| Identification | Back Directory | [Name]
UNCARINE C | [CAS]
5629-60-7 | [Synonyms]
UNCARINE C
PTEROPODINE
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)- | [Molecular Formula]
C21H24N2O4 | [MDL Number]
MFCD03788764 | [MOL File]
5629-60-7.mol | [Molecular Weight]
368.43 |
| Hazard Information | Back Directory | [Description]
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. | [Uses]
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. | [Definition]
ChEBI: Uncarine C is a member of indolizines. | [References]
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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