An Unprecedented Neolignan Skeleton from Chimarrhis turbinata

Author(s)

Cardoso, Carmen L. ^[1] ; Castro-Gamboa, Ian ^[2] ; Bergamini, Giovana M. ^[3] ; Cavalheiro, Alberto J. ^[2] ; Silva, Dulce H. S. ^[2] ; Lopes, Marcia N. ^[2] ; Araujo, Angela R. ^[2] ; Furlan, Maysa ^[2] ; Verli, Hugo ^{[3, 4]} ; Bolzani, Vanderlan da S. ^[2]

Affiliation

^[1] Univ Sao Paulo, Dept Quim, Fac Filosofia Ciencias & Letras Ribeirao Preto, BR-14040901 Sao Paulo - Brazil

^[2] Sao Paulo State Univ, Inst Chem, UNESP, BR-14800900 Araraquara, SP - Brazil

^[3] Univ Fed Rio Grande do Sul, Fac Pharm, UFRGS, BR-90610000 Porto Alegre, RS - Brazil

^[4] Univ Fed Rio Grande do Sul, Ctr Biotechnol, UFRGS, BR-90610000 Porto Alegre, RS - Brazil

• Document type: Journal article
• Source: Journal of Natural Products; v. 74, n. 3, p. 487-491, MAR 2011.
• Web of Science Citations: 8

Abstract

A lignan with a new skeleton named chimarrhinin (1) was isolated from an extract of the leaves of Chimarrhis turbinata, a Rubiaceae plant species. (13)C NMR spectrometric techniques including 1D and 2D experiments and HRESIMS provided unequivocal structural confirmation of this new C(6).C(3) skeleton type. The relative configuration of 1 was established by 2D (1)H-H analysis and J couplings, while its conformation was evaluated through molecular modeling using the RM1 semiempirical method, with the aid of coupling constants obtained by NMR analysis. The antioxidant activity of the new derivative 1 and two known and previously isolated phenolic derivatives (2 and 3) was investigated. An IC(50) value of 7.50 +/- 0.5 mu mol L(-1) was obtained for the new derivative 1, while 2 and 3 showed IC(50) values of 18.60 +/- 0.4 and 18.50 +/- 0.6 mu mol, respectively. (AU)

• FAPESP's process: 03/02176-7 - Conservation and sustainable use of the diversity from Cerrado and Atlantic Forest: chemical diversity and prospecting for potential drugs - phase II
• Grantee: Vanderlan da Silva Bolzani
• Support Opportunities: BIOTA-FAPESP Program - Thematic Grants