Peltogynoids and 2-Phenoxychromones from Peltophorum
                        pterocarpum and Evaluation of Their Estrogenic Activity

Johanne Polasek; Emerson Ferreira Queiroz; Laurence Marcourt; Aggeliki K. Meligova; Maria Halabalaki; Alexios-Leandros Skaltsounis; Michael N. Alexis; Bambang Prajogo; Jean-Luc Wolfender; Kurt Hostettmann

doi:10.1055/s-0032-1328299

Planta Medica, Table of Contents

Planta Med 2013; 79(06): 480-486
DOI: 10.1055/s-0032-1328299

Natural Product Chemistry

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Peltogynoids and 2-Phenoxychromones from Peltophorum pterocarpum and Evaluation of Their Estrogenic Activity

Johanne Polasek

¹School of Pharmaceutical Sciences, Phytochemistry and Bioactive Natural Products, University of Geneva, University of Lausanne, Geneva, Switzerland

,

Emerson Ferreira Queiroz

¹School of Pharmaceutical Sciences, Phytochemistry and Bioactive Natural Products, University of Geneva, University of Lausanne, Geneva, Switzerland

,

Laurence Marcourt

¹School of Pharmaceutical Sciences, Phytochemistry and Bioactive Natural Products, University of Geneva, University of Lausanne, Geneva, Switzerland

,

Aggeliki K. Meligova

²Institute of Biology, Medicinal Chemistry and Biotechnology, National Hellenic Research Foundation, Athens, Greece

,

Maria Halabalaki

³Laboratory of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, University of Athens, Athens, Greece

,

Alexios-Leandros Skaltsounis

³Laboratory of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, University of Athens, Athens, Greece

,

Michael N. Alexis

²Institute of Biology, Medicinal Chemistry and Biotechnology, National Hellenic Research Foundation, Athens, Greece

,

Bambang Prajogo

⁴University of Airlangga, Surabaya, Indonesia

,

Jean-Luc Wolfender

¹School of Pharmaceutical Sciences, Phytochemistry and Bioactive Natural Products, University of Geneva, University of Lausanne, Geneva, Switzerland

,

Kurt Hostettmann

¹School of Pharmaceutical Sciences, Phytochemistry and Bioactive Natural Products, University of Geneva, University of Lausanne, Geneva, Switzerland

› Author Affiliations

Abstract

Phytochemical investigation of the dichloromethane extract of the leaves of Peltophorum pterocarpum, a tropical ornamental tree, led to the isolation of twelve compounds (1–12). One new derivative of peltogynoid ophioglonin (1) and a new 2-phenoxychromone (2) with its 3′-O-β-D-glucoside derivative (3) are described here for the first time. In addition, nine flavonoid derivatives, including peltogynoid ophioglonin (4), were isolated for the first time from this plant. The structures were determined by spectroscopic and chemical methods. Evaluation of the estrogenic activities of 1, 2, and 4 using different model cell systems revealed that 4 was estrogenic and that 2 was largely inactive. Interestingly, 1 was unable to stimulate the proliferation of breast and endometrial cancer cells but exhibited substantial estrogen receptor α-mediated activation of gene expression. This observation indicates that 1 can be further evaluated for its cancer chemopreventive potential.

Key words

Peltophorum pterocarpum - Fabaceae - peltogynoid - phenoxychromone - estrogenic activity

Full Text

References

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