PHENANTHRENES AND BIBENZYLS FROM THE STEMS OF DENDROBIUM SONIA ‘RED JO’ AND THEIR ANTI-INFLAMMATORY ACTIVITY
Keywords:
Dendrobium Sonia ‘Jo Daeng’ orchid, orchidaceae, phenanthrenes, bibenzyls, anti-inflammatory activityAbstract
Dendrobium orchids are one of the important economic crops in Thailand and most of them are used as cut flowers or ornamental plants. Several Dendrobium species have been utilized as folk medicines since ancient times in Asian countries for treatments of gastric disorders, fever, diabetes and for tonic purposes. However, the pharmacological applications of Thai Dendrobium orchids have not been reported. The aims of this study are to investigate the chemical constituents from Dendrobium Sonia ‘Jo Daeng’ (Orchidaceae) and to evaluate the anti-inflammatory properties of the isolated compounds in order to promote Thai Dendrobium orchids with valued-added medical features. As a result, the isolation of the ethyl acetate fraction from the stems of D. Sonia ‘Jo Daeng’ by using repeated chromatography techniques provided five stilbenoid derivatives including three phenanthrenes: nudol (1), confusarin (2) and lusianthridin (3), and two bibenzyls: gigantol (4) and tristin (5). Their structures were determined on the basis of MS and NMR spectroscopic data. The isolated compounds (1-5) were evaluated for their anti-inflammatory effects by inhibiting nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. Among these, confusarin (2) and gigantol (4) were found to exhibit promising anti-inflammatory activity with 79.42% and 71.57% inhibition, respectively, at 5 µg/mL without cytotoxicity. Therefore, this study supports the possibility of using D. Sonia ‘Jo Daeng’ as an anti-inflammatory inhibitor source.
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References
Hou, Beiwei; Luo, Jing; Zhang, Yusi; Niu, Zhitao; Xue, Qingyun, and Ding, Xiaoyu. (2017, March). Iteration expansion and regional evolution: phylogeography of Dendrobium officinale and four related taxa in southern China. Scientific reports, 7, Article ID: 43525.
Wood, Howard P. (2006). The Dendrobriums. 1st ed. Oregon: Timber Press.
Xiaohua, Jin; Singchi, Chen, and Yibo, Luo. (2009, March). Taxonomic revision of Dendrobium moniliforme complex (Orchidaceae). Scientia Horticulturae, 120(1), 143-145.
Hossain, Mohammad M. (2011, March). Therapeutic orchids: traditional uses and recent advances - an overview. Fitoterapia, 82(2), 102-140.
Ng, Tzi B.; Liu, Jingyi; Wong, Jack H.; Ye, Xiujuan.; Wing Sze, Stephen C.; Tong, Yao, and Zhang, Kalin Y. (2012, March). Review of research on Dendrobium, a prized folk medicine. Applied Microbiology and Biotechnology, 93(5), 1795-1803.
Cheng, Jin; Dang, Pie-Pie; Zhao, Zhe; Yuan, Liang-Chen; Zhou, Zhi-Hua; Wolf, Daniel, and Luo, Yi-Bo. (2019, January). An assessment of the Chinese medicinal Dendrobium industry: supply, demand and sustainability. Journal of Ethnopharmacology, 229, 81-88.
Bulpitt, Christopher J.; Li, Yan; Bulpitt, Pauline F., and Wang, Jiguang. (2007, December). The use of orchids in Chinese medicine. Journal of the Royal Society of Medicine, 100(12), 558-563.
Wei, Wei; Feng, Lei; Bao, Wan-Rong; Ma, Dik-Lung; Leung, Chung-Hang; Nie, Shao-Ping, and Han, Quan-Bin. (2016, February). Structure characterization and immunomodulating effects of polysaccharides isolated from Dendrobium officinale. Journal of Agricultural and Food Chemistry, 64(4), 881-889.
Cheng, Lei; Guo, Da-Le; Zhang, Mao-Sheng; Linghu, Lang; Fu, Shao-Bin; Deng, Yun; He, Yu-Qi, and Xiao, Shi-Ji. (2020, June). Dihydrophenanthrofurans and bisbibenzyl derivatives from the stems of Dendrobium nobile. Fitoterapia, 143, Article ID: 104586.
Zhao, Gui Yun; Deng, Bo Wen; Zhang, Chong Yu; Cui, Yi Da; Bi, Jia Yi, and Zhang, Guo Gang. (2018, January). New phenanthrene and 9, 10-dihydrophenanthrene derivatives from the stems of Dendrobium officinale with their cytotoxic activities. Journal of Natural Medicines, 72(1), 246-251.
Zhou, Xue-Ming; Zheng, Cai-Juan; Gan, Li-She; Chen, Guang-Ying; Zhang, Xiao-Peng; Song, Xiao-Ping; Li, Gao-Nan, and Sun, Chong-Ge. (2016, July). Bioactive phenanthrene and bibenzyl derivatives from the stems of Dendrobium nobile. Journal of Natural Products, 79(7), 1791-1797.
Wang, Pei; Chen, Xin; Wang, Hao; Huang, Shengzhuo; Cai, Caihong; Yuan, Jingzhe; Zhu, Guoliang; Xu, Xinglian; Mei, Wenli, and Dai, Haofu. (2019, November). Four new picrotoxane-type sesquiterpenes from Dendrobium nobile Lindl. Frontiers in Chemistry, 7, 812.
Wang, Pei; Chen, Xin; Cai, Cai-Hong; Kong, Fan-Dong; Huang, Sheng-Zhuo; Yuan, Jing-Zhe; Xu, Xing-Lian; Mei, Wen-Li, and Dai, Hao-Fu. (2020, December). A new picrotoxane-type sesquiterpene from Dendrobium nobile Lindl. Natural Product Research. Retrieved January, 20, 2021, from https://doi.org/10.1080/14786419.2020.1851224
Lam, Yau; Ng, Tzi B.; Yao, Ren M.; Shi, Jun; Xu, Kai; Wing Sze, Stephen C., and Zhang, Kalin Y. (2015, April). Evaluation of chemical constituents and important mechanism of pharmacological biology in Dendrobium plants. Evidence-Based Complementary and Alternative Medicine, 2015, Article ID: 841752.
Chu, Chu; Li, Tuo; Pedersen, Hans A.; Kongstad, Kenneth T.; Yan, Jizhong, and Staerk, Dan. (2019, June). Antidiabetic constituents of Dendrobium officinale as determined by high-resolution profiling of radical scavenging and α-glucosidase and α-amylase inhibition combined with HPLC-PDA-HRMS-SPE-NMR analysis. Phytochemistry Letters, 31, 47-52.
He, Li; Su, Qian; Bai, Lan; Li, Meifeng; Liu, Juanru; Liu, Xiaomei; Zhang, Cunyan; Jiang, Zhongliang; He, Jun; Shi, Jianyou; Huang, Shan, and Guo, Li. (2020, October). Recent research progress on natural small molecule bibenzyls and its derivatives in Dendrobium species. European Journal of Medicinal Chemistry, 204, Article ID: 112530.
Nie, Xuqiang; Chen, Yu; Li, Wei, and Lu, Yanliu. (2020, July). Anti-aging properties of Dendrobium nobile Lindl.: From molecular mechanisms to potential treatments. Journal of Ethnopharmacology, 257, Article ID: 112839.
Paudel, Mukti R.; Bhattarai, Hari D., and Pant, Bijaya. (2020). Traditionally used medicinal Dendrobium: A promising source of active anticancer constituents. In Orchids Phytochemistry, Biology and Horticulture, Reference Series in Phytochemistry, (Merillon, Jean-Michel; and Kodja, Hippolyte, eds.), pp. 1-26. Cham: Springer.
Teixeira da Silva, Jaime A., and Ng, Tzi B. (2017, March). The medicinal and pharmaceutical importance of Dendrobium species. Applied Microbiology and Biotechnology, 101(6), 2227-2239.
Maksup, Sarunyaporn, and Obsuwan, Kullanart. (2020). Flavonoid contents and antityrosinase activity in various parts of Dendrobium 'Sonia Jo Daeng' and Dendrobium 'Khao Sanan' at different growth stages. In Acta Horticulturae, V. 1298, pp. 517-522. Bangkok: International Society for Horticultural Science.
Obsuwan, Kullanart; Jeong, Byoung R., and Maksup, Sarunyaporn. (2019, May-August). Analysis of bioactive compounds, polysaccharides and antioxidant activity in different parts of Dendrobium 'Sonia Jo Daeng'. Science, Engineering and Health Studies, 13(2), 73-82.
Qinyi, Zhu; Lu, Jiang, and Xipeng Wang. (2017, June). The expression of Duffy antigen receptor for chemokines by epithelial ovarian cancer decreases growth potential. Oncology Letters, 13(6), 4302-4306.
Chen, Y.G.; Yu, H., and Lian, X. (2015, November). Isolation of stilbenoids and lignans from Dendrobium hongdie. Tropical Journal of Pharmaceutical Research, 14(11), 2055-2059.
Majumder, P.L., and Kar, Amita. (1987, March). Confusarin and confusaridin two phenanthrene derivatives of the orchid Eria Confusa. Phytochemistry, 26(4), 1127-1129. doi:10.1016/s0031-9422(00)82363-8
Blitzke, Torsten; Masaoud, Mohamed, and Schmidt, Jürgen. (2000, September). Constituents of Eulophia petersii. Fitoterapia, 71(5), 593-594.
Woo, Kyeong W.; Park, Jong E.; Choi, Sang U.; Kim, Ki H., and Lee, Kang R. (2014, January). Phytochemical constituents of Bletilla striata and their cytotoxic activity. Natural Product Science, 20(2), 91-94.
Chen, Yegao; Xu, Junju; Yu, Hong; Qing, Chen; Zhang, Yanli; Wang, Liqin; Lui, Ying, and Wang, Jihua. (2008, March). Cytotoxic phenolics from Bulbophyllum odoratissimum. Food Chemistry, 107(1), 169-173.
Zhang, X.; Xu, J. K.; Wang, J.; Wang, N. L.; Kurihara, H.; Kitanaka, S., and Yao, X. S. (2007, January). Bioactive bibenzyl derivatives and fluorenones from Dendrobium nobile. Journal of Natural Products, 70(1), 24-28.
Zhang, Yuying; Zhang, Qianqian; Xin, Wie; Liu, Na, and Zhang, Hua. (2019). Nudol, a phenanthrene derivative from Dendrobium nobile, induces cell cycle arrest and apoptosis and inhibits migration in osteosarcoma cells. Drug design, Development and Therapy, 2019(13), 2591-2601.
Réthy, Borbála; Kovács, Adriána; Zupkó, István; Forgo, Peter; Vasas, Andrea; Falkay, György, and Hohmann, Judit. (2006, June). Cytotoxic phenanthrenes from the rhizomes of Tamus communis. Planta Medica, 72(8), 767-770.
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