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Arborisidine and Arbornamine are two monoterpenoid indole alkaloids that were isolated from the Malayan Kopsia arborea plant. This review provides valuable information about the total and formal syntheses of these alkaloids. The synthesis strategies discussed in this review, such as Pictet-Spengler cyclization, chemo- and stereoselective oxidative cyclization, Michael/Mannich cascade process, and intramolecular N-alkylation, can be useful for developing new methods to synthesize these and other similar compounds.
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http://dx.doi.org/10.1007/s11030-024-10978-7 | DOI Listing |
Acc Chem Res
September 2025
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510641, China.
ConspectusMonoterpenoid indole alkaloids constitute one of the largest natural product families, with over 3000 members reported to date. , a genus of about 30 species, is notable for its rich alkaloid diversity. These plants produce unique monoterpenoid indole alkaloids with intriguing structures and bioactive properties, making them a key focus in synthetic chemistry research over the years.
View Article and Find Full Text PDFMol Divers
June 2025
Department of Chemistry, SRM Institute of Science & Technology, Delhi-NCR Campus, Modinagar, Ghaziabad, 201204, India.
Arborisidine and Arbornamine are two monoterpenoid indole alkaloids that were isolated from the Malayan Kopsia arborea plant. This review provides valuable information about the total and formal syntheses of these alkaloids. The synthesis strategies discussed in this review, such as Pictet-Spengler cyclization, chemo- and stereoselective oxidative cyclization, Michael/Mannich cascade process, and intramolecular N-alkylation, can be useful for developing new methods to synthesize these and other similar compounds.
View Article and Find Full Text PDFAlkaloids Chem Biol
March 2020
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune, India. Electronic address:
The tryptamine-derived polycyclic bridged bioactive indole alkaloids subincanadines A-G were isolated in 2002 by Ohsaki and coworkers from the bark of the Brazilian medicinal plant Aspidosperma subincanum. Kobayashi proposed that subincanadines D-F could be biosynthetically resulting from stemmadenine via two different pathways and, furthermore, that the subincanadines A-C could be biogenetically resulting from subincanadines D and E. Kam and coworkers, in their focused efforts, isolated five indole alkaloids from Malaysian Kopsia arborea species, namely valparicine, apparicine, arboridinine, arborisidine, and arbornamine in combination with subincanadine E.
View Article and Find Full Text PDFOrg Lett
April 2016
Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia.
Two new monoterpene indole alkaloids, characterized by previously unencountered natural product skeletons, viz., arborisidine (1), incorporating indolizidine and cyclohexanone moieties fused to an indole unit, and arbornamine (2), incorporating an unprecedented 6/5/6/5/6 "arbornane" skeleton (distinct from the eburnan or tacaman skeleton), were isolated from a Malayan Kopsia arborea. The structures of the alkaloids were determined based on analysis of the NMR and MS data.
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