STRUCTURAL MODIFICATION OF CYTOTOXIC SERRATENEDIOL FROM LYCOPODIACEAE PLANT
Article Sidebar
Main Article Content
Abstract
Serratenediol (1), cytotoxic natural product, from L.phlegmaria (traditional herbal medicine) were isolated and purified by chromatographic method. Structural modification of isolated serratenediols (1) was studied by oxidation reaction, which included the oxidation of hydroxyl groups and epoxidation of carbon double bond, to provide the new carbonyl compound (2) and oxirane derivatives (3). The obtained product 2 and 3 were identified by spectroscopic method. The carbonyl product 2 was obtained in 67.8% by using chromium trioxide in the presence of pyridine at room temperature. Meanwhile, the epoxidation reaction was carried out by using meta-chloroperbenzoic acid to produce product 3 in 62.9%. This work achieved to find the reaction conditions to create new derivatives of serratenediol (2, 3)
Article Details
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
Journal of TCI is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence, unless otherwise stated. Please read our Policies page for more information.
References
Boonya-udtayan S, Chaiphattharakit N, Thasana N, Ruek-ngam N, Ruchirawat S, Techasakul S. 2017. Phytochemical investigation of Lycopodium nummularifolium Blume and their antibacterial activity. The Sci. J. Phetchaburi Rajabhat Univ. 14(1): 26-33.
Doi K, Sakai K, Tanaka R, Toma K, Yamaguchi T, Wei M, et al. 2010. Chemopreventive effects of 13α, 14α-epoxy-3β-methoxyserratan-21β-ol (PJJ-34), a serratane-type triterpenoid, in a rat multi-organ carcinogenesis bioassay. Cancer Lett. 289(2):161-9.
Ham YM, Yoon WJ, Park SY, Jung YH, Kim D, Jeon YJ, et al. 2012. Investigation of the component of Lycopodium serratum extract that inhibits proliferation and mediates apoptosis of human HL-60 leukemia cells. Food Chem. Toxicol. 50(8): 2629-34.
Shi H, Li ZY, Guo YW. 2005. A new serratane-type triterpene from Lycopodium phlegmaria. Nat. Prod. Res. 19(8): 777-81.
Tanaka R, Minami T, Ishikawa Y, Matsunaga S, Tokuda H, Nishino H. 2003. Cancer chemopreventive activity of serratane-type triterpenoids on two-stage mouse skin carcinogenesis. Cancer Lett. 196(2): 121-6.
Tanaka R, Minami T, Tokuda H. 2006. Anti‐initiating activity of 3β‐methoxy‐13α, 14α‐epoxyserratan‐21β‐ol (PJJ‐34) from the stem bark of Picea jezoensis Carr. var. jezoensis. Chem. Biodivers. 3(7): 818-24.
Tanaka R, Tsujimoto K, In Y, Ishida T, Matsunaga S, Terada Y. 2001. Structure and stereochemistry of epoxyserratanes from the cuticle of Picea jezoensis var. jezoensis. J. Nat. Prod. 64(8): 1044-7.
Tanaka R, Ishikawa Y, Minami T, Minoura K, Tokuda H, Matsunaga S. 2003. Two new anti-tumor promoting serratane-type triterpenoids from the stem bark of Picea jezoensis var. jezoensis. Planta Med. 69(11): 1041-7.
Wittayalai S, Sathalalai S, Thorroad S, Worawittayanon P, Ruchirawat S, Thasana N. 2012. Lycophlegmariols A–D: Cytotoxic serratene triterpenoids from the club moss Lycopodium phlegmaria L. Phytochemistry 76: 117-23.
Yan J, Zhang XM, Li ZR, Zhou L, Chen JC, Sun LR, Qiu MH. 2005. Three new triterpenoids from Lycopodium japonicum Thunb. Helvetica Chimica Acta. 88(2): 240-4.
Yan J, Yi P, Chen B, Lu L, Li Z, Zhang X, Zhou L, Qiu M. 2008. Polyhydroxyserratane triterpenoids from Diphasiastrum complanatum. Phytochemistry 69(2): 506-10.
Zhang Z, ElSohly HN, Jacob MR, Pasco DS, Walker LA, Clark AM. 2002. Natural products inhibiting Candida albicans secreted aspartic proteases from Tovomita krukovii. Planta Med. 68(1): 49-54.
Zhang Y, Yi P, Chen Y, Mei Z, Hu X, Yang G. 2014. Lycojaponicuminol A–F: Cytotoxic serratene triterpenoids from Lycopodium japonicum. Fitoterapia 96: 95-102.
Zhou H, Li YS, Tong XT, Liu HQ, Jiang SH, Zhu DY. 2004. Serratane-type triterpenoids from Huperzia serrata. Nat. Prod. Res. 18(5): 453-9.