimers of dammarane type saponins named ginsenoside I and II. The structures of the epimers were characterized on the basis of chemical and spectral evidence as 3-O-[β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl]-20-S-O-β-D-glucopyranosyl-3β12β20(S)-trihydroxy-24ξ-hydroperoxydammar-25-ene, except for their C-24 configurations. Ginsenoside I is a new triterpene glycoside, and ginsenoside II is a known compound first isolated from a natural plant.