Isolation of a New Potential Antitumor Compound From Wedelia asperrima

Oelrichs, Peter B.; Vallely, Peter J.; MacLeod, John K.; Lewis, Ivor A. S.

doi:10.1021/np50009a014

Cited by 15 publications

(4 citation statements)

References 2 publications

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“…Toxicity testing.-This was carried out as previously reported (10). Both compounds 2 and 3 were toxic to mice and rats down to the 1 mg/kg level.…”

Section: Methodsmentioning

confidence: 99%

“…The presence in the spectrum of an ion at mtz 179 (C7H6OTMSi) placed the hydroxy group on either the phenyl ring or C-3 of the phenylpropanoate group. Treatment of 3 with CH2N2 followed by NaOMe/MeOH yielded, after hplc purification, methyl 3-hydroxy-3-phenylpropanoate [10], identical by ms and 1H nmr to an authentic racemic sample, while its [ot]D value established the absolute stereochemistry of the chiral center as S (8). The residual compound 8 on methanolysis gave 1-0-methyl ot-L-rhamnopy- ranoside [15], which had a 13C-nmr spectrum and optical rotation identical to authentic 1-0-methyl -L-rhamnopyranoside (7,9).…”

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confidence: 99%

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The Toxic Extractives from Wedelia asperrima, III. Structures of Two Naturally Occurring Rhamnosyl Analogues of Wedeloside

MacLeod

Lewis²,

Moeller³

et al. 1990

J. Nat. Prod.

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Ass?aAcr.-The structures of two new toxic 4'-O-rhamnosyl analogues of wedeloside [l], from W d l i a a.~pmimu, have been determined by a combination of chemical, nmr, and mass spectrometric analysis.In previous papers, we described the structural elucidation of the diterpene aminoglycoside wedeloside [I), the major toxic constituent of Wedelia asperrim Benth. (Compositae) (1,2). Subsequent biochemical studies (3) have shown wedeloside to be a powerful inhibitor of ADP/ATP transport across the mitochondrial membrane, with a binding affinity to the carrier protein comparable to that of the related diterpene glycoside, carboxyatractyloside 14) (4). We now report the structures of two additional toxic components 2 and 3 from W. asperrim. RESULTSAND DISCUSSION For the structure of 0-a-L-rhamnosyl-( 1"~4')-wedeloside {2), the fab mass spectrum of 2 showed an [MH)+ ion at d z 904 and an [MNa)+ ion at d z 926, which mass-B R'

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“…Toxicity testing.-This was carried out as previously reported (10). Both compounds 2 and 3 were toxic to mice and rats down to the 1 mg/kg level.…”

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

The Toxic Extractives from Wedelia asperrima, III. Structures of Two Naturally Occurring Rhamnosyl Analogues of Wedeloside

MacLeod

Lewis²,

Moeller³

et al. 1990

J. Nat. Prod.

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“…centrolobular necrosis, was similar to that seen in domestic animals poisoned by the plant under field and experimental conditions as also reported by Cole et al 59 Apart from Atractylis gummifera, atractylosides have also been found in roasted coffee beans (Coffea arabica) as well as the South African plant Gzllilepis laureola.68 More recently, carboxyatractyligenin has been found in the highly toxic glycoside wedeloside (VII), isolated from the Australian plant Wedelia aspem'ma. 69 It seems possible that similar such compounds may be found in other acutely toxic compositaceous plants.…”

Section: Slaframinementioning

confidence: 95%

Toxic substances in the food of animals: Some recent findings of australian poisonous plant investigations

Seawright

Hrdlicka

Lee

et al. 1982

J of Applied Toxicology

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Some of the more interesting and significant recent Australian studies of plant toxins are those dealing with furanosesquiterpenoid essential oils, irritant diterpene esters, thiaminase I, trihydroxyindolizidine, carboxyatractyloside and oxalates. Furanosesquiterpenes, found mainly in Myoporum spp., require activation by microsomal mixed-function oxygenases in order to produce injury in the tissues in which they accumulate. One such compound isolated from M. deserti, deisopropylngaione, causes necrotizing lesions in the liver, kidney and lung. The native pteridophyte Marsilea drummondii contains thiaminase I at such a high level of activity that it can cause clinical thiamine deficiency in adult sheep which graze it at times of the year when it is growing profusely. Potent diterpene esters (which have been found t o be potent cocarcinogens in mice) are to be found in thymelaeaceous plants such as Pimelea spp. One such compound, simplexin, also causes marked contraction of vascular smooth muscle, giving rise to the cardiopulmonary and hepatic circulatory disorder in cattle, known as St. George Disease. Carboxyatractyloside has recently been found to be the toxin in Xanthium spp. The compound is a hypoglycaemic agent, an inhibitor of mitochondria1 oxidative phosphorylation and causes acute liver necrosis. Swainsona spp. contain the a-mannosidase inhibitor trihydroxyindolizidine. Consumption of the plants by animals results in the typical lysosomal storage disease a-mannosidosis. Oxalate or acid oxalate ions in plants normally cause toxicity per se in grazing animals, but when present in low levels in various native and introduced grasses eaten by horses, they can produce negative calcium balance and secondary nutritional hyperparathyroidism within several months. 0 Heyden The constituents of Australian Pimelea simplex I. The isolation and structure of the toxin of Pimelea simplex and P. trichostochya Form B responsible for St. George Disease of cattle. Aust. J. Chem.,

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“…In 1980, Oelrichs et al [30] isolated the toxin wedeloside (85) from W. asperrima, which, in preliminary experiments, was found to inhibit tumors produced by aflatoxin B 1 in rats. Antitumor Effects.…”

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Structures and Biological Properties of the Chemical Constituents from the Genus Wedelia

Dong

Liu

et al. 2007

ChemInform

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Isolation of a New Potential Antitumor Compound From Wedelia asperrima

Cited by 15 publications

References 2 publications

The Toxic Extractives from Wedelia asperrima, III. Structures of Two Naturally Occurring Rhamnosyl Analogues of Wedeloside

The Toxic Extractives from Wedelia asperrima, III. Structures of Two Naturally Occurring Rhamnosyl Analogues of Wedeloside

Toxic substances in the food of animals: Some recent findings of australian poisonous plant investigations

Structures and Biological Properties of the Chemical Constituents from the Genus Wedelia

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