Vincarostine A, a novel anti-malarial trimeric monoterpenoid indole alkaloid from Catharanthus roseus

Yusuke Hirasawa; Yusuke Kakizoe; Takahiro Tougan; Nahoko Uchiyama; Toshihiro Horii; Hiroshi Morita

doi:10.1007/s11418-024-01795-1

Vincarostine A, a novel anti-malarial trimeric monoterpenoid indole alkaloid from Catharanthus roseus

J Nat Med. 2024 Jun;78(3):768-773. doi: 10.1007/s11418-024-01795-1. Epub 2024 Apr 2.

Authors

Yusuke Hirasawa^#¹, Yusuke Kakizoe², Takahiro Tougan³, Nahoko Uchiyama⁴, Toshihiro Horii⁵, Hiroshi Morita^#⁶

Affiliations

¹ Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa-Ku, Tokyo, 142-8501, Japan. y-hirasawa@hoshi.ac.jp.
² Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa-Ku, Tokyo, 142-8501, Japan.
³ Research Center for Infectious Disease Control, Research Institute for Microbial Diseases, Osaka University, 3-1 Yamadaoka, Suita, Osaka, 565-0871, Japan.
⁴ National Institute of Health Sciences, 3-25-26 Tonomachi, Kawasaki-Ku, Kawasaki, Kanagawa, 210-9501, Japan.
⁵ Department of Malaria Vaccine Development, Research Institute for Microbial Diseases, Osaka University, 3-1 Yamadaoka, Suita, Osaka, 565-0871, Japan.
⁶ Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa-Ku, Tokyo, 142-8501, Japan. moritah@hoshi.ac.jp.

^# Contributed equally.

PMID: 38564155
DOI: 10.1007/s11418-024-01795-1

Abstract

A novel trimeric monoterpenoid indole alkaloid, vincarostine A (1) consisting of an aspidosperma-iboga-aspidosperma type skeleton, was isolated from the whole plant of Catharanthus roseus. The structure including absolute stereochemistry was elucidated on the basis of 2D NMR data and CD spectrum. Vincarostine A (1) showed anti-malarial activity.

Keywords: Catharanthus roseus; Anti-malarial activity; Trimeric monoterpenoid indole alkaloid; Vincarostine A.

MeSH terms

Antimalarials* / chemistry
Antimalarials* / pharmacology
Catharanthus* / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Plant Extracts / chemistry
Plasmodium falciparum / drug effects
Secologanin Tryptamine Alkaloids* / chemistry
Secologanin Tryptamine Alkaloids* / isolation & purification