Abstract
Three new coumarin types were isolated from the aerial parts of the wild medicinal plant Ammi majus, which was collected from western Asia (Saudi Arabia), including pyrano coumarin, namely, 5-isobutylcoumarin-6-C-glucoside (1); furanocoumarin, namely, 6,7,9-Trimethoxy-3-(8′-methoxy-2′-oxo-2H-chromen-3-yl)-2H-furo[3,2-g]chromen-2(3H)-one (2); and pyrone coumarin, namely, 6-hydroxy-3-(2-hydroxypropyl)-7-methoxy-4 methyl coumarin (3). The structures were determined by spectroscopic methods, mainly 1D- and 2D-NMR. In vitro cytotoxicity was evaluated by 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl-tetrazolium bromide (MTT) assay. The results of cytotoxicity depending on their structure features showed that compound 3 had high activity on different cell lines, while compound 1 showed no activity against HCT116. Compound 2 had high activity towards HCT116 cell line.
Acknowledgment
The authors are thankful to the Bioassay-Cell Culture Laboratory, National Research Centre, El-Tahrir St., Dokki, Cairo 12622, Egypt, for conducting the analysis and determining the results of biology.
Conflict of interest statement: The authors declare no conflict of interest.
References
1. Hakim RE. Rediscovery of a treatment for vitiligo. Clio Medica 1969;4:277–89.Search in Google Scholar
2. Anonymous. Wealth of India.1-A, PID, CSIR, Hillside Road, New Delhi, 1985.Search in Google Scholar
3. Parwaiz A, Mohd AM, Sharma Md, Waris HH, Babar A, Nisha C, et al. Development of quality standards of Ammi majus L. Fruit. J Exp Sci 2010;11:20–4.Search in Google Scholar
4. Sener BE, Baykal T. Separation and determination of Khellin and visnagin in Ammi majus L. fruits by HPLC. Gazi Unversitesi-Eczacilik-Fakultesi-Dergisi 1986;3:149–52.Search in Google Scholar
5. Pande D, Purohit M, Srivastava PS. Variation in xanthotoxin content in Ammi majus L. cultures during in vitro flowering and fruiting. Plant Sci (Shannon, Ireland) 2002;162:583–7.10.1016/S0168-9452(01)00597-0Search in Google Scholar
6. Yasser AS, Nabil HO. Anti-inflammatory new coumarin from the Ammi majus L. Org Med Chem Lett 2012;2:1–4.10.1186/2191-2858-2-1Search in Google Scholar PubMed
7. Bencheraiet RH, Kherrab A, Kabouche Z, Jay M. Flavonols and antioxidant activity of Ammi visnaga L. (Apiaceae). Rec Nat Prod 2011;5:52–5.Search in Google Scholar
8. Finn GJ, Creaven BS, Egan DA. Daphnetin induced differentiation of human renal carcinoma cells and its mediation by p38 mitogen-activated protein kinase. Biochem Pharmacol 2004;67:1779–88.10.1016/j.bcp.2004.01.014Search in Google Scholar PubMed
9. Duddeck H, Kaiser M. Regioselektivität der Baeyer-Villiger-Oxidation substituierter Adamantanone. Z Naturforsch 1982;37b:1672.10.1515/znb-1982-1237Search in Google Scholar
10. Miserez F, Potterat, O, Marston A, Mungai GM, Hostettmann K. Flavonol glycosides from Vernonia galamensis ssp. nairobiensis. Phytochemistry 1996;43:283–6.10.1016/0031-9422(96)00252-XSearch in Google Scholar
11. Sajjadi SE, Noroozi p. Isolation and identification of xanthotoxin (8-methoxypsoralen) from the fruits Heracleum persicum Desf. Ex Fischer. Res Pharm Sci 2007;2:13–6.Search in Google Scholar
12. Hilal SH, Haggag MY. A thin-layer chromatography (TLC) colorimetric assay of furocoumarins. Egypt J Pharm Sci 1975;16:495–9.Search in Google Scholar
13. Rajesh NG, Sharad GJ. Antioxidant activities and cytotoxicity of selected coumarin derivatives preliminary results of a structure activity relationship study using computational tools. J Exp Clin Med 2012;4:165–9.10.1016/j.jecm.2012.04.007Search in Google Scholar
14. Mosmann T. Rapid colorimetric assays for cellular growth and survival, application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63.10.1016/0022-1759(83)90303-4Search in Google Scholar PubMed
15. Skehan P, Storeng R, Scudiero D, Monks A, Mcmahon J, Vistica D, et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990;82:1107–12.10.1093/jnci/82.13.1107Search in Google Scholar PubMed
16. Amany B, Mohamed AA. New benzothiazole/benzoxazole-pyrazole hybrids with potential as COX inhibitors: design, synthesis and anticancer activity evaluation. Res Chem Intermed 2017;43:3859–72.10.1007/s11164-016-2851-xSearch in Google Scholar
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The online version of this article offers supplementary material (https://doi.org/10.1515/znc-2017-0068).
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