Discovery of Unusual Ajmaline‐Macroline Type Bisindole Alkaloids from Alstonia macrophylla by Building Blocks‐Based Molecular Networking

Author:

Li Zi‐Wei123,Fan Chun‐Lin123,Sun Biao123,Huang Lan123,Wang Zi‐Qi123,Huang Xiao‐Jun123,Zhang Shi‐Qing123,Ye Wen‐Cai123ORCID,Wu Zhen‐Long123,Zhang Xiao‐Qi123

Affiliation:

1. State Key Laboratory of Bioactive Molecules and Druggability Assessment Jinan University Guangzhou 510632 P.R. China

2. Center for Bioactive Natural Molecules and Innovative Drugs Research and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM & New Drugs Research Jinan University Guangzhou 510632 P.R. China

3. Guangdong Provincial Engineering Research Center for Modernization of TCM College of Pharmacy Jinan University Guangzhou 510632 P.R. China

Abstract

AbstractThree unusual ajmaline‐macroline type bisindole alkaloids, alsmaphylines A–C, together with their postulated biogenetic precursors, were isolated from the stem barks and leaves of Alstonia macrophylla via the building blocks‐based molecular network (BBMN) strategy. Alsmaphyline A represents a rare ajmaline‐macroline type bisindole alkaloid with an S‐shape polycyclic ring system. Alsmaphylines B and C are two novel ajmaline‐macroline type bisindole alkaloids with N‐1−C‐21′ linkages, and the former possesses an unconventional stacked conformation due to the presence of intramolecular noncovalent interactions. The chemical structures including absolute configurations of alsmaphylines A–C were established by comprehensive spectroscopic analyses, electronic circular dichroism (ECD) calculations, and single‐crystal X‐ray crystallography. In addition, a plausible biosynthetic pathway of these bisindole alkaloids as well as their ability to promote the protein synthesis on HT22 cells were discussed.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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