Isolation and structural elucidation of heliangolidin, a new sesquiterpene lactone from artemisia canariensis

Bretón, J.; Camps, Francisco; Coll, Josep Pujol i; Eguren, Liliana; Gavín, José A.; González, Albano; Martorell, X.; Miravitlles, C.; Molins, Elı́es; Torramilans, J.

doi:10.1016/s0040-4020(01)96668-2

Cited by 16 publications

(4 citation statements)

References 9 publications

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“…The coupling constants across the protons at positions H-5-H-7 (J 5,6 =11.0 Hz and J 6,7 was very small and not measurable) were equivalent to the literature values for heliangolides such as provincialin, heliangolidin, and ajanolide A. [21][22][23] Further relative stereochemistry of 2 was confirmed by NOESY experiment. The NOE correlations (Fig.…”

Section: Resultssupporting

confidence: 78%

Sesquiterpenes and Other Constituents from Dendranthema zawadskii var. latilobum

Shin

Lee

Kim

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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Six new germacranolides, zawadskinolides A-F (1-6), and a new eudesmane glucoside, chrysantiloboside (7) were isolated from the aerial parts of Dendranthema zawadskii var. latilobum, along with thirteen known constituents. Their structures were elucidated by means of spectroscopic evidence. Bioassay showed that flavonoids such as apigenin (9) farnesyl protein transferase (FPTase) inhibition, 12) and quinone reductase modulation.13) In addition, the 70% EtOH extract and its hexane-soluble fraction were reported to strongly inhibit inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) activity.14) In the course of our studies on the constituents of the MeOH extract of the aerial parts of D. zawadskii var. latilobum, six new sesquiterpene lactones, zawadskinolides A-F (1-6), and a new eudesmane glucoside, chrysantiloboside (7), together with thirteen known compounds were isolated. Since NO and prostaglandin E 2 are considered the major inflammatory mediators and in keeping with the traditional medical applications of this herb 2) and the previous report on its anti-inflammatory activity, 14) the isolates were evaluated for their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells. In this paper, we report the isolation, structural elucidation and biological evaluation of these compounds. Results and DiscussionDried aerial parts of D. zawadskii var. latilobum were extracted with MeOH and then fractionated with hexane, CH 2 Cl 2 , EtOAc, n-BuOH and water. By combined chromatographic separations of these extracts, seven new and thirteen known compounds were isolated. Their structures were elucidated using physicochemical and spectroscopic methods.

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Section: Resultssupporting

confidence: 78%

Sesquiterpenes and Other Constituents from Dendranthema zawadskii var. latilobum

Shin

Lee

Kim

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Breton et al ( 1985); (d) Camps, Coil, Conchillo, Messeguer, Molins & Miravitlles (1985); (e) Braekman, Daloze, Dupont, Tursch, Declercq, Germain & Van Meerssche (1981).…”

Section: Translation Searchunclassified

An automated full-symmetry Patterson search method

Rius¹,

Miravitlles²

1987

J Appl Cryst

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A full-symmetry Patterson search method is presented that performs a molecular coarse rotation search in vector space and orientation refinement using the o-function. The oriented molecule is positioned using the fast translation function Zo, which is based on the automated interpretation of z projections using the sum function. This strategy reduces the number of Patterson-function values to be stored in the rotation search, and the use of the ~o function minimizes the required time for the development of all probable rotation search solutions. The application of this method to five representative test examples is shown.

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“…61 An aldehyde (1 lo), previously prepared from caryophyllene, has been isolated from Helenium amarum. 62 Eight new silphinene derivatives (1 11)-- (118) have been obtained from Cineraria geifolia var. glabra.…”

Section: Caryophyllane and Related Compoundsmentioning

confidence: 99%