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Chemical constituents of Trichosanthes kirilowii and their cytotoxic activities

Abstract

One new lignan, trichobenzolignan (1), and seven known compounds, ligballinol (2), (−)-pinoresinol (3), ehletianol C (4), luteolin 7-O-β-D-glucopyranoside (5), chrysoeriol-7- O-β-D-glucopyranoside (6), 10α-cucurbita-5,24-dien-3β-ol (7), and arvenin I (8). Their structures were established on the basis of spectral and chemical evidence, which were in agreement with those reported in literature. The cytotoxic activities of these compounds were evaluated on four cancer cell lines such as A-549 (human lung cancer), HT-29 (human colon adenocarcinoma), OVCAR (human ovarian carcinoma), and MCF-7 (human breast cancer). As the results, compound 7 showed significant activity on HT-29 and OVCAR cancer cell lines with IC50 of 4.1 and 6.5 µM, respectively. Compounds 1, 5, 6, and 8 exhibited moderate activities in all cancer cell lines with IC50 ranging from 11.3 to 42.8 µM.

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References

  • Akihisa, T., W.C.M.C. Kokke, J.A. Krause, D.S. Eggleston, S.-I. Katayama, Y. Kimura, and T. Tamura. 1992. 5-Dehydrokarounidiol [D:C-Friedo-oleana-5, 7, 9(11)-triene-3α, 29-diol], a novel triterpene from Trichosanthes kirilowii MAXIM. Chemical & Pharmaceutical Bulletin 40: 3280–3283.

    CAS  Article  Google Scholar 

  • Akihisa, T., K. Yasukawa, Y. Kimura, M. Takido, W.C.M.C. Kokke, and T. Tamura. 1994. Five D: C-Friedo-oleanane triterpenes from the seeds of Trichosanthes kirilowii MAXIM. and their anti-inflammatory effects. Chemical & Pharmaceutical Bulletin 42: 1101–1105.

    CAS  Article  Google Scholar 

  • Chi, V. V. 2012. The Dictionary of Medicinal Plants in Vietnam. Hanoi: Medical Publishing House, Vol 1.

  • Chiruvella, K.K., A. Mohammed, G. Dampuri, R.G. Ghanta, and S.C. Raghavan. 2007. Phytochemical and antimicrobial studies of methyl angolensate and luteolin-7-O-glucoside isolated from callus cultures of Soymida febrifuga. International Journal of Biomedical Science 3: 269–278.

    CAS  PubMed Central  PubMed  Google Scholar 

  • Jang, K.C., J.H. Lee, S.C. Kim, E.Y. Song, N.Y. Ro, D.Y. Moon, Y.C. Um, and K.H. Park. 2007. Antibacterial and radical scavenging activities of 1-C-(p-hydroxyphenyl)-glycerol from Trichosanthes kirilowii. Journal of Applied Biological Chemistry 50: 17–21.

    CAS  Google Scholar 

  • Kawahara, N., A. Kurata, T. Hakamatsuka, S. Sekita, and M. Satake. 2004. Two new cucurbitacin glucosides, opercurins A and B, from the Brazilian folk medicine “Buchinha” (Luffa operculata). Chemical & Pharmaceutical Bulletin 52: 1018–1020.

    CAS  Article  Google Scholar 

  • Kimura, Y., T. Akihisa, K. Yasukawa, M. Takido, and T. Tamura. 1995. Structures of five hydroxylated sterol from the seeds of Trichosanthes kirilowii MAXIM. Chemical & Pharmaceutical Bulletin 43: 1813–1817.

    CAS  Article  Google Scholar 

  • Kondo, T., M. Inoue, H. Mizukami, and Y. Ogihara. 1995. Cytotoxic activity of bryonolic acid isolated from transformed hairy roots of Trichosanthes kirilowii var. japonica. Biological and Pharmaceutical Bulletin 18: 726–729.

    CAS  PubMed  Article  Google Scholar 

  • Moon, S.S., A.A. Rahman, J.Y. Kim, and S.H. Kee. 2008. Hanultarin, a cytotoxic lignan as an inhibitor of actin cytoskeleton polymerization from the seeds of Trichosanthes kirilowii. Bioorganic & Medicinal Chemistry 16: 7264–7269.

    CAS  Article  Google Scholar 

  • Nes, W.D., R.Y. Wong, M. Benson, and T. Akihisa. 1991. Conformational analysis of 10α-cucurbitadienol. Chemical Communications 0: 1272–1274.

    CAS  Article  Google Scholar 

  • Nhiem, N.X., N.H. Tung, P.V. Kiem, C.V. Minh, Y. Ding, J.H. Hyun, H.K. Kang, and Y.H. Kim. 2009. Lupane triterpene glycosides from leave of Acanthopanax koreanum and their cytotoxic activity. Chemical & Pharmaceutical Bulletin 57: 986–989.

    Article  Google Scholar 

  • Rahman, M.A.A., and S.S. Moon. 2007. Isoetin 5’-methyl ether, a cytotoxic flavone from Trichosanthes kirilowii. Bulletin of Korean Chemical Society 28: 1261–1264.

    CAS  Article  Google Scholar 

  • Ryu, S.Y., S.H. Lee, S.U. Choi, C.O. Lee, Z. No, and J.W. Ahn. 1994. Antitumor activity of Trichosanthes kirilowii. Archives of Pharmacal Research 17: 348–353.

    CAS  Article  Google Scholar 

  • Schwaiger, S., C. Seger, B. Wiesbauer, P. Schneider, E.P. Ellmerer, S. Sturm, and H. Stuppner. 2006. Development of an HPLC-PAD-MS assay for the identification and quantification of major phenolic edelweiss (Leontopodium alpium Cass.) constituents. Phytochemical Analysis 17: 291–298.

    CAS  PubMed  Article  Google Scholar 

  • Takahashi, N., Y. Yoshida, T. Sugiura, K. Matsuno, A. Fujino, and U. Yamashita. 2009. Cucurbitacin D isolated from Trichosanthes kirilowii induces apoptosis in human hepatocellular carcinoma cells in vitro. International Immunopharmacology 9: 508–513.

    CAS  PubMed  Article  Google Scholar 

  • Wang, X.W., H.P. Zhang, F. Chen, X. Wang, and W.Y. Wen. 2009. A new lignan from Gynostemma pentaphyllum. Chinese Chemical Letters 20: 589–591.

    CAS  Article  Google Scholar 

  • Xu, J.F., D.H. Cao, N.H. Tan, Z.L. Liu, Y.M. Zhang, and Y.B. Yang. 2006. New lignan glycosides from Cupressus duclouxian (Cupessaceae). Journal of Asian Natural Products Research 8: 181–185.

    CAS  PubMed  Article  Google Scholar 

  • Yoshikawa, K., H. Kageyama, and S. Arihara. 1995. Phenolic glucosides and lignans from Ehretia ovalifolia. Phytochemistry 39: 659–664.

    CAS  Article  Google Scholar 

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Acknowledgments

This research was supported by Vietnam National Foundation for Science and Technology Development (NAFOSTED) under grant number 104.01-2011.23 and Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (NRF-2011-0025129).

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Correspondence to Seung Hyun Kim.

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Minh, C.V., Nhiem, N.X., Yen, H.T. et al. Chemical constituents of Trichosanthes kirilowii and their cytotoxic activities. Arch. Pharm. Res. 38, 1443–1448 (2015). https://doi.org/10.1007/s12272-014-0490-6

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  • DOI: https://doi.org/10.1007/s12272-014-0490-6

Keywords

  • Trichosanthes kirilowii
  • Cucurbitaceae
  • Trichobenzolignan
  • Cytotoxic activity