Monoglycosides from Isoplexis chalcantha

Trujillo, Juan Pedro Pérez; Hernández, O; Navarro, Eduardo

doi:10.1021/np50067a024

Cited by 11 publications

(3 citation statements)

References 5 publications

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“…complexity in steroids higher than previously published since 3 and 4 were not found in I. chalcantha (González et al, 1985;Trujillo et al, 1990), and 2 was not found in I. canariensis Boada et al, 1984). In I. Isabelliana, genins 1-3 were detected as has been previously reported in this species (Freitag et al, 1967), although the reported presence of gitoxigenin was not confirmed in our extracts.…”

contrasting

confidence: 69%

“…According to previous phytochemical studies (Freitag et al, 1967;Spengel et al, 1967;Boada et al, 1984;González et al, 1985;Trujillo et al, 1990) these three Isoplexis species mainly produce glycosides derived from 5a-configured cardenolides [uzarigenin (1)] or from the unsaturated analogues of these steroids [xysmalogenin (3) and canarigenin (4)]. Together with these, 5bcardenolides [digitoxigenin (2) and/or gitoxigenin derivatives] have been found in I. chalcantha (González et al, 1985;Trujillo et al, 1990) and I. isabelliana (Freitag et al, 1967), but such secondary metabolites have never been reported in I. canariensis Boada et al, 1984).…”

Section: Introductionmentioning

confidence: 95%

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LC‐NMR applied to the characterisation of cardiac glycosides from three micropropagated Isoplexis species

Gavidia¹,

Seitz²,

Pérez‐Bermúdez³

et al. 2002

Phytochemical Analysis

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Species of the genus Isoplexis are of particular interest with respect to the biochemical pathway leading to the cardenolides. It is important to determine whether or not 5beta-configured compounds, typically produced by Digitalis species and used in medicine, are present together with their respective alpha-isomers in Isoplexis spp. Structure elucidation by LC-NMR of the products isolated from in vitro regenerated Isoplexis canariensis, I. chalcantha and I. isabelliana was carried out, and similarities were observed among the products of the three species, including the presence of digitoxigenin-type cardenolides in I. canariensis and xysmalogenin and canarigenin derivatives in I. chalcantha never previously reported in these species. Pregnane glycosides not found until now either in Isoplexis or Digitalis were also detected.

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contrasting

confidence: 69%

Section: Introductionmentioning

confidence: 95%

LC‐NMR applied to the characterisation of cardiac glycosides from three micropropagated Isoplexis species

Gavidia¹,

Seitz²,

Pérez‐Bermúdez³

et al. 2002

Phytochemical Analysis

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“…The cardenolides found in Isoplexis may also be regarded as ªmore primitiveº than those of Digitalis, because only monoand diglycosides are produced. Early phytochemical studies [7], [8], [9], [10] indicated the presence of 5a-configurated cardenolides (uzarigenin-type) and of D 4 -and D 5 -unsaturated cardenolides of the xysmalogenin-and canarigenin-types, respectively. Schaller and Kreis [30] were the first to report the occurrence of 5b-cardenolides in I. canariensis.…”

Section: Introductionmentioning

confidence: 99%

Cardenolide Genin Pattern in Isoplexis Plants and Shoot Cultures

Schaller¹,

Kreis²

2006

Planta med

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An HPLC method for the quantitative analysis of cardenolides was developed and applied. The procedure was optimised for analysing small samples (40 mg dw) of plant and tissue culture material. ISOPLEXIS CANARIENSIS plants obtained from seeds accumulated cardenolides to about 20 - 40 micromol g (-1) dw as calculated from the levels of cardenolide genins released after acidic hydrolysis of methanolic extracts. The relative contents of xysmalogenin, digitoxigenin, uzarigenin and canarigenin were 5 - 15 %, 0 - 5 %, 10 - 15 % and 70 - 90 %, respectively. Shoot cultures were initiated from seeds, established as permanent cultures and cultivated on agar-solidified or in liquid medium. Shoot cultures maintained on solid medium contained an average of about 6 micromol cardenolides g (-1) dw. A relatively high proportion of digitoxigenin was found in two-thirds of the shoot cultures examined. The cardenolide content of amphibian shoot cultures averaged to about 1 micromol g (-1) dw. Plants regenerated from shoot cultures and maintained under hydroponic conditions accumulated the same amount of cardenolides as plants collected in the field. No cardenolides could be detected in callus cultures.

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Evatromonoside

2006

Spectroscopic Data of Steroid Glycosides: Spirostanes, Bufanolides, Cardenolides

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Monoglycosides from Isoplexis chalcantha

Cited by 11 publications

References 5 publications

LC‐NMR applied to the characterisation of cardiac glycosides from three micropropagated Isoplexis species

LC‐NMR applied to the characterisation of cardiac glycosides from three micropropagated Isoplexis species

Cardenolide Genin Pattern in Isoplexis Plants and Shoot Cultures

Evatromonoside

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