| Full text | |
| Author(s): Show less - |
Batista, Jr., Joao M.
[1]
;
Batista, Andrea N. L.
[1]
;
Rinaldo, Daniel
[1]
;
Vilegas, Wagner
[1]
;
Ambrosio, Daniela L.
[2]
;
Cicarelli, Regina M. B.
[2]
;
Bolzani, Vanderlan S.
[1]
;
Kato, Massuo J.
[3]
;
Nafie, Laurence A.
[4]
;
Lopez, Silvia N.
[5]
;
Furlan, Maysa
[1]
Total Authors: 11
|
| Affiliation: | [1] Univ Estadual Paulista UNESP, Inst Quim, Dept Quim Organ, BR-14800900 Araraquara, SP - Brazil
[2] Univ Estadual Paulista UNESP, Fac Ciencias Farmaceut, BR-14801902 Araraquara, SP - Brazil
[3] Univ Sao Paulo USP, Inst Quim, BR-05508900 Sao Paulo - Brazil
[4] Syracuse Univ, Dept Chem, Syracuse, NY 13244 - USA
[5] Univ Nacl Rosario, Fac Ciencias Bioquim & Farmaceut, RA-2000 Rosario, Santa Fe - Argentina
Total Affiliations: 5
|
| Document type: | Journal article |
| Source: | Journal of Natural Products; v. 74, n. 5, p. 1154-1160, MAY 2011. |
| Web of Science Citations: | 32 |
| Abstract | |
Gaudichaudianic acid, a prenylated chromene isolated from Piper gaudichaudianum, has been described as a potent trypanocidal compound against the Y-strain of Trypanosoma cruzi. We herein describe its isolation as a racemic mixture followed by enantiomeric resolution using chiral HPLC and determination of the absolute configuration of the enantiomers as (+)-S and (-)-R by means of a combination of electronic and vibrational circular dichroism using density functional theory calculations. Investigation of the EtOAc extract of the roots, stems, and leaves from both adult specimens and seedlings of P. gaudichaudianum revealed that gaudichaudianic acid is biosynthesized as a racemic mixture from the seedling stage onward. Moreover, gaudichaudianic acid was found exclusively in the roots of seedlings, while it is present in all organs of the adult plant. Trypanocidal assays indicated that the (+)-enantiomer was more active than its antipode. Interestingly, mixtures of enantiomers stowed a synergistic effect, with the racemic mixture being the most active. (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 |