两种细胞毒性马良酰胺 C 的立体异构体，8-表马良酰胺 C 和 8-O-乙酰基-8-表马良酰胺 C，来自海洋蓝细菌 Lyngbya majuscula。
Two cytotoxic stereoisomers of malyngamide C, 8-epi-malyngamide C and 8-O-acetyl-8-epi-malyngamide C, from the marine cyanobacterium Lyngbya majuscula.
机构信息
Institute for Pharmaceutical Biology, University of Bonn, Bonn, Germany.
出版信息
Phytochemistry. 2010 Oct;71(14-15):1729-35. doi: 10.1016/j.phytochem.2010.07.001. Epub 2010 Aug 9.
Abstract
Two epimers of malyngamide C, 8-O-acetyl-8-epi-malyngamide C (1) and 8-epi-malyngamide C (3) have been isolated along with known compounds 6-O-acetylmalyngamide F (5), H (6), J (7) K (8), and characterized from a Grenada field collection of the marine cyanobacterium Lyngbya majuscula. The structures of these compounds were deduced by 1D and 2D NMR spectroscopic and mass spectral data interpretation. Absolute configurations were determined by a combination of CD-spectroscopy, chemical degradation and the variable temperature Mosher's method. Compounds 1-5, 7 and 8 displayed moderate cytotoxicity to NCI-H460 human lung tumor and neuro-2a cancer cell lines, with IC(50) values ranging between 0.5 and 20 microg/mL.
摘要
两种马良酰胺 C 的差向异构体，8-O-乙酰-8-差向马良酰胺 C（1）和 8-差向马良酰胺 C（3），以及已知化合物 6-O-乙酰马良酰胺 F（5）、H（6）、J（7）、K（8），从格林纳达海洋蓝细菌 Lyngbya majuscula 的实地采集物中分离出来并进行了表征。这些化合物的结构通过 1D 和 2D NMR 光谱和质谱数据解释推导得出。通过 CD 光谱、化学降解和变温 Mosher 法的组合确定了绝对构型。化合物 1-5、7 和 8 对 NCI-H460 人肺癌肿瘤和神经-2a 癌细胞系表现出中等的细胞毒性，IC50 值在 0.5 和 20 μg/mL 之间。
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本文引用的文献
1
Isolation and biological evaluation of 8-epi-malyngamide C from the Floridian marine cyanobacterium Lyngbya majuscula.从佛罗里达海洋蓝藻 Lyngbya majuscula 中分离并生物评价 8-表马缨丹酰胺 C。
J Nat Prod. 2010 Mar 26;73(3):463-6. doi: 10.1021/np900614n.
2
Palmyramide A, a cyclic depsipeptide from a Palmyra Atoll collection of the marine cyanobacterium Lyngbya majuscula.从 Palmyra 环礁收集的海洋蓝细菌 Lyngbya majuscula 中分离得到的环肽 Palmyramide A。
J Nat Prod. 2010 Mar 26;73(3):393-8. doi: 10.1021/np900428h.
3
Malyngamide X: the first (7R)-lyngbic acid that connects to a new tripeptide backbone from the Thai sea hare Bursatella leachii.马琳酰胺X：首个来自泰国海兔（Bursatella leachii）的与新三肽骨架相连的(7R)-灵菌酸。
Chem Asian J. 2007 Jan 8;2(1):114-22. doi: 10.1002/asia.200600219.
4
Bioactive natural products from marine cyanobacteria for drug discovery.用于药物研发的海洋蓝藻生物活性天然产物
Phytochemistry. 2007 Apr;68(7):954-79. doi: 10.1016/j.phytochem.2007.01.012. Epub 2007 Mar 2.
5
Structure and biosynthesis of the jamaicamides, new mixed polyketide-peptide neurotoxins from the marine cyanobacterium Lyngbya majuscula.来自海洋蓝藻巨大鞘丝藻的新型聚酮肽混合神经毒素——牙买加酰胺的结构与生物合成
Chem Biol. 2004 Jun;11(6):817-33. doi: 10.1016/j.chembiol.2004.03.030.
6
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J Exp Ther Oncol. 2002 Jul-Aug;2(4):228-36. doi: 10.1046/j.1359-4117.2002.01038.x.
7
Nitrogen-containing metabolites from marine cyanobacteria.来自海洋蓝藻细菌的含氮代谢产物。
Alkaloids Chem Biol. 2001;57:75-184. doi: 10.1016/s0099-9598(01)57003-0.
8
New malyngamides from the Hawaiian cyanobacterium Lyngbya majuscula.来自夏威夷蓝藻巨大鞘丝藻的新型马琳酰胺类化合物。
J Nat Prod. 2000 Dec;63(12):1599-602. doi: 10.1021/np000250t.
9
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10
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