Abstract
Ten steroids and iridoids were isolated from the tubers of Alocasia cucullata (Lour.) G. Don. Among them, alocasgenin A (1) and alocasgenoside B–C (2–3) were new compounds and the aglycone of compound 1, obtained from the acid hydrolysis of 1, was named alocasgenol (1a). Also, for the first time, tenacigenin B (4), 17β-tenacigenin-B (5), 3-O-6-deoxy-3-O-methyl-β-d-allopyranosyl-(1→4)-β-d-oleandropyranosyl-tenacigenin C (6), marsdenoside A–B (7–8) and tenacigenoside A–B (9–10) were isolated from the genus Alocasia. The chemical structures were elucidated by the extensive analysis of spectral data and compared with the literature. By evaluation of the cytotoxic and tyrosine kinase inhibition, compounds 1–10, 1a and compound 2 showed significant growth inhibition against two tumour cell lines, MGC-803 and HT-29, while compounds 1, 1a, 3, 6 and 8 presented moderate inhibition. Furthermore, compound 2 had the inhibitory property against the enzyme activity biochemically.
Similar content being viewed by others
References
Wu ZY (1990) The Chinese flora. Science Press, Beijing, 75 pp
Yang X, Guan PC (1998) Purification and characterization of a lectin from Alocasia cucullata. J South China Agric Univ 19:106–111
Han HC, Chen PF (2007) Research progress of the anti-cancer effect of the varieties of Chinese medicine “Seliugu”. Yunnan J Tradit Chin Med Mater Med 7:51–53
Lei X, Xu ZH, Wang Y, Feng Y, Zheng XW (2013) Advances in chemical constituents and biological activity of Alocasia. Chin J New Drugs A 3:2–5
Lei X, Feng Y, Liang S, Wang Y, Zheng XW (2012) Antitumor effect and chemical study of the petroleum ether fraction from the rhizome of Alocasia cucullata (Lour). Schott. Chin J Pharm 43:340–343
Peng Q, Cai H, Sun X, Li X, Mo Z, Shi J (2013) Alocasia cucullata exhibits strong antitumor effect in vivo by activating antitumor immunity. PLoS One 8:e75328
Peng W, Chen ZY, Tang X, Zheng XW (2015) Antitumor effect and apoptosis induction of Alocasia cucullata (Lour.) G. Don in human gastric cancer cells in vitro and in vivo. BMC Complement Altern Med 15:1–11
Lei X, Feng Y, Liang S, Zheng XW (2014) Chemical components of the tuber of Alocasia cucullata. Chem Nat Comp 50:133–136
Kaur A, Kamboj SS, Singh J, Saxena AK, Dhuna V (2005) Isolation of a novel N-acetyl-d-lactosamine specific lectin from Alocasia cucullata (Schott.). Biotechnol Lett 27:1815–1820
Deng J, Liao ZX, Chen DF (2005) Two new C21 steroids from Marsdenia tenacissima. Chin Chem Lett 16:487–490
Chen JJ, Zhang ZX, Zhou J (1999) New C21 steroidal glycosides from Marsdenia tenacissima. Acta Bot Yunn 21:369–377
Yu DQ, Yang JS (1999) Handbook of analytical chemistry, 7th edn. Chemical Industrial Press, Beijing, 901 pp
Lei YS, Li ZL, Yang SS, Liu ZL, Hua HM (2008) C21 steroids from the stems of Marsdenia tenacissima. Acta Pharm Sin 43:509–512
Hu JF, Starks CM, Williams RB, Rice SM, Norman VL, Olson KM, Hough GW, Goering MG, O’Neil‐Johnson M, Eldridge GR (2009) Secoiridoid glycosides from the pitcher plant Sarracenia alata. Helv Chim Acta 92:273–280
Deng J, Liao Z, Chen D (2005) Marsdenosides A–H, polyoxypregnane glycosides from Marsdenia tenacissima. Phytochemistry 66:1040–1051
Wang XL, Li QF, Yu KB, Peng SL, Zhou Y, Ding LS (2006) Four new pregnane glycosides from the stems of Marsdenia tenacissima. Helv Chim Acta 89:2738–2744
Handjieva N, Tersieva L, Popov S, Evstatieva L (1995) Two iridoid glucosides, 5-o-menthiafoloylkickxioside and kickxin, from Kickxia Dum. species. Phytochemistry 39:925–927
Geran RI, Greenberg NH, MacDonald MM, Schumacher AM, Abbott BJ (1972) Protocols for screening chemical agents and natural products against animal tumors and other biological systems. Cancer Chemother Rep 3:1–103
Acknowledgements
This study was supported by grant A1-20140371 from Project of Shanghai Education Commission within budget.
Author information
Authors and Affiliations
Corresponding author
Additional information
W. Peng, S. Liang, Z. Chen and X. Zheng contributed equally to this work.
Rights and permissions
About this article
Cite this article
Peng, W., Liang, S., Hu, J. et al. The cytotoxic and tyrosine kinase inhibitory properties of C21 steroids and iridoids from the tubers of Alocasia cucullata . J Nat Med 70, 602–609 (2016). https://doi.org/10.1007/s11418-016-0982-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11418-016-0982-4