Triterpenoid saponins from Dipsacus asper and their activities in vitro

Two new triterpenoid saponins 1 and 2, along with six known saponins 3-8, were isolated from the roots of Dipsacus asper. The structures of new compounds were established as 3-O-β-d-glucopyranosyl-(1?→?4)-[α-l-rhamnopyranosyl-(1?→?3)]-β-d-glucopyranosyl-(1?→?3)-α-l-rhamnopyranosyl-(1?→?2)-α-l-arabinopyranosyl-hederagenin-28-O-β-d-glucopyranoside (dipsacus saponin J, 1) and 3-O-α-l-arabinopyranosyl-hederagenin-28-O-β-d-glucopyranosyl-(1?→?6)-β-d-glucopyranosyl-(1?→?6)-β-d-glucopyranoside (dipsacus saponin K, 2). The structures were determined by extensive analysis of their spectroscopic data. Compounds 6 and 7 could significantly stimulate UMR106 cell proliferation and increase alkaline phosphatase activities in UMR106 cell at the concentration of 4?μM.     

Wound Healing Properties of Triterpenes from Buddleia scordioides in Diabetic Rats

Abstract

The pentacyclic triterpenes 3-O-α-l-rhamnopyranosyl-(1 → 4)-β -d-glucopyranosyl-(1 → 3)-[β -d-glucopyranosyl-(1 → 2)]-β -d- fucopyranosyl-23,28-dihydroxy-oleane-11, 13(18)-diene (1) and 3-O-α-l-rhamnopyranosyl-(1 → 4)-β -d-glucopyranosyl-(1 → 3)-[β -d-glucopyranosyl-(1 → 2)]-β -d-fucopyranosyl-16,23,28-trihydroxy-oleane-11,13(18)-diene (2) isolated from leaves of Buddleia scordioides Kunth (Loganiaceae) were studied for the effect on wound healing, using excision and incision wound modes. Significant increase in granulation tissue, tensile strength, hydroxyproline, total protein, and collagen contents was observed. There was significant reduction in the wound area measurement of the test group compared with that of controls. The efficacious prohealing effect may be due to increased collagen deposition as well as to better alignment and maturation.     

Three new isoflavone glycosides from Tongmai granules

Three new isoflavone glycosides, 3'-methoxydaidzein-7,4'-di-O-β-d-glucopyranoside (1), biochanin A-8-C-β-d-apiofuranosyl-(1?→?6)-O-β-d-glucopyranoside (2), daidzein-7-O-β-d-glucopyranosyl-(1?→?4)-O-β-d-glucopyranoside (3), and a new natural isoflavone glycoside, daidzein-7-O-α-d-glucopyranosyl-(1?→?4)-O-β-d-glucopyranoside (4) were isolated along with 18 known isoflavones from the EtOAc and n-BuOH fractions of the aqueous extraction of Tongmai granules. All the isoflavones were obtained and determined for the first time from Tongmai granules. The structures of these compounds were elucidated by spectral methods. It was confirmed that the compounds 1-4 were originally from Puerariae Lobatae Radix based on HPLC-DAD analysis of the crude drug extract. The isoflavones isolated were tested for their antioxidative activities by measuring the capacities of scavenging the 2,2'-diphenyl-1-picrylhydrazyl radical.     

New steroidal glycosides from Tribulus terrestris L

Two new steroidal glycosides were isolated from Tribulus terrestris L. Their structures were elucidated as 26-O-β-d-glucopyranosyl-5α-furostan-12-one-20(22)-ene-3β,23,26-triol-3-O-β-d-xylopyranosyl-(1?→?2)-[β-d-xylopyranosyl-(1?→?3)]-β-d-glucopyranosyl-(1?→?4)-[α-l-rhamnopyranosyl-(1?→?2)]-β-d-galactopyranoside (1) and 26-O-β-d-glucopyranosyl-5α-furostan-20(22)-ene-3β,23,26-triol-3-O-β-d-xylopyranosyl-(1?→?2)-[β-d-xylopyranosyl-(1?→?3)]-β-d-glucopyranosyl-(1?→?4)-[α-l-rhamnopyranosyl-(1?→?2)]-β-d-galactopyranoside (2) by spectroscopic methods including 1D and 2D NMR experiments.     

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.     

Puberosides C-E, triterpenoid saponins from Glochidion puberum

Three new triterpenoid glycosides, named puberosides C-E (1-3), were isolated from the water-soluble fraction of Glochidion puberum (Linn.) Hutch. Their structures were determined as 3α-[(O-β-d-glucopyranosyl-(1?→?3)-O-α-l-arabinopyranosyl)oxy]-22α-trans-cinnamoyl-olean-12-ene-16α,28-diol, 3α-[(O-β-d-glucopyranosyl-(1?→?3)-O-α-l-arabinopyranosyl)oxy]-22α-cis-cinnamoyl-olean-12-ene-16α,28-diol, and 3α-[(O-β-d-glucopyranosyl-(1?→?3)-O-β-d-glucopyranosyl)oxy]-22α-benzoyloxy-olean-12-ene-16α,28-diol by the combination of 1D, 2D NMR, and MS spectral analyses.     

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。     

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。     

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。     

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)。     

Design, synthesis, and biological evaluation of novel potent and selective alphavbeta3/alphavbeta5 integrin dual inhibitors with improved bioavailability. Selection of the molecular core

A novel series of potent and selective alpha(v)beta(3)/alpha(v)beta(5) dual( )()inhibitors was designed, synthesized, and evaluated against several integrins. These compounds were synthesized through a Mitsunobu reaction between the guanidinium mimetics and the corresponding central templates. Guanidinium mimetics with enhaced rigidity (i.e., (2-pyridylamino)propoxy versus the 2-(6-methylamino-2-pyridyl)ethoxy) led to improved activity toward alpha(v)beta(3). Exemplary oral bioavailability in mice was achieved using the indole central scaffold. Although, oral bioavailability was maintained when the indole molecular core was replace with the bioisosteric benzofuran or benzothiophene ring systems, it was found to not significantly impact the integrin activity or selectivity. However, the indole series displayed the best in vivo pharmacokinetic properties. Thus, the indole series was selected for further structure-activity relationships to obtain more potent alpha(v)beta(3)/alpha(v)beta(5) dual antagonist with improved oral bioavailability.     

川产九节龙皂甙的化学研究

从川产九节龙(Ardisea pusilla A. DC)的正丁醇提取物中分离到两个三萜皂甙。经化学和光谱(IR,MS,¹HNRM,¹³CNMR和两种新的核磁技术)分析,两个化合物的结构分别鉴定为3-O-[α-L-吡喃鼠李糖(1→2)-β-D-吡喃葡萄糖(1→3)][B-D-吡喃葡萄糖(1→2)]-α-L-阿拉伯糖-西克拉敏A(Ⅰ)和3-O-[β-D-吡喃木糖(1→2)-B-D-吡喃葡萄糖-(1→4)][B-D-吡喃葡萄糖-(1→2)-β-D-吡喃葡萄糖(1→2)]-α-L-吡喃阿拉伯糖-西克拉敏A(Ⅱ)。二者均为新皂甙,依次命名为九节龙皂甙Ⅰ(ardipusilloside Ⅰ)和九节龙皂甙Ⅱ(ardipusillosidc Ⅱ)。     

延龄草化学成分的分离与鉴定

目的研究延龄草(Trillium tschonoskii Maxim.)根及根茎的化学成分。方法利用硅胶柱色谱、凝胶柱色谱、ODS(反相C18键合硅胶)柱色谱、高效液相色谱等色谱技术对延龄草的化学成分进行分离和纯化,通过理化性质和NMR等波谱数据分析确定化合物的结构。结果从延龄草根及根茎70%(φ)乙醇提取物中分离得到11个已知成分,分别确定为重楼皂苷Ⅵ(chonglouosideⅥ,1)、偏诺皂苷元-3β-O-α-L-吡喃鼠李糖基-(1→4)-[O-α-L-吡喃鼠李糖基-(1→2)]-O-β-D-吡喃葡萄糖苷(penogenin-3β-O-α-L-rhamnopyranosyl-(1→4)-[O-α-L-rhamnopyranosyl-(1→2)]-O-β-D-glu-copyranoside,2)、重楼皂苷Ⅶ(chonglouosideⅦ,3)、偏诺皂苷元-3β-O-β-D-吡喃葡萄糖基-(1→6)-[O-α-L-吡喃鼠李糖基-(1→2)]-O-β-D-吡喃葡萄糖苷(trikamsteroside B,4)、(25S)-27-羟基偏诺皂苷元-3β-O-α-L-吡喃鼠李糖基-(1→2)-O-β-D-吡喃葡萄糖苷((25S)-27-hydroxypenogenin-3β-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranoside,5)、(25S)-27-羟基偏诺皂苷元-3β-O-α-L-吡喃鼠李糖基-(1→4)-[O-α-L-吡喃鼠李糖基-(1→2)]-O-β-D-吡喃葡萄糖苷((25S)-27-hydroxypenogenin-3β-O-α-L-rhamnopyranosyl-(1→4)-[O-α-L-rhamnopyranosyl-(1→2)]-O-β-D-glucopyranoside,6)、(25S)-27-羟基偏诺皂苷元-3β-O-α-L-吡喃鼠李糖基-(1→4)-O-α-L-吡喃鼠李糖基-(1→4)-[O-α-L-吡喃鼠李糖基-(1→2)]-O-β-D-吡喃葡萄糖苷(polyphyllosideⅢ,7)、(23S,24S,25S)-螺甾-5-烯-1β,3β,21,23,24-五羟基-1β-O-β-D-呋喃芹糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→2)-[O-β-D-吡喃木糖基-(1→3)]-O-α-L-吡喃阿拉伯糖苷(trikamsteroside E,8)、3β-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranosylhomo-aro-cholest-5-ene-26-O-β-D-glucopyranoside(parispseudoside B,9)、3β-O-α-L-rhamnopyranosyl-(1→4)-[O-α-L-rhamnopyranosyl-(1→2)]-O-β-D-glucopyranosylhomo-aro-cholest-5-ene-26-O-β-D-glucopyranoside(aethioside A,10)、3β-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rham-nopyranosyl-(1→4)-[O-α-L-rhamnopyranosyl-(1→2)]-O-β-D-glucopyranosylhomo-aro-cholest-5-ene-26-O-β-D-glucopyranoside(parispseudoside A,11)。结论化合物9-11为首次从百合科植物中分离得到,7为首次从延龄草属植物中分离得到,4-6、8为首次从延龄草中分离得到。     

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)。     

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。     

Three new steroidal saponins from Fritillaria pallidiflora

Three new steroidal saponins, pallidiflosides A (1), B (2), and C (3), have been isolated from the dry bulbs of Fritillaria pallidiflora Schrenk. Their structures were elucidated as 26-O-β-d-glucopyranosyl-(25R)-furost-5,20(22)-dien-3β,26-diol-3-O-β-d-xylopyranosyl(1?→?4)-[α-l-rhamnopyranosyl(1?→?2)]-β-d-glucopyranoside (1); 26-O-β-d-glucopyranosyl-3β,26-dihydroxyl-20,22-seco-25(R)-furost-5-en-20,22-dione-3-O-α-l-rhamnopyranosyl(1?→?2)-β-d-glucopyranoside (2); and (25R)-spirost-5-ene-3β,17α-diol-3-O-β-d-glucopyranosyl(1?→?4)-β-d-galactopyranoside (3) by spectroscopic techniques and chemical means.     

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。     

广东紫珠中黄酮碳苷的分离与结构鉴定及初步体外抗炎活性研究

利用AB-8大孔树脂、Sephadex LH-20、C18及硅胶等柱色谱法分离纯化了广东紫珠的抗炎活性部位。根据理化性质和波谱方法(1H NMR、13C NMR、HMBC、ESI-MS等)鉴定化合物的结构。结果从中分离鉴定了5个黄酮碳苷化合物,分别为5,7,3’,4’-四羟基-8-C-β-D-葡萄糖黄酮碳苷(Ⅰ)、5,7,3’,4’-四羟基-6-C-[α-L-鼠李糖-(1→2)]-β-D-葡萄糖黄酮碳苷(Ⅱ)、5,7,3’,4v-四羟基-8-甲氧基-6-C-β-D-葡萄糖黄酮碳苷(Ⅲ)、5,4’-二羟基-6,7-二甲氧基-8-C-[β-D-木糖-(1→2)]-β-D-葡萄糖黄酮碳苷(Ⅳ)及5,4’-二羟基-6,7-二甲氧基-8-C-β-D-葡萄糖黄酮碳苷(Ⅴ)。化合物Ⅰ为首次从该植物中分离得到,其余4个化合物均为首次从紫珠属植物中分离得到。考察了5个化合物的抗环氧合酶-2活性,结果化合物Ⅰ、Ⅱ、Ⅲ均显示较强的体外抗炎活性。     

New triterpenoid saponins from Patrinia scabiosifolia

Phytochemical investigation of methanol extract from the whole plants of Patrinia scabiosifolia Fisch. resulted in the isolation of three new triterpenoid saponins (1-3) along with twelve known triterpenoids (4-15). The structures of the new compounds were established as 11α, 12α-epoxy-3-O-β-D-xylopyranosyl-olean-28, 13β-olide (1), 11α, 12α-epoxy-3-O-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl-olean-28, 13β-olide (2), and 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl oleanolic acid 28-O-β-D-glucopyranoside (3) on the basis of various spectroscopic analyses (including different 1D and 2D NMR spectroscopies and high-resolution electrospray ionization mass spectrometry) and chemical evidences.     

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.