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Absolute configuration and selective trypanocidal activity of gaudichaudianic acid enantiomers.
J Nat Prod. 2011 May 27; 74(5):1154-60.JN

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 showed a synergistic effect, with the racemic mixture being the most active.

Authors+Show Affiliations

Departamento de Química Orgânica, Instituto de Química, Universidade Estadual Paulista (UNESP), Araraquara, SP 14800-900, Brazil. joaombj@hotmail.comNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21506530

Citation

Batista, João M., et al. "Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers." Journal of Natural Products, vol. 74, no. 5, 2011, pp. 1154-60.
Batista JM, Batista AN, Rinaldo D, et al. Absolute configuration and selective trypanocidal activity of gaudichaudianic acid enantiomers. J Nat Prod. 2011;74(5):1154-60.
Batista, J. M., Batista, A. N., Rinaldo, D., Vilegas, W., Ambrósio, D. L., Cicarelli, R. M., Bolzani, V. S., Kato, M. J., Nafie, L. A., López, S. N., & Furlan, M. (2011). Absolute configuration and selective trypanocidal activity of gaudichaudianic acid enantiomers. Journal of Natural Products, 74(5), 1154-60. https://doi.org/10.1021/np200085h
Batista JM, et al. Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers. J Nat Prod. 2011 May 27;74(5):1154-60. PubMed PMID: 21506530.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Absolute configuration and selective trypanocidal activity of gaudichaudianic acid enantiomers. AU - Batista,João M, AU - Batista,Andrea N L, AU - Rinaldo,Daniel, AU - Vilegas,Wagner, AU - Ambrósio,Daniela L, AU - Cicarelli,Regina M B, AU - Bolzani,Vanderlan S, AU - Kato,Massuo J, AU - Nafie,Laurence A, AU - López,Silvia N, AU - Furlan,Maysa, Y1 - 2011/04/20/ PY - 2011/4/22/entrez PY - 2011/4/22/pubmed PY - 2011/8/19/medline SP - 1154 EP - 60 JF - Journal of natural products JO - J Nat Prod VL - 74 IS - 5 N2 - 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 showed a synergistic effect, with the racemic mixture being the most active. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/21506530/Absolute_configuration_and_selective_trypanocidal_activity_of_gaudichaudianic_acid_enantiomers_ L2 - https://doi.org/10.1021/np200085h DB - PRIME DP - Unbound Medicine ER -