中国南海矮小短指软珊瑚(Sinularia nanolobata)的化学成分研究

运用硅胶柱色谱、凝胶柱色谱和高效液相色谱等分离技术,对中国南海西瑁岛矮小短指软珊瑚的丙酮提取物中的化学成分进行了系统研究,从中分离得到10个化合物,并采用多种波谱技术确定了这些化合物的化学结构.分别鉴定为罗伯塔特(1)、(17R)-loba-8,10,13(15)-triene-17,18-diol(2)、α-生育醌(3)、(1E,3Z,7E,11R,12R)-11-羟基-12-甲氧基-1-异丙基-4,8,12-三甲基-环十四碳-1,3,7-三烯(4)、(+)-(1E,3E,7E,11R,12S)-11,12-epoxy-11,12-dihydrocembrene-C(5)、(1E,3E,7R,8S,11E)-7,8-环氧-1-异丙基-4,8,12-三甲基-环十四碳-1,3,11-三烯(6)、24-亚甲基-胆固醇(7)、孕烯醇酮(8)、3β,6α,11-三羟基-24-亚甲基-9,11-断-5α-胆甾-7-烯-9-酮(9), Sinugrandisterol A (10).其中化合物1为新的异戊烯基榄烷型二萜化合物.生物活性实验结果表明,化合物3对蛋白酪氨酸磷酸酶1B (PTP1B)的酶...     

新三羟基-西松烯二萜内酯

本文从采自海南三亚的条状短指软珊瑚(sinulariacapillosa)中分离得四个西松烯二萜内酯(1～4)。化合物(1)是新的三羟基西松烯内酯,通过波谱方法测定了它的结构。     

柔软肉芝软珊瑚中的新二萜内酯

肉芝软珊瑚Sarcophytum是珊瑚纲,八放珊瑚亚纲,软珊瑚目中的一个属,软珊瑚肉质柔软而不被海洋中的动物所吞食,这被认为是与其次生代谢产物中含有能驱赶其它生物的化学防御物质有关,从而引起了化学家和药物学家的重视^[1,2],例如从乳白肉芝软珊瑚Sarcophytum glaucum和第氏肉芝办珊瑚Sarcophyton decasyi中均分离得到细胞毒活性相当强的二萜内脂Sarcophine^[3-5],Bernstein^[3]认为这类物质可能是软珊瑚的化学防御物质之一,最近我们在研究柔软肉芝软珊瑚Sarcophyton molle Tix.Dur.的次生代谢产物过程中,分离到两个在生源上与Sarcophine有密切关系的二萜内酯 Sarcophinone(1)^[6,7]和iso-Sarcophinone(2),其中2是新化合物。体外的生理活性试验显示,化合物1和2对艾氏腹水瘤细胞和水鼠S180肿瘤细胞均有显著抑制作用,本文报道了Sarcophinone(1)和iso-Sarcophinone(2)的分离和结构测定。     

鹿角短指软珊瑚Sinularia Cervicornis Tix-Dur 中的一个新糖甙-Cervicoside

珊瑚属腔肠动物门 ( Clelenterata) ,海鸡冠目 ( Alcyonacea) ,是一种热带与亚热带海洋中广泛分布Scheme 1　 Structure of cervicoside(1 )的低等海洋生物 .软珊瑚的次生代谢物中含有萜类和甾体类等各类生理活性物质[1～ 5] .我们在对鹿角短指软珊瑚的次生代谢产物研究中 ,分离到一个新三糖甙 ,命名为 Cervicoside( 1 ) ,结构见 Scheme 1 .该化合物具有较强的体外抗癌活性 .1　实验部分1 .1　样品　鹿角短指软珊瑚采自海南岛三亚海域 .样品储藏于中山大学化学与化学工程学院天然有机化学研究室 ,编号为 98- SY- 3.种属由中国科学院南海…     

软珊瑚Sarcophyton sp.中一个新的西松烷二萜内酯的分离及结构测定

肉芝软珊瑚 Sarcophyton富含二萜 ,从这类软珊瑚生物体中已经分离出许多含十四元环结构的西Scheme 1　 Sturcture of Sarcophydiol 1松烷二萜内酯 ,例如 Sarcophinone[1] ,iso-Sarcophinone[2 ] ,Sarcophine[3,4 ] ,Sartrochine[5] 和 iso-Sarcophine[6 ,7] .这些西松烷二萜内酯均有较强的细胞毒性 .在对采自南中国海的一种肉芝软珊瑚 Sar-cophyton sp.次生代谢产物的研究过程中 ,我们分离得到一个在生源上与 iso- Sarcophine有密切关系的新西松烷二萜内酯 Sarcophydiol 1 (结构见Scheme 1 ) .本文报道其分离方法及结构测定结果 .1　…     

海南豆荚软珊瑚Lobophytum sp.中的新西松烷二萜

从海南豆荚软珊瑚Lobophytum sp. 中分离得到四个新的西松烷类型的二萜[19-hydroxy-sarcocrassolide (1), 18-deacetyldeepoxy lobolide (2), 13-hydroxy-sinularial A (3) 和 16-hydroxy-sinulariol C (4)], 以及四个已知的相同类型化合物(5-8)。所有化合物的结构及其相对构型都是通过分析它们的一维和二维波谱学数据,和将这些数据与文献中的报道的数据相比较来确定的。     

南海软珊瑚Sarcophyton molle化学成分的研究

从中国南海软肉芝软珊瑚(Sarcophyton molle)中分离到七个化合物, 经紫外光谱(UV), 红外光谱(IR), 质谱(MS)和核磁共振光谱(1H NMR, 13C NMR)分析, 确定了其化学结构。它们是: 异新西松烯(1), (E, E, E)-7, 8-环氧-1-异丙基-4, 8, 12-三甲基-十四环-1,3, 11-三烯(2), 正十八烷酸(3), 鲨肝醇(4), 神经酰胺(5), 胸腺嘧啶(6), 胸腺嘧啶脱氧核苷(7)。其中化合物(2)为新化合物。本文是第一次报道软珊瑚Sarcophyton molle的化学成分。     

珊瑚中五环半缩醛甾体的结构解析

为研究珊瑚Sinularia sp.中五环半缩醛甾醇的分离与结构,运用普通色谱及高效液相色谱等色谱方法对珊瑚Sinularia sp.中五环半缩醛甾醇化合物进行分离纯化,通过分析该化合物的核磁共振谱与质谱确定其平面结构,测定并比较圆二色光谱计算值确定化合物的立体构型。结果从珊瑚Sinularia sp.中首次分离纯化得到结构独特的五环半缩醛甾醇化合物(8R,9S,10R,13R,14S,17R,18R,20S,22R)-胆甾-1,4-二烯-18-乙酰基-22-氧-3-酮-18,22-环缩醛。     

肉芝软珊瑚Sarcophyton sp中次生代谢产物的研究

从中国海南岛三亚附近海域采集的肉芝软珊瑚Sarcophyton sp中,分离得5个结晶化合物。通过化学和波谱方法鉴定出他们的结构分别是：24亚甲基胆甾-1α,3β,5α,6β-四醇(1);24-亚甲基胆甾14-烯-3β,6β-二醇(2);2．十六碳酰胺基-十八-4(E),8(E)-二烯-1,3-二醇(3);(2S,3S,5R)-2-十六碳酰胺基-十八-1,3,5-三醇(4);柳珊瑚甾醇(5)。生理活性试验表明,化合物1对人体鼻咽癌(CNE2)和胃癌(NGC-803)细胞有强抑制活性;化合物2对P-388肿瘤细胞有强抑制活性;柳珊瑚甾醇(5)有明显的抗心律失常和减慢心率等作用。     

中国南海软珊瑚Scleronephthya sp.化学成分的研究

对中国南海的软珊瑚Scleronephthya sp.的化学成分进行研究,从有免疫调节活性的乙醚可溶物中分离鉴定了13个化合物,经1H NMR,13C NMR,HMQC,HMBC,1H-1H COSY和MS等光谱分析并结合文献数据,确证其结构分别为:3β-羟基-20-烯孕甾烷乙酸酯(1),3β-羟基-5,20-二烯孕甾烷乙酸酯(2),3-酮-20-烯孕甾烷(3),1,2-环氧-3-酮-20-烯孕甾烷(4),1,20-二烯-3-酮孕甾烷(5),1-烯-3-酮-20S-甲基-21-羟基孕甾烷乙酸酯(6),1-烯-3-酮-20β-羟基孕甾烷乙酸酯(7),1-烯-3,22-二酮胆甾烷(8),1,24-二烯-3-酮-22,23-二羟基胆甾烷(9),O-methylisogrifolin(10),(1R,3S,4S,7E,11E)-3α,4α-环氧-7,11,15-三烯西松烷(11),玉米黄素12和6-溴-3-羧酸吲哚(13),其中化合物4,6和10是首次从自然界分离得到.首次对化合物6,7和10的波谱数据进行了报道,而且利用2D NMR对其进行了全归属.对化合物1～7可能的生源关系也进行了探讨.化合物6和7对人宫颈癌细胞(HELA)有抑制活性,IC50分别为3.3和6.3 mol/L;化合物7对肝癌细胞(BE7402)和人白血病细胞(HL-60)也显示抑制活性,IC50分别为3.1和0.26mol/L;化合物11对COX-2显示强烈的抑制活性,IC50为0.455 mol/L.     

Complete assignments of 1H and 13C NMR spectral data for three sesquiterpenoids from Inula helenium

The complete assignments of all the (1)H and (13)C NMR signals of three sesquiterpene lactones, 4-oxo-5(6),11-eudesmadiene-8,12-olide (1), 4-oxo-11-eudesmaene-8,12-olide (2) and (1(10)E)-5beta-Hydroxygermacra-1(10),4(15),11-trien-8, 12-olide (3), were carried out by various 2D NMR experiments. Compounds 1-3 were isolated from the roots of Inula helenium for the first time. Among them, 1 was identified as a new nor-sesquiterpene lactone, and 2 was isolated from a natural source for the first time. The (13)C-NMR data of compound 3 was also reported for the first time.     

Anti-babesial compounds from Curcuma xanthorrhiza

Anti-babesial ingredients, (12R)- and (12S)-12,13-dihydro-12,13-dihydroxyxanthorrhizols, were isolated from Curcuma xanthorrhiza. The structures were established by the extensive NMR techniques. The assignments of (1)H NMR data of (12R)-12,13-dihydro-12,13-dihydroxyxanthorrhizol was revised, and (12S)-12,13-dihydro-12,13-dihydroxyxanthorrhizol was isolated as a pure form for the first time. The IC(50) of the active compounds were compared with that of commercial drug, diminazene aceturate (Ganaseg). IC(50) values of Ganaseg, (12R)-, and (12S)-12,13-dihydro-12,13-dihydroxyxanthorrhizols were 0.6 microg mL(-1), 8.3 microg mL(-1) and 11.6 microg mL(-1), respectively.     

Studies on Nepalese crude drugs. XXIX. Chemical constituents of Dronapuspi, the whole herb of Leucas cephalotes SPRENG

From the whole herb of Leucas cephalotes SPRENG., new labdane-, norlabdane- and abietane-type diterpenes named leucasdins A (1), B (2) and C (3), respectively, and two protostane-type triterpenes named leucastrins A (4) and B (5) were isolated, together with a known triterpene, oleanolic acid, five sterols, 7-oxositosterol, 7-oxostigmasterol, 7alpha-hydroxysitosterol, 7alpha-hydroxystigmasterol and stigmasterol, and eight flavones, 5-hydroxy-7,4'-dimethoxyflavone, pillion, gonzalitosin I, tricin, cosmosin, apigenin 7-O-beta-D-(6-O-p-coumaroyl)glucopyranoside, anisofolin A and luteolin 4'-O-beta-D-glucuronopyranoside. The structures of 1--5 were determined as (3S,6R,8R,9R,13S,16S)-9,13,15,16-bisepoxy-3,16-diacetoxy-6-formyloxylabdane, (3S,6R)-3-acetoxy-6-formyloxy-iso-ambreinolide, (4R,9S,12R,13R)-12,13-dihydroxyabiet-7-en-18-oic acid, (3S,17S,20S,24S)-3,20-dihydroxy-24-methylprotost-25-en, and (3S,17S,20S,24S)-3,20,24-trihydroxyprotost-25-en respectively, based on spectral and chemical data.     

Simiranes A and B: erythroxylanes diterpenes and other compounds from Simira eliezeriana (Rubiaceae)

The first phytochemical study of Simira eliezeriana Peixoto (Rubiaceae) allowed the isolation and structural determination of two new diterpenes named simirane A [(5R,6R,8R,9R,10S,11S,13S)-6β,11β-dihydroxy-2,4(18),15-erythroxylatrien-1-one] (1) and simirane B [(5S,8R,9R,10S,11S,13S)-11β-hydroxy-2,4(18),15-erythroxylatrien-1-one] (2), together with seven known compounds: sitosterol (3), stigmasterol (4), campesterol (5), coniferaldehyde (6), vanillin (7), pinoresinol (8) and harman (9) from the bark of the plant. The structures of the compounds were established on the basis of spectroscopic methods, including 1-D and 2-D NMR, HRESI-MS and CD analysis and comparisons with available literature data of known compounds.     

Tobacco Chemistry.29. (7S)-10-Oxo-4xi-methyl-7-isopropyl-5E-undecen-4-olide, a New Thunbergan-type Nor-isoprenoid isolated from Greek Nicotiana tabacum L.

The structure of a new C15-lactone, (7S)-10-oxo-4xi-methyl-7-isopropyl-5E-undecen-4-olide, isolated from Greek tobacco, has been determined mainly be 1H NMR, 13C NMR and high resolution MS, and its absolute configuration established by degradation to (2S)-5-oxo-2-isopropylhexanal. The carbon skeleton of the new compound indicated that it is derived from a thunbergane precursor and constitutes the first C15 nor-thunberganoid in tobacco.     

Labdane diterpenes from the rhizomes of Hedychium coronarium

A new labdane diterpenoid, (E)-labda-8(17),12-dien-15,16-olide (1) together with eight known compounds, coronarin D (2), coronarin D methyl ether (3), coronarin D ethyl ether (4), isocoronarin D (5), coronarin B (6), labda-8(17),11,13-trien-15,16-olide (7), (E)-labda-8(17),12-diene-15,16-dial (8) and 16-hydroxylabda-8(17),11,13-trien-15,16-olide (9), are isolated from the rhizomes of Hedychium coronarium. Compounds 2-4, 5 and 9 are isolated as mixtures of C-15, C-14 and C-16 epimers, respectively. Their structures are determined on the basis of their spectroscopic data. The epimeric mixtures of 2 and 3 have not been reported before. Some of them were evaluated for their cytotoxicity.     

Two new eremophilanolides from Xanthium sibiricum

Two new eremophilanolides, sibiriolides A (1) and B (2), were isolated from the aerial parts of Xanthium sibiricum. The structures of the new compounds were identified as 4S,5R,7R,8R, 11R-2-oxo-1(10)-eremophilen-12,8-olide (1) and 4S,5R,7R,8R,11S-2-oxo-1(10)-eremophilen-12,8-olide (2) by HREIMS and NMR spectroscopic techniques in combination with X-ray crystallographic analysis and CD measurements.     

Two new sesquiterpene lactones from Ixeris chinensis

Phytochemical investigation of Ixeris chinensis NAKAI (Asteraceae) has resulted in the isolation of a new guaianolide-type sesquiterpene lactone, ixerochinolide (1) as well as the related glucoside, ixerochinoside (2). In addition, the known guaianolides, 8beta-hydroxy-3-oxo-guaia-4(15),10(14),11(13)-trien-1alpha,5alpha,6beta,7alphaH-12,6-olide (8beta-hydroxydehydrozaluzanin), 8beta,15-dihydroxy-2-oxo-guaia-1(10),3,11(13)-trien-5alpha,6beta,7alphaH-12,6-olide (lactucin), 3beta,8alpha,10alpha-trihydroxy-guaia-4(15),11(13)-dien-1alpha,5alpha,6beta,7alphaH-12,6-olide (10alpha-hydroxy-10,14-dihydro-desacylcynaropicrin) and 3beta-D-glucopyranosyloxy-8beta-(p-hydroxyphenylacetyloxy)-guaia-4(15),10(14),11(13)-trien-1alpha,5alpha,6beta,7alphaH-12,6-olide (8-epicrepioside) were identified. The structures were determined on the basis of spectral analyses, especially 1- and 2D NMR. Compound 1 exhibited significant cytotoxicity against human PC-3 tumor cells.     

Wedelolides A and B: novel sesquiterpene delta-lactones, (9R)-eudesman-9,12-olides, from Wedelia trilobata

Two new sesquiterpene lactones, wedelolides A (1) and B (2), were isolated by bioassay-guided fractionation from the leaves of Wedelia trilobata, together with known trilobolides 6-O-isobutyrate (3) and 6-O-methacrylate (4). The compounds 1 and 2 were the first examples of an unprecedented framework: a novel sesquiterpene delta-lactone, (9R)-eudesman-9,12-olide. The structures of the antimalarial wedelolides A (1) and B (2) were determined on the basis of MS and 2D NMR spectral analysis. The absolute configuration of eight carbon stereocenters of compounds 1 and 2 was determined to be 1S,4S,5S,6R,7S,8S,9R,10S by mean of auxiliary chiral MTPA derivatives.     

Sesquiterpene lactones from Saussurea alata

Two new guaianolides, namely, 3beta,8alpha-dihydroxy-13-methoxyl-4(14),10(15)-dien-(1alphaH,5alphaH,6beta H,11betaH)-12,6-olide (1) and 3beta,8alpha-dihydroxy-13-methoxyl-4(14),10(15)-dien-(1alphaH,5alphaH,6beta H,11alphaH)-12,6-olide (2), together with six known guaianolides, 8-hydroxyzaluzanin C, austricin, chlorojanerin, cynaropicrin, chlorohyssopifolin E and chlorohyssopifolin A were isolated from the aerial parts of Saussurea alata. The structures were established mainly based on spectral analysis, especially 2D NMR techniques.