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Quercetin as the Active Principle of Hypericum hircinum Exerts a Selective Inhibitory Activity against MAO-A: Extraction, Biological Analysis, and Computational Study

Supporting Info

Franco Chimenti,^† Filippo Cottiglia,^‡ Leonardo Bonsignore,^‡ Laura Casu,^‡ Mariano Casu,^§ Costantino Floris,^§ Daniela Secci,*^† Adriana Bolasco,^† Paola Chimenti,^† Arianna Granese,^† Olivia Befani, Paola Turini, Stefano Alcaro, Francesco Ortuso, Giuseppe Trombetta, Alberto Loizzo, and Irene Guarino

Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Universit degli Studi di Roma La Sapienza, P.le A. Moro 5, 00185 Rome, Italy, Dipartimento Farmaco Chimico Tecnologico, Universit degli Studi di Cagliari, Via Ospedale 72, 09124 Cagliari, Italy, Dipartimento di Scienze Chimiche, Universit di Cagliari, Complesso di Monserrato, SS 554, Km 4.5, 09042 Monserrato (CA), Italy, Dipartimento di Scienze Biochimiche A. Rossi Fanelli and Centro di Biologia Molecolare del CNR Universit degli Studi di Roma La Sapienza, P.le A. Moro 5, 00185 Rome, Italy, Dipartimento di Scienze Farmaco Biologiche Complesso Nin Barbieri, Universit degli Studi di Catanzaro Magna Graecia, 88021 Roccelletta di Borgia (CZ), Italy, and Istituto Superiore di Sanit, Viale Regina Elena 299, 00161 Rome, Italy

J. Nat. Prod., 2006, 69 (6), pp 945–949

DOI: 10.1021/np060015w

Publication Date (Web): May 24, 2006

†

Dip. S.C.T.S.B.A., University of Rome “La Sapienza”.

‡

Dip. Farmaco Chimico Tecnologico, University of Cagliari.

Dip. Scienze Chimiche, University of Cagliari.

To whom correspondence should be addressed. E-mail: daniela.secci@uniroma1.it. Tel and Fax: +39 06 4991 3763.

Dip. Scienze Biochimiche “A.Rossi Fanelli”, University of Rome “La Sapienza”.

Dip. Scienze Farmaco Biologiche, University of Catanzaro.

Istituto Superiore di Sanità.

Abstract

The methanol extract from Hypericum hircinum leaves exhibited in vitro inhibition of monoamine oxidases (MAO). Bioassay-guided fractionation led to the isolation of quercetin and five compounds identified for the first time from H. hircinum. Quercetin was the only compound with a selective inhibitory activity against MAO-A, with an IC₅₀ value of 0.010 μM. To explain MAO selective inhibition at the molecular level, a computational study was carried out by conformational search and docking techniques using recently determined crystallographic models of both enzymatic isoforms. An in vivo study in mice was carried out using the forced swimming test in order to elucidate the behavioral effects of quercetin.

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