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平卧凹顶藻中的劳伦德卡玛琳烯A - B和劳伦德卡玛炔烯A - B,卤代非萜类C(15) - 聚酮化合物。

Laurendecumallenes A-B and laurendecumenynes A-B, halogenated nonterpenoid C(15)-acetogenins from the marine red alga Laurencia decumbens.

作者信息

Ji Nai-Yun, Li Xiao-Ming, Li Ke, Wang Bin-Gui

机构信息

Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Qingdao, People's Republic of China.

出版信息

J Nat Prod. 2007 Sep;70(9):1499-502. doi: 10.1021/np0701172. Epub 2007 Aug 22.

Abstract

Four new halogenated nonterpenoid C(15)-acetogenins, 4:7,6:13-bisepoxy-9,10-diol-1,12-dibromopentadeca-1,2-diene (1, laurendecumallene A), 4:7,6:12-bisepoxy-9,10-diol-1,13-dibromopentadeca-1,2-diene (2, laurendecumallene B), (3Z)-6:10,7:13-bisepoxy-12-bromo-9-hydroperoxylpentadeca-3-en-1-yne (3, laurendecumenyne A), and (3Z)-6:10,9:13-bisepoxy-12-bromo-7-chloropentadeca-3-en-1-yne (4, laurendecumenyne B), together with one known halogenated C(15)-acetogenin elatenyne (5) were isolated and identified from the organic extract of the marine red alga Laurencia decumbens. Their structures and relative stereochemistry were established by means of spectroscopic analysis including UV, IR, high-resolution electrospray ionization mass spectrometry (HRESIMS), and 1D and 2D NMR techniques. All these metabolites were submitted for the cytotoxic assay against tumor cell line A549 (human lung adenocarcinoma), but all of them were found inactive (IC(50) > 10 microg/mL).

摘要

从平卧凹顶藻的有机提取物中分离并鉴定出四种新的卤代非萜类C(15)-产乙酸素,即4:7,6:13-双环氧-9,10-二醇-1,12-二溴十五碳-1,2-二烯(1,劳伦癸三烯A)、4:7,6:12-双环氧-9,10-二醇-1,13-二溴十五碳-1,2-二烯(2,劳伦癸三烯B)、(3Z)-6:10,7:13-双环氧-12-溴-9-氢过氧十五碳-3-烯-1-炔(3,劳伦癸炔A)和(3Z)-6:10,9:13-双环氧-12-溴-7-氯十五碳-3-烯-1-炔(4,劳伦癸炔B),以及一种已知的卤代C(15)-产乙酸素elatenyne(5)。通过紫外光谱(UV)、红外光谱(IR)、高分辨电喷雾电离质谱(HRESIMS)以及一维和二维核磁共振技术等光谱分析手段确定了它们的结构和相对立体化学。所有这些代谢产物均针对肿瘤细胞系A549(人肺腺癌)进行了细胞毒性试验,但发现它们均无活性(半数抑制浓度IC(50)>10 μg/mL)。

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