Secorubenine, a Monoterpenoid Indole Alkaloid Glycoside from Adina rubescens: Isolation, Structure Elucidation, and Enantioselective Total Synthesis

Nanako Nakashima; Jukiya Sakamoto; Kenta Rakumitsu; Mariko Kitajima; Lia Dewi Juliawaty; Hayato Ishikawa

doi:10.1248/cpb.c21-00931

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Secorubenine, a Monoterpenoid Indole Alkaloid Glycoside from Adina rubescens: Isolation, Structure Elucidation, and Enantioselective Total Synthesis

Nanako Nakashima, Jukiya Sakamoto, Kenta Rakumitsu, Mariko Kitajima, Lia Dewi Juliawaty, Hayato Ishikawa

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Keywords: secorubenine, Adina rubescens, monoterpenoid indole alkaloid, bioinspired total synthesis, alkaloid glycoside, structure elucidation

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2022 Volume 70 Issue 2 Pages 187-191

DOI https://doi.org/10.1248/cpb.c21-00931

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Abstract

A new pentacyclic monoterpenoid indole alkaloid glycoside named secorubenine (1) was isolated from the heartwood of Adina rubescens, collected in Indonesia. The structure was elucidated by spectroscopic analysis and chemical modification of isolated secorubenine (1). The bioinspired enantioselective total synthesis of 1 was accomplished in 12 steps, whereafter its structure was determined and the absolute stereochemistry was confirmed.

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