Six New Cembranolides from the Hainan Soft Coral Lobophytum sp.

Six new cembrane diterpenes, lobophytolides A–F ( 1 – 6 , resp.), along with six known related cembranoids, 7 – 12 , were isolated from the Hainan soft coral Lobophytum sp. Their structures, including their relative configuration, were elucidated by extensive analyses of the spectroscopic data and by comparison with related known compounds.     

Cembranolides and Related Constituents from the Soft Coral Sarcophyton cinereum

In an attempt to explore the bioactive metabolites of the soft coral Sarcophyton cinereum, three new cembranolides, cinerenolides A–C (1–3), and 16 known compounds were isolated and identified from the EtOAc extract. The structures of the new cembranolides were elucidated on the basis of spectroscopic analysis, and the NOE analysis of cinerenolide A (1) was performed with the assistance of the calculated lowest-energy molecular model. The relative configuration of cinerenolide C (3) was determined by the quantum chemical NMR calculation, followed by applying DP4+ analysis. In addition, the cytotoxic assays disclosed that some compounds exhibited moderate to potent activities in the proliferation of P388, DLD-1, HuCCT-1, and CCD966SK cell lines.     

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。     

Further New Cembrane Diterpenes from the Hainan Soft Coral Sarcophyton latum

Two new cembranoid diterpenes, diepoxysarcophytonene ( 1 ) and sarconphytonol ( 2 ), were isolated from the Hainan soft coral Sarcophyton latum. Their structures including relative stereochemistry were established by 1D and 2D NMR spectroscopic techniques. Compound 1 showed weak inhibitory activity against COX‐2 in vitro at the concentration of 10^?5 µmol·L^?1 with the inhibitory rate of 55%.     

Further New Bis‐cembranoids from the Hainan Soft Coral Sarcophyton tortuosum

Two new bis‐cembranoids, ximaolides F ( 1 ) and G ( 2 ), were isolated from the Hainan soft coral Sarcophyton tortuosum. The structures and relative configurations of the two new compounds were elucidated by the combination of spectroscopic methods, chemical conversion of ximaolide F ( 1 ) into ximaolide G ( 2 ), and comparison with related model compounds.     

Further New Cembranoid Diterpenes from the Hainan Soft Coral Sarcophyton latum

Four new cembranoid diterpenes, sarcophytonolides I–L ( 1 – 4 ), were isolated from the Hainan soft coral Sarcophyton latum. Their structures were established by detailed analysis of 1D and 2D NMR spectra and by comparison with related model compounds.     

Sarcophytolides G–L,New Biscembranoids from the Soft Coral Sarcophyton elegans

Six new biscembranoids, namely, sarcophytolides G–L ( 1 – 6 , resp.), together with six known analogs, were isolated from a marine soft coral Sarcophyton elegans. The structures of the new compounds were established on the basis of 1D‐ and 2D‐NMR (COSY, HSQC, HMBC, and NOESY) spectroscopic analysis together with the aid of MS, CD, and IR data. The unusual isobiscembranoid sarcophytolide G ( 1 ) was found for the first time in the genus Sarcophyton.     

Two New Polyhydroxylated Steroids from the Hainan Soft Coral Sinularia sp.

Two new polyhydroxylated steroids, (2β,3β,4α,5α,8β,11β)‐4‐methylergost‐24(28)‐ene‐2,3,8,11‐tetrol‐( 1 ) and (3β,5α,6β)‐ergosta‐22,24(28)‐diene‐3,5,6,19‐tetrol ( 3 ), together with the six known related steroids 2 and 4 – 8 , were isolated from the Hainan soft coral Sinularia sp. Their structures were elucidated on the basis of spectroscopic analysis and by comparison with previously reported data. The structure of the known compound 9 (hyrtiosterol) was revised as 2 by extensive analysis of the ROESY data and by the NOE difference experiment.     

Xishaglaucumins A—J,New Cembranoids with Anti-Inflammatory Activities from the South China Sea Soft Coral Sarcophyton glaucum

Ten new cembrane-type diterpenoids,namely xishaglaucumins A—J(1—10),along with ten known related ones(11—20),have been isolated from the soft coral Sarcophyton glaucum collected off the Xisha Island in the South China Sea.Their structures were elucidated by extensive spectroscopic analysis,quantum mechanical nuclear magnetic resonance(QM-NMR)methods,X-ray diffraction analysis,chemical methods and comparison with the reported data in the literature.The absolute configuration of new compounds 1,5 and known compounds 11,12,16 and 20 were determined either by chemical methods or by X-ray diffraction analysis using Cu Kα(λ=1.5417A).In in vitro bioassay,compound 4 exhibited inhibitory effects on lipopolysaccharide(LPS)-induced inflammatory responses in BV-2 microglial cells.     

Sarcoglycosides A – C,New O‐Glycosylglycerol Derivatives from the South China Sea Soft Coral Sarcophyton infundibuliforme

Chemical examination of the soft coral Sarcophyton infundibuliforme collected from the South China Sea resulted in the isolation of the three new O‐glycosylglycerol derivatives sarcoglycosides A–C ( 1 – 3 ), together with two known compounds, chimyl alcohol ( 4 ) and hexadecanol ( 5 ). Their structures were elucidated by combined spectral and chemical methods. All the compounds showed moderate toxicity to brine shrimps Artemia salina.     

Metabolites of Marine Fungus Aspergillus sp. Collected from Soft Coral Sarcophyton tortuosum

Fungus Aspergillus sp., which was isolated from soft coral Sarcophyton tortuosum, was cultured in the GPY medium containing glucose 10 g/L, peptone 5 g/L, yeast extract 2 g/L, sea water 1 L, at pH=7.5. Four com- pounds, 3,6-diisobutyl-2(1H)-pyrazinone(1), 3-isobutyl-6-(1-hydroxy-2-methylpropyl)-2(1H)-pyrazinone(2), 3-meth- oxy-4-methyl-2,4-dien-pentanoic acid(3) and penicillic acid(4) were obtained from the AcOEt extract of the culture broth. Their structures were elucidated mainly based on the NMR, HR-EI-MS and X-ray single crystal diffraction experimental data. Compound 3 is a new compound. Compound 1 was previously proposed to be the tautomer of flavacol(3,6-diisobutylpyrazin-2-ol, 5). However, the evaluation of the NMR and X-ray single crystal diffraction experimental data permitted us to propose that compound 1 existed as amide form instead of tautomers. Compound 1 is stable both in solution and crystal due to strong intermolecular hydrogen bonds. Incidentally supplying anthracenone to the GPY medium with a dose of 100 mg/L, the yield of penicillic acid(4) in the culture broth of the strain Aspergillus sp. was increased dramatically from 6 mg/L to 57 mg/L.     

Yalongenes A and B,Two New Cembranoids with Cytoprotective Effects from the Hainan Soft Coral Sarcophyton trocheliophorum Marenzeller

Two new cembranoids, yalongenes A ( 1 ) and B ( 2 ), were isolated from the South China Sea soft coral Sarcophyton trocheliophorum Marenzeller . Their structures were elucidated by detailed spectroscopic analysis (IR, MS, and NMR) and by comparison with a related model compound. Yalongenes 1 and 2 were evaluated for their cytoprotective effects on SH‐SY5Y cell injury induced by H₂O₂ in vitro, and the result showed that only compound 1 had a significant cytoprotective activity at the concentration of 1 μM .     

Sardisterol,A New Polyhydroxylated Sterol from the Soft Coral Sarcophyton digitatum Moser

A new polyhydroxylated sterol, named sardisterol, was isolated from the soft coral Sarcophyton digitatum Moser. Its structure was determined as (22R, 24ξ)‐methylcholest‐5‐en‐3β, 22, 25, 28‐tetraol‐3‐acetate on the basis of spectroscopic methods.     

南海肉芝软珊瑚中的次生代谢产物分析

从采自海南岛三亚湾的一种肉芝软珊瑚Sarcopyton sp中分离到1个新的对苯二甲酸二酯衍生物,通过波谱方法和化学转变测定其结构为对苯二甲酸-1-异丁基-4-(2′-乙基-正己基)-二酯(1);另外,还分离鉴定得2个多羟基甾醇,24α-甲基一胆甾-5(6)-烯-3β,7α-二醇(2),24-亚甲基-胆甾-3β,5α,6β-三醇(3)和α-十六酸-鲨肝醇酯(4);化合物2和3对肿瘤细胞有明显抑制作用,4具有升白血球作用。     

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。     

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。     

Japonicumins A–D: Four New Compounds from Lycopodium japonicum

Three new serratane‐type triterpenoids, japonicumins A–C ( 1 – 3 ), as well as a unique, new C₁₃ terpenoid, japonicumin D ( 4 ), were isolated from the dried whole plants of Lycopodium japonicum, together with the known compound lycoclavanol ( 5 ). Their structures were identified by extensive mass‐spectrometric and spectroscopic (especially 2D‐NMR) experiments. Compounds 1 – 5 exhibited no activity against human‐tumor A 549 cells.     

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　…