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N-N-Coupled Indolo-sesquiterpene Atropo-Diastereomers from a Marine-Derived Actinomycete
Zhang, QB; Mandi, A; Li, SM; Chen, YC; Zhang, WJ; Tian, XP; Zhang, HB; Li, HX; Zhang, WM; Zhang, S; Ju, JH; Kurtan, T; Zhang, CS;;
AbstractFour new indolo-sesquiterpenes dixiamycins A (1) and B (2), oxiamycin (3), and chloroxiamycin (4) were isolated from a marine-derived Actinomycete and characterized, together with the known compound xiamycin A (5). Dixiamycins A (1) and B (2) are the first examples of atropisomerism of naturally occurring N-N-coupled atropo-diastereomers, with a dimeric indolo-sesquiterpene skeleton and a stereogenic N-N axis between sp3-hybridized nitrogen atoms. Solution TDDFT ECD calculations were utilized to ascertain the axial chirality of 1 and 2, and rotational barriers and transitions states of the inversion were calculated. Oxiamycin (3) contains a seven-membered 2,3,4,5-tetrahydrooxepine ring. The two dimeric compounds 1 and 2 showed better antibacterial activities than the monomers 35.
Department[Mandi, Attila; Kurtan, Tibor] Debrecen Univ Med, Dept Organ Chem, H-4010 Debrecen, Hungary; [Zhang, Qingbo; Li, Sumei; Zhang, Wenjun; Tian, Xinpeng; Zhang, Haibo; Li, Huixian; Zhang, Si; Ju, Jianhua; Zhang, Changsheng] Chinese Acad Sci, Key Lab Marine Bioresources Sustainable Utilizat, RNAM Ctr Marine Microbiol, Guangdong Key Lab Marine Mat Med,S China Sea Inst, Guangzhou 510301, Guangdong, Peoples R China; [Zhang, Qingbo] Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China; [Chen, Yuchan; Zhang, Weimin] Guangdong Inst Microbiol, Guangzhou 510070, Guangdong, Peoples R China
KeywordNatural Products Terpenoids Xiamycin Atropisomerism Configuration Determination Density Functional Calculations
Subject AreaChemistry, Organic
Funding ProjectLMB
WOS IDWOS:000308580800016
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Document Type期刊论文
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GB/T 7714
Zhang, QB,Mandi, A,Li, SM,et al. N-N-Coupled Indolo-sesquiterpene Atropo-Diastereomers from a Marine-Derived Actinomycete[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2012(27):5256-5262.
APA Zhang, QB.,Mandi, A.,Li, SM.,Chen, YC.,Zhang, WJ.,...& Indolo-sesquiterpene Atropo-Diastereomers from a Marine-Derived Actinomycete.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(27),5256-5262.
MLA Zhang, QB,et al."N-N-Coupled Indolo-sesquiterpene Atropo-Diastereomers from a Marine-Derived Actinomycete".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .27(2012):5256-5262.
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