Molecules 2013, 18(11), 13520-13529; doi:10.3390/molecules181113520
Article

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

1 Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, 21941-902, Brazil 2 Instituto de Tecnologia em Fármacos, FAR-MANGUINHOS, Fiocruz, Rio de Janeiro, RJ, 22775-903, Brazil 3 Departamento de Produtos Naturais e Alimentos, Faculdade de Farmácia, Universidade Federal do Rio de Janeiro, 21941-590, Rio de Janeiro, RJ, Brazil
* Author to whom correspondence should be addressed.
Received: 12 September 2013; in revised form: 24 October 2013 / Accepted: 29 October 2013 / Published: 31 October 2013
(This article belongs to the Section Natural Products)
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Abstract: 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 24.
Keywords: 3-ishwarone; structure elucidation; IR spectra simulation; NMR chemical shift calculation; molecular modeling

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MDPI and ACS Style

dos S. Junior, F.M.; Velozo, L.S.M.; de Carvalho, E.M.; Marques, A.M.; Borges, R.M.; Trindade, A.P.F.; dos Santos, M.I.S.; de Albuquerque, A.C.F.; Costa, F.L.; Kaplan, M.A.C.; de Amorim, M.B. 3-Ishwarone, a Rare Ishwarane Sesquiterpene from Peperomia scandens Ruiz & Pavon: Structural Elucidation through a Joint Experimental and Theoretical Study. Molecules 2013, 18, 13520-13529.

AMA Style

dos S. Junior FM, Velozo LSM, de Carvalho EM, Marques AM, Borges RM, Trindade APF, dos Santos MIS, de Albuquerque ACF, Costa FL, Kaplan MAC, de Amorim MB. 3-Ishwarone, a Rare Ishwarane Sesquiterpene from Peperomia scandens Ruiz & Pavon: Structural Elucidation through a Joint Experimental and Theoretical Study. Molecules. 2013; 18(11):13520-13529.

Chicago/Turabian Style

dos S. Junior, Fernando M.; Velozo, Leosvaldo S.M.; de Carvalho, Erika M.; Marques, André M.; Borges, Ricardo M.; Trindade, Ana P.F.; dos Santos, Maria I.S.; de Albuquerque, Ana C.F.; Costa, Fabio L.; Kaplan, Maria A.C.; de Amorim, Mauro B. 2013. "3-Ishwarone, a Rare Ishwarane Sesquiterpene from Peperomia scandens Ruiz & Pavon: Structural Elucidation through a Joint Experimental and Theoretical Study." Molecules 18, no. 11: 13520-13529.

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