Tumor inhibitors. XLI. Structural elucidation of tumor inhibitory sesquiterpene lactones from Eupatorium rotundifolium

Kupchan, S. Morris; Kelsey, John E.; Muruyama, Masao; Cassady, John M.; Hemingway, J. C.; Knox, John R.

doi:10.1021/jo01264a029

Cited by 74 publications

(28 citation statements)

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“…In a preliminary pharmacological test ( Table 3), it was found that compounds 8, 9, and 11 inhibit the proliferation of T and B lymphocytes of mice in vitro at concentrations of 1 10 ± 7 , 110 ± 6 , and/or 1 10 ±5 M without obvious cytotoxicity, while compounds 6, 7, and 10 exhibited cytotoxicity at concentration of 1 10 ± 5 M or lower. Cytotoxicity of guaiane-type sesquiterpenes with a-methylene-g-lactone were also reported by Sun and Zidorn [13], [14], [15].…”

Section: Resultssupporting

confidence: 57%

“…The 1 H-13 C long-range correlation signals between H glc-1 and C-3, and between H glc-3 and C-8¢ in the HMBC spectrum of 2 revealed the connecting positions of the glucose moiety with the sesquiterpene skeleton and the p- The 1D and 2D NMR spectra of 3 were superimposed to those of 2 except for the disappearance of the oxygenated methine signal at d C = 72.7 (C-8 of compound 2) and appearance of an additional methylene at d C = 30.9, which suggested the absence of OH substitution at C-8 in 3. Further analysis of 1 H-NMR, 13 C-NMR, 1 H-1 H COSY, HMQC, HMBC, and NOESY spectra of 3 confirmed its structure to be 3b-[3-(4-hydroxyphenyl)acetyl-b-D-glucopyranosyloxy]-4(15),10(14),11(13)-guaiatrien-12,6-olide. To our best knowledge, compound 3 is a new natural product, and has been assigned the trivial name youngiajaponicoside B.…”

Section: Anti-inflammatory Test Male Kunming Mice Weighing 24 1 G (Shmentioning

confidence: 81%

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New Guaiane, Megastigmane and Eudesmane-Type Sesquiterpenoids and Anti-Inflammatory Constituents fromYoungia japonica

Chen¹,

Liu²,

Wang³

et al. 2006

Planta Med

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Eleven sesquiterpenoids have been isolated from the whole plants of Youngia japonica (Asteraceae). Among these sesquiterpenoids, five were identified as new compounds on the basis of spectroscopic methods and chemical analysis. Their structures were 3-oxo-8alpha-(4-hydoxyphenyl)acetoxy-10(14),11(13)-guaiadien-12,6-olide ( 1), 3beta-[3-(4-hydroxyphenyl)acetyl-beta- D-glucopyranosyloxy]-8alpha-hydroxy-4(15),10(14),11(13)-guaiatrien-12,6-olide ( 2), 3beta-[3-(4-hydroxyphenyl)acetyl-beta- D-glucopyranosyloxy]-4(15),10(14),11(13)-guaiatrien-12,6-olide ( 3), 3alpha,5beta,6alpha-trihydroxy-4alpha-(beta- D-glucopyranosyloxy)-7-megastigmen-9-one ( 4), and 3alpha-(beta- D-glucopyranosyloxy)-4(15),11(13)-eudesmadien-12-oic acid ( 5). The three known components 3beta-(beta- D-glucopyranosyloxy)-8alpha-(4-hydroxyphenyl)acetoxy-4(15),10(14),11(13)-guaiatrien-12,6-olide ( 8), 3beta-(beta- D-glucopyranosyloxy)-4(15),10(14),11 (13)-guaiatrien-12,6-olide ( 9), and 3alpha-hydroxy-4alpha-(beta- D-glucopyranosyloxy)-5,7-megastigmadien-9-one ( 11) showed inhibitory activity against the proliferation of T and B lymphocytes of mice in vitro at concentrations of 1 x 10 ( - 7), 1 x 10 ( - 6), and/or 1 x 10 ( - 5) M without obvious cytotoxicity. Compound 9, the major component of the plant extract, exhibited weak anti-inflammatory activity at a dosage of 50 mg/kg ( p. o.) in in vivo anti-inflammatory experiments of mice.

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Section: Resultssupporting

confidence: 57%

Section: Anti-inflammatory Test Male Kunming Mice Weighing 24 1 G (Shmentioning

confidence: 81%

New Guaiane, Megastigmane and Eudesmane-Type Sesquiterpenoids and Anti-Inflammatory Constituents fromYoungia japonica

Chen¹,

Liu²,

Wang³

et al. 2006

Planta Med

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“…Indeed, among the more than 130 chlorinecontaining plant constituents reviewed by Engvild [ 19861, the vast majority are chlorohydrins, and a recent update on organohalogen compounds gives a similar picture for the 39 chlorine containing compounds reported from higher plants between 1980 and1992 [Gribble, 19921. It is, therefore, surprising that so little effort has been made to verify the genuineness of these plant derived chlorohydrins. In cases where the genuineness of chlorohydrins was confirmed, the methodology used (i.e., extraction and isolation excluding chlorinated solvents, tandem MS-MS of crude extracts) [Kupchan et al, 1969;Roush Pachuta et al, 1986ljustifies that the findings are to be considered with caution. Indeed, the choice of extraction procedure may have profound effects on the composition of the extract.…”

Section: Discussionmentioning

confidence: 99%

Search for chlorinated sesquiterpene lactones in the neurotoxic thistle Centaurea solstitialis by liquid chromatography‐mass spectrometry, and model studies on their possible artifactual formation

1993

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An HPLC method has been developed for the analysis of sesquiterpene lactones of the neurotoxic plant Centaurea solstitialis (Asteraceae). The presence of sesquiterpene lactone chlorohydrins in extracts was investigated by means of liquid chromatography-thermospray mass spectrometry. In contrast to earlier reports of a series of mono- and dichlorohydrins from this plant, traces only of two monochlorohydrins could be detected in lipophilic extracts. Model studies carried out with extracts and with the genuine sesquiterpene diepoxide repin and its epimer subluteolide showed that (i) monochlorohydrins can be formed in CHCl3 under usual laboratory conditions; (ii) the epoxide moiety at C-4 of the sesquiterpenes is extremely labile, reacting immediately and quantitatively with traces of HCl to the corresponding monohydrins; (iii) epoxide ring opening at the acyl side chain occurs only at higher HCl concentrations. Confirmation of the peak identity was obtained by the isotope ratio of chlorinated compounds and comparison with authentic samples. The structures of the mono- and dichlorohydrins were established by NMR spectroscopy.

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“…(Garcia et al, 1990;Muschietti et al, 1994). E. cuneifolium, E. rotundifolium and E. semiserratum have been traditionally used for the treatment of cancer (Herz et al, 1981, Kupchan et al, 1967, 1969Woerdenbag, 1993). E. formosanum is used in Formosan folk medicine for its antileukemic, antipyretic, anti-inflammatory and anticancer properties (Lee et al, 1972(Lee et al, , 1977Woerdenbag, 1993).…”

Section: Other Speciesmentioning

confidence: 99%

A review of the toxicosis and biological properties of the genus Eupatorium

et al. 1998

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Eupatorium genus grows wild in many parts of the world. A number of species of Eupatorium are toxic to grazing animals. Milk sickness in humans is caused by ingestion of milk of the animals reared on the pastures infested with Eupatorium rugosum (white snakeroot). While some information is available on the toxins in various species of Eupatorium, ambiguities still persist in extrapolation of the data to field incidence of toxicosis. Eupatorium genus has been used for its medicinal properties for many decades. A number of bioactive natural products have been reported in the extracts of Eupatorium spp. and the genus is a promising bioresource for preparation of drugs and value-added products.

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Tumor inhibitors. XLI. Structural elucidation of tumor inhibitory sesquiterpene lactones from Eupatorium rotundifolium

Cited by 74 publications

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New Guaiane, Megastigmane and Eudesmane-Type Sesquiterpenoids and Anti-Inflammatory Constituents fromYoungia japonica

New Guaiane, Megastigmane and Eudesmane-Type Sesquiterpenoids and Anti-Inflammatory Constituents fromYoungia japonica

Search for chlorinated sesquiterpene lactones in the neurotoxic thistle Centaurea solstitialis by liquid chromatography‐mass spectrometry, and model studies on their possible artifactual formation

A review of the toxicosis and biological properties of the genus Eupatorium

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