Elsevier

Phytochemistry

Volume 50, Issue 6, 20 March 1999, Pages 1061-1062
Phytochemistry

Guaianolides from Calycocorsus stipitatus and Crepis tingitanafn1

https://doi.org/10.1016/S0031-9422(98)00637-2Get rights and content

Abstract

The dichloromethane extract of subaerial parts of Crepis tingitana L. afforded two sesquiterpene lactones, 8-epidesacylcynaropicrin-3-O-β-d-glucoside and ixerisoside A, already known from other members from the Lactuceae tribe of the Asteraceae family. The dichloromethane extract of subaerial parts of Calycocorsus stipitatus (Jacq.) Rauschert revealed a closely related new substance. The structure of the new compound has been established by MS, 1H and 13C NMR experiments as 3β- (β-d-glucopyranosyloxy)-8β- (4″-methoxyphenylacetoxy)-guaia-4 (15), 10 (14), 11 (13)-trien-1a, 5a, 6β, 7aH-12,6-olide.

Introduction

Phytochemical analysis of some of the 70 species of Crepis in Europe (Sell, 1976) led so far to the isolation and identification of several guaianolide type sesquiterpene lactones (Kisiel, 1983, Kisiel, 1984, Kisiel, 1993; Kisiel and Kohlmunzer, 1987, Kisiel and Kohlmunzer, 1989; Kisiel et al., 1994; Kisiel and Barszcz, 1996). Crepis tingitana, an endemic of southern Spain and Morocco, has not been investigated yet. The genus Calycocorsus is closely related to Crepis and represented by one European species, Calycocorsus stipitatus, which grows in southern Central Europe, Crna Gora, Albania and the eastern Pyreneés (Sell, 1976). So far nothing is known about secondary metabolites of Calycocorsus.

Section snippets

Results and discussion

The dichloromethane extract of the air dried subaerial parts of C. tingitana was repeatedly chromatographed on silica gel to give two guaianolides, 8-epidesacylcynaropicrin-3-O-β-d-glucoside (1) and ixerisoside A (2). Identification of compounds 1 and 2 was based on comparison of mass spectra (positive ESI m/z: 447 [M+Na]+ and 581 [M+Na]+, respectively) and 1H and 13C NMR data with those given in literature (Kisiel, 1983; Warashina et al., 1990).

Substance 3 was isolated from the dichloromethane

Plant material

C. tingitana was collected in April 1997 near Majada Madrid/Andalucia/Spain. C. stipitatus was gathered at the Wildmoosalm near Seefeld/Tyrol/Austria. Voucher specimens are deposited at the Institute of Pharmacognosy.

Extraction and isolation of compound 13

Air dried subaerial parts of C. tingitana (120 g) and C. stipitatus (90 g) were ground and extracted exhaustively at room temperature with CH2Cl2 yielding 1.3 and 2.1 g of residue after evaporation in vacuum, respectively. 1 (95 mg) and 2 (25 mg) were isolated by repeated silica

Acknowledgements

The authors thank C. Pölzleitner [Inst. f. Pharmakognosie, Innsbruck (A)] for technical assistance.

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fn1

Dedicated to Professor Dr. G. Heinisch (Institut für Pharmazeutische Chemie der Universität Innsbruck) on the occasion of his 60th birthday.

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