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5629-60-7
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???C
???(??):
???C
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UNCARINE C
???(??):
UNCARINE C;PTEROPODINE;Uncarine C-RM;Isospeciophylline;(20α)-19α-Methyl-2-oxoformosanan-16-carboxylic acid methyl ester;methyl 1-methyl-2'-oxospiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-carboxylate;methyl 1-methyl-2'-oxo-spiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-carboxylate;2'-keto-1-methyl-spiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-indoline]-4-carboxylic acid methyl ester;Spiro[3H-indole-3,6'(4'aH)-[1H]pyrano[3,4-f]indolizine]-4'-carboxylic acid, 1,2,5',5'a,7',8',10',10'a-octahydro-1'-methyl-2-oxo-, methyl ester, (1'S,3R,4'aS,5'aS,10'aS)-
CBNumber:
CB7326387
???:
C21H24N2O4
??? ??:
368.43
MOL ??:
5629-60-7.mol

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217-219℃
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1.33±0.1 g/cm3 (20 ºC 760 Torr)
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Isolated from Uncaria pteropoda, this alkaloid is probably stereoisomeric withMitraphylline (q.v.). It forms colourless plates when crystallized from MeOH and has [α]29DJ 9 - 102.5° (c 1.0, CHC13). The ultraviolet spectrum in MeOH has an absorption maximum at 246 mp. with a shoulder at 280 mp.. A crystalline picrate, m.p. 143-6°C; [α]D - 9.6° (c 0.5, EtOH) and a methiodide, m.p. 209-211°C after softening at 204°C; [α]D - 149° (c 0.53, EtOH) have been prepared. A solution of the alkaloid in pyridine forms an equilibrium mixture with 70 per cent isopteropodine when heated.

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Uncarine C is a compound extracted from Uncaria tomentosa leaves. The compounds extracted from these leaves have exhibited immunomodulating, antiinflammatory and anti-cancer activity, attributed to the presence of tetra/pentacyclic oxindole alkaloids.

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Yeoh, Chan, Morsingh., Tetrahedron Lett., 931 (1966)
Chan, Morsingh, Yeoh., 1. Chem. Soc., C, 2245 (1966)
Stereochemistry: Shamma et al., 1. Amer. Chem. Soc., 89, 1739, 2799 (1967)

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