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从一种未描述过的菲律宾强枝海绵属海洋海绵中分离出的一种新的间二萜二聚体。

A new meroditerpenoid dimer from an undescribed Philippine marine sponge of the genus Strongylophora.

作者信息

Balbin-Oliveros M, Edrada R A, Proksch P, Wray V, Witte L, Van Soest R W

机构信息

College of Pharmacy, University of the Philippines Manila, Taft Avenue, Manila, Philippines.

出版信息

J Nat Prod. 1998 Jul;61(7):948-52. doi: 10.1021/np980005y.

DOI:10.1021/np980005y
PMID:9677282
Abstract

An undescribed Philippine marine sponge of the genus Strongylophora yielded a new meroditerpenoid-strongylophorine dimer (1) and the known meroditerpenoids, strongylophorine-2 (2), strongylophorine-3 (3), and strongylophorine-4 (4). The structures of the compounds were established on the basis of NMR spectroscopic and mass spectrometric data. The position of the inter-unit linkage in the new compound was elucidated after methylation and 1D 1H NOE difference experiments. This is the first report wherein the1H and 13C NMR data of the strongylophorine congeners are fully and unambiguously assigned on the basis of 2D NMR spectroscopy. Compounds 2 and 3 exhibited slight activity against Micrococcus luteus and Salmonella typhii, respectively. Compound 3 was active against the phytopathogenic fungusCladosporium cucumerinum and also against the neonate larvae of the polyphagous pest insectSpodoptera littoralis (EC50 of 69 [+/-0.48 (S.E.)] ppm) when incorporated into artificial diet. Compound 1 was found to be the most active in the brine shrimp lethality test with a LC50 of 10.5 [+/-0.43 (S.E.)] microg/mL.

摘要

一种未被描述的菲律宾强叶海绵属海洋海绵产生了一种新的半萜类化合物——强叶海绵素二聚体(1)以及已知的半萜类化合物强叶海绵素 -2(2)、强叶海绵素 -3(3)和强叶海绵素 -4(4)。这些化合物的结构是基于核磁共振光谱和质谱数据确定的。在甲基化和一维氢核Overhauser效应(1D 1H NOE)差异实验后,阐明了新化合物中单元间连接的位置。这是首次基于二维核磁共振光谱对强叶海绵素同系物的氢谱和碳谱数据进行全面且明确归属的报道。化合物2和3分别对藤黄微球菌和伤寒沙门氏菌表现出轻微活性。当将化合物3掺入人工饲料中时,它对植物致病真菌黄瓜枝孢以及多食性害虫斜纹夜蛾的新生幼虫具有活性(半数有效浓度(EC50)为69 [±0.48(标准误差)] ppm)。在卤虫致死试验中发现化合物1活性最高,其半数致死浓度(LC50)为10.5 [±0.43(标准误差)] μg/mL。

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