Elsevier

Phytochemistry

Volume 47, Issue 8, April 1998, Pages 1551-1560
Phytochemistry

Chemotaxonomy
Pyrrolizidine alkaloids of Ipomoea hederifolia and related species

https://doi.org/10.1016/S0031-9422(97)01082-0Get rights and content

Abstract

The common necine base of the novel pyrrolizidine alkaloids (ipangulines) isolated recently from Ipomoea hederifolia is not turneforcidine but its 1β-epimer, platynecine. Three novel ipangulines were isolated from the aerial parts of I. hederifolia and identified as 9-O-[2-hydroxy-3-(2-acetoxy)-2-methylbutyryl]-7-O-salicyloylplatynecine (ipanguline B2), 9-O-[2-hydroxy-3-(2-methylbutyryloxy)-2-methylbutyryl]-platynecine (ipanguline D10) and 9-O-salicyloylplatynecine (ipanguline D11). Comprehensive GC-mass spectrometric analysis also revealed a great variety of >38 platynecine monoesters and diesters. They are classified as ipangulines A (diesters with one phenylacetic acid moiety), ipangulines B (diesters with one salicylic acid moiety), ipangulines C (diesters with two aliphatic moieties) and ipangulines D (either 7- or 9-monoesters). In shoot tips and young leaves, total ipangulines concentrations are up to 0.45% (on dry wt basis). The ipangulines are stored as tertiary alkaloids and not as N-oxides. Seeds of different provenance showed similar alkaloid patterns. Taxonomically related species, such as I. neei and I. × perigrenium, also contain platynecine esters in their vegetative tissues.

Three novel ipangulines (platynecine mono- and diesters) were isolated from I. hederifolia. A large series of related compounds were characterised by GC-MS in different parts of I. hederifolia, I. neei and I. x perigrenium.

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      In the case of young plants of Heliotropium spathulatum, leaves are the main organs for the biosynthesis of necine, as demonstrated by exposure of the plant to 14CO2.187 For Ipomoea hederifolia (Convolvulaceae), the shoots are the site of PA biosynthesis.188 In PA-producing orchids, such as Phalaenopsis, these alkaloids are synthesized in young root tips and young flower buds.154

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