Guaianolides from Calycocorsus stipitatus and Crepis tingitanafn1
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 1–3
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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2019, Biochemical Systematics and EcologyCitation Excerpt :González et al., 1970). Integrifolin 3-O-β-D-glucopyranoside (5) is one of the most common secondary metabolites of the tribe Cichorieae, isolated, so far, from many Crepis spp., namely C. capillaris (Kisiel, 1983), C. dioscoridis (Tsoukalas et al., 2014), C. lacera (Russo et al., 2018), C. mollis (Kisiel et al., 2000), C. pyrenaica (L.) Greuter (Kisiel and Barszcz, 1995), C. sibirica (Kisiel, 1995), C. tingitana Ball (Zidorn et al., 1999). and C. zacintha (L.) Babc. (Kisiel et al., 2002).
Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan Peninsula and their chemosystematic significance
2018, PhytochemistryCitation Excerpt :The H-3 and C-3, H-1′ and C-1′ signals assignments were in agreement with a previously reported eudesmanolide glucoside (Grass et al., 2004). Its β-glycosidic linkage was additionally deduced from the large coupling constant (7.9 Hz) of anomeric proton signal, in good agreement with 8-epidesacylcynaropicrin 3-O-β-D-glucoside (integrifolin 3-O-β-D-glucoside) from Crepis tingitana Ball (Zidorn et al., 1999), and C. pyrenaica (L.) W. Greuter (Kisiel and Barszcz, 1995). The absence of exocyclic methylene protons and carbon signals from α-methylene-γ-lactone structure, which are present in 1H and 13C spectra of related eudesmanolides (Grass et al., 2004; Hasbun et al., 1982), indicated that proline was added on α-methylene-γ-lactone by Michael addition, as it was also previously reported for saussureamines and pulchellamines (Matsuda et al., 2003; Yang et al., 2008).
Sesquiterpene lactones from Crepis aurea (Asteraceae, Cichorieae)
2013, Biochemical Systematics and EcologyCitation Excerpt :The isolated compounds were identified as 8-epi-deacylcynaropicrin (1), its 3-O-β-glucopyranoside (2), ixerin N (3), ixerin M (4), ixerisoside A (5) and its p-methoxyphenylacetyl analogue (6), the methanol addition product (7), 8β-hydroxy-4β,15-dihydrozaluzanin C (8), 8-epiisolippidiol (9) and its 3-O-β-glucopyranoside (10) as well as syringin and 5-methoxyeugenyl-4-O-β-glucopyranoside. The identities of 3 (Nishimura et al., 1985), 5 (Warashina et al., 1990) and 6 (Zidorn et al., 1999) were established by comparison of their spectroscopic data with those reported. The remaining compounds were identified by direct comparison of their 1H NMR spectra and retention time values with those of compounds isolated from Crepis and Taraxacum (syringin) species in earlier studies: 1 (Kisiel, 1983; Kisiel et al., 1994), 2 (Kisiel and Barszcz, 1995), 3 (Kisiel et al., 2002), 7 (Marco et al., 1994; Kisiel et al., 2000), 8 (Kisiel and Michalska, 2001), 9 (Kisiel and Michalska, 2001), 10 (Kisiel and Barszcz, 1995), syringin (Michalska et al., 2010) and 5-methoxyeugenyl-4-O-β-glucopyranoside (Kisiel et al., 2000; Kisiel and Michalska, 2001).
Sesquiterpenoids and phenolics from Crepis mollis
2000, PhytochemistryStudy on chemical constituents from Ixeris dentata
2023, Vietnam Journal of Science and Technology
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Dedicated to Professor Dr. G. Heinisch (Institut für Pharmazeutische Chemie der Universität Innsbruck) on the occasion of his 60th birthday.