Isolation of Apoptosis-Inducing Stilbenoids from Four Members of the Orchidaceae Family

Russell B. Williams; Steven M. Martin; Jin-Feng Hu; Eliane Garo; Stephanie M. Rice; Vanessa L. Norman; Julie A. Lawrence; Grayson W. Hough; Matt G. Goering; Mark O'Neil-Johnson; Gary R. Eldridge; Courtney M. Starks

doi:10.1055/s-0031-1280293

Planta Medica, Table of Contents

Planta Med 2012; 78(2): 160-165
DOI: 10.1055/s-0031-1280293

Natural Product Chemistry

Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Isolation of Apoptosis-Inducing Stilbenoids from Four Members of the Orchidaceae Family

Russell B. Williams¹ , Steven M. Martin¹ , Jin-Feng Hu¹ , Eliane Garo¹ , Stephanie M. Rice¹ , Vanessa L. Norman¹ , Julie A. Lawrence¹ , Grayson W. Hough¹ , Matt G. Goering¹ , Mark O'Neil-Johnson¹ , Gary R. Eldridge¹ , Courtney M. Starks¹

¹Lead Discovery and Rapid Structure Elucidation Group, Sequoia Sciences, Inc., St. Louis, Missouri, USA

Abstract

High-throughput natural product research produced a suite of anticancer hits among several species of the Orchidaceae family (Oncidium microchilum, O. isthmi, and Myrmecophila humboldtii). A commercial Oncidium sp. was also examined as a convenient source of additional material. Isolation and structure elucidation led to the identification of fifteen stilbenoids including a new phenanthraquinone and two new dihydrostilbenes. NMR data for structure elucidation and dereplication were acquired utilizing a Bruker BioSpin TCI 1.7-mm MicroCryoProbe or a 5-µL CapNMR capillary microcoil. Several compounds inhibited proliferation of NCI-H460 and M14 cancer cell lines. All compounds were also examined for their ability to induce apoptosis. Apoptosis induction was determined by measuring caspase 3/7 activation and LDH release in a NCI-H460 cell line. Based on these results, a portion of the extract from a commercially available Oncidium sp. was chemically modified in an attempt to obtain additional phenanthraquinones.

Key words

Orchidaceae - Oncidium - Myrmecophila - phenanthraquinone - stilbenoid - apoptosis

Full Text

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Dr. Russell B. Williams

Sequoia Sciences, Inc.

1912 Innerbelt Business Center Drive

St. Louis, Missouri, 63114

USA

Phone: +1 314 373 51 81

Fax: +1 314 373 51 86

Email: rwilliams@sequoiasciences.com

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