Guaianolides from Calycocorsus stipitatus and Crepis tingitanafn1fn1Dedicated to Professor Dr. G. Heinisch (Institut für Pharmazeutische Chemie der Universität Innsbruck) on the occasion of his 60th birthday.

Zidorn, Christian; Ellmerer-Müller, Ernst P.; Stuppner, Hermann

doi:10.1016/s0031-9422(98)00637-2

Cited by 14 publications

(3 citation statements)

References 8 publications

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“…Compound 2 Table 1) to those of 3b-(b-D-glucopyranosyloxy)-8b -(4Љ-methoxyphenylacetoxy)-guaia-4(15),10(14),11(13)-trien-1a,5a,6b,7aH-12,6-olide 19) supported the proposed configuration at the former positions. The HMBC correlation between the anomeric signal at d 4.36 (H-1Љ) and a carbon signal at d 81.9 (C-3) located the sugar moiety at C-3.…”

Section: Resultsmentioning

confidence: 54%

Two New Sesquiterpene Lactones from Ixeris chinensis

Khalil

Shen

Guh

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Phytochemical investigation of Ixeris chinensis NAKAI (Asteraceae) has resulted in the isolation of a new guaianolide-type sesquiterpene lactone, ixerochinolide (1) as well as the related glucoside, ixerochinoside (2). In addition, the known guaianolides, 8b b-hydroxy-3-oxo-guaia-4(15),10(14),11(13)-trien-1a a,5a a,6b b,7a aH-12,6-olide (8b b-hydroxydehydrozaluzanin), 8b b,15-dihydroxy-2-oxo-guaia-1(10),3,11(13)-trien-5a a,6b b,7a aH-12,6-olide (lactucin), 3b b,8a a,10a a-trihydroxy-guaia-4(15),11(13)-dien-1a a,5a a,6b b,7a aH-12,6-olide (10a a-hydroxy-10,14-dihydro-desacylcynaropicrin) and 3b b-D-glucopyranosyloxy-8b b-(p-hydroxyphenylacetyloxy)-guaia-4(15),10(14),11(13)-trien1a a,5a a,6b b,7a aH-12,6-olide (8-epicrepioside) were identified. The structures were determined on the basis of spectral analyses, especially 1-and 2D NMR. Compound 1 exhibited significant cytotoxicity against human PC-3 tumor cells.

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Section: Resultsmentioning

confidence: 54%

Two New Sesquiterpene Lactones from Ixeris chinensis

Khalil

Shen

Guh

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…These signals clearly showed that the para coupling protons pattern at [( H 6.97 (d, J = 8 Hz), H-2′′, H-6′′); and ( H 6.67 (d, J = 8 Hz), H-3′′, H-5′′)] and acetylphenyl signals at  C 172.9 and 41.2 in the NMR spectrum of 7. The comparison of the NMR data of compound 7 with the reference [18] suggested that 7 was ixerisoside A.…”

Section: Resultsmentioning

confidence: 90%

Study on chemical constituents from Ixeris dentata

Huyen

Dũng

2023

Vietnam J. Sci. Technol.

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Ixeris dentata (Thunb. ex Thunb.) Nakai (family Asteraceae) a plant widely distributed in Viet Nam, is a perennial herb that grows to a height of 0.5 m. It has been used as a medicinal herb medicine since ancient times for the treatment of calculi, dyspepsia, indigestion, pneumonia, hepatitis, contusion, and tumors in Northeast Asia. The biological activities of this plant have been shown to be neuroprotective, anti-mutagenic, anti-hyperlipidemic, anti-inflammatory, anti-allergic, and anti-proliferative activities. It is also composed of aliphatics, triterpenoids, sesquiterpene, and glycosides. However, research on the phytochemistry of this plant has yet to be conducted in Viet Nam. In this study, five phenolics including chlorogenic acid (1), 3,5-di-O-caffeoylquinic acid (2), 4,5-di-O-caffeoylquinic acid (3), citrusin C (4), 4-allyl-2,6-dimethoxyphenol O-β-D-glupyranoside (5), and two sesquiterpene lactones, 8-epidesacylcynaropicrin glucoside (6) and ixerisoside A (7) were isolated from the methanol extract of the leaves of Ixeris dentata using combined chromatographic methods. Their chemical structures were determined by analysis of MS, NMR spectra data as well as comparison with those reported in the literature.

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“…This paper presents the isolation of root constituents from this plant, which includes somewhat unusual new ester ( 1 ) of the known guaianolide 8‐epideacylcynaropicrin‐3‐ O‐β ‐glucopyranoside ( 2 ). Compound 2 , first reported from Crepis capillaris (L.) Wallr., is the most common sesquiterpene lactone in Crepis species, and its esters at C‐8 with aliphatic and aromatic acids have previously been isolated from a few members of the genus . The stereostructure of 8‐epideacylcynaropicrin was confirmed by x‐ray diffraction analysis .…”

Section: Introductionmentioning

confidence: 93%