Abstract
A new xanthone, 1,2-dihydroxy-6,7,8-trimethoxyxanthone, together with ten known xanthones and nine other compounds was isolated from the stem of Securidaca inappendiculata. The structure of the new compound was elucidated based on spectroscopic data analyses, and other compounds were identified by comparison with data from the literature. The anti-tumor activities of the xanthones were evaluated by MTT assay on human lung adenocarcinoma epithelial cell line A549, and a primary structure–activity relationship analysis was carried out based on results from MTT assay. It is revealed that all the xanthones possessed anti-tumor activity in vitro in a concentration-dependent manner. The IC50 values varied a lot among xanthones. 1,7-Dihydroxy-3,4-dimethoxyxanthone was proved to be the most efficient anti-tumor agent with IC50 of 50.66 μM, while 1,3,7-trihydroxy-2,8-dimethoxyxanthone and 1,7-dihydroxyxanthone possessed the weakest activities. The structure–activity relationship analysis revealed that the anti-tumor activity of xanthones was affected mostly by the position and number of hydroxyl and methoxyl groups. Free hydroxyl and ortho-methoxyl groups were believed to possess important potentials to the activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Chidouh A, Aouadi S, Heyraud A (2014) Extraction, fractionation and characterization of water-soluble polysaccharide fractions from myrtle (Myrtus communis L.) fruit. Food Hydrocoll 35:733–739
Dao TT, Dang TT, Nguyen PH, Kimb E, Thuong PT, Oh WK (2012) Xanthones from Polygala karensium inhibit neuraminidases from influenza A viruses. Bioorg Med Chem Lett 22:3688–3692
Dibwe DF, Awale S, Kadota S, Morita H, Tezuka Y (2013) Heptaoxygenated xanthones as anti-austerity agents from Securidaca longepedunculata. Bioorg Med Chem Lett 21:7663–7668
Duan LX, Feng BM, Chen F, Liu JY, Li F, Wang YQ (2007) Sinapic acid derivatives from the seeds of Raphanus nussatirus L. J Asian Nat Prod Res 9:557–561
Han QB, Qiao CF, Song JZ, Yang NY, Cao XW, Peng Y, Yang DJ, Chen SL, Xu HX (2007) Cytotoxic prenylated phenolic compounds from the twig barks of Garcinia xanthochymus. Chem Biodivers 4:940–946
Han QB, Yang NY, Tian HL, Qiao CF, Song JZ, Chang DC, Chen SL, Luo KQ, Xu HX (2008) Xanthones with growth inhibition against HeLa cells from Garcinia xipshuanbannaensis. Phytochemistry 69:2187–2192
Hansen MB, Nielsen SE, Berg K (1989) Re-examination and further development of a precise and rapid dye methods for measuring cell growth/cell kill. J Immunol Methods 119:203–210
Khonkarna R, Mankhetkornb S, Talelli M, Henninkc WE, Okonogi S (2012) Cytostatic effect of xanthone-loaded mPEG-b-p(HPMAm-Lac2) micelles towards doxorubicin sensitive and resistant cancer cells. Colloids Surf B 94:266–273
Kuetea V, Sandjoc LP, Ouetec JLN, Fouotsac H, Wiencha B, Effertha T (2013) Cytotoxicity and modes of action of three naturally occurring xanthones (8-hydroxycudraxanthone G, morusignin I and cudraxanthone I) against sensitive and multidrug-resistant cancer cell lines. Phytomedicine. doi:10.1016/j.phymed.2013.08.018
Li CF (2008) Studies on the antioxidant activities and volatile constituents of medicinal plants. Master’s Dissertation, Henan University, pp 4–15
Luo CT, Mao SS, Liu FL, Yang MX, Chen HR, Kurihara H, Li YL (2013) Antioxidant xanthones from Swertiamussotii, a high altitude plant. Fitoterapia 91:140–147
Meli AL, Komguem J, Ngounou FN, Tangmouo JG, Lontsi D, Ajaz A (2005) Bangangxanthone A and B, two xanthones from the stem bark of Garcinia polyantha Oliv. Phytochemistry 66:2351–2415
Niu SL, Li ZL, Ji F, Liu GY, Zhao N, Liu XQ, Jing YK, Hua HM (2012) Xanthones from the stem bark of Garcinia bracteata with growth inhibitory effects against HL-60 cells. Phytochemistry 77:280–286
Saxena V, Hussain MD (2012) Poloxamer 407/TPGS mixed micelles for delivery of gambogic acid to breast and multidrug-resistant cancer. Int J Nanomed 7:713–721
Tanaka N, Kashiwada Y, Kima SY, Sekiya M, Ikeshiro Y, Takaishi Y (2009) Xanthones from Hypericum chinense and their cytotoxicity evaluation. Phytochemistry 70:1456–1461
Wang JJ, Sanderson BJS, Wei Z (2011) Cytotoxic effect of xanthones from pericarp of the tropical fruit mangosteen (Garcinia mangostana Linn.) on human melanoma cells. Food Chem Toxicol 49:2385–2391
Yang XD (2001) Studies on the chemical constituents and bioactivities of medicinal plant Securidaca inappendiculata Hassk. Ph.D. Dissertation, Peking Union Medical College, pp 70–93
Yunnan Institute of Botany, Chinese Academy of Science (1983) Flora of Yunnan. Science, Peking, p 261
Zhang LJ (2005) Studies on the chemical constituents of medicinal plant Securidaca inappendiculata Hassk. Ph.D. Dissertation, Peking Union Medical College, pp 93–97
Zuo J, Xia Y, Li X, Chen JW (2014) Therapeutic effects of dichloromethane fraction of Securidaca inappendiculata on adjuvant-induced arthritis in rat. J Ethnopharmacol. doi:10.1016/j.jep.2014.02.015
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Zuo, J., Mao, Kj., Yuan, F. et al. Xanthones with anti-tumor activity isolated from Securidaca inappendiculata . Med Chem Res 23, 4865–4871 (2014). https://doi.org/10.1007/s00044-014-1051-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-014-1051-8