Benzoic acid derivatives, acetophenones, and anti-inflammatory constituents from Melicope semecarpifolia

Two new benzoic acid derivatives, (E)-3-acetyl-6-(3,7-dimethylocta-2,6-dienyloxy)-2,4-dihydroxybenzoic acid (1) and (E)-3-acetyl-4-(3,7-dimethylocta-2,6-dienyloxy)-2,6-dihydroxybenzoic acid (2), and three new acetophenones, (E)-1-(5-(3,7-dimethylocta-2,6-dienyloxy)-7-hydroxy-2,2-dimethyl-2 H-chromen-8-yl)ethanone (3), (E)-1-(5-(3,7-dimethylocta-2,6-dienyloxy)-7-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2 H-chromen-8-yl)ethanone (4), and (R,E)-1-(5-(3,7-dimethylocta-2,6-dienyloxy)-3,7-dihydroxy-2,2-dimethylchroman-8-yl)ethanone (5), have been isolated from the fruits of Melicope semecarpifolia, together with eight known compounds. The structures were determined through in-depth NMR and mass spectrometric analyses. Among the isolated compounds, 2-(1'-geranyloxy)-4,6,beta-trihydroxyacetophenone (8), 4-(1'-geranyloxy)-2,6,beta-trihydroxyacetophenone (9), 5-hydroxy-3,7,3',4'-tetramethoxyflavone (10), 5,4'-dihydroxy-3,7,3'-trimethoxyflavone (11), and 5,4'-dihydroxy-3,7-dimethoxyflavone (12) exhibited potent inhibition (IC50<4 microg/mL) on superoxide anion generation and elastase release by human neutrophils in response to fMet-Leu-Phe/cytochalasin B.     

Grahamines A-E, cyclobutane-centered tropane alkaloids from the aerial parts of Schizanthus grahamii

Schizanthus grahamii is an endemic Chilean plant that is known to contain tropane alkaloids. Five new alkaloids, grahamines A-E (1-5), were isolated and characterized by extensive spectroscopic analysis. Their structures were determined to be 2-{[(3α-hydroxytropo-6β-yl)oxy]carbonyl}-2-methyl-3-{[((6β-angeloyloxy)-3α-yl)oxy]carbonyl}-4-phenylcyclobutanecarboxylic acid (1), 2-{[(3α-hydroxytropo-6β-yl)oxy]carbonyl}-2-methyl-3-{[((6β-tigloyloxy)-3α-yl)oxy]carbonyl}-4-phenylcyclobutanecarboxylic acid (2), 1-methyl-2-{[(3α-hydroxytropo-6β-yl)oxy]carbonyl}-4-{[((6β-angeloyloxy)-3α-yl)oxy]carbonyl}-3-phenylcyclobutanecarboxylic acid (3), 1,2-bis{[(3α-hydroxytropo-6β-yl)oxy]carbonyl}-2-methyl-3-{[((6β-angeloyloxy)-3α-yl)oxy]carbonyl}-4-phenylcyclobutanecarboxylate (4), and 1-{[(3α-mesaconyloxytropo-6β-yl)oxy]carbonyl}-2-{[(3α-hydroxytropo-6β-yl)oxy]carbonyl}-2-methyl-3-{[((6β-angeloyloxy)-3α-yl)oxy]carbonyl}-4-phenylcyclobutanecarboxylate (5).     

南海沿海海藻内生真菌ZJ27次级代谢产物研究

目的:对南海沿海海藻内生真菌ZJ27次级代谢产物进行研究。方法:采用色谱技术进行分离纯化,结合理化性质和波谱分析技术确定化合物的结构。结果:从真菌ZJ27次级代谢产物中分离得到5个化合物,分别为:核丛青霉素(1)、ochrephilone(2)、6-((3E,5E)-5,7-二甲基-2-酮基-3,5-壬二烯基)-2,4-二羟基-3-甲基苯甲醛(3)、(2E,4E)-4,6-二甲基-2,4-辛二烯酸(4)、pencolide(5)。结论:化合物1量特别大,达11 g,化合物2也有66 mg,因此本菌经优化培养可望成为药源微生物。     

小黄皮茎的化学成分及生物活性研究

目的研究小黄皮Clausenaemarginata茎的化学成分及其保肝活性。方法采用硅藻土、硅胶等多种柱色谱、中压制备液相色谱(MPLC)及制备型HPLC等方法对小黄皮茎的化学成分进行分离纯化,根据化合物理化性质结合现代波谱学方法鉴定化合物结构;并测试其对DL-半乳糖胺诱导肝细胞损伤的保护活性及其对脂多糖(LPS)诱导小鼠小胶质BV2细胞产生一氧化氮(NO)的抑制活性。结果从小黄皮茎的95%乙醇提取物的氯仿部位分离得到11个化合物,分别鉴定为nordentatin(1)、oxanordentatin(2)、5′-羟基葡萄内酯(3)、7-[(E)-7′-羟基-3′,7′-二甲基-2′,5′-二烯]-香豆素(4)、7-羟基香豆素(5)、claulamine A(6)、γ-崖椒碱(7)、开环异落叶松脂素(8)、2-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenoxy}propane-1,3-diol(9)、2-[4-(3-hydroxy-1-propenyl)-2-methoxyphenoxy]-1,3-propanediol(10)、甲基-2-O-β-D-吡喃葡萄糖基苯甲酸(11)。其中,化合物1~5为香豆素类化合物,6为咔唑生物碱,7为呋喃喹啉类生物碱,8为木脂素类化合物,9、10为苯丙素类化合物,11为酚酸类化合物。结论化合物2~4、7~11为首次从该植物中分离得到,化合物5和7对DL-半乳糖胺诱导的肝细胞损伤具有一定的保护活性,化合物11对LPS诱导BV2细胞产生NO具有一定的抑制作用。     

花椒果皮化学成分分离鉴定

目的:研究花椒Zanthoxylum bungeanum果皮的化学成分。方法:将花椒干燥果皮粉碎后用95%乙醇冷浸提取浓缩得到总浸膏,将总浸膏吸附于硅藻土上,依次用不同极性溶剂进行洗脱,浓缩得到相应洗脱部位。对二氯甲烷部位和正丁醇部位分别采用硅胶柱色谱,LH-20型羟丙基葡聚糖凝胶(Sephadex LH-20)凝胶柱色谱,ODS柱色谱,半制备HPLC等方法进行分离纯化,并结合理化性质和多种波谱学方法鉴定其结构。结果:从花椒果皮二氯甲烷部位和正丁醇部位分离得到14个化合物,分别鉴定为(1S,3S)-1-甲基-1,2,3,4-四氢-β-咔啉-3-羧酸(1),(3S)-1,2,3,4-四氢-β-咔啉-3-羧酸(2),芹菜素-7,4’-二甲醚(3),芫花素(4),淫羊藿次苷F2(5),breyniaionoside A(6),3-甲氧基苯乙醇-4-O-β-D-葡萄糖苷(7),3-甲氧基-5-羟基苯-1-O-β-D-葡萄糖苷(8),苔黑酚葡萄糖苷(9),紫丁香苷(10),4-[(3S)-3-羟基丁基]-2-甲氧基苯-β-D-吡喃葡萄糖苷(11),(+)-南烛木树脂酚-3a-O-β-D-葡萄糖苷(12),2-甲基丙基-6-O-β-D-呋喃芹糖基-β-D-吡喃葡萄糖苷(13)和(E)-6-羟基-2,6-二甲基辛-2,7-二烯酸(14)。结论:以上所有化合物均为首次从花椒植物中分离得到,其中化合物1~4,12,14为首次从花椒属植物中分离得到。     

Pseudotrienic acids A and B, two bioactive metabolites from Pseudomonas sp. MF381-IODS

Bioassay-guided fractionation of the liquid culture broth of Pseudomonas sp. MF381-IODS yielded two new antimicrobial substances, identified as (2E,4E,6E)-9-[((2S,3R)-3-hydroxy-4-{[(3E,5E,7RS)-7-hydroxy-4-methylhexadeca-3,5-dienoyl]amino}-2-methylbutanoyl)amino]nona-2,4,6-trienoic acid and the tetradeca equivalent, named pseudotrienic acids A (1) and B (2), respectively. The compounds are prone to lactone formation, and their structures suggest them to be derived from ring opening of a macrolide. Pseudotrienic acids A and B inhibited growth of Staphylococcus aureus (MIC 70 microg/mL) and Pseudomonas syringae pv. syringae (MIC 70 microg/mL). Two known antimicrobial compounds, the polyketide 2,3-deepoxy-2,3-didehydrorhizoxin (3) and the tryptophan-derived pyrrolnitrin (4), were also identified.     

贯叶金丝桃化学成分研究

目的:研究贯叶金丝桃Hypericum perforatum的化学成分。方法:通过各种柱色谱进行分离纯化,根据理化性质和波谱数据对所得化合物进行结构鉴定;测定化合物对基因重组人PTP1B的抑制率。结果:从中分离并鉴定了10个化合物:D-甘露醇(1),邻苯二甲酸二异丁酯(2),(7E,6R,9S)-9-hydroxy-4,7-megastigmadien-3-one(3),(6S,9R)-roseoside(4),2,6-dim-ethoxy-4-hydroquinone-1-O-β-D-glucopyranoside(5),2,6-dimethoxy-4-hydroxybenzyl alcohol 1-O-β-D-glucopyranoside(6),syringate4-O-β-glucopyranoside(7),金丝桃素(8),skyrin-6-O-β-D-glucopyranoside(9),(R)-3,4-二羟基-苯甲酸-1’-丙三醇酯(10)。在2μmol.L-1时,化合物9对基因重组人PTP1B的抑制率为96.4%,IC50为2.5μmol.L-1。结论:化合物10为新化合物,化合物2～4,7为首次从该属中分离得到,化合物5,6从该植物中首次得到。体外活性筛选表明化合物8具有显著的PTP1B抑制作用。     

Phytochemical constituents from Salsola tetrandra

The new norisoprenoid 3beta-hydroxy-5alpha,6alpha-epoxy-beta-ionone-2alpha-O-beta-d-glucopyranoside (1) and the long-chain hydroxy fatty acids 9,12,13-trihydroxyoctadeca-10(E),15(Z)-dienoic acid (2) and 9,12,13-trihydroxyoctadeca-10(E)-dienoic acid (3) were isolated from Salsola tetrandra aerial parts, together with 3,4,5-trimethoxyphenyl-beta-d-glucopyranoside (4), 9-hydroxylinaloyl glucoside (5), taxiphyllin (6), trans-N-feruloyltyramine (7), and S-(-)-trans-N-feruloyloctopamine (8). Their structures were elucidated by extensive spectroscopic analysis and chemical methods. Compounds 6 and 8 displayed mild antibacterial activity against Staphylococcus aureus, whereas compound 6 showed the highest activity in the Artemia salina bioassay.     

�ɽ��Ļ�ѧ�ɷ��о�

??OBJECTIVE To study the chemical constituents of Rhizoma Zingiberis. METHODS Diaion HP-20, Toyopearl HW-40, ODS, silica gel column and semi-preparation liquid were used to separate and purify the structure, and the structure was identified according to the physical and chemical properties and spectral data of the compound. RESULTS Fifteen compounds were isolated and identified from Rhizoma Zingiberis, which were renealtin A(1),kravanhol A(2),1, 7-bis(3,4-di-hydroxyphenyl)-3-heptanone(3),dihydrocannabinone C(4), 1, 7-bis(3, 2), 1, 7-bis(3,4-di-hydroxyphenyl) 4-dihydroxyphenyl) heptane-3-ylacetate(5),(5R)-1,7-bis(3, 4-dihydroxy)-3-hydroxyphenylheptane(6), citrus acid(7), citrate 4-(1-methoxyethyl)-phenol(8), 3-indolecarboxy(9), 3, 4-dimethoxyphenylacetic acid(10),(2E,6E)-2,6-dimethylocta-2, 6-dienedioicacid(11), cyclo-(D-Leu-L-Trp)(12), cyclo-(S-Pro-S-Phe)(13), 8-hydroxygeraniol(14) and (Z)-2, 6-dimethyloct-6-ene-1, 8-dihydroxy(15). CONCLUSION Compounds 1-15 were isolated from the plant for the first time.     

Cytotoxic and antimicrobial benzophenones from the leaves of Tovomita longifolia

Bioassay-guided fractionation of the chloroform and ethanol extracts of Tovomita longifolia leaves using cytotoxic and antimicrobial assays resulted in the isolation of four new benzophenones, (E)-3-(2-hydroxy-7-methyl-3-methyleneoct-6-enyl)-2,4,6-trihydroxybenzophenone (1), (E)-3-(6-hydroxy-3,7-dimethylocta-2,7-dienyl)-2,4,6-trihydroxybenzophenone (2), 8-benzoyl-2-(4-methylpenten-3-yl)chromane-3,5,7-triol (3), and 5-benzoyl-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene-6,8-diol (4), and two known benzophenones, 4-geranyloxy-2,6-dihydroxybenzophenone (5) and 3-geranyl-2,4,6-trihydroxybenzophenone (6). The structures of 1-4 were established by spectroscopic means and by molecular modeling calculations. Compounds 1 and 3-5 demonstrated cytotoxic activities against breast (MCF-7), central nervous system (SF-268), and lung (H-460) human cancer cell lines, while compounds 3-6 showed antimicrobial activity against Klebsiella pneumoniae, Mycobacterium smegmatis, Pseudomonas aeruginosa, Salmonella gallinarum, and Staphylococcus aureus.     

Potential antitumor-promoting diterpenes from the cones of Pinus luchuensis

A new nor-labdane-type diterpene, 15-nor-labda-8(17),12E-dien-13,19-dienoic acid (1), along with five known diterpenes, 15-nor-14-oxolabda-8(17),12E-dien-19-oic acid (2), trans-communic acid (3), sandaracopimaric acid (4), dehydroabietic acid (5), and abieta-8,11,13-triene-15,18-diol (6), was isolated from the cones of Pinus luchuensis. The structure of 1 was established by chemical and spectroscopic methods. Among these isolates, compounds 2, 4, and 6 showed potent inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol 13-acetate.     

Inhibition of respiratory burst in human neutrophils and lipoxygenase enzyme by compounds from Haloxylon griffithii

Secondary metabolites, ferulic acid (1), 2,6-dimethoxy-4-hydroxy acetophenone (2), herniarin (3), p-hydroxy acetophenone (4), methyl 3,4-dihydroxycinnamate (5), and methyl 4-hydroxy-3-methoxycinnamate (6) were isolated from Haloxylon griffithii, a member of the family Chenopodiaceae. The structures of compounds 1-6 were identified with the help of spectroscopic techniques. These compounds were isolated for the first time from this plant. The lipoxygenase and respiratory burst inhibitory activities were determined. Compound 5 was found to be the most potent inhibitory activity against respiratory burst in human neutrophils among all the compounds as well as exhibited moderate lipoxygenase inhibitory activity from this plant.     

10-membered macrolides from the insect pathogenic fungus Cordyceps militaris BCC 2816

Three new 10-membered macrolides (1-3) have been isolated from the entomopathogenic fungus Cordyceps militaris BCC 2816, together with six known compounds, cepharosporolides C (4), E (5), and F (6), 2-carboxymethyl-4-(3'-hydroxybutyl)furan (7), cordycepin (8), and pyridine-2,6-dicarboxylic acid. The structures were determined by analysis of NMR data, and an X-ray analysis was performed to confirm the structure of 1. The antimalarial activity of 1-4 and 8 against Plasmodium falciparum K1 was evaluated.     

狗牙根化学成分的研究

目的研究狗牙根的化学成分。方法狗牙根95%乙醇提取物正丁醇部位采用MCI、Rp-C18、半制备HPLC进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。结果从中分离得到13个化合物,分别鉴定为monocerin (1)、绿原酸甲酯(2)、4-O-香豆酰基奎宁酸甲酯(3)、5-O-阿魏酰奎宁酸(4)、异血红酸(5)、麦芽酚-β-D-吡喃葡萄糖苷(6)、1, 4-二甲氧基吩嗪(7)、19α-羟基齐墩果酮酸(8)、3-羟基-1-(4-羟基-3,5-二甲氧基苯基)-2-[4-(3-羟基-1-(E)-丙烯基)-2,6-二甲氧基苯氧基]丙基-β-D-吡喃葡萄糖苷(9)、4,5-二咖啡酰基奎宁酸甲酯(10)、苯甲酸(11)、4-羟基-邻茴香醛(12)、阿替匹林C(13)。结论所有化合物均为首次从该植物中分离得到。     

丝棉木种子化学成分及其抗肿瘤活性

目的 研究丝棉木Euonymus maackii Rupr.种子的化学成分及其抗肿瘤活性.方法 丝棉木种子95%乙醇提取物乙酸乙酯部位采用硅胶、D101、反相HPLC进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构.MTT法测定其抗肿瘤活性.结果 从中分离得到10个化合物,分别鉴定为1β-甲基正丁酰氧基-2β-苯甲酰氧基-4α-羟基-6α-呋喃酰氧基-9β,12-二乙酰氧基-β-二氢沉香呋喃(1)、6α,9β,12-三乙酰氧基-1β,2β,8β-三苯甲酰氧基-β-二氢沉香呋喃(2)、6α,9β,12-三乙酰氧基-1β,8β-二苯甲酰氧基-2β-正己酰氧基-β-二氢沉香呋喃(3)、6α,9β,12-三乙酰氧基-1β,8β-二苯甲酰氧基-2β-正辛酰氧基-β-二氢沉香呋喃(4)、6α,9β,12-三乙酰氧基-1β,8β-二苯甲酰氧基-2β-正癸酰氧基-β-二氢沉香呋喃(5)、卫矛羰碱(6)、6α,12-二乙酸基-1β,9α-二乙酸(β-呋喃羧氧基)-4α-羟基-2β-2-甲基丁酯-β-二氢沉香呋喃(7)、6α,9β,12-三乙酰氧基-1β,8β-二苯甲酰氧基-2β-羟基-β-二氢沉香呋喃(8)、6α,12-二乙酸基-1β,9 α-二乙酸(β-呋喃羧氧基)-4α-羟基-1β-2-甲基丁酯-β-二氢沉香呋喃(9)、6α,9β,12-四乙酰氧基-1β,8β-二苯甲酰氧基-β-二氢沉香呋喃(10).化合物6对Hela细胞有明显的抑制作用,IC50为9.76 μg/mL.结论 化合物1为新化合物.化合物6有一定的抗肿瘤活性.     

白花前胡化学成分研究Ⅱ

目的：分离鉴定河南产白花前胡的化学成分。方法：用乙醇提取,经大孔树脂、硅胶和反相硅胶ODS柱色谱分离化合物,利用质谱、核磁共振等现代波谱技术鉴定结构。结果：分离鉴定了8个化合物,分别为(-)sclerodin(1),棕榈酸(palmitic acid,2),白花前胡E素［(+)-praeruptorin E,3］,佛手柑内酯(bergapten,4),欧前胡素(imperatorin,5),2,6-二甲基喹啉(2,6-dimethyl quinoline,6),二十四烷酸(tetracosanoic acid,7),胡萝卜苷(daucosterol,8)。结论：化合物1,6为首次从伞形科植物中分离得到；5,7为首次从该植物中分离得到。     

Daryamides A-C, weakly cytotoxic polyketides from a marine-derived actinomycete of the genus Streptomyces strain CNQ-085

In the course of our continuing search for new antitumor-antibiotics from marine-derived actinomycete bacteria, four new cytotoxic compounds, designated as daryamides A (1), B (2), and C (3) and (2E,4E)-7-methylocta-2,4-dienoic acid amide (4), were isolated from the culture broth of a marine-derived Streptomyces strain CNQ-085. The structures of these new compounds were assigned by detailed interpretation of spectroscopic data. The relative configuration of 1 was determined by comprehensive NMR analysis, while the absolute configuration of 1 was determined as 4S,5R using the modified Mosher method. The daryamides show weak to moderate cytotoxic activity against the human colon carcinoma cell line HCT-116 and very weak antifungal activities against Candida albicans.     

Coumarins from Phebalium tuberculosum ssp. megaphyllum and Phebalium filifolium.

A total of 14 coumarins have been isolated from the aerial parts of Phebalium tuberculosum ssp. megaphyllum and 9 from Phebalium filifolium (Rutaceae). Three of the coumarins obtained from P. tuberculosum ssp. megaphyllum are novel and have been characterized, on the basis of spectroscopic analysis, as (E)-7-(6-hydroperoxy-3,7-dimethylocta-2,7- dienyloxy)coumarin [3], (E)-8-(6-hydroperoxy-3,7-dimethylocta-2,7-dienyloxy)psoralen [16] and (E,E)-8-(7-hydroxy-3,7-dimethylocta-2,5-dienyloxy)psoralen [15] In addition, both species yielded the simple acetophenone xanthoxylin, and P. tuberculosum ssp. megaphyllum gave (E)-betulin-3-p-coumarate [20] and (Z)-betulin-3-p-coumarate [21], both of which appear to be novel. The chemotaxonomic implications of coumarin distribution in the two species are discussed.     

粟米草三萜类化学成分及其活性研究

目的研究粟米草Mollugo pentaphylla中的三萜类化学成分,寻找其中具有细胞毒活性化合物。方法综合运用大孔吸附树脂、硅胶柱色谱、半制备型高效液相及SephadexLH-20凝胶柱色谱等各种色谱技术进行系统化学研究,根据其理化性质和MS、NMR等波谱数据鉴定化合物结构,同时对所得的三萜皂苷进行细胞毒活性测试。结果从粟米草干燥地上部分醇提取物中共分离得到6个三萜类化合物,分别鉴定为粟米草苷E(1)、3-O-[α-L-rhamnopyranosy1(1→2)-α-L-arabinopyranosyl]-28-O-[β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl] oleanolic acid(2)、竹节香附皂苷R8(3)、竹节香附素A(4)、mollugogenolsA(5)、齐墩果酸(6)。细胞毒活性显示,化合物1~5对人前列腺癌DU145细胞、人宫颈癌HeLa细胞及人早幼粒白血病HL-60细胞均显示一定的抑制作用,尤其是对人早幼粒急性白血病HL-60细胞,其IC50分别为10.21、38.43、40.28、20.59、83.16μmol/L。结论化合物1为新的齐墩果酸型三萜皂苷,2~4为首次从该植物中分离得到。细胞毒活性显示,化合物1~5对人前列腺癌DU145细胞、人宫颈癌HeLa细胞及人早幼粒白血病HL-60细胞均显示一定的抑制作用。     

Inhibitory effects on HIV-1 protease of constituents from the wood of Xanthoceras sorbifolia

From a methanolic extract of the wood of Xanthoceras sorbifolia, two new compounds, 29-hydroxy-3-oxotirucalla-7,24-dien-21-oic acid (3, xanthocerasic acid) and epigallocatechin-(4beta-->8, 2beta-->O-7)-epicatechin (6), were isolated, together with 11 known compounds. Of the isolated compounds, 3-oxotirucalla-7, 24-dien-21-oic acid (2), oleanolic acid (4), and 6 were found to be inhibitory substances against human immunodeficiency virus (HIV-1) protease, with their 50% inhibitory concentrations (IC(50)) being 20, 10, and 70 microg/mL, respectively. Condensed tannins of high molecular weights with epicatechin and epiafzelechin as the main extender units were found to be the most active principles of this plant (IC(50) values ca. 6.0 microg/mL).