• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

利马西平A - F,来自印度尼西亚微球菌属的吡咯并[1,4]苯二氮䓬类抗生素

Limazepines A-F, pyrrolo[1,4]benzodiazepine Antibiotics from an Indonesian Micrococcus sp.

作者信息

Fotso Serge, Zabriskie T Mark, Proteau Philip J, Flatt Patricia M, Santosa Dwi Andreas, Mahmud Taifo

机构信息

Department of Pharmaceutical Sciences, College of Pharmacy, Oregon State University, Corvallis, Oregon 97331-3507, USA

出版信息

J Nat Prod. 2009 Apr;72(4):690-5. doi: 10.1021/np800827w.

DOI:10.1021/np800827w
PMID:19388705
Abstract

In our screening of Indonesian microorganisms for novel bioactive natural products we have isolated seven new compounds, designated as limazepines A, B1 and B2 (isolated as an isomeric mixture), C, D, E, and F, from the culture broth of Micrococcus sp. strain ICBB 8177. In addition, the known natural products prothracarcin and 7-O-succinylmacrolactin A, as well as two previously reported synthetic compounds, 2-amino-3-hydroxy-4-methoxybenzoic acid methyl ester and 4-ethylpyrrole-2-carboxaldehyde, were obtained from the extract. Chemical structures were determined by spectroscopic methods and by comparison with the NMR data of structurally related compounds. The limazepines belong to the growing group of the pyrrolo[1,4]benzodiazepine antitumor antibiotics isolated from various soil bacteria. Limazepines B1/B2 mixture, C, and E were active against the Gram-positive bacterium Staphylococcus aureus and the Gram-negative bacterium Escherichia coli. Limazepine D was also active against S. aureus, but was not active against E. coli. Interestingly, only the limazepines B1/B2 mixture and D were active against Pseudomonas aeruginosa.

摘要

在我们对印度尼西亚微生物进行新型生物活性天然产物筛选的过程中,我们从微球菌属菌株ICBB 8177的培养液中分离出了7种新化合物,分别命名为利马泽平A、B1和B2(以异构体混合物形式分离)、C、D、E和F。此外,还从提取物中获得了已知的天然产物原蒽环素和7 - O - 琥珀酰大环内酯A,以及两种先前报道的合成化合物,2 - 氨基 - 3 - 羟基 - 4 - 甲氧基苯甲酸甲酯和4 - 乙基吡咯 - 2 - 甲醛。通过光谱方法并与结构相关化合物的核磁共振数据进行比较确定了化学结构。利马泽平属于从各种土壤细菌中分离出的不断增加的吡咯并[1,4]苯并二氮杂䓬类抗肿瘤抗生素。利马泽平B1/B2混合物、C和E对革兰氏阳性菌金黄色葡萄球菌和革兰氏阴性菌大肠杆菌有活性。利马泽平D对金黄色葡萄球菌也有活性,但对大肠杆菌无活性。有趣的是,只有利马泽平B1/B2混合物和D对铜绿假单胞菌有活性。

相似文献

1
Limazepines A-F, pyrrolo[1,4]benzodiazepine Antibiotics from an Indonesian Micrococcus sp.利马西平A - F,来自印度尼西亚微球菌属的吡咯并[1,4]苯二氮䓬类抗生素
J Nat Prod. 2009 Apr;72(4):690-5. doi: 10.1021/np800827w.
2
Two new members of streptothricin class antibiotics from Streptomyces qinlingensis sp. nov.来自秦岭链霉菌新种的两种新的链丝菌素类抗生素成员
J Antibiot (Tokyo). 2007 Dec;60(12):739-44. doi: 10.1038/ja.2007.96.
3
Aranciamycins I and J, Antimycobacterial Anthracyclines from an Australian Marine-Derived Streptomyces sp.橙青霉素 I 和 J,一种来源于澳大利亚海洋衍生链霉菌的抗分枝杆菌蒽环类抗生素
J Nat Prod. 2015 Apr 24;78(4):949-52. doi: 10.1021/acs.jnatprod.5b00095. Epub 2015 Mar 19.
4
Antimicrobial activity of some heterocyclic derivatives.一些杂环衍生物的抗菌活性。
Microbios. 1995;82(331):87-93.
5
Abyssomicin I, a modified polycyclic polyketide from Streptomyces sp. CHI39.阿博霉素 I,一种来源于链霉菌 CHI39 的改良多环聚酮化合物。
J Nat Prod. 2010 Nov 29;73(11):1943-6. doi: 10.1021/np100292h. Epub 2010 Oct 28.
6
Wollamides: antimycobacterial cyclic hexapeptides from an Australian soil Streptomyces.沃拉米德类:源自澳大利亚土壤链霉菌的抗分枝杆菌环六肽。
Org Lett. 2014 Oct 3;16(19):5120-3. doi: 10.1021/ol502472c. Epub 2014 Sep 17.
7
Maklamicin, an antibacterial polyketide from an endophytic Micromonospora sp.马卡霉素,一种来自内生枝顶孢属的抗菌聚酮化合物
J Nat Prod. 2011 Apr 25;74(4):670-4. doi: 10.1021/np100727h. Epub 2011 Mar 9.
8
Triterpenoid saponins from Symplocos lancifolia.石笔木中的三萜皂苷。
J Nat Prod. 2011 Feb 25;74(2):163-8. doi: 10.1021/np100502y. Epub 2011 Feb 2.
9
Lyngbyazothrins A-D, antimicrobial cyclic undecapeptides from the cultured Cyanobacterium lyngbya sp.林氏藻毒素A-D,从培养的鞘丝藻属蓝细菌中提取的具有抗菌活性的环状十一肽
J Nat Prod. 2009 Aug;72(8):1373-8. doi: 10.1021/np8007792.
10
Antibacterial action of a heat-stable form of L-amino acid oxidase isolated from king cobra (Ophiophagus hannah) venom.从眼镜王蛇(Ophiophagus hannah)毒液中分离得到的热稳定型 L-氨基酸氧化酶的抗菌作用。
Comp Biochem Physiol C Toxicol Pharmacol. 2011 Mar;153(2):237-42. doi: 10.1016/j.cbpc.2010.11.001. Epub 2010 Nov 6.

引用本文的文献

1
Synthesis of 2,2'-bipyrrole-5-carboxaldehydes and their application in the synthesis of B-ring functionalized prodiginines and tambjamines.2,2'-联吡咯-5-甲醛的合成及其在B环官能化的灵菌红素和坦贝胺合成中的应用。
Tetrahedron. 2014 Sep 30;69(39):8375-8385. doi: 10.1016/j.tet.2013.07.067. Epub 2013 Jul 26.
2
Unveiling the bioactive potential of Actinomycetota from the Tagus River estuary.揭示塔古斯河口放线菌门的生物活性潜力。
Int Microbiol. 2024 Oct;27(5):1357-1372. doi: 10.1007/s10123-024-00483-0. Epub 2024 Jan 18.
3
An ultrasound assisted, ionic liquid-molecular iodine synergy driven efficient green synthesis of pyrrolobenzodiazepine-triazole hybrids as potential anticancer agents.
超声辅助、离子液体-分子碘协同驱动高效绿色合成吡咯并苯二氮卓-三唑杂化物作为潜在抗癌剂。
Front Pharmacol. 2023 May 5;14:1168566. doi: 10.3389/fphar.2023.1168566. eCollection 2023.
4
Amycolatopsis camponoti sp. nov., new tetracenomycin-producing actinomycete isolated from carpenter ant Camponotus vagus.新型放线菌 Amycolatopsis camponoti sp. nov.,可产生tetracenomycin,从木匠蚁 Camponotus vagus 中分离得到。
Antonie Van Leeuwenhoek. 2022 Apr;115(4):533-544. doi: 10.1007/s10482-022-01716-w. Epub 2022 Feb 26.
5
Mining Indonesian Microbial Biodiversity for Novel Natural Compounds by a Combined Genome Mining and Molecular Networking Approach.通过组合基因组挖掘和分子网络方法挖掘印度尼西亚微生物生物多样性中的新型天然化合物。
Mar Drugs. 2021 May 28;19(6):316. doi: 10.3390/md19060316.
6
Draft Genome Sequence of the Pristinamycin-Producing Strain Streptomyces sp. SW4, Isolated from Soil in Nusa Kambangan, Indonesia.从印度尼西亚努山塔拉坎邦土壤中分离出的产普那霉素菌株链霉菌SW4的基因组序列草图
Microbiol Resour Announc. 2018 Aug 23;7(7). doi: 10.1128/MRA.00912-18. eCollection 2018 Aug.
7
Novel pathway of 3-hydroxyanthranilic acid formation in limazepine biosynthesis reveals evolutionary relation between phenazines and pyrrolobenzodiazepines.在利马嗪生物合成中 3-羟基邻氨基苯甲酸形成的新途径揭示了吩嗪类化合物和吡咯并苯二氮䓬类化合物之间的进化关系。
Sci Rep. 2018 May 17;8(1):7810. doi: 10.1038/s41598-018-26179-w.
8
An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines.吡咯并[1,4]苯并二氮杂卓合成的最新进展
Molecules. 2016 Jan 28;21(2):154. doi: 10.3390/molecules21020154.
9
Pyrrolobenzodiazepines (PBDs) do not bind to DNA G-quadruplexes.吡咯并苯二氮卓类化合物(PBDs)不与DNA G-四链体结合。
PLoS One. 2014 Aug 18;9(8):e105021. doi: 10.1371/journal.pone.0105021. eCollection 2014.
10
Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines.吡咯并苯二氮䓬类的生物合成、合成和生物活性。
Med Res Rev. 2012 Mar;32(2):254-93. doi: 10.1002/med.20212. Epub 2010 Jun 13.