Asclepias curassavica

F. Abe, Y. Mori, and T. Yamauchi, 3 -epi-19-Norafroside and 12./l-hydroxycoroglauci-genin from Asclepias curassavica, Chem. Pharm. Bull. (Tokio), 39 (1991) 2709-2711. 

Groeneveld, H., van den Berg, B., Elings, J. and Seykens, D. (1990) Cardenolide biosynthesis from malonate in Asclepias curassavica. Phytochemistry, 29,3479-86. 

The cardenolides of the Asclepiadaceae differ from those of the Apocynaceae and the Scrophulariaceae, in that the former have a 5cL trans A/B) and the latter a 5(3(cw A/B) ring junction. The latter type is useful clinically in humans, whereas the former normally is not (Seiber et al., 1984). At least 30% of the cardiac glycosides of young plants of Asclepias curassavica occurs in the latex (Groeneveld et al., 1991). 

Several cardiac glycosides have been reported to have antiviral properties (Vanden Berghe et al., 1985). Others have been reported to have antitumor or cytotoxic properties. Among these are calotropin (25) from Asclepias curassavica (Kupchan et al, 1964) and neriifolin (31) and 2 -acetylnerii-folin from Thevetia thevetioides (Apocynaceae) seeds (McLaughlin et al, 1980). 

Groeneveld, H. W., A. Binnekamp, and D. Seykens, Cardenolide biosynthesis from acetate in Asclepias curassavica. Phytochemistry, 30, 2577-2585 (1991). 

Lee, S. M. and J. N. Seiber, Biosynthetic preparation of cardenolides from [l- C]acetic acid by stem discs of the milkweed Asclepias curassavica, Ph3dochemistry, 22, 923-927 (1983). 

Recent studies on Asclepias curassavica [197], and Bersama abyssinica [198, 199] have shown that bufadienolides and cardenolides are cytotoxic and that hellebrigenin 3-acetate (XLIX) inhibits W 256 at 8 mg/kg. Structure-activity relationship studies on bufadienolides and cardenolides have failed to reveal the structural features required for activity [194]. 

A doubly linked 4,6-dideoxy-D-j/ rgo-hexos-2-ulose residue was identified in the cardenolide glycoside (1) isolated from Asclepias curassavica stems, and a branched hexos-4-ulose derivative isolated from Pittosporum tobira flowers is covered in Chapter 14. Oxidation (MCPBAAleOH) of unsaturated derivative (2) (obtained by base treatment of methyl 3,4-0-isopropylidene-2,6-di-0-methyl-P-D-galactopyranoside) afforded L-arabino-hexos-S-ulose derivative (3) and then (4) after acid hydrolysis. The hexopyranosid-3-uloses (5) have been prepared by oxidation (Cr03/Ac20/pyridine) of the corresponding 3-alcohols. ... 

Herbarium managers bemoan collections of common tropical weeds - bans on accessions of some species, like Asclepias curassavica L., are sometimes mooted. But this can carry risks recent work on the widespread weedy tree genus Trema (Yesson et al., 2004) revealed that hidden in what everyone had assumed was a single trash weed, were two quite different taxa with different life histories and biology. Assumptions can be dangerous ... 

N OCHg N OCHs N 0CH3 pyrazines from Asclepias curassavica... 

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