Bioassay-guided isolation of the antidiabetic principle from Sorbus decora (Rosaceae) used traditionally by the Eeyou Istchee Cree First Nations.
Bioassay-guided fractionation of a crude extract (80% EtOH in H(2)O) of stem bark of Sorbus decora led the isolation of three new pentacycle triterpenes (compounds 1-3). The structures of 1-3 were established on the basis of spectroscopic methods (IR, HREIMS, 1D and 2D NMR) as 23,28-dihydroxyursan-12-ene-3β-caffeate, 23,28-dihydroxylupan-20(29)-ene-3β-caffeate, and 3β,23,28-trihydroxy-12-ursene, respectively. Compound 2 significantly enhanced glucose uptake in C2C12 cells, but compounds 1 and 3 did not. In addition, triterpenoids 4-8, catechin, and epicatechin were also isolated. This is the first comprehensive report of the phytochemical constituents of S. decora since the initial study by Narashmachari and von Rudloff (1962) and includes evaluation of their antidiabetic activity.
Guerrero-Analco
José A
JA
Centre for Advanced Research in Environmental Genomics, University of Ottawa, Ottawa, ON, K1N6N5, Canada.
Martineau
Louis
L
Saleem
Ammar
A
Madiraju
Padma
P
Muhammad
Asim
A
Durst
Tony
T
Haddad
Pierre
P
Arnason
John Thor
JT
D000818:Animals; D007004:Hypoglycemic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D024301:Plant Bark / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D011792:Quebec; D031994:Sorbus / Q000737:chemistry*; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
C552979:23,28-dihydroxylupan-20(29)-ene-3beta-caffeate; C552978:23,28-dihydroxyursan-12-ene-3beta-caffeate; C552980:3beta,23,28-trihydroxy-12-ursene; D007004:Hypoglycemic Agents; D014315:Triterpenes