Studies on Bignoniaceae: Newbouldiosides D – F, Minor Phenylethanoid Glycosides from Newbouldia laevis, and New Flavonoids from Markhamia zanzibarica and Spathodea campanulata ^{[ # ]}

Abstract

Continued examination of the stem bark of Newbouldia laevis afforded three minor phenylethanoid glycosides, designated as newbouldiosides D – F. Their structures were elucidated by spectroscopic methods as β-(3,4-dihydroxyphenyl)ethyl 5-O-syringoyl-β-D-apiofuranosyloxy-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 3)]-6-O-E-sinapoyl-β-D-glucopyranoside, β-(3,4-dihydroxyphenyl)ethyl β-D-apiofuranosyloxy-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 3)]-6-O-E-sinapoyl-β-D-glucopyranoside, and β-(3,4-dihydroxyphenyl)ethyl β-D-apiofuranosyloxy-(1 → 2)-O-α-L-rhamnopyranosyl-(1 → 2)-6-O-E-sinapoyl-β-D-glucopyranoside, respectively. These metabolites are the first members possessing a sinapoyl structural element. In addition, the series of naturally occurring flavonoids is extended by the identification of 3′,4′,5,7-tetrahydroxy-5′-methoxyflavanone and apigenin-5-O-α-L-rhamnopyranosyl-7-O-β-D-glucopyranoside obtained from leaf extracts of Markhamia zanzibarica and aromadendrin-7-O-(2″-O-formyl)-β-D-glucopyranoside isolated from Spathodea campanulata. The latter compound is the first example of a flavonoid possessing a formylated glucosyl moiety.

Key words

Newbouldia laevis - Markhamia zanzibarica - Spathodea campanulata - Bignoniaceae - phenylethanoid glycosides - newbouldiosides - flavonoids

^# Dedicated to Professor Arnold Vlietinck on the occasion of his 80th birthday.

Publication History

Received: 06 July 2020

Accepted after revision: 15 September 2020

Article published online:
06 November 2020

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