3-Ishwarone, a Rare Ishwarane Sesquiterpene from Peperomia scandens Ruiz & Pavon: Structural Elucidation through a Joint Experimental and Theoretical Study

Molecules

Fernando M. dos S. Junior³  Leosvaldo S. M. Velozo³  Erika M. de Carvalho²  André M. Marques³  Ricardo M. Borges³  Ana Paula F. Trindade³  Maria Isabel S. dos Santos¹  Ana Carolina F. de Albuquerque³  Fabio L.P. Costa³  Maria Auxiliadora C. Kaplan³ 

[1]Departamento de Produtos Naturais e Alimentos, Faculdade de Farmácia, Universidade Federal do Rio de Janeiro, 21941-590, Rio de Janeiro, RJ, Brazil

[2] E-Mail:

[3]Instituto de Tecnologia em Fármacos, FAR-MANGUINHOS, Fiocruz, Rio de Janeiro, RJ, 22775-903, Brazil

[4] E-Mail:

[5]Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, 21941-902, Brazil

[6] E-Mails:

关键词: 3-ishwarone;    structure elucidation;    IR spectra simulation;    NMR chemical shift calculation;    molecular modeling;   

DOI  :  10.3390/molecules181113520

来源: mdpi

【 摘 要 】

3-Ishwarone, (1), a sesquiterpene with a rare ishwarane skeleton, was isolated from Peperomia scandens Ruiz & Pavon (Piperaceae). Its structure was unambiguously determined by 1D- and 2D-NMR and infrared analyses, as well as by comparative theoretical studies which involved calculations of ¹³C-NMR chemical shifts, using the Density Functional Theory (DFT) with the mPW1PW91 hybrid functional and Pople’s 6-31G(d) basis set, and of vibrational frequencies, using the B3LYP hybrid functional and triple ζ Dunning’s correlation consistent basis set (cc-pVTZ), of (1) and three of its possible diastereomers, compounds 2–4.

【 授权许可】

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© 2013 by the authors; licensee MDPI, Basel, Switzerland.