Cathagines A-D, new bisindole alkaloids from Catharanthus roseus

Yusuke Hirasawa; Chiaki Kasagi; Erika Koyama; Hitomi Myojin; Takahiro Tougan; Toshihiro Horii; Nahoko Uchiyama; Toshio Kaneda; Hiroshi Morita

doi:10.1007/s11418-024-01857-4

Cathagines A-D, new bisindole alkaloids from Catharanthus roseus

J Nat Med. 2025 Jan;79(1):134-142. doi: 10.1007/s11418-024-01857-4. Epub 2024 Nov 14.

Authors

Yusuke Hirasawa¹, Chiaki Kasagi², Erika Koyama², Hitomi Myojin², Takahiro Tougan³, Toshihiro Horii⁴, Nahoko Uchiyama⁵, Toshio Kaneda², Hiroshi Morita⁶

Affiliations

¹ Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa-ku, Tokyo, 142-8501, Japan. [email protected].
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 Department of Malaria Vaccine Development, Research Institute for Microbial Diseases, Osaka University, 3-1 Yamadaoka, Suita, Osaka, 565-0871, Japan.
⁵ National Institute of Health Sciences, 3-25-26 Tonomachi, Kawasaki-ku, Kawasaki, Kanagawa, 210-9501, Japan.
⁶ Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa-ku, Tokyo, 142-8501, Japan. [email protected].

PMID: 39540962
DOI: 10.1007/s11418-024-01857-4

Abstract

Four new bisindole alkaloids, cathagines A (1)-D (4) consisting of an aspidosperma and the fused tetracyclic 3-spirooxindole derived from an iboga type skeleton were isolated from the whole plant of Catharanthus roseus. The structures including absolute stereochemistry were elucidated on the basis of 2D NMR data and CD spectra. Cathagine B (2) showed moderate anti-malarial activity against Plasmodium falciparum 3D7.

Keywords: Catharanthus roseus; 3-spirooxindole; Antiplasmodial activity; Apocynaceae; Aspidosperma; Bisindole alkaloid; Cathagines A–D.

MeSH terms

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

Substances

Indole Alkaloids
Antimalarials
Plant Extracts