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(+/-)-Meliviticines A and B: Rearranged prenylated acetophenone derivatives from Melicope viticina and their antimicrobial activity
Li, Wei2; Rao, Li; Liu, Yu; He, Qian; Fan, Yue; You, Yun-Xia; Su, Yu; Hu, Feng; Xu, You-Kai; Lin, Bin4; Yin, Sheng2; Zhang, Chuan-Rui
2019
Source PublicationBIOORGANIC CHEMISTRY
ISSN0045-2068
Volume90Issue:xPages:-
Abstract

Two new prenylated acetophenone derivatives racemates, meliviticines A (1) and B (2) with unprecedented rearranged skeletons, were isolated from Melicope viticina. Subsequent chiral resolution led to the separation of two pairs of enantiomers, (+/-)-meliviticines A (1a/1b) and (+/-)-meliviticines B (2a/2b). Their structures including absolute configurations were elucidated by extensive spectroscopic data, electronic circular dichroism analysis, and X-ray crystallography. A plausible biosynthetic pathway of 1 and 2, involving ring cleavage and rearrangement of the prenylated acetophenone backbone was proposed. All the isolates showed moderate antimicrobial activities with MIC values of 25-50 mu g/mL against several bacterial and fungal strains.

KeywordMelicope viticina Prenylated acetophenone derivatives Absolute configuration Antimicrobial activity
Subject AreaBiochemistry & Molecular Biology ; Chemistry
DOI10.1016/j.bioorg.2019.103099
Indexed BySCI
Language英语
WOS IDWOS:000479184600031
Citation statistics
Document Type期刊论文
Identifierhttps://ir.xtbg.ac.cn/handle/353005/11460
Collection民族植物学研究组
Affiliation1.Chongqing Univ, Sch Pharmaceut Sci, Chongqing Key Lab Nat Prod Synth & Drug Res, Chongqing 401331, Peoples R China
2.Chongqing Univ, Sch Pharmaceut Sci, Chem Biol Res Ctr, Chongqing 401331, Peoples R China
3.Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China
4.Chinese Acad Sci, Key Lab Trop Plant Resource & Sustainable Use, Xishuangbanna Trop Bot Garden, Menglun 666303, Yunnan, Peoples R China
5.Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Shenyang 110016, Liaoning, Peoples R China
Recommended Citation
GB/T 7714
Li, Wei,Rao, Li,Liu, Yu,et al. (+/-)-Meliviticines A and B: Rearranged prenylated acetophenone derivatives from Melicope viticina and their antimicrobial activity[J]. BIOORGANIC CHEMISTRY,2019,90(x):-.
APA Li, Wei.,Rao, Li.,Liu, Yu.,He, Qian.,Fan, Yue.,...&Zhang, Chuan-Rui.(2019).(+/-)-Meliviticines A and B: Rearranged prenylated acetophenone derivatives from Melicope viticina and their antimicrobial activity.BIOORGANIC CHEMISTRY,90(x),-.
MLA Li, Wei,et al."(+/-)-Meliviticines A and B: Rearranged prenylated acetophenone derivatives from Melicope viticina and their antimicrobial activity".BIOORGANIC CHEMISTRY 90.x(2019):-.
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