Chemodiversity of tryptamine-derived alkaloids in six Costa Rican Palicourea species (Rubiaceae–Palicoureeae). (November 2017)

• Record Type: Journal Article
• Authors: Berger, Andreas; Tanuhadi, Elias; Brecker, Lothar; Schinnerl, Johann; Valant-Vetschera, Karin
• Is Part Of: Phytochemistry. Volume 143(2017)
• Page Start: 124
• Page End: 131
• Publication Date: 2017-11
• Subjects: Palicourea -- Rubiaceae -- Alkaloids -- Chemodiversity -- Chemosystematics -- Deoxostrictosamide; WOCCAHAMOCJPBR-YUXCFCGHSA-N -- XVYUPRKBCBOLNH-UFBUDHMGSA-N -- BEAMQDGOWBZORD-UIDCBYKHSA-N -- FZHZQHNKCPJTNQ-UHFFFAOYSA-N -- QAZFGOZXMUMPIZ-AEKHMMLTSA-N -- BVNLOLBWJBPPSN-NSCXOBDTSA-N -- BEAMQDGOWBZORD-KLCZDXPNSA-N -- AEVNZYJYJYDVSH-FGKKIZGCSA-N -- LBRPLJCNRZUXLS-WRYSRTJPSA-N -- SNNPBMCFZUSNAP-UYMRSQGBSA-N -- VRCIJFPURKMFQI-UYMRSQGBSA-N -- DNWUSGICDUHIRY-CKVIAXGWSA-N; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2017.07.016
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: We report 14 harmala and tryptamine-iridoid alkaloids with various tri-, tetra- and pentacyclic cores from leaves and stem bark of six species of the large and complex neotropical genus Palicourea . Among them is the previously undescribed compound deoxostrictosamide which is related to strictosamide, a key intermediate in camptothecin biosynthesis. In addition, we describe the occurrence of 1, 2, 3, 4-tetrahydronorharman-1-one for the first time within Rubiaceae and ophiorine A and B, two alkaloids with an unusual core bearing a betaine function and a zwitterion as new for the genus. Although the other compounds are already known from other species, their degree of structural diversity highlights the remarkable biosynthetic capabilities of the genus Palicourea . Furthermore, the present paper provides additional support for the hypothesis that tryptamine-iridoid alkaloids represent a distinct chemosystematic feature for the genus Palicourea . Graphical abstract: The previously undescribed alkaloid deoxostrictosamide was isolated from leaves of Palicourea winkleri (Rubiaceae). In total, 14 tryptamine-derived alkaloids were isolated from six species of Palicourea . Their structures were elucidated by NMR and MS techniques. Highlights: We report 14 tryptamine-derived alkaloids from six species of Palicourea . These contain various tri-, tetra- and pentacyclic cores. A previously undescribed alkaloid named deoxostrictosamide is described. Structural diversity and chemosystematic significance of alkaloids are discussed.