Solasodine

• Catalog No.: Bio-0257
• CAS Number: 126-17-0
• M. F.: C27H43NO2
• M. W.: 413.63582

SYNONYMS

• IUPAC name: (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosane-6,2'-piperidin]-18-en-16-ol
• IUPAC Traditional name: (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosane-6,2'-piperidin]-18-en-16-ol
• Synonyms: Solancarpine; Purapuridine; Solanidine S; Solancarpidine

DATABASE IDS

• CAS Number: 126-17-0

PROPERTIES

• Application(s): Antineoplastic agent
• Application(s): Antiandrogenic
• Application(s): Antiinflammatory
• Application(s): Antispermatogenic props.
• Biological Source: Aglycone from many Solanum spp. and from Fritillaria camtschatcensis. Occurs free in Solanum trilobatum and Solanum dulcamara (Liliaceae, Solanaceae)
• Description: Racemic
• Mechanism of Action: Inhibitor of spermatogenesis and sperm motility
• Mechanism of Action: Inhibitor of testosterone release
• Mechanism of Action: Regulations of TNFR I and II expression

REFERENCES

• Uhle, F.C., J.A.C.S., 1954, 76, 4245, (synth, struct)
• Budzikiewicz, H., Tetrahedron, 1964, 2267, (ms)
• Schreiber, K. et al., Tetrahedron, 1964, 20, 1939; 1966, 22, 3591, (struct, synth)
• Boll, P.M. et al., Acta Chem. Scand., 1965, 19, 1365, (pmr, config)
• Wolters, B., Planta Med., 1966, 14, 392-401, (activity)
• Puroshathaman, K.K. et al., Aust. J. Chem., 1969, 22, 2153
• Kessar, S.V. et al., Tetrahedron, 1971, 27, 2153-2159, (synth)
• Weston, R.J. et al., Aust. J. Chem., 1977, 30, 917, (cmr)
• Bird, G.J. et al., Aust. J. Chem., 1979, 32, 783, (cmr)
• Ripperger, H. et al., Alkaloids (N.Y.), 1981, 19, 81, (rev)
• Ripperger, H. et al., Phytochemistry, 1997, 46, 1279-1282, (Solasuaveoline, Isosolasuaveoline)
• Hu, K. et al., Planta Med., 1999, 65, 35-38, (isol, activity)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, POJ000