Hunterines A–C, Three Unusual Monoterpenoid Indole Alkaloids from Hunteria zeylanica

Three new monoterpenoid indole alkaloids (MIAs), hunterines A–C (1–3), were isolated from Hunteria zeylanica. Compound 1 possesses a unique skeleton with an unprecedented azabicyclo[4.3.1]­decane ring system. Compounds 2 and 3 are a pair of epimeric vobasinylindole alkaloid heterodimers. Their struc...

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Veröffentlicht in:Journal of organic chemistry 2019-11, Vol.84 (22), p.14892-14897
Hauptverfasser: Zhang, Jian, Liu, Zhi-Wen, Ao, Yun-Lin, Hu, Li-Jun, Wei, Cui-Jie, Zhang, Qing-Hua, Yuan, Meng-Fei, Wang, Ying, Zhang, Qing-Wen, Ye, Wen-Cai, Zhang, Xiao-Qi
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Sprache:eng
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Zusammenfassung:Three new monoterpenoid indole alkaloids (MIAs), hunterines A–C (1–3), were isolated from Hunteria zeylanica. Compound 1 possesses a unique skeleton with an unprecedented azabicyclo[4.3.1]­decane ring system. Compounds 2 and 3 are a pair of epimeric vobasinylindole alkaloid heterodimers. Their structures including absolute configurations were established by spectroscopic analyses, X-ray diffraction, computational calculation, and the modified Mosher’s method. Plausible biogenetic pathways of 1–3 were also proposed. Alkaloid 1 showed moderate cytotoxic activity against the HepG2 cell line.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01835