Фармация и фармакология

Расширенный поиск


Полный текст:

Об авторах

Д. А. Коновалов
Пятигорский медико-фармацевтический институт – филиал ВолгГМУ Минздрава России
доктор фармацевтических наук, профессор, заместитель директора по науке

О. М. Шевчук

доктор биологических наук, заведующий лабораторией ароматических и лекарственных растений,

 пгт. Никита, Республика Крым

Л. А. Логвиненко

научный сотрудник лаборатории ароматических и лекарственных растений,

пгт. Никита, Республика Крым

А. А. Хамилонов
Пятигорский медико-фармацевтический институт – филиал ВолгГМУ Минздрава России
аспирант кафедры фармакогнозии

Список литературы

1. Klayman D.L. Qinghaosu (artemisinin): an antimalarial drug from China // Science. 1985. Vol. 228. P. 1049–1055.

2. Li Y., Wu Y.L. How Chinese scientists discovered qinghaosu (artemisinin) and developed its derivatives. What are the future perspectives? // Med. Trop. 1998. Vol. 58. Р. 9S-12S.

3. Liu J.-M., Ni M.-Y., Fan Y.-F., Tu Y.-Y., Wu Z.-H., Wu Y.-L., ChouW.-S. Structure and reactions of arteannuin // Huaxue Xuebao. 1979. Vol. 37. Is.2. P. 129–141.

4. Xu X.-X., Zhu J., Huang D.-Z., Zhou W.-S. Total synthesis of (+)-yingzhaosu A // Tetrahedron Lett. 1991. Vol. 32. P. 5785–5788.

5. Jeremic D., Jokic A., Behbud A., Stefanovic M. A new type of sesqiterpene lactone isolated from artemisia annua L. arteannuin B // Tetrahedron Lett. 1973. Vol. 32. P. 3039–3042.

6. Uskokovie M. R., Williams T. H., Blount J. F. The structure and absolute configuration of arteannuin B // Helv. Chim. Acta. 1974. Vol. 57, no.3. P. 600–602.

7. Qinghaosu Antimalarial Coordinating Research Group et al. Institute of Biophysics, CAS. The crystal structure and absolute configuration of qinghaosu // Scientia Sinica. 1979. Vol. 11. P. 1114– 1128.

8. Yeung S., Pongtavornpinyo W., Hastings I.M., Mills A.J., White N.J. Anti-malarial drug resistance, artemisinin-based combination therapy, and the contribution of modeling to elucidating policy choices // Am. J. Trop. Med. Hyg. 2004. Vol. 71. P. 179–186.

9. Tu Y.-Y., Ni M.-Y., Zhong Y.-R., Li L.- N., Cui S.-L., Zhang M.-Q., Wang X.- Z., Liang X.-T. Studies on the chemical constituents of Artemisia annua L. // Acta Pharmaceutica Sinica. 1981. Vol. 16, no.5. P. 366–370.

10. Tu Y.-Y., Ni M.-Y., Zhong Y.-R., Li L.- N., Cui S.-L., Zhang M.-Q., Wang X.- Z., Liang X.-T. Studies on the constituents of Artemisia annua. Part II. // Planta Medica. 1982. Vol. 44. P. 143–145.

11. Zhu D.-Y, Deng D.-A., Zhang S.-G, Xu R.-S. Structure of artemisilactone // Acta Chim. Sinica. 1984. Vol. 42, no.9. P. 937–939.

12. Wu Z.-H., Wang Y.-Y. Structure and synthesis of arteannuin and related compounds. XI. Identification of epoxyarteannuinic acid // Acta Chim. Sinica. 1984. Vol. 42. P. 596.

13. Tu Y.-Y., Ni M.-Y., Chung Y.-Y., Li L.-N. Chemical constituents in Artemisia annua L. and the derivatives of artemisinine // Zhong Yao T’ong Bao (Bull. Chin. Nat. Med.). 1981. Vol. 6, no.2. P. 31.

14. Zhu D.-Y., Zhang S.-G., Liu B.-N., Fan G.-J., Liu J., Xu R.-S. Study on antibacterial constituents of Qing Hao (Artemisia annua L.) // Zhongcaoyao (Chin. Trad. Herb. Drug). 1982. Vol. 13, no.2. P. 54.

15. Huang J.-J., Xia Z.-Q., Wu L.-F. Constituents of Artemisia annua L. I. Isolation and identification of 11R-(-)-dihydroarteannuic acid // Acta Chim. Sin. 1987. Vol. 45. P. 609–612.

16. Tian Y., Wei Z.-Y., Wu Z.-H. Studies on the chemical constituents of Qing Hao (Artemisia annua), a traditional Chinese herb // Zhongcaoyao. 1982. Vol. 13. P. 249–251.

17. Roth R. J., Acton N. Isolation of arteannuic acid from Artemisia annua // Planta Med. 1987. Vol. 53. P. 501–502.

18. Zaman S.-S., Sharma R.-P. Some aspects of the chemistry and biological activity of artemisinin and related antimalarials // Heterocycles. 1991. Vol. 32. Is.8. P. 1593–1637.

19. Misra L.N. Arteannuin C, a sesquiterpene lactone from Artemisia annua // Phytochemistry. 1986. Vol. 25. Is.12. P. 2892–2893.

20. Acton N., Klayman D.L. Artemisitene, a new sesquiterpene lactone endoperoxide from Artemisia annua // Planta Med. 1985. Vol. 5. P. 441–442.

21. El-Feraly F.-S., Al-Meshal I. A., Khalifa S. I. epi-Deoxyarteannuin B and 6,7-dehydroartemisinic acid from Artemisia annua // J. Nat. Prod. 1989. Vol. 52. P. 196–198.

22. Wei Z.X., Pan J.P., Li Y. Artemisinin-G – a sesquiterpene from Artemisia annua // Planta Med. 1992. Vol. 58. Is. 3. P. 300.

23. Brown G. D. Annulide, a sesquiterpene lactone from Artemisia-Annua // Phytochemistry. 1993. Vol. 32. Is. 2. P. 391–393.

24. Sy L.K., Brown G.D. Deoxyarteannuin-B, dihydro-deoxyarteannuin-B and tans-5-hydroxy-2-isopropenyl-5-methylhex-3-en-1-ol from Artemisia anuua // Phytochemistry. 2001. Vol. 58. Is. 8. P. 1159–1166.

25. Sy L. K., Brown G. D., Haynes R. A novel endoperoxide and related sesquiterpenes from Artemisia annua which are possibly derived from allylic hydroperoxides // Tetrahedron. 1998. Vol. 54. Is.17. P. 4345–4356.

26. Brown G. D. Two new compounds from Artemisia annua // J. Nat. Prod. 1992. Vol. 55. Is.12. P. 1756–1760.

27. Brown G. D. Cadinanes from Artemisia annua that may be intermediates in the biosynthesis of artemisinin // Phytochemistry. 1994. Vol. 36. Is.3. P. 637–641.

28. Duke M.V., Paul R.N., Elsohly H.N., Sturtz G., Duke S.O. Localization of artemisinin and artemisitene in foliar tissues of glanded and glandless biotypes of Artemisia annua I. // Int. J. Plant Sci. 1994. Vol. 155. P. 365–372.

29. Vandenberghe D. R., Vergauwe A. N., Van Montagu M., Van Den Eeckout E. G. Simultaneous Determination of Artemisinin and Its Bioprecursors in Artemisia annua // J. Nat. Prod. 1995. Vol. 58. P. 798–803.

30. Woerdenbag H.J., Pras N., Nguyen G.C., Bui T.B., Bos R., Van Uden W., Pham V.Y., Nguyen V.B., Batterman S., Lugt C.B. Artemisinin related sesquiterpenes and essential oils in Artemisia annua during a vegetation period in Vietnam // Planta Med. 1994. Vol. 60. P. 272–275.

31. Pathak A. K., Jain D. C., Bhakuni R. S., Chaudhuri P. K., Sharma R. P. Deepoxidation of arteannuin-B with chlorotrimethylsilane and sodium-iodide // J. Nat. Prod. 1994. Vol. 57. Is. 12. P. 1708–1710.

32. Sy L. K., Cheung K. K., Zhu N. Y., Brown G. D. Structure elucidation of Arteannuin-O, a novel cadinane diol from Artemisia annua and the synthesis of Arteannuin-K, Arteannuin-L, Arteannuin-M and Arteannuin-O // Tetrahedron. 2001. Vol. 57. Is. 40. P. 8481–8493.

33. Akhila A., Kumkum R., Thakur R.S. Biosynthesis of artemisinic acid in Artemisia annua // Phytochemistry.1990. Vol.29. P. 2129–2132.

34. Bouwmeester H.J., Wallaart T.E., Janssen M.H.A. et al. Amorpha-4,11-diene synthase catalyses the first probable step in artemisinin biosynthesis // Phytochemistry. 1999. Vol. 52. P. 843–854.

35. Bertea C.M., Freije J.R., van der Woude H. et al. Identification of intermediates and enzymes involved in the early steps of artemisinin biosynthesis in Artemisia annua L. // Planta Med. 2005. Vol. 71. P. 40–47.

36. Wallaart T.E., Pras N., Beekman A.C., Quax W.J. Seasonal variation of artemisinin and its biosynthetic precursors in plants of Artemisia annua of different geographical origin; proof for the existence of chemotypes // Planta Med. 2000. Vol. 66. P. 57–62.

37. Woerdenbag H. J., Lugt C. B., Pras N. Artemisia annua L.: a source of novel antimalarial drugs // Pharmaceutisch Weekblad. – 1990. – Vol. 12, no. 5. – P. 169–181.

38. Brown G.D., Sy L.K. In vivo transformations of dihydroartemisinic acid in Artemisia annua plants // Tetrahedron. 2004. Vol. 60. P. 1139–1159.

39. Sangwan R.S., Agarwal K., Luthra R., Thakur R.S., Singh-Sangwan N. Biotransformation of arteannuic acid into arteannuin-B and artemisinin in Artemisia annua // Phytochemistry. 1993. Vol. 34. P. 1301–1302.

40. Martinez B.C., Staba E.J: The production of artemisinin in Artemisia annua L. tissue cultures // Adv. Cell. Cult. 1988. Vol. 6. P. 69–87.

41. Nair M.S.R., Basile D.V. Bioconversion of arteannuin B to artemisinin // J. Nat. Prod. 1993. Vol. 56. P. 1559–1566.

42. Rydén A.-M., Ruyter-Spira C., Quax W.J., Osada H., Muranaka T., Kayser O., Bouwmeester H. The Molecular cloning of dihydroartemisinic aldehyde reductase and its implication in artemisinin biosynthesis in Artemisia annua // Planta med. 2010. Vol. 76. Is.15. P. 1778–1783.

43. Brown G.D., Sy L.K. In vivo transformations of artemisinic acid in Artemisia annua plants // Tetrahedron. 2006. Vol. 63. P. 9548–9566.

44. Dhingra V., Narasu M.L. Purification and characterization of an enzyme involved in biochemical transformation of arteannuin B to artemisinin from Artemisia annua // Biochem. Biophys. Res. Commun. 2001. Vol. 281. P. 558–561.

45. Olofsson, L., Engström, A., Lundgren, A., Brodelius, P. Relative expression of genes of terpene metabolism in different tissues of Artemisia annua L. // BMC Plant Biology. 2011. Vol. 11. P. 45–56.

46. Acton N., Klayman D.L., Rollmann I.J. Reductive electrochemical HPLC assay for artemisinin (qinghaosu) // Planta Med. 1985. Vol. 5. P. 445–446.

47. Charles D.J., Simon J.E., Wood K.V., Heinstein P. Germplasm variation in artemisinin content of Artemisia annua using an alternative method of artemisinin analysis from crude plant extracts // Journal of Natural Products. 1990. Vol. 53. P. 157–160.

48. Ferreira J.F.S., Simon J.E., Janick J. Developmental studies of Artemisia annua: flowering and artemisinin production under greenhouse and field conditions // Planta medica. 1995. Vol. 61, no. 2. P. 167–170.

49. Duke S.O., Paul R.N. Development and fine structure of the glandular trichomes of Artemisia annua L. // Int. J. Plant Sci. 1993. Vol. 154. P. 107–118.

50. Gupta S.K., Singh P., Bajpai P. et al. Morphogenetic variation for artemisinin and volatile oil in Artemisia annua // Ind. Crop. Prod. 2002. Vol. 16. P. 217–224.

51. Liersch R., Soicke H., Stehr C., Tullner H.U. Formation of artemisinin in Artemisia annua during one vegetation period // Planta Med. 1986. Vol.52. P. 387–390.

52. Laughlin J.C. The influence of distribution of antimalarial constituents in Artemisia annua L. on time and method of harvest // Acta Hortic. 1995. Vol.390. P. 67–73.

53. Lommen W.J.M., Schenk E., Bouwmeester H.J., Verstappen F.W.A. Trichome dynamics and artemisinin acumination during development and senescence of Artemisia annua leaves // Planta med. 2006. Vol. 72. P. 336–345.

54. Ferreira J.F.S., Simon J.E., Janick J. Relationship of artemisinin content of tissue cultured, greenhouse grown, and field grown plants of Artemisia annua // Planta Med. 1995. Vol. 61. P. 351–355.

55. Weathers P.J., Cheetham R.D., Follansbee E., Theoharides K. Artemisinin production by transformed roots of Artemisia annua // Biotechnol Lett. 1994. Vol. 16. P. 1281–1286.

56. Meshnick S.R. Artemisinin mechanisms of action, resistance and toxicity // Int. J. Parasitology. 2002. Vol. 32. P. 1655–1660.

57. Abdin M. Z., Israr M., Rehman R. U., Jain S. K. Artemisinin, a novel antimalarial drug: biochemical and molecular approaches for enhanced production // Planta medica. 2003. Vol. 69. Is. 04. P. 289–299.

58. Takatsuki S., Narui T., Ekimoto H. et al. Studies on cytotoxic activity of animal and plant crude drugs // Nat. Med. 1996. Vol. 50, no. 2. P. 145–157.

59. Kroes B.H., Quaries H.C., Van Ufford Q., Tinbergen-De Boer R.L., Van Den Berg A.J.J., Beukelman C.J., Labadie R.P., Van Dijk H. Modulatory effects of Artemisia annua extracts on human complement, neutrophil oxidative burst and proliferation of T lymphocytes // Phytotherapy Research. 1995. Vol. 9. Is. 8. P. 551–554.

60. Zeng Q. P., Zhang P. Z. Artesunate mitigates proliferation of tumor cells by alkylating heme-harboring nitric oxide synthase // Nitric Oxide. 2011. Vol. 24, no. 2. P. 110–112.

61. Bao F., Wu P., Xiao N., Qiu F., Zeng Q.P. Nitric oxide-driven hypoxia initiates synovial angiogenesis, hyperplasia and inflammatory lesions in mice // PloS one. 2012. Vol. 7, no. 3. P. e34494.

62. Michaelsena Fr.W., Saeed M.E.M., Schwarzkopf J., Efferth Th. Activity of Artemisia annua and artemisinin derivatives, in prostate carcinoma // Phytomedicine. 2015. Vol. 22. P. 1223–1231.

63. Du J.H., Zhang H.D., Ma Z.J., Ji K.M. Artesunate induces oncosis-like cell death in vitro and has antitumor activity against pancreatic cancer xenografts in vivo // Cancer Chemother. Pharmacol. 2010. Vol. 65. P. 895–902.

64. Ma H., Yao Q., Zhang A.M., Lin S., Wang X.X., Wu L., Sun J.G., Chen Z.T. The effects of artesunate on the expression of EGFR and ABCG2 in A549 human lung cancer cells and axenograft model // Molecules. 2011. Vol. 16. P. 10556–10569.

65. Ng D.S., Liao W., Tan W.S., Chan T.K., Loh X.Y., Wong, W.S. Anti-malarial drug artesunate protects against cigarette smoke-induced lungi njury in mice // Phy-tomedicine. 2014. Vol. 21. P. 1638–1644.

66. Breuer E., Efferth T. Treatment of Iron-Loaded Veterinary Sarcoma by Artemisia annua // Nat. Prod. Bioprospect. 2014. Vol. 4. P.113–118.

67. Krishna S., Ganapathi S., Ster I.C., Saeed M.E., Cowan M., Finlayson C., Kovacsevics H., Jansen H., Kremsner P.G., Efferth T., Kumar D. A randomised, double blind, placebo-controlled pilot study of oral artesunate therapy for colorectal cancer // EBioMed. 2015. Vol. 2. P. 82–90.

68. Foglio M. A., Dias P. C., Antônio M. A., Possenti A., Rodrigues R. A. F., da Silva É. F. et al. Antiulcerogenic activity of some sesquiterpene lactones isolated from Artemisia annua // Planta medica. 2002. Vol. 68, no.6. P. 515–518.

69. Tripathi A. K., Prajapati V., Aggarwal K. K., Kumar S. Toxicity, feeding deterrence, and effect of activity of 1, 8-cineole from Artemisia annuaon progeny production of Tribolium castanaeum (Coleoptera: Tenebrionidae) //Journal of Economic Entomology. 2001. Vol. 94, no. 4. P. 979–983.

70. Luo X.D., Shen C.C. The chemistry, pharmacology, and clinical applications of qinghaosu (artemisinin) and its derivatives // Med. Res. Rev. 1987. Vol. 7. P. 29–52.

71. Zheng M., Li L., Chen S. Chemical transformations of qinghaosu, a peroxidic antimalarial // Tetrahedron. 1983. Vol. 36. P. 2941–2946.

72. Zhao S.S., Zeng M. Spectrometric high pressure liquid chromatography (HPLC) studies on the analysis of Qinghaosu // J. Med. Plant. Res. 1985. Vol. 3. P. 233– 237.

73. Theoharides A.D., Smyth M.H., Ashmore R.W., Halverson J.M., Zhou Z.M., Ridder W.E., Lin A.J. Determination of dihydroqinghaosu [dihydroartemisinin] in blood by pyrolysis gas chromatography-mass spectrometry // Anal. Chem. 1988. Vol. 60. P. 115–120.

74. Zhou Z.M., Anders J.C., Chung H., Theoharides A.D. Analysis of artesunic acid and dihydroQHS in blood by HPLC with reductive EC detection // J. Chromatogr. 1987. Vol. 414. P. 77–90.

75. El Domiaty M.M., Al Meshal I.A., El Feraly F.S. Reversed-phase HPLC determination of artemisitene in artemisinin // J. Liq. Chromatogr. 1991. Vol. 14. P. 2317–2330.

76. Zhou Z., Huang Y., Xie G., Sun X., Wang Y., Fu L., Jian H., Guo X., Li G. HPLC with polarographic detection of artemisinin and its derivatives and application of the method to the pharmacokinetic study of artemether // J. Liq. Chromatogr. 1988. Vol. 11. P. 1117–1137.

77. Sipahimalani A.T., Fulzele D.P., Heble M.R. Rapid method for the detection and determination of artemisinin by gas chromatography // J. Chromatogr. 1991. Vol. 538. P. 452–455.

78. Ranasinghe A., Sweatlock J.D., Cooks R.G. A rapid screening method for artemisinin and its congeners using Ms/Ms: Search for new analogues in Artemisia annua // Journal of natural products. 1993. Vol. 56, no. 4. P. 552–563.

79. Woerdenbag H.J., Luers J.F.J., Van Uden W., Pras N., Malingre Th., Alfermann A.W. Production of the new antimalarial drug in shoot cultures of Artemisia annua L. // Plant Cell Tiss. Org. Cult. 1993. Vol.32. P. 247–257.


Для цитирования:

Коновалов Д.А., Шевчук О.М., Логвиненко Л.А., Хамилонов А.А. БИОЛОГИЧЕСКИ АКТИВНЫЕ СОЕДИНЕНИЯ ПОЛЫНИ ОДНОЛЕТНЕЙ. СЕСКВИТЕРПЕНОВЫЕ ЛАКТОНЫ. Фармация и фармакология. 2016;4(5):4-35.

For citation:

Konovalov D.A., Shevchuk O.M., Logvinenko L.A., Khamilo A.A. BIOLOGICALLY ACTIVE COMPOUNDS OF ARTEMISIA ANNUA. SESQUITERPENE LACTONES. Pharmacy & Pharmacology. 2016;4(5):4-35. (In Russ.)

Просмотров: 1457

Creative Commons License
Контент доступен под лицензией Creative Commons Attribution 4.0 License.

ISSN 2307-9266 (Print)
ISSN 2413-2241 (Online)