A new acyclic thiophene sesterterpene from the Sikao Bay sponge, Xestospongia sp

Bioactivity-guided fractionation of the ethyl acetate extract of a marine sponge, Xestospongia sp., led to the isolation of a new thiophene-S-oxide acyclic sesterterpene (1). The chemical structure was extensively analyzed using NMR and mass spectral data. Compound 1 showed weak cytotoxicity against Vero cells.     

锉海绵属海绵Xestospongia sp.甾体类成分研究

目的 对广西涠洲岛北部湾海域来源的锉海绵属（Xestospongia）海绵中获得的结构新颖、活性良好的甾体类成分进行研究。方法 根据甾体类化合物的结构特性,利用多种柱色谱和高效液相色谱（HPLC）等方法,通过高分辨质谱（HRMS）、核磁共振（NMR）和旋光（ORD）等方法并结合文献对照对化合物进行结构鉴定。结果 从锉海绵属海绵中分离得到9个甾体化合物,分别为7-ketocholesterol (1)、3β-Hydroxy-24-methylene-5-cholesten-7-one (2)、(22E)-3β-Hydroxychoiesta-5,22-dien-7-one (3)、(22E)-3β-Hydroxychiest-5,22-diene-7,24-dione (4)、Dictyopterisin G (5)、Dictyopterisins D (6)、Dictyopterisins E (7)、antrocarine E (8)和Fucosterol (9)。结论 化合物2-8均为首次从该属海绵中分离得到,6和7母核上C-7位为少见的甲氧基,8是首次从海绵中分离得到5-OH和7羰基的甾体化合物。     

A new brominated polyacetylene from Chinese marine sponge Xestospongia testudinaria

A new brominated polyacetylene xestonariene J (1), bearing a rare 2,4-dibromo-1-ene-3-yne terminal in the molecule, along with two known related analogues (2 and 3), was obtained from Chinese marine sponge Xestospongia testudinaria. Its structure was determined on the basis of detailed spectroscopic analysis and comparison with literature data.

     

A new bioactive steroidal ketone from the South China Sea sponge Xestospongia testudinaria

A new steroidal ketone (1), with an ergosta-22,25-diene side chain, was obtained from the South China Sea marine sponge Xestospongia testudinaria. The structure of 1 was determined on the basis of detailed spectroscopic analysis and by comparison with literature. Compound 1 exhibited significant inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), a key target for the treatment of type II diabetes and obesity, with an IC₅₀ value of 4.27 ± 0.55 μM, which is comparable with the positive control oleanolic acid (IC₅₀ = 2.63 ± 0.22 μM).     

Brominated polyunsaturated lipids with protein tyrosine phosphatase-1B inhibitory activity from Chinese marine sponge Xestospongia testudinaria

A new brominated polyunsaturated lipid, methyl (E,E)-14,14-dibromo-4,6,13-tetradecatrienoate (1), along with three known related analogues (2–4), were isolated from the Et₂O-soluble portion of the acetone extract of Chinese marine sponge Xestospongia testudinaria treated with diazomethane. The structure of the new compound was elucidated by detailed spectroscopic analysis and by comparison with literature data. Compound 3 exhibited significant inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), a key target for the treatment of type II diabetes and obesity, with an IC₅₀ value of 5.30 ± 0.61 μM, when compared to the positive control oleanolic acid (IC₅₀ = 2.39 ± 0.26 μM).     

Leucanone A and naamine J,glycerol ether lipid and imidazole alkaloid from the marine sponge Leucandra sp.

Chemical investigation on CH₂Cl₂ extract of the marine sponge Leucandra sp. afforded two new compounds named leucanone A (1) and naamine J (2), together with eight known compounds (3–10). Their structures were elucidated on the basis of NMR spectroscopic analyses, and comparing with the literature. The cytotoxic activities of the compounds were evaluated against four cancer cell lines, and compound 2 showed mild cytotoxic activities against MCF-7, A549, HeLa, and PC9 cancer cell lines with IC₅₀ values in the range of 20.1–45.3 μM.     

A new thiophene and two new monoterpenoids from Xanthium sibiricum

Three new compounds (1–3), together with six known compounds (4–9), were isolated from the fruits of Xanthium sibiricum. The structures and the absolute configurations of sibiricumthionol (1), (+)-(5Z)-6-methyl-2-ethenyl-5-hepten-1,2,7-triol [(+)-2], ( ? )-(5Z)-6-methyl-2-ethenyl-5-hepten-1,2,7-triol [( ? )-2], (2E,4E,1′S, 2′R, 4′S, 6′R)-dihydrophaseic acid (3), (+)-xanthienopyran [(+)-4] and ( ? )-xanthienopyran [( ? )-4] were established by extensive spectroscopic analyses, X-ray crystallographic analysis, ECCD analysis and ECD calculations. Caffeic acid (7) and caffeic acid ethyl ester (8) weekly inhibited α-glucosidase enzymatic activity by 44.5% and 40.2%, respectively, at 40 μM. Protocatechuic acid (9) selectively exhibited cytotoxicity against HepG2 cell lines, with an IC₅₀ value of 2.92 μM.     

中国南海海绵Spheciospongia sp.中的甾体化合物

目的研究中国南海海绵Spheciospongia sp.的化学成分。方法采用多种色谱方法分离纯化,依据理化性质、波谱数据和文献对照的方法鉴定结构。结果从中国南海海绵Spheciospongia sp.石油醚提取物中分离鉴定了6个甾体类化合物:胆甾醇(cholesterol,1),胆甾-4-稀-3-酮(cho-lest-4-en-3-one,2),胆甾-3,6-二酮(cholest-3,6-dione,3),3β-羟基-胆甾-5-稀-7-酮(3β-hydroxy-cholest-5-en-7-one,4),6β-羟基-胆甾-4-稀-3-酮(6β-hydroxy-cholest-4-en-3-one,5),胆甾-3β,5α,6β-三醇(cholest-3β,5α,6β-triol,6)。结论化合物2-6为首次从该属海绵中分离得到。     

3-Oxo-axisonitrile-3, a new sesquiterpene isocyanide from the Chinese marine sponge Acanthella sp.

A new sesquiterpene isocyanide, 3-oxo-axisonitrile-3 (1), with a spiro [5 Alvi, K.A., Tenenbaum, L. and Crews, P. 1991. J. Nat. Prod., 54: 71[Crossref], [PubMed], [Web of Science ®] , [Google Scholar],6 Burgoyne, D.L. and Dumdei, E.J. 1993. Tetrahedron, 49: 4503 [Google Scholar]] decane skeleton (spiroaxane) together with a known related sesquiterpene isonitrile (2), sesquiterpene isothiocyanates (3–8) and two diterpene isonitriles (9, 10) have been isolated from the Chinese marine sponge Acanthella sp. The structure of 1 has been determined on the basis of spectroscopic analysis.     

Three new polyunsaturated lipids from a Guangxi marine sponge Haliclona sp.

Three new polyunsaturated lipids, (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraen-3-one (1), (6Z,9Z,12Z,15Z)-1-bromooctadeca-6,9,12,15-tetraen-3-one (2), and (Z)-ethyl docos-5-enoate (3), together with two known polyunsaturated lipids, 4(Z),7(Z),10(Z)-tridecatrienoic acid (4) and (6Z,9Z,12Z,15Z)-octadeca-1,6,9,12,15-pentaen-3-one (5), were isolated from the marine sponge Haliclona sp., which was collected from Guangxi, using HSCCC and HPLC methods. Chemical structures of the five compounds were elucidated by spectroscopic techniques.     

Brominated derivatives from the Chinese sponge Pseudoceratina sp.

Chemical examination of the marine sponge Pseudoceratina sp. resulted in the isolation and characterization of two new dibromotyrosine-derived metabolites (1-2), and a new histamine-derived alkaloid (3), along with eight known dibromotyrosine based products. Their structures were elucidated on the basis of IR, 1D and 2D NMR, and MS spectral data analyses.     

Seimisochromenes A and B: two new dihydroisochromenes from the endophytic fungus,Seimatosporium sp.

Two new dihydroisochromenes, named seimisochromenes A and B (1 and 2), were isolated from an endophytic fungus, Seimatosporium sp. The structures of seimisochromenes A and B have been determined from 1D (¹H and ¹³C NMR spectra) and 2D (COSY, HMQC, HMBC, and NOESY) NMR experiments.     

3-Oxo-axisonitrile-3, a new sesquiterpene isocyanide from the Chinese marine sponge Acanthella sp

A new sesquiterpene isocyanide, 3-oxo-axisonitrile-3 (1), with a spiro [5,6] decane skeleton (spiroaxane) together with a known related sesquiterpene isonitrile (2), sesquiterpene isothiocyanates (3-8) and two diterpene isonitriles (9, 10) have been isolated from the Chinese marine sponge Acanthella sp. The structure of 1 has been determined on the basis of spectroscopic analysis.     

O-methyl nakafuran-8 lactone, a new sesquiterpenoid from a hainan marine sponge Dysidea sp

A new sesquiterpenoid, O-methyl nakafuran-8 lactone (1) has been isolated from a Hainan sponge Dysidea sp. and the structure of the new compound proposed by spectral data, was confirmed by X-ray diffraction analysis. The complete ¹H- and ¹³C-NMR assignments were made on the basis of detailed 2D NMR spectral analysis.

Compound 1 showed strong inhibitory bioactivity against PTP1B with IC₅₀ value of 1.58 μM.     

中国南海海绵Cinachyrella sp.的化学成分研究

目的 研究中国南海海绵Cinachyrella sp.的化学成分。方法 采用硅胶柱色谱、Sephadex LH-20凝胶色谱及半制备型高效液相色谱对Cinachyrella sp.海绵中的化学成分进行分离和纯化,通过核磁共振、质谱、紫外等解析化合物结构并结合文献中的数据对比鉴定所得化合物,并且对分离得到的化合物进行抗菌活性测试。结果 从Cinachyrella sp.海绵中分离鉴定了15个化合物：喹啉-4-甲醛肟(1)、环(L-脯氨酸-L-缬氨酸)二肽(2)、环(L-脯氨酸-L-亮氨酸)二肽 (3)、环(L-脯氨酸-L-异亮氨酸)二肽(4)、苯甲酸(5)、苯乙酸(6)、苯乙酰胺(7)、胸腺嘧啶(8)、尿嘧啶 (9)、腺嘌呤核苷(10)、胸腺嘧啶脱氧核苷(11)、尿嘧啶苷(12)、3-吲哚甲醛(13)、吲哚乙酰胺(14)、吲哚-3-甲酸(15)。结论 化合物1～4均为首次从该属海绵中分离得到;抗菌活性测试中化合物2～4对6种细菌MIC值均大于64 μg/mL,提示其抑菌活性较弱。     

西沙群岛海绵Pseudoceratina sp.化学成分研究

目的 对中国南海西沙群岛海绵Pseudoceratina sp.的化学成分进行研究。方法 利用薄层色谱、硅胶柱层析、高效液相色谱（HPLC）和中压制备色谱（MPLC）等方法对海绵粗提物中的化学成分进行分离纯化;运用核磁共振、质谱等方法,并与文献中的理化数据比对,鉴定化合物的结构。结果 从西沙海绵Pseudoceratina sp.中分离鉴定到11个二倍半萜类化合物：sesterstatin 7(1)、crystalline 12-epi-scalarin(2)、12-epi-scalarin(3)、hyrtiolide(4)、25-dehydroxy-12-epi-scalarin(5)、scalarolide acetate(6)、sesterstatin 6(7)、(Z)-neomanoalide(8)、(+)-(6E)-neomanoalide(9)、luffariellolide(10a,b)、acantholide C(11a,b)。结论 从西沙海绵Pseudoceratina sp.中分离得到了11个已知的二倍半萜类化合物,分别属于scalarane型和manoalide-...     

海绵共附生放线菌Saccharopolyspora sp.nov中抗肿瘤活性成分的研究

羽毛山海绵（Mycale plumose）来源的糖多孢菌（Saccharopolyspora sp.nov SP2-10）具有诱导肿瘤细胞坏死的活性。本文对其发酵产物的活性部位乙酸乙酯层进行活性追踪分离．共得到7个化合物；利用理化性质和波谱学方法鉴定它们的结构分别为胆甾醇、邻苯二甲酸二异丁酯、4（2，4-二羟基苯甲酰氨基）苯甲酸、苯丙胺酸、脱氧鸟苷、鸟苷和N-乙酰酪胺I并初步评价上述化合物的抗肿瘤活性，结果表明，邻苯二甲酸二异丁酯显示强细胞毒活性。     

Fasciospyrinadine,a novel sesquiterpene pyridine alkaloid from a Guangxi sponge Fasciospongia sp.

Fasciospyrinadine (1), a novel sesquiterpene pyridine alkaloid with a previously unreported skeleton featuring a monocyclicfarnesane moiety attached to a 3-methylenepyridine residue, was isolated from the sponge Fasciospongia sp. from Weizhou Island, Guangxi Autonomous Region. The structure and the relative stereochemistry of 1 were elucidated on the basis of extensive analysis of its 1D and 2D NMR spectroscopic techniques.     

西沙海绵Dysidea granulosa 化学成分研究

目的 研究中国西沙群岛海绵Dysidea granulosa的化学成分。 方法 利用薄层色谱、硅胶色谱、Sephadex LH-20色谱、MPLC、半制备HPLC等方法对化学成分进行分离纯化;通过NMR、MS等方法,并结合文献,鉴定化合物的结构。结果 从西沙海绵Dysidea granulosa的甲醇粗提取物中,分离得到6个化合物： Honulactone A (1), Honulactone B(2), Honulactone E (3), Honulactone F (4), 2-(2’,4’-Dibromophenoxy)-4,6-dibromophenol (5), 3,5-Dibromo-6-chloro-2-(2,4- dibromophenoxy)phenol (6)。结论 化合物1、2、3、4均为首次从该种海绵中分离得到。