Low-dose action of tryptanthrin and its derivatives against developing embryos of the sea urchin Strongylocentrotus intermedius
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Nine tryptanthrin derivatives, including tryptanthrin itself, were synthesized using different methods, including oxidation of the corresponding isatins to obtain 1–4, the reaction of tryptanthrin 1 with hydrazine and its derivatives to obtain 5–7, and aldol condensation of 1 with acetone and methylethylketone to obtain 8 and 9. The action of 1–9 in doses corresponding to the IC50 against developing embryos of the sea urchin Strongylocentrotus intermedius and in the sperm test allowed us to estimate to potency of all the compounds and to determine which were cytotoxic. In addition, these studies showed that compounds 3, 4, 8, and 9 had a stimulatory effect at lower doses. In particular, the tryptanthrin derivatives stimulated the larval stages of development in surviving embryos at concentrations lower than the IC50.
KeywordsThryptanthrin Sea urchin embryos Cytotoxicity Stimulatory effects
This study was partially supported by a grant from the Russian Scientific Fund (project no. 14-25-00037) and FEBRAS Grant No. 15 - I - 5- 006.
- Chavda, V. (2015). “Cannonball tree”: the alchemist plant. Innoriginal International Journal of Sciences, 2(5), 6–9.Google Scholar
- Kobayashi, N., Hori, M., Kan, K., Yasuzawa, T., Matsusi, M., Suzuki, S., & Kitagawa, I. (1991). Marine natural products. XXVII. Distribution of lanostane-type triterpene oligo glycosides in ten kinds of Okinawan sea cucumbers. Chemical and Pharmaceutical Bulletin, 39, 2282–2287. https://doi.org/10.1248/cpb.39.2282.CrossRefGoogle Scholar
- Koya-Miyata, S., Kimoto, T., Micallef, M., Hino, K., Taniguchi, M., Ushio, S., Iwaki, K., Ikeda, M., & Kurimoto, M. (2001). Prevention of azoxymethane-induced intestinal tumors by a crude ethyl acetate-extract and tryptanthrin extracted from Polygonum tinctorium Lour. Anticancer Research, 21(5), 3295–3300 ISSN:0250-7005.Google Scholar
- Mitscher, L., & Baker, W. (1998). Tuberculosis: a search for novel therapy starting with natural products. Medicinal Research Reviews, 18, 363–374. https://doi.org/10.1002/(SICI)1098-1128(199811)18:6<363:AID-MED1>3.0.CO;2-I.CrossRefGoogle Scholar
- Pergola, C., Jazzar, B., Rossi, A., Northoff, H., Hamburger, M., Sautebin, L., & Werz, O. (2012). On the inhibition of 5–lipoxygenase product formation by tryptanthrin: mechanistic studies and efficiency in vivo. British Journal of Pharmacology, 165(3), 765–776 http://edoc.unibas.ch/dok/A6001502.CrossRefGoogle Scholar
- Shim, W., Hong, S., Agafonova, I., & Aminin, D. (2006). Comparative toxicities of organotin compounds fertilization and development of sea urchin (Anthocidaris crassispina). Bulletin of Environmental Contamination and Toxicology, 77, 755–762. https://doi.org/10.1007/s00128-006-1128-2.CrossRefGoogle Scholar
- Utkina, N. (2008). Aromatic metabolites from marine sponges and echinoderms. In 1st Far Eastern Intern. Symp. Life Sci., Vladivostok, September, 2–7, 66.Google Scholar
- Wagner-Dober, I., Rheims, H., Felske, A., El-Ghezal, A., Flade-Schhoder, D., Laatsch, H., Lang, S., Pukall, R., & Tindall, B. (2004). Oceanibulbus indolifex gen. nov. North Sea alpha–proteobacterium that produced bioactive metabolites. International Journal of Systematic and Evolutionary Microbiology, 54, 1177–1182. https://doi.org/10.1099/ijs.0.02850-0.CrossRefGoogle Scholar