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

By Jian Zhang, Zhi-Wen Liu, Yun-Lin Ao, Li-Jun Hu, Cui-Jie Wei, Qing-Hua Zhang, Meng-Fei Yuan, Ying Wang, Qing-Wen Zhang, Wen-Cai Ye, Xiao-Qi Zhang

November 13, 2019

  • Year

  • Technique

  • Industry

Title

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

Author

Jian Zhang, Zhi-Wen Liu, Yun-Lin Ao, Li-Jun Hu, Cui-Jie Wei, Qing-Hua Zhang, Meng-Fei Yuan, Ying Wang, Qing-Wen Zhang, Wen-Cai Ye, Xiao-Qi Zhang

Year

2019

Journal

The Journal of Organic Chemistry

Abstract

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.

Full Article

https://pubs.acs.org/doi/abs/10.1021/acs.joc.9b01835

Instrument

V-550, J-810

Keywords

Circular dichroism, Absorption, Absolute configuration, Quantitation, Natural products, Medicinal