A new type of monoterpenoid indole alkaloid precursor from Alstonia rostrata

Xiang-Hai Cai; Mei-Fen Bao; Yu Zhang; Chun-Xia Zeng; Ya-Ping Liu; Xiao-Dong Luo

doi:10.1021/ol200996a

A new type of monoterpenoid indole alkaloid precursor from Alstonia rostrata

Org Lett. 2011 Jul 15;13(14):3568-71. doi: 10.1021/ol200996a. Epub 2011 Jun 21.

Authors

Xiang-Hai Cai¹, Mei-Fen Bao, Yu Zhang, Chun-Xia Zeng, Ya-Ping Liu, Xiao-Dong Luo

Affiliation

¹ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, China. [email protected]

PMID: 21688858
DOI: 10.1021/ol200996a

Abstract

Currently, all monoterpenoid indole alkaloids (MIAs) have been derived from strictosidine, which originates from the condensation of tryptophan with secologanin in a 1:1 ratio. However, our phytochemical research on Alstonia rostrata revealed a potential new precursor for these compounds. We isolated the alstrostines A and B, and it was determined that they were derived from tryptophan and secologanin in a 1:2 ratio, which supported the presence of a new type of MIA precursor.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alstonia / chemistry*
Antineoplastic Agents, Phytogenic* / chemical synthesis
Antineoplastic Agents, Phytogenic* / chemistry
Antineoplastic Agents, Phytogenic* / isolation & purification
Antineoplastic Agents, Phytogenic* / pharmacology
Drug Screening Assays, Antitumor
HL-60 Cells
Humans
Iridoid Glucosides / chemistry
Molecular Structure
Secologanin Tryptamine Alkaloids* / chemical synthesis
Secologanin Tryptamine Alkaloids* / chemistry
Secologanin Tryptamine Alkaloids* / isolation & purification
Secologanin Tryptamine Alkaloids* / pharmacology
Tryptophan / chemistry
Vinca Alkaloids / chemistry*

Substances

Antineoplastic Agents, Phytogenic
Iridoid Glucosides
Secologanin Tryptamine Alkaloids
Vinca Alkaloids
alstrostine A
alstrostine B
secologanin
strictosidine
Tryptophan