Synthesis and composition of vitamin D-3 metabolites in Solanum malacoxylon

Esparza, Margarita S.; Vega, Manuel A.; Boland, Ricardo

doi:10.1016/0304-4165(82)90254-9

Cited by 42 publications

(24 citation statements)

References 23 publications

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“…Other glycoside forms of vitamin D have also been found in Sg , including 25D 3 and vitamin D 3 itself, but they are much less abundant, and are less important than glycosides of 1,25D 3 with regards to the hypercalcemic activity of the plant [43, 44]. Substantial evidence documents that the plant and/or plant extracts are active in monogastrics, and if given in high amounts can serve as a means of increasing plasma 1,25D 3 concentrations [34, 36, 45-50].…”

Section: Disucussionmentioning

confidence: 99%

Targeted delivery of 1,25-dihydroxyvitamin D3 to colon tissue and identification of a major 1,25-dihydroxyvitamin D3 glycoside from Solanum glaucophyllum plant leaves

Zimmerman

Koszewski

Hoy

et al. 2015

The Journal of Steroid Biochemistry and Molecular Biology

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Leaves of the Solanum glaucophyllum (Sg) plant, indigenous to South America, have long been known for their calcinogenic toxicity in ruminant animals. It was determined the leaves contained glycosidic derivatives of 1,25-dihydroxyvitamin D3 (1,25D3) and liberation of the free hormone by rumen bacterial populations elicited a hypercalcemic response. Our interest in the leaves is predicated on the concept that the glycoside forms of 1,25D3 would target release of the active hormone in the lower gut of non-ruminant mammals. This would provide a means of delivering 1,25D3 directly to the colon, where the hormone has been shown to have beneficial effects in models of inflammatory bowel disease (IBD) and colon cancer. We fed mice for 10 days with variable amounts of Sg leaf. Feeding 7-333 ug leaf/day produced no changes in plasma Ca2+ and 1,25D3 concentrations, and only at > 1000 ug leaf/day did these values become significantly elevated compared to controls. Gene expression studies from colon tissue indicated a linear relationship between the amount of leaf consumed and expression of the Cyp24a1 gene. In contrast, Cyp24a1 gene expression in the duodenums and ileums of these mice was unchanged compared to controls. One of the major 1,25D3-glycosides was isolated from leaves following extraction and purification by Sep-Pak cartridges and HPLC fractionation. Ultraviolet absorbance was consistent with modification of the 1-hydroxyl group, and positive ion ESI mass spectrometry indicated a diglycoside of 1,25D3. 2-Dimensional NMR analyses were carried out and established the C1 proton of the A-ring was interacting with a C1’ sugar proton, while the C3 proton of the A-ring was linked with a second C1’ sugar proton. The structure of the isolated compound is therefore consistent with a beta-linked 1,3-diglycoside of 1,25D3. Thus, Sg leaf administered to mice at up to 333 ug/day can elicit colon-specific enhancement of Cyp24a1 gene expression without inducing hypercalcemia, and the 1,3-diglycoside is one of the major forms of 1,25D3 found in the leaf.

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Section: Disucussionmentioning

confidence: 99%

Targeted delivery of 1,25-dihydroxyvitamin D3 to colon tissue and identification of a major 1,25-dihydroxyvitamin D3 glycoside from Solanum glaucophyllum plant leaves

Zimmerman

Koszewski

Hoy

et al. 2015

The Journal of Steroid Biochemistry and Molecular Biology

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“…also identified as Solanum glaucophyllum Desf., and its biological activity in animals has been extensively studied. This plant which grows in South America, contains the glycosides of la,25-(OH)2 vitamin D 3 (Wasserman 1976), of 25-(OH) VitD 3, and vitamin D 3 (Esparza 1982). Moreover the calcinogenic activity, earlier reported primarily in leaves, has also been found in berries, stems and roots of Solanum glaucophyllurn plants in both aglycone and glycoside forms (Weissemberg 1989).…”

Section: Introductionmentioning

confidence: 99%

In vitro cultures of Solanum malacoxylon Sendt.: nutritional requirements and sterol production

Suardi¹,

Bernasconi²,

Pelizzoni³

et al. 1994

Plant Cell Tiss Organ Cult

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Callus cultures were established from hypocotyl, root and leaf explants of Solanum malacoxylon. The growth rate of calli was evaluated on Murashige and Skoog medium as well as Gamborg's B5 medium. Sterols were isolated from calli grown on both media however the B5 proved to be more effective in promoting the production of these metabolites. No calcitriol was found in the cultures. Feeding experiments with vitamin D 3 were scarcely effective in promoting the production of vitamin D 3 hydroxylated metabolites.

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“…In fact, Sm contains not only 1,25(OH) 2 D 3 but also other metabolites, like vitamin D 3 and 25(OH)D 3 (Esparza et al 1982).…”

Section: Introduction Introduction Introduction Introduction Introducmentioning

confidence: 99%

Bone changes caused by experimental Solanum malacoxylon poisoning in rabbits

et al. 2005

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The aim of this study was to describe the bone changes observed after a daily oral administration of the calcinogenic plant Solanum malacoxylon (syn. S. glaucophyllum) (Sm) during 9 days. The Sm-poisoned rabbits had an increase of bone resorption in the endosteal surface of the cortical zone and also in the surface covered by osteoblasts of the primary and secondary spongiosa of the trabecular bone compartment. Moreover, the epiphyseal growth plates in long bones appeared narrower than in the control rabbits, with reduction of the proliferative and hyperthrophic chondrocyte zones. The electron microscopic study revealed a significant decrease of proteoglycans in the hyperthrophic chondrocyte zone evidenced by a significant reduction of rutenium red positive granules in the poisoned rabbit. Altogether, these data suggest that cell differentiation may play a pivotal role in the pathogenesis of Sm-induced bone lesions

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Synthesis and composition of vitamin D-3 metabolites in Solanum malacoxylon

Cited by 42 publications

References 23 publications

Targeted delivery of 1,25-dihydroxyvitamin D3 to colon tissue and identification of a major 1,25-dihydroxyvitamin D3 glycoside from Solanum glaucophyllum plant leaves

Targeted delivery of 1,25-dihydroxyvitamin D3 to colon tissue and identification of a major 1,25-dihydroxyvitamin D3 glycoside from Solanum glaucophyllum plant leaves

In vitro cultures of Solanum malacoxylon Sendt.: nutritional requirements and sterol production

Bone changes caused by experimental Solanum malacoxylon poisoning in rabbits

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