Quantitative variations in the cardiac glycosides of oleander

Yamauchi, Tatsuo; Abe, Fumiko; Tachibana, Yoshishige; Atal, C.K.; Sharma, Brij Mohan; Imre, Zeliha

doi:10.1016/s0031-9422(00)80149-1

Cited by 24 publications

(19 citation statements)

References 5 publications

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“…Biological activities of both the methyl ester of 3 (compound 16) and natural products possessing one more hydroxyl group at C-27 or C-13 of 3 (compounds 4 and 5) decreased. Oleanolic acid (10) showed moderate inhibitory activity on induction of ICAM-1 under concentrations that did not decrease cell viability. Betulinic acid (12) and methyl oleanolate (17) showed moderate inhibitory activity on induction of ICAM-1 and cell growth of lung carcinoma A 549 cells.…”

Section: Resultsmentioning

confidence: 94%

Three New Triterpenes from Nerium oleander and Biological Activity of the Isolated Compounds

Zhang

et al. 2005

J. Nat. Prod.

118

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New ursane-type triterpene 1, oleanane-type triterpene 2, and dammarane-type triterpene 15 were isolated from the leaves of Nerium oleander together with 12 known triterpenes, 3beta-hydroxy-12-ursen-28-oic acid (ursolic acid, 3), 3beta,27-dihydroxy-12-ursen-28-oic acid (4), 3beta,13beta-dihydroxyurs-11-en-28-oic acid (5), 3beta-hydroxyurs-12-en-28-aldehyde (6), 28-norurs-12-en-3beta-ol (7), urs-12-en-3beta-ol (8), urs-12-ene-3beta,28-diol (9), 3beta-hydroxy-12-oleanen-28-oic acid (oleanolic acid, 10), 3beta,27-dihydroxy-12-oleanen-28-oic acid (11), 3beta-hydroxy-20(29)-lupen-28-oic acid (betulinic acid, 12), 20(29)-lupene-3beta,28-diol (betulin, 13), and (20S,24R)-epoxydammarane-3beta,25-diol (14). On the basis of their spectroscopic data, the structures of the new compounds 1, 2, and 15 were established as 3beta,20alpha-dihydroxyurs-21-en-28-oic acid, 3beta,12alpha-dihydroxyoleanan-28,13beta-olide, and (20S,24S)-epoxydammarane-3beta,25-diol, respectively. The anti-inflammatory activity of the seven isolated compounds and methyl esters of ursolic acid and oleanoic acid in vitro was examined on the basis of inhibitory activity against the induction of the intercellular adhesion molecule-1 (ICAM-1). The anticancer activity of the 14 isolated compounds, including 1, 2, 15, and methyl esters of ursolic acid and oleanolic acid in vitro was examined on the basis of the cell growth inhibitory activities toward three kinds of human cell lines.

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Section: Resultsmentioning

confidence: 94%

Three New Triterpenes from Nerium oleander and Biological Activity of the Isolated Compounds

Zhang

et al. 2005

J. Nat. Prod.

118

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“…To our knowledge, our observation represents the first report of an oleander intoxication with conclusive identification of oleandrin in the patient's blood by mass spectrometry. This improvement may be of limited interest for emergency practitioners wishing to assess the severity of a poisoning, considering the existence in oleander of many other components, present at various concentrations and sharing oleandrin toxicity [1,2,19]. However HPLC/MS should be recognized as the reference method in all cases (e.g.…”

Section: Resultsmentioning

confidence: 99%

Confirmation of oleander poisoning by HPLC/MS

Tracqui

Kintz

Branche³

et al. 1997

International Journal of Legal Medicine

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A non-fatal case of Nerium oleander (common oleander) self-poisoning in a 45-year-old female is presented. Initial symptoms were nausea and vomiting, abdominal pain, phosphenes, cardiovascular shock and sinus brady-cardia. Blood and urine were assayed for oleandrin, the major cardiac glycoside of N. oleander, using a highly specific HPLC/MS procedure. The blood concentration of oleandrin at admission was 1.1 ng/ml. This is the first report of an oleander intoxication ascertained by the mass spectrometric identification of oleandrin in blood. HPLC/MS appears to be the method of choice for the forensic-toxicological investigation of poisonings by cardiac glycosides.

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“…However, the whole plant, including its sap, is toxic containing several cardiac glycosides (e.g. oleandrin, oleandrigenin, desacetyloleandrin, glucosyloleandrin, gentiobiosyloleandrin, nerigoside, odorosides, oleasides) at various concentrations and sharing toxicity [1,2]. A lethal dose of 5 to 15 leaves of oleandrin is described for adults [1].…”

Section: Introductionmentioning

confidence: 99%

A non-fatal oleander poisoning

et al. 2005

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The study presents a case of non-fatal poisoning with oleander blooms in a 47-year-old female, with emphasis on the importance of toxicological service in a clinical emergency. After repeated vomiting at home, the patient was admitted at the hospital with cardiac symptoms more than 18 h after the ingestion. Serum samples were assayed immunochemically for digitoxin-related compounds by electrochemiluminescent immunoassay, and using HPLC/MS/MS analysis for oleandrin, the main cardiac glycoside of Nerium oleander. Confirming the non-specific immunoassay results, which are often clinically over-interpreted, oleandrin was detected by HPLC/MS/MS in the serum sample in a concentration of 1.6 ng/ml upon admission. Comparison with previous reports indicates that single compound analysis only permits a toxicological assessment for oleander poisoning and results in the proposal to classify an oleandrin level between 1.0 and 2.0 ng/ml as toxic blood plasma/serum concentration.

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Quantitative variations in the cardiac glycosides of oleander

Cited by 24 publications

References 5 publications

Three New Triterpenes from Nerium oleander and Biological Activity of the Isolated Compounds

Three New Triterpenes from Nerium oleander and Biological Activity of the Isolated Compounds

Confirmation of oleander poisoning by HPLC/MS

A non-fatal oleander poisoning

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