Structure and absolute configuration of a secolignan from Peperomia blanda |
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| Authors: | Lidiane G Felippe João M Batista Jr Debora C Baldoqui Isabele R Nascimento Massuo J Kato Vanderlan S Bolzani Maysa Furlan |
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| Institution: | aInstituto de Química, Univ. Estadual Paulista - UNESP, CP 355, 14800-900 Araraquara, SP, Brazil;bDepartamento de Química, Universidade Estadual de Maringá, Av. Colombo 5790, 87020-900, Maringá, PR, Brazil;cInstituto de Química, Universidade de São Paulo, CP 26077, 05599-970 São Paulo, SP, Brazil |
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| Abstract: | A secolignan, (−)-2-methyl-3-bis(3′,4′-methylenedioxy-5′-methoxyphenyl) methyl]butyrolactone (1), with a rare cis configuration was isolated from the aerial parts of Peperomia blanda (Piperaceae). The structure of this compound was elucidated by a combination of spectroscopic methods, including ultraviolet, infrared, 1D- and 2D- nuclear magnetic resonance as well as high resolution mass spectrometry data. The absolute configuration of (−)-1 was determined as (2R,3S) by the comparison of experimental electronic circular dichroism (ECD) spectroscopy and time-dependent density functional theory (TDDFT) calculations. |
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| Keywords: | Peperomia blanda Piperaceae Secolignan Absolute configuration Electronic circular dichroism Density functional theory |
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