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Alkaloid Glycosides

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Helmut Ripperger – One of the best experts on this subject based on the ideXlab platform.

  • Steroidal Alkaloid Glycosides from Solanum suaveolens
    Phytochemistry, 1997
    Co-Authors: Helmut Ripperger, Andrea Porzel
    Abstract:

    Abstract In addition to khasianine, solamargine, xylosylsolamargine and solasonine, three steroidal Alkaloid Glycosides, solasuaveoline, dihydrosolasuaveoline and isosolasuaveoline, have been isolated from aerial parts of Solanum suaveolens. The structures have been assigned by NMR investigations as (25R)-3β-{O-β- d -glucopyranosyl-(1 → 2)-O-β- d -glucopyranosyl-(1 → 4)-[O-α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-22αN-spirosol-5-ene, (25R)-3β-{O-β- d -glucopyranosyl-(1 → 2)-O-β- d -glucopyranosyl-(1 → 4)-[O-α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-5α,22αN-spirosolane and (25R)-3β-{O-β- d -glucopyranosyl-(1 → 6)-O-β- d -glucopyranosyl-(1 → 3)-[O-α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-22αN-spirosol-5-ene, respectively.

  • Steroidal Alkaloid Glycosides from Solanum uporo
    Phytochemistry, 1997
    Co-Authors: Helmut Ripperger
    Abstract:

    In addition to solamargine, anguivine and isoanguivine, two new steroidal Alkaloid Glycosides, (23S)-23-hydroxyanguivine and (23S)-23-hydroxyisoanguivine, have been isolated from roots of Solanum uporo, the structures of which have been assigned by comparison with literature data as (23S,25R)-3 beta-[O-alpha-L-rhamnopyranosyl-(1–>2)-O- [beta-D-xylopyranosyl-(1–>3)]-beta-D-glucopyranosyloxy]-22 alpha N-spirosol-5-en-23-ol and (23S,25R)-3 beta-[O-alpha-L-rhamnopyranosyl-(1–>2)-O-[beta-D- xylopyranosyl-(1–>3)]-beta-D-galactopyranosyloxy]-22 alpha N-spirosol-5-en-23-ol.

  • steroid Alkaloid Glycosides from solanum coccineum
    Phytochemistry, 1996
    Co-Authors: Susan Lorey, Andrea Porzel, Helmut Ripperger
    Abstract:

    Abstract In addition to solamargine, isoanguivine and solasonine, two new steroid Alkaloid Glycosides, xylosyl-solamargine and xylosyl-β-solamarine, have been isolated from the aerial parts of Solanum coccineum, the structures of which have been elucidated as (25R)-3β-{O-β- d – xylopyranosyl -(1 → 2)-O-α- l – rhamnopyranosyl -(1 → 4)-O-[α- l – rhamnopyranosyl -(1 → 2)]-β- d – glucopyranosyloxy }-22αN- spirosol-5-ene and (25S)-3β-O-β- d – xylopyranosyl -(1 → 2)-O-α- l – rhamnopyranosyl -(1 → 4)-O-[α- l – rhamnopyranosyl -(1 → 2)]-β – d – glucopyranosyloxy }-22βN- spirosol-5-ene .

Andrea Porzel – One of the best experts on this subject based on the ideXlab platform.

  • Steroidal Alkaloid Glycosides from Solanum suaveolens
    Phytochemistry, 1997
    Co-Authors: Helmut Ripperger, Andrea Porzel
    Abstract:

    Abstract In addition to khasianine, solamargine, xylosylsolamargine and solasonine, three steroidal Alkaloid Glycosides, solasuaveoline, dihydrosolasuaveoline and isosolasuaveoline, have been isolated from aerial parts of Solanum suaveolens. The structures have been assigned by NMR investigations as (25R)-3β-{O-β- d -glucopyranosyl-(1 → 2)-O-β- d -glucopyranosyl-(1 → 4)-[O-α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-22αN-spirosol-5-ene, (25R)-3β-{O-β- d -glucopyranosyl-(1 → 2)-O-β- d -glucopyranosyl-(1 → 4)-[O-α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-5α,22αN-spirosolane and (25R)-3β-{O-β- d -glucopyranosyl-(1 → 6)-O-β- d -glucopyranosyl-(1 → 3)-[O-α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-22αN-spirosol-5-ene, respectively.

  • steroid Alkaloid Glycosides from solanum coccineum
    Phytochemistry, 1996
    Co-Authors: Susan Lorey, Andrea Porzel, Helmut Ripperger
    Abstract:

    Abstract In addition to solamargine, isoanguivine and solasonine, two new steroid Alkaloid Glycosides, xylosyl-solamargine and xylosyl-β-solamarine, have been isolated from the aerial parts of Solanum coccineum, the structures of which have been elucidated as (25R)-3β-{O-β- d – xylopyranosyl -(1 → 2)-O-α- l – rhamnopyranosyl -(1 → 4)-O-[α- l – rhamnopyranosyl -(1 → 2)]-β- d – glucopyranosyloxy }-22αN- spirosol-5-ene and (25S)-3β-O-β- d – xylopyranosyl -(1 → 2)-O-α- l – rhamnopyranosyl -(1 → 4)-O-[α- l – rhamnopyranosyl -(1 → 2)]-β – d – glucopyranosyloxy }-22βN- spirosol-5-ene .

  • solanum Alkaloids 128 steroid Alkaloid Glycosides from solanum robustum
    European Journal of Organic Chemistry, 1994
    Co-Authors: Helmut Ripperger, Andrea Porzel
    Abstract:

    β1-Solamargine and three new glycoAlkaloids, robustine, N-hydroxyrobustine, and 25-acetoxyrobustine, have been isolated from the roots of Solanum robustum, the structures of which have been elucidated as 3-O-{O-α-L-arabinopyranosyl-(13)-O-[α-L-rhamnopyranosyl-(12)]- O-[α-L-rhamnopyranosyl-(14)]-(β-D-glucopyranosyl}solasodine (3)), its N-hydroxy, and its 25-acetoxy derivative. These compounds have characteristic structures in comparison with the hitherto known Solanum glycoAlkaloids.

Jian-gong Shi – One of the best experts on this subject based on the ideXlab platform.

Toshihiro Nohara – One of the best experts on this subject based on the ideXlab platform.

William Gaffield – One of the best experts on this subject based on the ideXlab platform.

  • Spirosolane-containing Solanum species and induction of congenital craniofacial malformations.
    Toxicon, 2002
    Co-Authors: Richard F Keeler, Dale C. Baker, William Gaffield
    Abstract:

    Comparison by GC analysis of purified Alkaloid extracts of Solanum species revealed no measurable free solasodine, other spirosolanes, or any non-spirosolane steroidal Alkaloid aglycones in unhydrolyzed total Alkaloid fractions of fruit of Solanum elaeagnifolium Cav. (silverleaf nightshade), Solanum sarrachoides (S. villosum Lam.—hairy nightshade), Solanum dulcamara L. (European bittersweet nightshade) or Solanum melongena L. (eggplant). All Alkaloidal material was apparently present as glycoside. Conversely, sprouts of Solanum tuberosum L. (potato) contained 67% of its Alkaloids as Glycosides, which was freed only upon hydrolysis with the remaining 33% present as free solanidine. GC/MS analysis of hydrolysates of purified extracts of the test Solanum species revealed that solasodine was a principal or sole aglycone of the Alkaloid Glycosides in each of the test species except Solanum tuberosum. In the latter, solanidine was the sole aglycone. Among the test species, exclusive of S. tuberosum, only S. dulcamara contained aglycones other than solasodine. In addition to solasodine, S. dulcamara contained appreciable amounts of an unknown spirosolane, an aglycone provisionally identified as soladulcidine. The induction of congenital craniofacial malformations in hamsters by high oral doses of the four Solanum species that contained mainly solasodine Glycosides—S. elaeagnifolium, S. dulcamara, S. sarrachoides and S. melongena was compared to inductions of malformations by Solanum tuberosum, that contained mainly solanidane Glycosides. Compared to controls, Solanum elaeagnifolium and Solanum dulcamara fruit both induced a high percentage incidence of deformed litters (20.4 and 16.3, respectively) that was statistically significant (P < 0.001 level) while percentage incidence of deformed litters induced by Solanum sarrachoides and Solanum melongena fruit (9.5 and 7.6 respectively) were both higher than controls (3.4%), in neither case was the incidence statistically significant (P < .05). Deformed litter incidence induced by sprouts of Solanum tuberosum was 24.0%, (P < 0.001).