来自深海阿拉斯加 Latrunculia 属海绵的抗感染 discorhabdins。
Anti-infective discorhabdins from a deep-water alaskan sponge of the genus Latrunculia.
机构信息
Department of Pharmacognosy and the National Center for Natural Products Research (NCNPR), School of Pharmacy, The University of Mississippi, University, Mississippi 38677, USA.
出版信息
J Nat Prod. 2010 Mar 26;73(3):383-7. doi: 10.1021/np900281r.
Abstract
Bioassay- and LC-MS-guided fractionation of a methanol extract from a new deep-water Alaskan sponge species of the genus Latrunculia resulted in the isolation of two new brominated pyrroloiminoquinones, dihydrodiscorhabdin B and discorhabdin Y (2), along with six known pyrroloiminoquinone alkaloids, discorhabdins A (3), C (4), E (5), and L (6), dihydrodiscorhabdin C (7), and the benzene derivative 8. Compounds 3, 4, and 7 exhibited anti-HCV activity, antimalarial activity, and selective antimicrobial activity. Although compounds 3 and 7 displayed potent and selective in vitro antiprotozoal activity, Plasmodium berghei-infected mice did not respond to these metabolites due to their toxicity in vivo.
摘要
从一种新的阿拉斯加深海海绵属拉特朗库利阿（Latrunculia）物种的甲醇提取物中进行生物测定和 LC-MS 引导的分段，分离得到两种新的溴化吡咯并 iminoquinone，二氢 discorhabdin B 和 discorhabdin Y（2），以及六种已知的吡咯并 iminoquinone 生物碱，discorhabdins A（3）、C（4）、E（5）和 L（6），二氢 discorhabdin C（7）和苯衍生物 8。化合物 3、4 和 7 表现出抗 HCV 活性、抗疟原虫活性和选择性抗菌活性。尽管化合物 3 和 7 表现出强大和选择性的体外抗原生动物活性，但感染疟原虫伯氏疟原虫（Plasmodium berghei）的小鼠对这些代谢物没有反应，因为它们在体内的毒性。
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1
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3
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J Org Chem. 2008 Nov 21;73(22):9133-6. doi: 10.1021/jo801622n. Epub 2008 Oct 15.
4
The current state of ab initio calculations of optical rotation and electronic circular dichroism spectra.
J Phys Chem A. 2007 Dec 6;111(48):12057-68. doi: 10.1021/jp075046u. Epub 2007 Nov 7.
5
Theoretical calculation of electronic circular dichroism of the rotationally restricted 3,8''-biflavonoid morelloflavone.
J Org Chem. 2007 Nov 23;72(24):9010-7. doi: 10.1021/jo071134z. Epub 2007 Oct 24.
6
Application of electronic circular dichroism in configurational and conformational analysis of organic compounds.
Chem Soc Rev. 2007 Jun;36(6):914-31. doi: 10.1039/b515476f. Epub 2007 Feb 5.
7
Determination of the absolute configuration of a chiral oxadiazol-3-one calcium channel blocker, resolved using chiral chromatography, via concerted density functional theory calculations of its vibrational circular dichroism, electronic circular dichroism, and optical rotation.
J Org Chem. 2007 Jun 22;72(13):4707-15. doi: 10.1021/jo070302k. Epub 2007 May 22.
8
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J Nat Prod. 2006 Jul;69(7):1034-40. doi: 10.1021/np0601399.
9
Pyrroloiminoquinone and related metabolites from marine sponges.
Nat Prod Rep. 2005 Feb;22(1):62-72. doi: 10.1039/b407299p. Epub 2005 Jan 4.
10
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Antimicrob Agents Chemother. 2004 Nov;48(11):4450-2. doi: 10.1128/AAC.48.11.4450-4452.2004.
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