seco-iridoids from Calycophyllum spruceanum (Rubiaceae).
Three seco-iridoids 7-methoxydiderroside, 6'-O-acetyldiderroside and 8-O-tigloyldiderroside, were isolated from the wood bark of Calycophyllum spruceanum together with the known iridoids loganetin, loganin and the seco-iridoids secoxyloganin, kingiside and diderroside. Their structures were elucidated by means of NMR and MS spectral data analysis. Using NOE correlations and coupling constants, the relative stereochemistry of the new derivatives was established. 7-Methoxydiderroside, 6'-O-acetyldiderroside and the known secoxyloganin and diderroside showed in vitro activity against trypomastigote forms of Trypanosoma cruzi, with IC(50) values of 59.0, 90.2, 74,2 and 84.9 microg/mL, respectively and were compared to the standard gentian violet (IC(50) 7.5 microg/ml).
Cardona Zuleta
Luz Margarita
LM
NuBBE-Núcleo de Bioensaios, Biossíntesse e Ecofisiologia de Produtos Naturais, Instituto de Química, Universidade Estadual Paulista, CP 355, CEP 14801-970, Araraquara, São Paulo, Brazil.
Cavalheiro
Alberto José
AJ
Siqueira Silva
Dulce Helena
DH
Furlan
Maysa
M
Marx Young
Maria Claudia
MC
Albuquerque
Sérgio
S
Castro-Gamboa
Ian
I
da Silva Bolzani
Vanderlan
V
D000818:Animals; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification; D057888:Iridoid Glucosides; D039823:Iridoids / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D019666:Rubiaceae / Q000737:chemistry*; D013237:Stereoisomerism; D014344:Trypanocidal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D014349:Trypanosoma cruzi / Q000187:drug effects / Q000235:genetics
D005960:Glucosides; D006027:Glycosides; D057888:Iridoid Glucosides; D039823:Iridoids; D014344:Trypanocidal Agents; C059515:secoxyloganin; C059516:loganin