Cucurbitacins as Constituents of Wilbrandia ebracteata

The methanolic extract from the roots of WILBRANDIA EBRACTEATA afforded, in addition to the known dihydrocucurbitacins B and E, dihydroisocucurbitacin B, Cucurbitacins B, D, E, G, H, P, and 22-deoxycucurbi-tacin D, four new compounds whose structures were elucidated as (20 R,24xi)-3)3beta,16alpha,20)24,25-pentahydroxy-10alpha-cucurbit-5-ene-2,11,22-trione (3- EPI-isocucurbitacin G) ( 8), (20 R,22xi)-2beta16a,20,22,25-pentahydroxy-10alpha-cucurbita-5,23 T-diene-3,11-dione ( 13), (20 R)-25-acetoxy-3,16alpha,20-trihydroxy-30- NOR-2-(beta- D-glucopyranosyloxy)-1,2,3,4,5,10-dehydrocucurbit-6-ene-11,22-dione ( 14), and dihydroisocucurbitacin B-3-glucoside ( 16).     

New antibiotics SF2315A and B produced by an Excellospora sp. II. The structural elucidation

The structures of antibiotics SF2315A and B were determined to be [4aR-(4a beta,12b beta)] or [4aS-(4a alpha,12b alpha)]-4a,5,6,12b-tetrahydro-4a,8-dihydroxy-3- methylbenz[a]anthracen-1,7,12(4H)-trione and [1S-(1 beta,4a beta,6a beta,12 beta,12a beta,12b beta)] or [1 R-(1 alpha,4a alpha,6a alpha,12 alpha,12a alpha,12b alpha)]- 1,4,4a,5,6,6a,12a,12b-octahydro-1,4a,8,12-tetrahydroxy-3-methyl-6a ,12a- epoxybenz[a]anthracen-7(12H)-one, respectively from their spectroscopic analyses and single crystal X-ray diffraction analyses.     

Triterpenoids and Sesquiterpenes from Mulgedium tataricum

The chemical investigation of Mulgedium tataricum afforded six new compounds which were identified as lanost-9(11),23 Z(24)-diene-3beta,25-diol (1), lanost-9(11),25-diene-3beta,24beta-diol (2), ursane-20-ene-3beta,22alpha-diol (3), 4 E,10 E-3beta,11beta-dihydroxygermacra-4(5),10(1)-dien-12,6alpha-olide (4), 4 E-1beta-hydroperoxy-3beta,11beta-dihydroxygermacra-4(5),10(14)-dien-12,6alpha-olide (5) and lactucin-8-O-P-methoxyphenyl acetate (6) by using a combination of MS and NMR techniques. Compound 6 exhibited significant cytotoxicity against cultured human hepatoma cells (SMMC-7721) and human acute promyelocytic leukemia cells (HL60). The antibacterial activity study indicated that 1 and 2 strongly inhibited the growth of Escherichia coli.     

Bioactive coumarin derivatives from the fern Cyclosorus interruptus

Three new coumarin derivatives, compounds 1-3, three new furanocoumarins, compounds 4-6, and a novel dioxocane derivative, compound 7, were isolated from the fern Cyclosorus interruptus (Willd.) H. It?. Based on spectrometric and spectroscopic analysis (FAB or El mass spectrometry as well as 1D and 2D NMR experiments) their structures were characterised as 5,7-dihydroxy-6-methyl-4-phenyl-8-(3-phenylpropionyl)-1-benzopyran-2-one (1), 5,7-dihydroxy-6-methyl-4-phenyl-8-(3-phenyl-trans-acryloyl)-1- benzopyran-2-one (2), 5,7-dihydroxy-8-(2-hydroxy-3-phenylpropionyl)-6-methyl-4-phenyl-1- benzopyran-2-one (3), 8-benzyl-5,8-dihydroxy-6-methyl-4-phenylfuro[2,3-h]-1-benzopyran-2,9- dione (4), 8-benzyl-5,8 beta,9 beta-trihydroxy-6-methyl-4-phenyl-8,9-dihydro- furo[2,3-h]-1-benzopyran-2-one (5), 8-benzyl-5,8 beta,9 alpha-trihydroxy-6-methyl-4-phenyl-8,9-dihydro- furo[2,3-h]-1-benzopyran-2-one (6) and 5,11-dihydroxy-6-methyl-4-phenyl-11-(1-phenylmethyl)-7,10-dioxocane [5,6-h]-1-benzopyran-2,12-dione (7). For these compounds we propose the trivial names interruptins A-F. Compounds 1, 5/6 and 7 showed antibacterial activity while compounds 1 and 2 were cytotoxic to a KB cell line.     

中国南海聚裂丛柳珊瑚化学成分研究

目的研究聚裂丛柳珊瑚Rumphella aggregata的化学成分。方法利用硅胶色谱、Sephadex LH-20凝胶色谱、HPLC等手段对化学成分进行分离纯化;通过理化性质、波谱分析方法结合文献对照,鉴定化合物的结构。结果从聚裂丛柳珊瑚甲醇提取物中,共分离鉴定了15个单体化合物:胆甾醇(1)、(22E)-胆甾-5,22-二烯-3β-醇(2)、(22E)-麦角甾-5,22-二烯-3β-醇(3)、麦角甾-5,24(28)-二烯-3β-醇(4)、豆甾-5,24(28)-二烯-3β-醇(5)、柳珊瑚甾醇(6)、胆甾-7-烯-3β,5α,6β-三醇(7)、(22E)-胆甾-7,22-二烯-3β,5α,6β-三醇(8)、麦角甾-7-烯-3β,5α,6β-三醇(9)、(22E)-麦角甾-7,22-二烯-3β,5α,6β-三醇(10)、豆甾-7-烯-3β,5α,6β-三醇(11)、(22E)-豆甾-7,22-二烯-3β,5α,6β-三醇(12)、尿嘧啶(13)、咖啡因(14)、hydratoperidinin(15)。结论化合物1～15均为首次从该属柳珊瑚中分离得到,并首次对化合物hydratoperidinin(15)的1HNMR及13 CNMR信号进行了全归属。化合物12在10μg.mL-1浓度水平,对K562肿瘤细胞株的抑制率为39.17%。     

杜仲叶中倍半萜及降碳倍半萜的分离与鉴定

目的 研究植物杜仲(Eucommia ulmoides Oliver)叶中的化学成分.方法 综合运用硅胶柱色谱、反相硅胶柱色谱和Sephadex LH-20凝胶柱色谱以及制备型高效液相色谱等方法进行系统分离,根据化合物的理化性质及其波谱数据确定化合物的结构.结果 从杜仲叶80％(体积分数)乙醇提取物中分离得到了12个倍...     

New ursane triterpenoids from <Emphasis Type="Italic">Ficus pandurata</Emphasis> and their binding affinity for human cannabinoid and opioid receptors

Phytochemical investigation of Ficus pandurata Hance (Moraceae) fruits has led to the isolation of two new triterpenoids, ficupanduratin A [1β-hydroxy-3β-acetoxy-11α-methoxy-urs-12-ene] (11) and ficupanduratin B [21α-hydroxy-3β-acetoxy-11α-methoxy-urs-12-ene] (17), along with 20 known compounds: α-amyrin acetate (1), α-amyrin (2), 3β-acetoxy-20-taraxasten-22-one (3), 3β-acetoxy-11α-methoxy-olean-12-ene (4), 3β-acetoxy-11α-methoxy-12-ursene (5), 11-oxo-α-amyrin acetate (6), 11-oxo-β-amyrin acetate (7), palmitic acid (8), stigmast-4,22-diene-3,6-dione (9), stigmast-4-ene-3,6-dione (10), stigmasterol (12), β-sitosterol (13), stigmast-22-ene-3,6-dione (14), stigmastane-3,6-dione (15), 3β,21β-dihydroxy-11α-methoxy-olean-12-ene (16), 3β-hydroxy-11α-methoxyurs-12-ene (18), 6-hydroxystigmast-4,22-diene-3-one (19), 6-hydroxystigmast-4-ene-3-one (20), 11α,21α-dihydroxy-3β-acetoxy-urs-12-ene (21), and β-sitosterol-3-O-β-d-glucopyranoside (22). Compound 21 is reported for the first time from a natural source. The structures of the 20 compounds were elucidated on the basis of IR, 1D (¹H and ¹³C), 2D (¹H–¹H COSY, HSQC, HMBC and NOESY) NMR and MS spectroscopic data, in addition to comparison with literature data. The isolated compounds were evaluated for their anti-microbial, anti-malarial, anti-leishmanial, and cytotoxic activities. In addition, their radioligand displacement affinity on opioid and cannabinoid receptors was assessed. Compounds 4, 11, and 15 exhibited good affinity towards the CB2 receptor, with displacement values of 69.7, 62.5 and 86.5 %, respectively. Furthermore, the binding mode of the active compounds in the active site of the CB2 cannabinoid receptors was investigated through molecular modelling.     

板栗壳化学成分研究

从板栗壳95%乙醇浸膏中分离鉴定了16个化合物,分别是β-谷甾醇(1)、β-胡萝卜苷(2)、豆甾-5-烯-3β,7α-醇(3)、麦角甾-6,22-二烯-3β,5α,8α-三醇(4)、齐墩果酸(5)、豆甾-4-烯-6a-醇-3-酮(6)、豆甾-4-烯-6β-醇-3-酮(7)、原儿茶酸(8)、水杨酸(9)、豆甾-5-烯-3β-羟基-7-酮(10)、对羟基桂皮酸甲酯(11)、没食子酸(12)、绿原酸(13)、香(艹卓)醛(14)、乳糖(15)和芦丁(16).其中化合物3、6、9、10、11、13、14、15、16等9个化合物均为首次从该植物中分离得到,所有化合物均为首次从板栗壳中分离得到.     

Transformation of ergosterol peroxide to cytotoxic substances by rat intestinal bacteria

Ergosterol peroxide (EPO, 1) is a major antitumor sterol produced by edible or medicinal mushrooms. Following oral administration of 1 to rats or anaerobic in vitro incubation of 1 with rat fecal bacteria, three metabolites were detected and their structures were identified to be 5alpha,6alpha-epoxyergosta-8(14),22-diene-3beta,7alpha-diol (M1, 2), 5alpha,6alpha-epoxyergosta-8,22-diene-3beta,7alpha-diol (M2, 3), and 5alpha,6alpha-epoxy-3beta-hydroxyergosta-22-ene-7-one (M3, 4) by spectroscopic analysis. Of these, M2 and M3 showed more potent inhibitory activity than the original compound 1 against proliferation of CACO-2, WiDr, DLD-1 and Colo320 human colorectal adenocarcinoma cells. These findings suggest that bacterial metabolites of EPO play a significant role in its cytotoxic activity against human colorectal cancer cells.     

Two new triterpenoids from the leaves and stems of Fritillaria hupehensis

Two new cycloartane-type triterpenoids 25-hydroxyl-9,19-cycloart-22-ene-3-one (1) and (23Z)-9,19-cycloart-23-ene-3α,25-diol (2) along with 9,19-cycloart-25-ene-3β, 24ξ-diol (3) and cycloeucalenol (4) have been isolated from the leaves and stems of Fritillaria hupehensis Hsiao et K.C. Hsia. Their structures were elucidated on the basis of spectroscopic analysis.     

Three new oxazoline alkaloids from Gymnotheca chinensis

Three novel oxazoline alkaloids, 1-oxa-3-azaspiro [4.5] dec-2-ene-8-one (1), 1-oxa-3-azaspiro [4.5] dec-2, 6-diene-8-one (2), and 1-oxa-3-azaspiro [4.5] dec-10-methoxy-2, 6-diene-8-one (3) were isolated from the methanol extract of the whole plant of Gymnotheca chinensis. The chemical structures were established by means of spectroscopic analysis including one- and two-dimensional NMR spectroscopy.     

不同基原八爪金龙药材中黄酮、香豆素类化学成分分析

目的:鉴定并分析不同基原八爪金龙药材中黄酮及香豆素类成分.方法:采用超高效液相色谱-四极杆-静电场轨道阱高分辨质谱法(UPLC-QE-HF-MS/MS).色谱柱为Zorbax Eclipse-C18,流动相为乙腈-0.1％甲酸水溶液(梯度洗脱),柱温为30℃,流速为0.3 mL/min,自动进样器温度为4℃,进样量为2...     

铁篱巴果中的三萜成分研究

为研究铁篱巴果的化学成分, 利用柱色谱技术进行分离纯化, 得到3个三萜类化合物, 根据理化性质、光谱数据鉴定其结构为: 22S, 23R-环氧-甘遂烷-7-烯-3α, 24, 25-三醇 (1), 21S, 23R-epoxy-21, 24S, 25-trihydroxy- apotirucalla-7-ene-3-one (2), 21R, 23R-epoxy-21-ethoxy-24S, 25-dihydroxy-apotirucalla-7-ene-3-one (3)。化合物1为新化合物, 化合物2和3为首次从该属植物中分离得到。     

唐古特山莨菪毛状根对去氢表雄酮的生物转化

目的通过生物转化对去氢表雄酮进行结构修饰，以期获得更有意义的转化产物。方法利用唐古特山莨菪毛状根液体悬浮培养体系对去氢表雄酮进行生物转化，通过柱色谱及制备薄层色谱进行分离纯化，利用核磁共振、ESI-MS等光谱鉴定结构。结果分离得到了5个转化产物，即：androst-4-ene-3,17-dione ( I)； 6α-hydroxyandrost-4-ene-3, 17-dione (II)；6α,17β-dihydroxyandrost-4-ene-3-one(III)； androst-4-ene-3,6,17-trione (IV)；17β-hydroxyandrost-4-ene-3-one (V)。结论所得到的5个化合物均为首次通过植物组织培养生物转化的方法从唐古特山莨菪毛状根液体培养体系中分离得到。     

Sesquiterpenes and other constituents from Achillea wilsoniana

From the methanol extract of the whole plant of Achillea wilsoniana, 23 compounds were isolated. Their structures were elucidated by spectroscopic methods and chemical transformations. Three of them are new: 4E, 10E-9beta-hydroxy-3-(2-methylbutyroyloxy)-germacra-4,10(1)-diene-12,6alpha-olide (1), 4E,10E-3-(2-methylbutyroyloxy)-germacra-4,10(1)-diene-12,6alpha-olide (2) and 1beta,6a-dihydroxy-10beta-methyl-5alphaH,7alphaH-eudesm-4-one (3). In addition, 1beta-hydroxy-alpha-xyperone (5) and 9beta-acetoxy-3-(2methylbutyroyloxy)-germacra-4,10(1)-diene-12,6alpha-olide (1a) exhibited effective antibacterial activity against Staphylococcus aureus.     

Search for constituents with neurotrophic factor-potentiating activity from the medicinal plants of paraguay and Thailand

20 medicinal plants of Paraguay and 3 medicinal plants of Thailand were examined on nerve growth factor (NGF)-potentiating activities in PC12D cells. The trail results demonstrated that the methanol extracts of four plants, Verbena littoralis, Scoparia dulcis, Artemisia absinthium and Garcinia xanthochymus, markedly enhanced the neurite outgrowth induced by NGF from PC12D cells. Furthermore, utilizing the bioactivity-guided separation we successfully isolated 32, 4 and 5 constituents from V. littoralis, S. dulcis and G. xanthochymus, respectively, including nine iridoid and iridoid glucosides (1-9), two dihydrochalcone dimers (10 and 11), two flavonoids and three flavonoid glycosides (12-16), two sterols (17 and 18), ten triterpenoids (19-28), five xanthones (29-33), one naphthoquinone (34), one benzenepropanamide (35), four phenylethanoid glycosides (36-39) and two other compounds (40 and 41). Among which, 15 compounds (1-4, 10-11, 14-18, 29-31 and 34) were new natural products. The results of pharmacological trails verified that littoralisone (1), gelsemiol (5), 7a-hydroxysemperoside aglucone (6), verbenachalcone (10), littorachalcone (11), stigmast-5-ene 3beta,7alpha,22alpha-triol (18), ursolic acid (19), 3beta-hydroxyurs-11-en-28,13beta-olide (24), oleanolic acid (25), 2alpha,3beta-dihydroxyolean-12-en-28-oic acid (26), 1,4,5,6-tetrahydroxy-7,8-di(3-methylbut-2-enyl)xanthone (29), 1,2,6-trihydroxy-5-methoxy-7-(3-methylbut-2-enyl)xanthone (30), 1,3,5,6-tetrahydroxy-4,7,8-tri(3-methyl-2-butenyl)xanthone (31), 12b-hydroxy-des-D-garcigerrin A (32), garciniaxanthone E (33) and (4R)-4,9-dihydroxy-8-methoxy-alpha-lapachone (34) elicited marked enhancement of NGF-mediated neurite outgrowth in PC12D cells. These substances may contribute to the basic study and the medicinal development for the neurodegenerative disorder.     

长毛籽远志根的化学成分研究

为长毛籽远志Polygala wattersii的质量控制和进一步的开发提供科学依据,我们对它的根进行了系统的化学成分研究。利用砖胶、SephadexLH-20、制备薄层色谱及半制备液相等多种色谱分离技术进行分离和纯化,应用El—MS、ESI—MS、1HNMR及13CNMR等现代波谱技术并与文献相对照等方法鉴定化合物的结构。共从长毛籽远志根中分离鉴定了23个化合物,包括11个[口山]酮类：1,3-二羟基[口山]酮（1）,1-羟基-3-甲氧基[口山]酮（2）,1,3-羟基-2-甲氧基[口山]酮（3）,1,3,7-三羟基-2-甲氧基[口山]酮（4）,1,3,6-三羟基-2,7-二甲氧基[口山]酮（5）,1,6,7-三羟基-2,3-二甲氧基[口山]酮（6）,1,7-二羟基-2,3-亚甲二氧基[口山]酮（7）,1,7-二甲氧基[口山]酮（8）,1,2,3-三甲氧基[口山]酮（9）,1-甲氧基-2,3-亚甲二氧基[口山]酮（10）,6-羟基-1-甲氧基-2,3-亚甲二氧基[口山]酮（11）;9个糖酯类：3＇-O-阿魏酰基-6-O-乙酰蔗糖（12）,arillatose B（13）,sibficoseA5（14）,sibricoseA6（1S）,3＇,6-二-O-芥子酰基蔗糖（16）,tenufolisideA（17）,3＇-O-3,4,5-三甲氧基肉桂酰基-6—O-对甲氧基苯甲酰基蔗糖（18）,glomeratoseA（19）,1-O--对香甄酰基葡萄糖（20）;两个三萜皂苷类：bayogenin-3—O-glucoside（21）和tenufolin（22）及1个苯丙素类：芥了酸（23）。其中,化合物2和12为首次从远志属中分离得到,除化合物16外其它所有化合物均为首次从该种植物中分离得到。     

Three new α-pyrone derivatives from the plant endophytic fungus Penicillium ochrochloronthe and their antibacterial,antifungal, and cytotoxic activities

Three new 3,4,6-trisubstituted α-pyrone derivatives, namely 6-(2′R-hydroxy-3′E,5′E-diene-1′-heptyl)-4-hydroxy-3-methyl-2H-pyran-2-one (1), 6-(2′S-hydroxy-5′E-ene-1′-heptyl)-4-hydroxy-3-methyl-2H-pyran-2-one (2), and 6-(2′S-hydroxy-1′-heptyl)-4 -hydroxy-3-methyl-2H-pyran-2-one (3), together with one known compound trichodermic acid (4), were isolated from the solid-substrate fermentation culture of Penicillium ochrochloronthe associated the roots of Taxus media. Compounds 1–4 displayed the antimicrobial activity selectively against tested fungal and bacterial strains with minimum inhibitory concentration (MIC) values ranging from 12.5 to 100 μg/ml. Furthermore, we found that only compound 4 exhibited moderate cytotoxicity against five human cancer cells (A549, LN229, MGC, LOVO, and MDA231) with IC₅₀ values of 51.45, 23.43, 39.16, 46.97, and 42.85 μg/ml, respectively.     

Synthesis of 2-Oxacortexone and its Effect on Ca2+ Uptake in Bovine Spermatozoa

Low temperature base catalyzed autoxidation (BCA) of the A-ring of 21-acetoxypregn-5-ene-3,20-dione 20-ethylene ketal ( 7 ) resulted in the saponification of the ester with the concomitant formation of 2,21-dihydroxypregna-1,4-diene-3,20-dione 20-ethylene ketal ( 8 ) Continued BCA at ambient temperature, converts the latter to 1,21-dihydroxy-2-oxaprogesterone 20-ethylene ketal ( 9 ), which is reduced by NaBH₄ to the 2-oxasteroid, 21-hydroxy-2-oxaprogesterone 20-ethylene ketal ( 10 ). Treatment of enol 8 , lactol 9 , 9 , and lactone 10 with aqueous acid generates the corresponding deprotected analogs 2,21-dihydroxypregna-1,4-diene-3,20-dione (enol 11 ), 1,21-dihydroxy-2-oxaprogesterone (lactol 12 ), and 2-oxacortexone (2-oxadesoxycorticosterone, 21-hydroxy-2-oxaprogesterone, lactone 13 ). In bovine spermatozoa, neither 2-oxasteroid ketal 10 nor its deprotected analog 13 stimulated Ca²⁺ uptake. In high concentration (0.5 mM), the inhibition of Ca²⁺ uptake is only 37% for 13 , as compared to 83% found with the parent steroid, cortexone (desoxycorticosterone, 21-hydroxyprogesterone, 5 ). The difference in molecular structure between 13 and 5 indicates the importance of the oxygen atom in ring A in achieving the protective effect of the steroid. Ketalization of the C-20 carbonyl is not important for protection. Thus it seems that by replacing C-2 by an oxygen atom we can reduce the biological damage caused by relatively high concentrations of steroid treatment. These results are highly significant when treatment of patients with high doses of steroids is considered.     

Three new triterpenoids from Fuscoporia obliqua

Three new lanostane triterpenoids, fuscoporianol A (1), B (2), and C (3) were isolated from the petroleum ether extracts of Fuscoporia obliqua and their structures have been determined on the basis of chemical, spectroscopic methods and X-ray crystallographic analysis as 25-methoxy-21, 22-cyclolanosta-8-ene-3beta, 21alpha-diol(1), 3beta, 22alpha-dihydroxy-lanosta-8, 23E-diene-25-peroxide (2), 3beta, 22alpha, 25-trihydroxy-lanosta-8, 23E-diene (3).