Neritaloside

Characterization of the anticancer properties of monoglycosidic cardenolides isolated from Nerium oleander and Streptocaulon tomentosum.[Pubmed:21291990]

J Ethnopharmacol. 2011 Apr 12;134(3):781-8.

AIM OF THE STUDY: For identification of the active constituents we investigated the anticancer activity of cardenolides from Streptocaulon tomentosum Wight & Arn. (Asclepiadaceae) and from Nerium oleander L. (Apocynaceae) which are both used against cancer in the traditional medicine in their region of origin. MATERIAL, METHODS AND RESULTS: The antiproliferative activity of cardenolides isolated from roots of Streptocaulon tomentosum (IC(50)<1-15.3 muM after 2 days in MCF7) and of cardenolide containing fractions from the cold aqueous extract of Nerium oleander leaves ("Breastin", mean IC(50) 0.85 mug/ml in a panel of 36 human tumor cell lines), their influence on the cellular viability and on the cell cycle (block at the G2/M-phase or at the S-phase in tumor cells, respectively) were determined using different cell lines. The murine cell line L929 and normal non-tumor cells were not affected. Bioactivity guided fractionation of Breastin resulted in the isolation of the monoglycosidic cardenolides oleandrine, oleandrigeninsarmentoside, Neritaloside, odoroside H, and odoroside A (IC(50)-values between 0.010 and 0.071 mug/ml). CONCLUSIONS: The observed anticancer activities of extracts and isolated cardenolides are in agreement with the ethnomedicinal use of Streptocaulon tomentosum and Nerium oleander. The most active anticancer compounds from both species are monoglycosidic cardenolides possessing the 3beta,14beta-dihydroxy-5beta-card-20(22)-enolide structure with or without an acetoxy group at C-16. The results indicate that the cytotoxic effects are induced by the inhibition of the plasma membrane bound Na(+)/K(+)-ATPase.

LC/MS/MS analyses of an oleander extract for cancer treatment.[Pubmed:10952541]

Anal Chem. 2000 Aug 1;72(15):3547-52.

An HPLC/MS/MS method has been developed for the characterization and quantification of the cardiac glycosides oleandrin, odoroside, Neritaloside and the aglycone oleandrigenin, all contained in a patented-hot-water extract of Nerium oleander L (Anvirzel). Qualitative analysis of such extracts was achieved using a hybrid tandem quadrupole time-of-flight (QqTOF) mass spectrometer. Collision-induced dissociation (CID) mass spectra of oleandrin, oleandrigenin, odoroside, and Neritaloside were obtained with greater than 5 ppm mass accuracy and resolution routinely in excess of 8000 (fwhm). The detection limit for oleandrin of 20 pg (injected) was realized when the precursor-to-product ion transition, m/z 577 --> 373, was monitored. We have also applied the analytical method to the determination of oleandrin, oleandrigenin, Neritaloside, and odoroside in human plasma following an intramuscular injection of Anvirzel.

Bio-active cardenolides from the leaves of Nerium oleander.[Pubmed:9933955]

Phytochemistry. 1999 Feb;50(3):435-8.

A bioactivity directed isolation of the methanolic extract of the fresh, uncrushed leaves of Nerium oleander showing a central nervous system (CNS) depressant effect in mice has been undertaken. As a result, four CNS depressant cardenolides including a new cardenolide, neridiginoside and three known constituents, nerizoside, Neritaloside and odoroside-H, have been isolated which exhibited CNS depressant activity in mice at a dose of 25 mg/kg. The structure of neridiginoside was elucidated as 3 beta-O-(D-diginosyl)-5 beta, 14 beta-dihydroxy-card-20(22)-enolide, using spectroscopic methods including one-dimensional and two-dimensional NMR (COSY-45, NOESY, J-resolved, HMQC and HMBC). The known compounds have been indentified through spectral studies and comparison of data with those reported in the literature.