Investigations of Homeopathic Drugs Derived from<i>Hippomane mancinella</i>and<i>Stillingia sylvatica</i>: A Potential latrogenic Risk of Cancer?

Zahn, Peter; Nonfon, Maria; Hecker, Erich

doi:10.1055/s-2006-959967

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“…It has the same structure as gnidilatidin from Cnidia latifolia (Kupchan et al, 1976) or G . kraussiana (Borris and Cordell, 1984) as well as odoracin from Daphne odora (Ohigashi et al, 1982) and Stillingia factor S6 from Stillingia sylvatica (Adolf and Hecker, 1980;Zahn et al, 1993). Yuanhuacine is used in China in birth and fertility regulation of large populations (Shanghai Clinical Group, 1979;Gu Zhi-ping et al, 1989).…”

Section: Chemotaxonomic Implicationsmentioning

confidence: 99%

Medicinal plants of euphorbiaceae occurring and utilized in thailand. V. Skin irritants of the daphnane and tigliane type in latex of Excoecaria bicolor and the uterotonic activity of the leaves of the tree

Karalai

Wiriyachitra

Sorg

et al. 1995

Phytotherapy Research

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From latex of Excoecuria bicolor (Euphorbiaceae) four TLC-homogeneous fractions highly enriched in diterpene esters were obtained . Fraction F3 by NMR was found to be a mixture of 9,13,14-orthoester-2O-esters (la) of 5/3-hydroxyresiniferonol-6a,7a-epoxide (I). Alkaline transesterification yielded from l a a mixture of 58-hydroxyresiniferonol-6a,7a-epoxide-9,13-14-orthoesters (If) carrying unsaturated orthoester groups as a TLC-homogeneous material (final isolation of Excoecuriu factors Bl/B2, B3 and B4). The transesterification mixture also contained, according to GC-MS, methyl n-carboxylates corresponding to the even numbered C22-CJo acids from 20-positions in la. Fraction F4 by NMR contained molecular species (2a) structurally closely related to la, carrying 5/l,12~-dihydroxyresiniferonol-6a,7a-epoxide (2) as the parent alcohol. From 2a, by alkaline transesterification, a two-component mixture of Excoecuriu factors B5/B6, i.e. 5/l,12&dihydroxy-resiniferonol-6a,7a-epoxide-9,13,14-ortho(2,4,6-hexadecatrienoate)/-(2,4,6,8-hexadecatetraenoate) (2b/2c) was obtained. GC-MS of the transesterification mixture revealed methyl n-carboxylates corresponding to even numbered c 1 6 -c 3 0 acids from 20-positions in 2a (omitting CI8 and Cm). Fractions F1 and F2 by alkaline transesterifications yielded 12-deoxyphorbol (3) and its 13-(3,54etradecadienoate) 3b (Excoecuriu factor B7). Moreover 4,12-dideoxy(4a)phorbol (4), its 13-(3,5-tetradecadienoate) 4b and the natural 4-epimer of 4b 4,12-dideoxyphorbol-13-(3,5-tetradecadienoate) (5a) (new Excoecuriu factor B8) were obtained. GC-MS of the transesterification mixtures revealed mainly methyl n-carboxylates corresponding to even numbered c 1 6 -c 3 0 acids. Thus the latex and the fractions F1 and F2 contain 13,20-diesters of the parent alcohols 12-dmxyphorbol (3) and 4,12-dideoxyphorbol (5). 4,12-dideoxy(4a)phorboI (4) and its derivatives may be considered artifacts from alkaline epimerization of 5. The daphnane type Excoecuriu factors Bl-B6 are structurally very closely related to diterpenes such as yuanhuacine occurring in certain Daphne and Wikstroerniu species. Daphnane type esters of this kind are currently used routinely in China for fertility regulation. Similarly, daphnane and tigliane type Excoecuriu factors present in the latex of E . bicolor may be responsible for the uterotonic activity of its leaves utilized in Thai herbal medicine.

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Section: Chemotaxonomic Implicationsmentioning

confidence: 99%