Abstract
A new friedelane type triterpene, 3,16-dioxo-12α-hydroxyfriedelane was isolated from the chloroform extract of branches of Maytenus gonoclada Martius (Celastraceae) together with nine known compounds: 3, 11-dioxofriedelane, 3, 16-dioxofriedelane, 3, 12-dioxofriedelane, 3-oxo-12α,29-dihydroxyfriedelane, 3-oxofriedelane (friedelin), 3β-hydroxyfriedelane, 3-oxo-12α-hydroxyfriedelane and 3β-hydroxylup-20(29)-ene (lupeol) and a mixture of long chain hydrocarbons. The structure and stereochemistry of the new friedelane triterpene were established from the 1H NMR and 13C NMR spectra including two-dimensional experiments (HSQC, HMBC and NOESY) and high resolution mass spectrometry.
References
1.
Roberts S.C.
, Nat. Chem. Biol. , 2007 , 3 , 387 .
2.
Patocka J.
, J. Appl. Biomed. , 2003 , 1 , 7 .
3.
Martucciello S.
,
Balestrieri M.L.
,
Felice F.
,
Estevam C.S.
,
Sant'Ana A.E.G.
,
Pizza C.
, and
Piacente S.
, Chem-Biol. Interac. , 2010 , 183 , 450 .
4.
Oliveira M.L.G.
,
Duarte L.P.
,
Silva G.D.F.
,
Vieira Filho S.A.
,
Knupp V.F.
, and
Silva F.C.
, Magn. Reson. Chem. , 2007 , 45 , 895 .
5.
Silva F.C.
,
Duarte L.P.
,
Silva G.D.F.
,
Vieira Filho S.A.
,
Lula I.S.
,
Takahashi J.A.
, and
Sallum W.S.T.
, J. Braz. Chem. Soc. , 2011 , 22 , 943 .
6.
Andrade S.F.
,
Comunello E.
,
Noldin V.F.
,
Monache F.D.
,
Cechinel Filho V.
,
Niero R.
, Arch. Pharm. Res. , 2008 , 31 , 41 .
7.
Orabi K.Y.
,
Al-Qasoumi S.I.
,
El-Olemy M.M.
,
Mossa J.S.
,
Muhammad I.
, Phytochemistry , 2001 , 58 , 475 .
8.
Mahato S.B.
, and
Kundu A.P.
, Phytochemistry , 1994 , 37 , 1517 .
9.
Chen M.X.
,
Wang D.Y.
;
Guo J.
, J. Chem. Res. , 2010 , 34 , 114 .
10.
Queiroga C.L.
,
Silva G.F.
,
Dias P.C.
,
Possenti A.
,
Carvalho J.E.
, J. Ethnopharmacol. , 2000 , 72 , 465 .
11.
Salazar G.C.M.
,
Silva G.D.F.
,
Duarte L.P.
,
Vieira-Filho S.A.
, and
Lula I.S.
, Magn. Reson. Chem. , 2000 , 38 , 977 .
12.
Monache F.D.
,
Marini-Bettòlo G.B.
,
Pomponi M.
,
Méllo J.F.
,
King T.J.
, and
Thomson R.H.
, J. Chem. Soc., Perkin Trans. 1 , 1979 , 2649 .
13.
Ghosh A.
,
Misra S.
,
Dutta A.K.
,
Choudhury A.
, Phytochemistry 1985 , 24 , 1725 .
14.
Silverstein R.M.
, and
Bassler G.
,
Clayton G.
, and
Morrill Terence C.
Spectrometric identificationn of organic compounds. 5th edn, 1991 . John Wiley , New York .
15.
Miles D.H.
,
Kokpol U.
, J. Pharm. Sci. 1976 , 65 , 284 .