title: Isolation of apoptosis-inducing stilbenoids from four members of the Orchidaceae family.
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.
authors: Lead Discovery and Rapid Structure Elucidation Group, Sequoia Sciences, Inc., St. Louis, Missouri, USA. rwilliams@sequoiasciences.com
authors: Russell B
authors: RB
authors: Williams
authors: Steven M
authors: SM
authors: Martin
authors: Jin-Feng
authors: JF
authors: Hu
authors: Eliane
authors: E
authors: Garo
authors: Stephanie M
authors: SM
authors: Rice
authors: Vanessa L
authors: VL
authors: Norman
authors: Julie A
authors: JA
authors: Lawrence
authors: Grayson W
authors: GW
authors: Hough
authors: Matt G
authors: MG
authors: Goering
authors: Mark
authors: M
authors: O'Neil-Johnson
authors: Gary R
authors: GR
authors: Eldridge
authors: Courtney M
authors: CM
authors: Starks
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D017209:Apoptosis / Q000187:drug effects*; D053148:Caspase 3 / Q000378:metabolism; D053179:Caspase 7 / Q000378:metabolism; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy* / Q000378:metabolism; D029595:Orchidaceae / Q000737:chemistry*; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use*; D013267:Stilbenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D010936:Plant Extracts; D013267:Stilbenes; D053148:Caspase 3; D053179:Caspase 7