New Serratene Triterpenoids from Palhinhaea cernua and Their Cytotoxic Activity

Jian Yan; Zhong-Yu Zhou; Mei Zhang; Jing Wang; Hao-Fu Dai; Jian-Wen Tan

doi:10.1055/s-0032-1314999

Planta Medica, Table of Contents

Planta Med 2012; 78(12): 1387-1391
DOI: 10.1055/s-0032-1314999

Natural Product Chemistry

Letters

Georg Thieme Verlag KG Stuttgart · New York

New Serratene Triterpenoids from Palhinhaea cernua and Their Cytotoxic Activity

Jian Yan

¹Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, China

,

Zhong-Yu Zhou

¹Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, China

,

Mei Zhang

¹Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, China

³Graduate School of the Chinese Academy of Sciences, Beijing, China

,

Jing Wang

¹Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, China

³Graduate School of the Chinese Academy of Sciences, Beijing, China

,

Hao-Fu Dai

²State Key Laboratory of Tropical Crops Biotechnology, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agriculture Sciences, Haikou, China

,

Jian-Wen Tan

¹Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, China

› Author Affiliations

Abstract

Four new serratene triterpenoids, 3β,21β,24-trihydroxyserrat-14-en-24-(4′-hydroxybenzoate) (1), 3β,21α,24-trihydroxyserrat-14-en-3-(4′-hydroxybenzoate) (2), 3β,14α,15α,21α-tetrahydroxyserrat-14-en-3-(3′-methoxyl-4′-hydroxybenzoate) (3), and 3β,14α,15α,21α-tetrahydroxyserrat-14-en-21-acetyl-3-(4′-hydroxybenzoate) (4), together with two known ones, 5 and 6, were isolated from whole plants of Palhinhaea cernua. The structures of these new compounds were elucidated by spectroscopic methods. All the six compounds were tested for their in vitro cytotoxicity against three human cancer cell lines (K562, SMMC-7721, and SGC7901). Compound 5 showed cytotoxicity against the three test cell lines with IC₅₀ values of 20.3, 34.0, and 22.5 ug/mL, respectively. Compound 1 showed slight cytotoxicity against K562 cell lines with IC₅₀ value of 56.1 ug/mL, while no obvious inhibitory effects were detected for other compounds.

Key words

Palhinhaea cernua - Lycopodiaceae - serratene - triterpenoid - cytotoxic activity

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References

References
1 Tanaka R, Minami T, Tokuda H. 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 2006; 3: 818-824
2 Tanaka R, Minami T, Ishikawa Y, Tokuda H, Matsunaga S. Cancer chemopreventive activity of serratane-type triterpenoids from Picea jezoensis . Chem Biodivers 2004; 1: 878-885
3 Zhang Z, Elsohly HN, Jacob MR, Pasco DS, Walker LA, Clark AM. Natural products inhibiting Candida albicans secreted aspartic proteases from Lycopodium cernuum . J Nat Prod 2002; 65: 979-985
4 Bhutani KK, Kapoor R, Atal CK. Three bridged 14β,26-epoxy-C-chomo-pentacycle triterpenes from Primula rosea . Phytochemistry 1984; 23: 403-406
5 Kulshreshtha MJ, Kulshreshtha DK, Rastogi RP. Review article: the triterpenoids. Phytochemistry 1972; 11: 2369-2381
6 Ghisalberti EL, DeSouza NJ, Rees HH, Goodwin TW. Biosynthesis of the triterpene hydrocarbons of Polypodium vulgare . Phytochemistry 1970; 9: 1817-1823
7 Ageta H, Shiojima K, Masuda K. Fern constituents: Onoceroid, α-onoceradiene, serratene and onoceranoxide, isolated from Lemmaphyllum microphyllum varieties. Chem Pharm Bull 1982; 30: 2272-2274
8 Yan J, Zhang XM, Li ZR, Zhou L, Chen JC, Sun LR, Qiu MH. Three new triterpenoids from Lycopodium japonicum Thunb. Helv Chim Acta 2005; 88: 240-244
9 Yan J, Yi P, Chen BH, Lu L, Li ZR, Zhang XM, Zhou L, Qiu MH. Five new serratane triterpenoids with poly-hydroxyl from Diphasiastrum complanatum . Phytochemistry 2008; 69: 506-510
10 Yan J, Sun LR, Zhang XM, Li ZR, Zhou L, Qiu MH. Serratene triterpenoids from Palhinhaea cernua var. sikkimensis . Chem Pharm Bull 2009; 57: 1381-1384
11 Yan J, Sun LR, Li W, Zhou L, Li ZR, Zhang XM, Yang L, Qiu MH. Cytotoxic serratane triterpenes from Diphasiastrum complanatum with a hydroxyl group at C-27. Planta Med 2010; 76: 353-357
12 Xiao PG. Modern Chinese materia medica. Beijing: Chemistry and Industry Press; 2002; 3: 135-139
13 Haruo S, Kazuo F, Xu GY, Cao X, Pan DJ. Assignment of the ¹H-and ¹³C-NMR spectra of four lycopodium triterpenoids by the application of new two-dimensional technique, heteronuclear multiple bond connectivity (HMBC). Agric Biol Chem 1988; 52: 1797-1801
14 Zhou H, Li YS, Tong XT, Liu HQ, Jiang SH, Zhu DY. Serratane-type triterpenoids from Huperzia serrata . Nat Prod Res 2004; 18: 453-459
15 Tanaka R, Ohmori K, Minoura K, Matsunaga S. Two new epoxyserratanes from the cuticle of Picea jeazoensis . J Nat Prod 1996; 59: 237-241
16 Tanaka R, Tsujimoto K, Muraoka O, Matsunaga S. Two serratane triterpenoids from the stem bark of Picea jezoensis var. hondoensis . Phytochemistry 1998; 47: 839-843
17 Mosmann T. Rapid colourimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65: 55-63

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