ANTHRAQUINONES AND BIOLOGICAL ACTIVITY OF SPECIES OF THE GENUS RHEUM L. (POLYGONACEAE) (REVIEW)
Abstract
The review of materials on the composition and biological activity of anthraquinones of species of the genus Rheum L. The most well-studied are the representatives of "forest rhubarb", which evolved in the forests of Central and Northern China: Rheum palmatum L., R. officinale Baill., R. emodi Wall. ex Meissn., R. rhabarbarum L. (= R. undulatum L.) and R. compactum L. (= R. rhaponticum L.). The official rhubarb is the Tungut rhubarb R. palmatum L. var. tanguticum Regel, known on the international pharmaceutical market as "Chinese rhubarb". The main aglykones of rhubarb anthraquinones are chrysofanol, emodin, aloe-emodin, fisсion and rhein. Particular attention is paid to various aspects of their impact on the processes that accompany oncological diseases. Emodin was found to inhibit cell proliferation, induce apoptosis induction, and prevent metastases. Emodin and aloe-emodin have high cytotoxic activity against oral squamous cell carcinoma and salivary gland cancer. Rhein inhibits the absorption of glucose in tumor cells and leads to their death. Anthraquinone glycosides, in contrast to aglycons, exhibit moderate cytotoxic activity. Other types of biological activity have been investigated - antimicrobial, antiviral, immunomodulating, antioxidant, molluscicidal etc. It follows from the presented materials that species of the genus Rheum containing anthracene derivatives are promising for practical use and further study.
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Grigor'ev Iu.S. Biul. MOIP, 1981, vol. 86, no. 5, pp. 72–82. (in Russ.).
Lozina-Lozinskaia A.S. Flora i sistematika vysshikh rastenii: trudy Botanicheskogo instituta AN SSSR. [Flora and Sys-tematics of Higher Plants: Proceedings of the Botanical Institute of the Academy of Sciences of the USSR]. Moscow; Leningrad, 1936, pp. 67–141. (in Russ.).
Lozina-Lozinskaia A.S. Flora SSSR. [Flora of the USSR]. Moscow; Leningrad, 1936, vol. 5, pp. 444–501. (in Russ.).
Cherepanov S.K. Sosudistye rasteniia Rossii i sopredel'nykh gosudarstv (v predelakh byvshego SSSR). [Vascular plants of Russia and neighboring countries (within the former USSR)]. St. Petersburg, 1995, 990 p. (in Russ.).
Krasnoborov I.M., Lomonosova M.N., Shaulo D.N., Vibe E.I., Zhirova O.S., Koroliuk E.A., Krasnikov A.A., Snytko O.N., Tupitsyna N.N. Opredelitel' rastenii Novosibirskoi oblasti. [The determinant of plants of the Novosibirsk region]. Novosibirsk, 2000, 492 p. (in Russ.).
Yuan Y., Zhao F., Tan L. Zhongcaoyao, 2000, vol. 31(7), pp. 508–509.
Wei Z.-j., Lin L., Ni J.-r. Gaoxiao Huaxue Gongcheng Xuebao, 2006, vol. 20 (2), pp. 197–202.
Wei Z., Lin L., Ni J. Huaxue Gongcheng, 2006, vol. 34 (8), pp. 63–66.
Su X., Hu L., Kong L., Lei X., Zou H. J. Chromatogr. A., 2007, vol. 1154 (1-2), pp. 132–137.
Chen Q., Dai H., Su X. Tianran Chanwu Yanjiu, 2001, vol. 13 (3), pp. 58–60.
Tian K., Wang Y., Chen Y., Chen X., Hu Z. Talanta, 2007, vol. 72 (2), pp. 587–593.
Ding J., Ning B., Fu G., Lu Y., Dong S. Chromatographia, 2000, vol. 52 (5/6), pp. 285–288.
Wei J., Wang N., Wu X., Wang H. Zhongcaoyao, 2001, vol. 32 (11), pp. 993–995.
Tong Sh., Yan J. J. Chromatogr. A., 2007, vol. 1176 (1-2), pp. 163–168.
Shi Y.-Q., Fukai T., Sakagami H., Kuroda J., Miyaoka R., Tamura M., Yoshida N., Nomura T. Anticancer Research, 2001, vol. 21 (4A), pp. 2847–2853.
Lu H., Zhao Ch., Wu H., Liang Y., Li Q. Zhongcaoyao, 2010, vol. 41 (3), pp. 412–415.
Huang Q., Lu G., Shen H.-M., Chung M.C.M., Ong Ch.N. Medicinal Research Reviews, 2007, vol. 27 (5), pp. 609–630.
Liu Zh.-H., Li L.-Sh., Hu W.-X., Zhou H. Zhongguo yaoli xuebao, 1996, vol. 17 (1), pp. 61–63.
Chen Y.-Ch., Shen Sh.-Ch., Lee W.-R., Hsu F.-L., Lin H.-Y., Ko Ch.-H., Tseng Sh.-W. Biochemical Pharmacology, 2002, vol. 64 (12), pp. 1713–1724.
Huang Q., Shen H.-M., Ong Ch.-N. Biochemical Pharmacology, 2004, vol. 68(2), pp. 361–371.
Huang Q., Shen H.-M., Ong C.-N. Cellular and Molecular Life Sciences, 2005, vol. 62 (10), pp. 1167–1175.
Su Y.-T., Chang H.-L., Shyue S.-K., Hsu Sh.-L. Biochemical Pharmacology, 2005, vol. 70 (2), pp. 229–241.
Lee H.-Z. British Journal of Pharmacology, 2001, vol. 134 (1), pp. 11–20.
Kwak H.-J., Park M.-J., Park Ch.-M., Moon S.-I., Yoo D.-H., Lee H.-Ch., Lee S.-H., Kim M.-S., Lee H.-W., Shin W.-S., Park I.-Ch., Rhee Ch.-H., Hong S.-I. Intern. Journal of Cancer, 2006, vol. 118 (11), pp. 2711–2720.
Yim H., Lee Y.H., Lee Ch.H., Lee S.K. Planta Med., 1999, vol. 65(1), pp. 9–13.
Li H.-L., Chen H.-L., Li H., Zhang K.-L., Chen X.-Y., Wang X.-W., Kong Q.-Y., Liu J. Intern. Journal of Molecular Medicine, 2005, vol. 16 (1), pp. 41–47.
Kazuhiro Sh., Masami M., Sumito O., Satoshi I., Kazuhiro G., Atushi I., Hiroshi S. Research Communications in Pharmacology and Toxicology, 2000, vol. 5 (3 & 4), pp. 179–189.
Lu G.D., Shen H.-M., Ong Ch.N., Chung M.C.M. Proteomics: Clinical Applications, 2007, vol. 1 (4), pp. 410–419.
Lee H.-Z., Hsu Sh.-L., Liu M.-Ch., Wu Ch.-H. European Journal of Pharmacology, 2001, vol. 431 (3), pp. 287–295.
Yeh F.-T., Wu, Ch.-H., Lee H.-Z. Intern. Journal of Cancer, 2003, vol. 106 (1), pp. 26–33.
Huang Q., Lu G., Shen H.-M., Chung M.C.M., Ong Ch.N. Medicinal Research Reviews, 2007, vol. 27 (5), pp. 609–630.
Zhou W., Bounda G.-A. Yu F. World Journal of Pharmaceutical Research, 2014, vol. 3 (3), pp. 3599–3626.
Kubo I., Murai Y., Soediro I., Soetarno S., Sastrodihardjo S. Phytochemistry, 1992, vol. 31 (3), pp. 1063–1065.
Murai Y. Foods Food Ingredients J. Jpn., 2000, vol. 184, pp. 69–74.
Su X., Hu L., Kong L., Lei X., Zou H. J. Chromatogr. A., 2007, vol. 1154 (1–2), pp. 132–137.
Liu S.Y., Sporer F., Wink M., Jourdane J., Henning R., Li Y.L., Ruppel A. Trop. Med. Int. Health., 1997, vol. 2(2), pp. 179–188.
Kasparova M., Siatka T. Ceska Slov. Farm., 1999, vol. 48 (6), pp. 256–261.
Yang Sh., Liu X., Guo D. Zhongcaoyao, 2004, vol. 35 (10), pp. 1171–1174.
Yang Sh., Liu X., Guo D., Zheng J. Zhongcaoyao, 2005, vol. 36 (7), pp. 1075–1078.
Siatka T., Kasparova M., Sicha J., Dusek J. Herba Polonica, 2003, vol. 49 (1/2), pp. 44–48.
Chang Zh., Guo D., Shen X., Wang Sh., Zheng J. Yaoxue Xuebao, 1998, vol. 33 (11), pp. 869–872.
Duc R., Vanek T., Soudek P., Schwitzguebel, J.-P. Int. J. Phytorem., 1999, vol. 1 (3), pp. 255–271.
Gosudarstvennaia farmakopeia SSSR. 11-e izd. [State Pharmacopoeia of the USSR. 11th ed]. Moscow, 1990, vol. 2, 400 p. (in Russ.).
Kurkin V.A. Farmakognoziia. [Pharmacognosy]. Samara, 2004, 1180 p. (in Russ.).
Murav'eva D.A., Samylina I.A., Iakovlev G.P. Farmakognoziia. [Pharmacognosy]. Moscow, 2002, 656 p. (in Russ.).
Chen T., Liu Y.-L., Chen Ch., Zou D.-L., You J.-M., Sun J., Li Y.-L. J. Chromatogr. B: Analytical Technologies in the Biomedical and Life Sciences, 2014, vol. 957, pp. 90–95.
Cao W., Liu Zh., Shao Y., Tao Y. Xibei Zhiwu Xuebao, 2004, vol. 24 (11), pp. 2140–2142.
Gu J.-W., Hasuo H., Takeya M., Akasu T. Neuropharmacology, 2005, vol. 49 (1), pp. 103–111.
Liu W.-zh., Zhang A.-x. Xibei Zhiwu Xuebao, 2000, vol. 20 (6), pp. 1082–1085.
Yang F., Zhang T., Tian G., Cao H., Liu Q., Ito Y. J. Chromatogr. A., 1999, vol. 858 (1), pp. 103–107.
Yang F., Zhang T., Xu G., Chou F.E., Ito Y. J. Liq. Chromatogr. and Relat. Technol., 2001, vol. 24 (11–12), pp. 1617–1628.
Liu R., Li A., Sun A. J. Chromatogr. A., 2004, vol. 1052 (1–2), pp. 217–221.
Hu R., Dai X., Xu X., Sun C., Pan Y. J. Chromatogr. A., 2011, vol. 1218 (36), pp. 6085–6091.
Hu X.-l., Liu Zh.-y., Rong H., Zhang H.-q., Yu A.-m. Jilin Nongye Daxue Xuebao, 2005, vol. 27 (2), pp. 194–196.
Fan J., Zhang Zh., Zhang L., Wu Y. Dier Junyi Daxue Xuebao, 2005, vol. 26 (10), pp. 1194–1195.
Li Y.-h. Zhongyao Yanjiu Yu Xinxi, 2005, vol. 7 (6), pp. 17–18.
Chen R., Zhang J., Hu Y., Wang Sh., Chen M., Wang Y. American Journal of Chinese Medicine, 2014, vol. 42 (2), pp. 275–288.
Sun M., Sakakibara H., Ashida H., Danno G-i., Kanazawa K. Biosci., Biotechnol. and Biochem., 2000, vol. 64 (7), pp. 1373–1378.
Cai Y., Sun M., Xing J., Corke H. Journal of Agricultural and Food Chemistry, 2004, vol. 52 (26), pp. 7884–7890.
Wu Y., Gao W., Xiao X., Yi L. Thermochimica Acta., 2005, vol. 429 (2), pp.167–170.
Gou K., Sun L., Lou W., Ling Ch., Wang Y. Zhongguo Yaoxue Zazhi (Beijing), 1997, vol. 32 (5), pp. 278–280.
Ho T.-Y., Wu Sh.-L., Chen J.-Ch., Li Ch.-Ch., Hsiang Ch.-Y. Antiviral Research, 2007, vol. 74 (2), pp. 92–101.
Tang T., Yin L., Yang J., Shan G. European Journal of Pharmacology, 2007, vol. 567 (3), pp. 177–185.
Yang X., Yang L., Wang Sh., Yu D., Ni H. Pest Management Science, 2007, vol. 63 (5), pp. 511–515.
Liu B., Ge X., Xie J., Xu P., He Y., Cui Y., Ming J., Zhou Q., Pan L. Fish & Shellfish Immunology, 2012, vol. 32 (1), pp. 1–7.
Liu B., Ge X., He Y., Xie J., Xu P., He Y., Zhou Q., Pan L., Chen R. Aquaculture, 2010, vol. 310 (1–2), pp. 13–19.
Liu B., Xie J., Ge X., Xu P., Wang A., He Y., Zhou Q., Pan L., Chen R. Fish & Shellfish Immunology, 2010, vol. 29 (1), pp. 49–57.
Singh S.S., Pandey S.C., Singh R., Agarwal S.K. Indian Journal of Chemistry, Section B: Organic Chemistry Includ-ing Medicinal Chemistry, 2005, vol. 44B (7), pp. 1494–1496.
Zargar B.A., Masoodi M.H., Ahmed B., Ganie Sh.A. Food Chemistry, 2011, vol. 128 (3), pp. 585–589.
Bilal S., Mir M.R., Parrah J.D., Tiwari B.K., Tripathi V., Singh P., Mehjabeenc, Abidi A.B. Intern. Journal of Phar-macy and Biological Sciences, 2013, vol. 3 (3), pp. 228–233.
Mishra S.K., Tiwari Sh., Shrivastava A., Srivastava Sh., Boudh G.K., Chourasia Sh.K., Chaturvedi U., Mir S.S., Saxena A.K., Bhatia G. Journal of Natural Medicines, 2014, vol. 68 (2), pp. 363–371.
Suresh B.K., Srinivas P.V., Praveen B., Hara K.K., Suryanarayana M.U., Madhusudana R.J. Phytochemistry, 2003, vol. 62 (2), pp. 203–207.
Krenn L., Pradhan R., Presser A., Reznicek G., Kopp B. Chemical & Pharmaceutical Bulletin, 2004, vol. 52 (4), pp. 391–393.
Agarwal S.K., Singh S.S., Verma S., Kumar S. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem., 1999, vol. 38B (6), pp. 749–751.
Krenn L., Presser A., Pradhan R., Bahr B., Paper D.H., Mayer K.K., Kopp B. Journal of Natural Products, 2003, vol. 66 (8), pp. 1107–1109.
Hao Sh., Zhang H., Liu L., Li Zh., Xu Z. Zhongcaoyao, 2002, vol. 33 (1), pp. 23–26.
Verma S.C., Singh N.P., Sinha A.K. J. Chromatogr. A., 2005, vol. 1097 (1–2), pp. 59–65.
Wasim A., Mohd M., Sayeed A., Zaidi S.M.A. Int. J. Drug Dev. and Res., 2013, vol. 5 (1), pp. 297–304.
Kumar D.R.N., George V.C., Suresh P.K., Kumar R.A. Pakistan Journal of Pharmaceutical Sciences, 2015, vol. 28 (1), pp. 83–93.
Naveen Kumar D.R., George V.C., Suresh P.K., Kumar R.A. EXCLI journal, 2013, pp. 12462–78.
Narender T., Sukanya P., Sharma K., Bathula S.R. Phytomedicine, 2013, vol. 20 (10), pp. 890–896.
Kaur A., Kaur S., Kaur M., Mahajan A., Bose S. World Journal of Pharmaceutical Research, 2015, vol. 4 (1), pp. 1892–1902.
Agarwal S.K., Singh S.S., Verma S., Kumar S. J. Ethnopharmacol., 2000, vol. 72 (1, 2), pp. 43–46.
Tripathi B., Bhatia R., Pandey A., Gaur J., Chawala G., Walia S., Choi E.H., Attri P. Journal of Chemistry, 2014, arti-cle ID 652526, 9 p.
Das D., Maulik S.R., Bhattacharya S.Ch. Indian J. Fibre and Text. Res., 2008, vol. 33 (2), pp. 163–170.
Choi S.Z., Lee S.O., Jang K.U., Chung S.H., Park S.H., Kang H.Ch., Yang E.Y., Cho H.J., Lee K.R. Archives of Pharm. Research, 2005, vol. 28 (9), pp. 1027–1030.
Matsuda H., Morikawa T., Toguchida I., Park J.-Y., Harima S., Yoshikawa M. Bioorg. Med. Chem., 2001, vol. 9 (1), pp. 41–50.
Kim J.-E., Kim H.-J., Pandit S., Chang K.-W., Jeon J.-G. Fitoterapia, 2011, vol. 82 (3), pp. 352–356.
Hu B., Zhang H., Meng X., Wang F., Wang P. J. Ethnopharmacol., 2014, vol. 153 (3), pp. 846–853.
Pussa T., Raudsepp P., Kuzina K., Raal A. Phytochemical Analysis, 2009, vol. 20 (2), pp. 98–103.
Raudsepp P., Anton D., Roasto M., Meremae K., Pedastsaar P., Maesaar M., Raal A., Laikoja K., Pussa T. Food Con-trol., 2013, vol. 31 (1), pp. 129–135.
Tosun F., Akyuz K.C. Ankara Universitesi Eczacilik Fakultesi Dergisi, 2003, vol. 32 (1), pp. 31–35.
Sepehr M.F., Ghorbanli M. Plant Cell, Tissue and Organ Culture, 2002, vol. 68 (2), pp. 171–175.
The Japanese Pharmacopoeia. 17th ed., Tokyo, 2016, 2630 p.
Pharmacopea of the people’s republic of China, Pekin, 2005, vol. 1, 668 p.
European Pharmacopeia. 7th ed., 2010, 4034 p.
Li J., Wang A., Li J., He W., Kong M. Zhongcaoyao, 2000, vol. 31 (5), pp. 321–324.
Tian K., Wang Y., Chen Y., Chen X., Hu Zh. Talanta, 2007, vol. 72 (2), pp. 587–593.
Li Y.-h. Zhongyao Yanjiu Yu Xinxi, 2005, vol. 7 (6), pp. 17–18.
Yang X., Zhao J., Zhang Y., Li J., Ma Ch., Hatori Y., Nanba T. Zhongcaoyao, 1998, vol. 29 (5), pp. 289–293.
Min D., Xu L., Zhang Zh., Wang H., Huang D., Guo D., Zheng J. Zhongguo Zhongyao Zazhi, 1998, vol. 23 (7), pp. 416–418.
Prasad P., Purohit M.C. Curr. Sci., 2001, vol. 80 (6), pp. 734–736.
Wei Y., Zhang Ch., Li Ch., Tao B. Zhongcaoyao, 2004, vol. 35 (7), pp. 732–734.
Rawat M.S.M., Negi D.S., Panwar M.S., Pant G., Shibata S., Okada Y., Oshima Y., Okuyama T. Pharmazie, 1989, vol. 44 (7), pp. 509–510.
Xiang L., Zheng J., Guo D., Kou J., Fan G., Duan Y., Qin Ch. Zhongcaoyao, 2001, vol. 32 (5), pp. 395–397.
Qiu Y.-K., Chen F.-F., Zhang L.-L., Yan X., Chen L., Fang M.-J., Wu Zh. Anal. Chem. Acta., 2014, vol. 820, pp. 176–186.
Chang Zh., Shen X., Guo D., Lu K., Wang Sh., Zheng J. Beijing Yike Daxue Xuebao, 1998, vol. 30 (5), pp. 413–415.
Rokaya M.B., Munzbergova Z., Timsina B., Bhattarai K.R. J. Ethnopharmacol., 2012, vol. 141 (3), pp. 761–774.
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