New cytotoxic triterpene acids from aboveground parts of Manihot esculenta from the Suriname rainforest

Two novel triterpene acids, esculentoic acid A ( 1) and B ( 2) as well as the seven known compounds 3 - 9 were isolated from an EtOAc extract of leaves, stems, and twigs of Manihot esculenta by bioassay-guided fractionation for cytotoxic activity. The structures of the two new compounds were established as 3alpha-hydroxytaraxer-14-en-29-oic acid ( 1) and 3-oxotaraxer-14-en-29-oic acid ( 2) on the basis of 1D and 2D NMR spectroscopic data interpretation and chemical conversions. The two new compounds 1 and 2 showed moderate cytotoxicity against the A2780 human ovarian cancer cell line.     

水杨柳根的化学成分

本文的目的是对水杨柳的根部进行化学成分研究， 采用硅胶柱色谱的方法分离和纯化化合物， 根据理化性质和波谱方法鉴定化合物结构。从水杨柳的根部分离得到了13个化合物， 包括1-羰基-油桐酸(1)， 油桐酸(2)， 3-乙酰氧基-油桐酸(3)， 蒲公英赛酮(4)， 蒲公英赛醇(5)， 3-乙酰氧基-12-齐墩果烯-28-酸甲酯(6)， 3-乙酰氧基-12-齐墩果烯-28-醇(7)， 熊果酸(8)， 羽扇豆醇(9)， 乙酰氧羽扇豆醇酯(10)， 臭矢菜素A(11)， 大黄酚(12)和没食子酸(13)。化合物1为新的蒲公英赛烷三萜类化合物， 化合物2～12均为首次从该植物中分离得到。并用MTT法测定了化合物1～3对AGZY 83-a和SMMC-7721细胞的抑制作用。证明化合物2对AGZY 83-a细胞有弱抑制作用(IC50 33.055 μg·mL^-1)。     

New cytotoxic oleanane saponins from the infructescences of Polyscias amplifolia from the Madagascar rainforest

Bioassay-guided fractionation of an ethanolic extract of the infructescences of Polyscias amplifolia resulted in the isolation of two new oleanolic acid saponins, polyfoliolides A (1) and B (2), in addition to the two known saponins 3-O-beta-D-galactopyranosyloleanolic acid (3) and 3-O-beta-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyloleanolic acid (4). The structures of the two new compounds were established as 3-O-beta- D-galactopyranosyl-(1-->4)-beta-D-xylopyranosyloleanolic acid (1) and 3-O-beta-D-galactopyranosyl-(1-->4)-alpha-L-arabinopyranosyloleanolic acid (2) on the basis of extensive 1D and 2D NMR spectroscopic data interpretation and chemical conversions. All the isolated compounds showed weak cytotoxicity against A2780 human ovarian cancer cell line, with IC50 values in the range 6.7 to 10.8 microg/mL.     

Phenolic compounds from the aqueous extract of Acacia catechu

Two new phenolic compounds, 5-hydroxy-2-[2-(4-hydroxyphenyl) acetyl]-3-methoxylbenzoic acid (1) and (2S,3S)-3,7,8,3',4'-pentahydroxyflavane (2), were obtained from the aqueous extract of Acacia catechu, along with four known compounds identified as rhamnetin (3), 4-hydroxyphenyl ethanol (4), 3,3',5,5',7-pentahydroxyflavane (5), and fisetinidol (6). Their structures were determined on the basis of spectroscopic analysis. Free radical-scavenging activities of the new compounds were evaluated.     

A new acylglycosyl sterol from quisqualis fructus

A new acylglycosyl sterol (4) was isolated from the MeOH extract of Quisqualis Fructus together with four known compounds. On the basis of spectroscopic data, their structures were elucidated as clerosterol (1), betulinic acid (2), methylursolate (3), 3-O-[6'-O-(8Z-octadecenoyl)-beta-D-glucopyranosyl]-clerosterol (4) and alpha-xylofuranosyluracil (5).     

Phenolic compounds obtained from stems of<Emphasis Type="Italic">couepia ulei</Emphasis> with the potential to induce quinone reductase

Activity-guided fractionation of the EtOAc-soluble extract of the stems of Couepia ulei, using a bioassay based on the induction of quinone reductase (QR) in cultured Hepa 1c1c7 mouse hepatoma cells led to the isolation of two active compounds, a new natural product, erythro-2,3-bis(4-hydroxy-3-methoxyphenyl)-3-ethoxypropan-1-ol (1), and a known compound, evofolin-B (2), along with five inactive compounds all of known structure, viz., betulinic acid, oleanolic acid, pomolic acid, (+/-)-syringaresinol, and ursolic acid. These isolates were identified by analysis of physical and spectral data. Compounds 1 and 2 exhibited QR inducing activity, with observed CD (concentration required to double induction) values of 16.7 and 16.4 microM, respectively.     

Cytotoxic constituents of the leaves of Ixeris sonchifolia

The ethyl acetate extract of the leaves of Ixeris sonchifolia afforded two new and two known sesquiterpene lactone glucosides of the guaiane-type, together with a known alkenol glucoside. The known compounds were identified as ixerin Z (1), ixerin Z-6'-p-hydroxyphenylacetate (2), and (Z)-3-hexen-1-ol-beta-D-glucopyranoside (3), respectively. The structures of the new compounds were elucidated as 11,13a-dihydroixerin Z [4, 3-hydroxy-2-oxo-guaia-1(10), 3-dien-5alpha,6beta,7alpha, 11betaH-12,6-olide-3-O-beta-D-glucopyranoside], and 3,10beta-dihydroxy-2-oxo-guaia-3,11(13)-dien-1alpha,5alpha,6alpha,7aH-12,6-olide-10-O-beta-D-glucopyranoside (5), respectively. The cytotoxicity of these compounds against human hepatocellular carcinoma cell (HepG2) and human melanoma cell (SK-MEL-2) was evaluated.     

Isolation and characterization of secondary metabolites from Plumeria obtusa

Chromatographic purification of the methanolic extract of Plumeria obtusa yielded two new iridoid obtusadoids A (1) and B (2), along with eight known compounds plumieridin A (3), plumieridine (4), 1α-plumieride (5), 15-demethylplumieride (6), rel-(3R,3'S,4R,4'S)-3,3',4,4'-tetrahydro-6,6'-dimethoxy[3,3'-bi-2H-benzopyran]-4,4'-diol (7), glochiflavanoside B (8), oleanolic acid (9), and methyl coumarate (10). The structures of all the isolates (1-10) were determined by NMR spectroscopy and mass spectrometry. The data of known compounds (3-10) were further compared with the reported data for these compounds.     

Gallotannins and related polyphenols from Pistacia weinmannifolia

Two new gallotannins, pistafolins A (1) and B (2), were isolated from the leaf extract of Pistacia weinmannifolia. Their structures were determined by spectral methods. Four known gallotannins (3-6), seven known flavonoid glycosides (7-13), along with 1-O-beta-D-(6'-O-galloyl)-glucopyranosyl-3-methoxy-5-hydroxybenzen e (14), gallic acid (15), methyl gallate (16), (+)-catechin (17), and (+)-gallocatechin (18), were also isolated. Some of these compounds were tested for their cytotoxicity toward K562 cells, and two small molecular phenolic compounds, 15 and 18, showed significant inhibitory effects with IC50 values less than 5 micrograms/ml.     

Cytotoxic constituents fromSolanum lyratum

Activity-guided fractionation of the ethanol extract of the whole plant from Solanum lyratum resulted in the isolation of a new pregnane derivative glycoside, 16-dehydropregnenolone 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosid uronic acid (2), as well as other six known compounds: 16-dehydropregnenolone (1), allopregenolone (3), protocatechuic acid (4), vanillic acid (5), caffeic acid (6), and scopoletin (7). The structures of the isolated compounds were elucidated on the basis of their spectral data and chemical evidences. Compounds 1, 3, 4 were isolated for the first time from this plant. Cytotoxic activities of the isolated compounds were evaluated. Compound 1 exhibited significant cytotoxic activity against A375-S2, HeLa, SGC-7901, and Bel-7402 with IC50 values of 13.1 +/- 0.9, 21.5 +/- 1.0, 40.2 +/- 0.7, and 49.8 +/- 1.2 microg/mL, respectively.     

Speciosaperoxide, a new triterpene acid, and other terpenoids from Chaenomeles speciosa

Investigation on the EtOH extract of the fruits of Chaenomeles speciosa led to the isolation of a new triterpene acid bearing an unusual hydroperoxyl substitute group at C-11, speciosaperoxide (1), along with six known triterpenoids, 3beta-acetoxyurs-11-en-13beta,28-olide (2), 3-O-acetyl ursolic acid (3), oleanolic acid (4), ursolic acid (5), masilinic acid (6), and tormentic acid (7), and three known norsesquiterpenoids, roseoside (8), vomifoliol (9) and (6S,7E,9R)-6,9-dihydroxy-4,7-megastigmadien-3-one 9-O-[beta-d-xylopyranosyl (1 --> 6)-glucopyranoside] (10). Their structures were elucidated on the basis of spectroscopic data and comparison with reference data. Besides compound 1, compounds 2, 8-10 were obtained from this genus for the first time. None of these compounds exhibited inhibitory activity against T-and B-lymphocyte proliferation.     

Diterpenoids from Turraeanthus mannii

Three new compounds, 15-acetoxy-12-hydroxy-16-methyl-labda-8(17),13E-diene (1), ent-labda-8(17),13-dien-15,16-olid-19-oic acid methyl ester (2), and 12-hydroxy-labda-8(17),13-dien-15,16-olide (3), together with two known compounds, 19-acetoxy-ent-labda-8(17),13-dien-15,16-olide (4), and 16-acetoxy-12,15-epoxy-15beta-hydroxy-labda-8(17),13(16)-diene (5) were isolated from the stem bark of Turraeanthus mannii (Meliaceae). The structures of compounds 1 - 3 were elucidated by analysis of the spectroscopic data. The crude methanol extract and compound 5 exhibited weak antibacterial and antifungal activity.     

New steroidal glycoside ester and aliphatic acid from the fruits of Lycium chinense

Two new compounds stigmast-5-en-3β-ol-3-O-β-D-(2'-n-triacontanoyl) glucopyranoside (1) and 19,21-dimethyl triacont-17,22,24,26,28-pentaene-1-oic acid (2), along with the three known compounds n-tetracosanyl octadec-9-enoate (3), β-sitosterol, and β-sitosterol-3-O-β-D-glucoside, have been isolated from the methanol extract of Lycium chinense fruits. The structures of these phytoconstituents have been established on the basis of spectral data analysis and chemical reactions.     

New macrocyclic lathyrane diterpenes, from Euphorbia lagascae, as inhibitors of multidrug resistance of tumour cells

The new macrocyclic lathyrane diterpenes latilagascenes A and B ( 1 and 2), the diacetylated derivative of 2, latilagascene C ( 3), and the known diterpenes ent-16alpha,17-dihydroxyatisan-3-one ( 4) and ent-16alpha,17-dihydroxykauran-3-one ( 5), isolated from the methanol extract of Euphorbia lagascae, were examined for their effects on the reversal of multidrug resistance (MDR) on mouse lymphoma cells. Among the active lathyrane derivatives 1 - 3, compound 2 displayed the highest inhibition of rhodamine 123 efflux of human MDR1 gene transfected mouse lymphoma cells when compared to the untreated cells or the positive control verapamil. The new compounds are the first macrocyclic lathyrane diterpenes showing oxidation at C-16, whose structures were characterized by extensive spectroscopic methods, including 2D NMR experiments ( (1)H- (1)H COSY, HMQC, HMBC and NOESY). The known phenolic compounds vanillic acid ( 6), p-salicylic acid ( 7), isofraxidin ( 8) and cleomiscosin A ( 9) were also isolated from this species.     

Two new lanostane triterpenoids from Poria cocos

Two new lanostane triterpenoids, 29-hydroxypolyporenic acid C (4) and 25-hydroxypachymic acid (5), together with three known compounds, ergosta-7,22-dien-3beta-ol (1), polyporenic acid C (2) and pachymic acid (3), were isolated from the 95% ethanolic extract of the sclerotium of Poria cocos (Schw.) Wolf. Their structures were determined by extensive spectroscopic analyses, including IR, UV, ESITOF-MS, HRESI-MS, 1D and 2D NMR data (1H NMR, 13C NMR, 1H-1H COSY, NOESY, HSQC and HMBC).     

Two novel triterpenoids with antiproliferative and apoptotic activities in human leukemia cells isolated from the resin of Garcinia hanburyi

Two new triterpenoids, 2alpha-hydroxy-3beta-O-acetyllup-20(29)-en-28-oic acid (1) and 3- O-(4'- O-acetyl)-alpha- L-arabinopyranosyloleanolic acid ( 2), together with two known triterpenoids, betulinic acid ( 3) and messagenic acid ( 4) were isolated from the CHCl3 extract of Garcinia hanburyi resin. The structures were elucidated by analysis of the NMR spectroscopic data. The antiproliferative effects and the apoptosis induction abilities of compounds 1 and 2 were determined in four human leukemia cell lines. Compound 2 was more potent than compound 1 in inhibiting cell growth with IC50 values of 2.45, 2.69, 2.42, and 4.15 microM in HL-60, NB4, U937 and K562 cells, respectively.     

猫儿刺的化学成分

猫儿刺(Ilex pernyi)为冬青科冬青属植物，民间常用于清热解毒，润肺止咳。本文对猫儿刺叶的化学成分进行研究，应用硅胶、Sephadex LH-20、反相硅胶和半制备RP-HPLC等分离纯化方法从其乙醇提取物中分离并鉴定了6个化合物：(E)-异丁香酚-α-L-吡喃阿拉伯糖基(1→6)- β-D-吡喃葡糖苷(1)，山柰酚-3-O-桑布双糖苷(2)，槲皮素-3-O-桑布双糖苷(3)，异槲皮苷(4)，丁香树脂酚葡糖苷(5)，反枝苋苷IV(6)。其中，化合物1为一新酚苷类化合物，命名为猫儿刺酚苷A。化合物2～6为首次从该植物中分离得到。     

西双版纳粗榧内生真菌菌株CM112中分离到的两个新bisabolane型倍半萜

目的 从西双版纳粗榧内生真菌菌株Aspergillus sp. CM112中分离和鉴定抗菌活性产物。方法 采用反相硅胶色谱、凝胶色谱和HPLC等分离技术,对菌株CM112的发酵产物进行分离纯化;通过1D、2D NMR、HR-ESI-MS以及旋光数据进行结构测定。结果 鉴定了5个bisabolane型倍半萜的结构,包括两个新化合物(7S,11S)-(+)-11-hydroxyl-sydonol(1)和(7S,11S)-(+)-11-hydroxyl aspergiterpenoid A(2)以及3个已知化合物(7S,11S)-(+)-11-hydroxysydonic acid(3), (7S,11S)-(+)-11,12-dihydroxysydonic acid (4)和(7S,11S)-(+)-12-hydroxysydonic acid(5);并通过纸片扩散法测试了它们对3株病原细菌的抗菌活性。结论 化合物1和2是新的bisabolane型倍半萜,2和3为抗菌活性成分。     

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).     

单麻叶千里光中的一个新化学成分

研究菊科千里光属植物单麻叶千里光Senecio cannabifolius var integrilifolius (Koidz.) Kitam.的化学成分。用硅胶、 Sephadex LH-20及反相C₁₈等柱色谱方法从其水提取物中分离得到11个化合物， 根据理化性质和光谱数据鉴定其结构， 分别为senecine(1)， 对羟基苯乙酸(2)， 原儿茶酸(3)， 2,5-二羟基苯乙酸(4)， 3,4-二羟基苯乙酸(5)， 香草酸(6)， 咖啡酸(7)， 丁二酸(8)， 2-糠酸(9)， 1,2,4,5-四氢-jacaranone(10)， 4-(吡咯烷-2-酮基)-苯基乙酸(11)。其中化合物1为新化合物， 2～11均为首次从该植物中分离得到。