Subscribe to RSS
DOI: 10.1055/s-0031-1280293
© Georg Thieme Verlag KG Stuttgart · New York
Isolation of Apoptosis-Inducing Stilbenoids from Four Members of the Orchidaceae Family
Publication History
received June 6, 2011
revised Sept. 1, 2011
accepted Sept. 20, 2011
Publication Date:
14 October 2011 (online)
![](https://www.thieme-connect.de/media/plantamedica/201202/lookinside/thumbnails/10.1055-s-0031-1280293-1.jpg)
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
References
- 1 Dressler R L. The orchids: natural history and classification. Cambridge, Mass.: Harvard University Press; 1990
- 2 Fay M F, Chase M W. Orchid biology: from Linnaeus via Darwin to the 21st century. Preface. Ann Bot. 2009; 104 359-364
- 3 Swarts N D, Dixon K W. Terrestrial orchid conservation in the age of extinction. Ann Bot. 2009; 104 543-556
- 4 Swarts N D, Dixon K W. Perspectives on orchid conservation in botanic gardens. Trends Plant Sci. 2009; 14 590-598
- 5 Myers N, Mittermeier R A, Mittermeier C G, Da F G A B, Kent J. Biodiversity hotspots for conservation priorities. Nature. 2000; 403 853-858
- 6 Gutierrez R M P. Orchids: a review of uses in traditional medicine, its phytochemistry and pharmacology. J Med Plants Res. 2010; 4 592-638
- 7 Garo E, Hu J-F, Goering M, Hough G, O'Neil-Johnson M, Eldridge G. Stilbenes from the Orchid Phragmipedium sp. J Nat Prod. 2007; 70 968-973
- 8 Hu J-F, Garo E, Yoo H-D, Cremin P A, Zeng L, Goering M G, O'Neil-Johnson M, Eldridge G R. Application of capillary-scale NMR for the structure determination of phytochemicals. Phytochem Anal. 2005; 16 127-133
- 9 Hernandez-Romero Y, Rojas J-I, Castillo R, Rojas A, Mata R. Spasmolytic effects, mode of action, and structure-activity relationships of Stilbenoids from Nidema boothii. J Nat Prod. 2004; 67 160-167
- 10 Yamaki M, Honda C. The stilbenoids from Dendrobium plicatile. Phytochemistry. 1996; 43 207-208
- 11 Tezuka Y, Hirano H, Kikuchi T, Xu G. Constituents of orchidaceous plants. X. Constituents of Ephemerantha lonchophylla; isolation and structure elucidation of new phenolic compounds, ephemeranthol-A, ephemeranthol-B, and ephemeranthoquinone, and of a new diterpene glucoside, ephemeranthoside. Chem Pharm Bull. 1991; 39 593-598
- 12 Bae E Y, Oh H, Oh W K, Kim M S, Kim B S, Kim B Y, Sohn C B, Osada H, Ahn J S. A new VHR dual-specificity protein tyrosine phosphatase inhibitor from Dendrobium moniliforme. Planta Med. 2004; 70 869-870
- 13 Shimizu M, Shogawa H, Hayashi T, Arisawa M, Suzuki S, Yoshizaki M, Morita N, Ferro E, Basualdo I, Berganza L H. Chemical and pharmaceutical studies on medicinal plants in Paraguay. Anti-inflammatory constituents of topically applied crude drugs. III. Constituents and anti-inflammatory effect of Paraguayan crude drug “Tamanda cuna” (Catasetum barbatum Lindle). Chem Pharm Bull. 1988; 36 4447-4452
- 14 Chen Y, Xu J, Yu H, Chen Q, Zhang Y, Wang L, Liu Y, Wang J. Cytotoxic phenolics from Bulbophyllum odoratissimum. Food Chem. 2008; 107 169-173
- 15 Honda C, Yamaki M. Phenanthrenes from Dendrobium plicatile. 2. Phytochemistry. 2000; 53 987-990
- 16 Leong Y-W, Kang C-C, Harrison L J, Powell A D. Phenanthrenes, dihydrophenanthrenes and bibenzyls from the orchid Bulbophyllum vaginatum. Phytochemistry. 1996; 44 157-165
- 17 Tuchinda P, Udchachon J, Khumtaveeporn K, Taylor W C, Engelhardt L M, White A H. Phenanthrenes of Eulophia nuda. Phytochemistry. 1988; 27 3267-3271
- 18 Majumder P L, Lahiri S. Lusianthrin and lusianthridin, two stilbenoids from the orchid Lusia indivisa. Phytochemistry. 1990; 29 621-624
- 19 Matsuda H, Morikawa T, Xie H, Yoshikawa M. Antiallergic phenanthrenes and stilbenes from the tubers of Gymnadenia conopsea. Planta Med. 2004; 70 847-855
- 20 Jones jr. W D, Ciske F L. A convenient synthesis of Dengibsin. J Org Chem. 1996; 61 3920-3922
- 21 Stermitz F R, Suess T R, Schauer C K, Anderson O P, Bye jr. R A. New and old phenanthrene derivatives from Oncidium cebolleta, a peyote-replacement plant. J Nat Prod. 1983; 46 417-423
- 22 Williams C A, De Brito A L T, Harborne J B, Eagles J, Waterman P G. Methylated C-glycosylflavones as taxonomic markers in orchids of the subtribe Ornithocephalinae. Phytochemistry. 1994; 37 1045-1053
- 23 Eldridge G R, Vervoort H C, Lee C M, Cremin P A, Williams C T, Hart S M, Goering M G, O'Neil-Johnson M, Zeng L. High-throughput method for the production and analysis of large natural product libraries for drug discovery. Anal Chem. 2002; 74 3963-3971
- 24 Bhaskar M U, Rao L J M, Rao N S P, Rao P R M. Ochrone A, a novel 9,10-dihydro-1,4-phenanthraquinone from Coelogyne ochracea. J Nat Prod. 1991; 54 386-389
- 25 Lee C-L, Nakagawa-Goto K, Yu D, Liu Y-N, Bastow K F, Morris-Natschke S L, Chang F-R, Wu Y-C, Lee K-H. Cytotoxic calanquinone A from Calanthe arisanensis and its first total synthesis. Bioorg Med Chem Lett. 2008; 18 4275-4277
- 26 Magwere T. Escaping immune surveillance in cancer: is denbinobin the panacea?. Br J Pharmacol. 2009; 157 1172-1174
- 27 Yang C R, Guh J H, Teng C M, Chen C C, Chen P H. Combined treatment with Denbinobin and Fas ligand has a synergistic cytotoxic effect in human pancreatic adenocarcinoma BxPC-3 cells. Br J Pharmacol. 2009; 157 1175-1185
- 28 Yang K-C, Uen Y-H, Suk F-M, Liang Y-C, Wang Y-J, Ho Y-S, Li I H, Lin S-Y. Molecular mechanisms of denbinobin-induced anti-tumorigenesis effect in colon cancer cells. World J Gastroenterol. 2005; 11 3040-3045
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