BIOLOGICALLY ACTIVE COMPOUNDS OF ARTEMISIA ANNUA. ESSENTIAL OIL
https://doi.org/10.19163/2307-9266-2016-4-4-4-33
Abstract
Artemisia annua is a herblike annual plant which has been used in Chinese folk medicine for more than 2,000 years. In 1970-s sesquiterpenic lactone of artemisinin was isolated from the above-ground part of this plant. Today it is the most efficient known natural and synthetic compound for malaria treatment. The purpose of the study was to review the data from the open sources about a component composition of Artemisia annua essential oil in the spectrum of its pharmacological activity. Methods. The study was carried out using information and searching sources (PubMed, ScholarGoogle), library data bases (eLibrary, Cyberleninca), as well as the results of our studies. Results. We have established that aboveground part of Artemisia annua have a significant amount of essential oil apart from the sesquiterpene lactones. Essential oil contains more than 120 components, which belong to different classes of natural compounds. The study for dynamics of the essential oil accumulation in the Artemisia annua herb showed that the amount of oil in the herb rises significantly during budding, reaching maximum value in blossom. Qualitative composition and quantitative content of certain components varies depending on ecological and geographical factors, plant growing phase, cultivation technology, drying methods etc. Well-known pharmacological studies of essential oil of the Artemisia annua characterize it as a prospective source for the development of new antimicrobial medicinal drugs. Besides, as the studies shown, it can be related to the 6 class according to K. Sidorov’s classification – “relatively non-hazardous substances”. Conclusion. The analysis of the open sources on the study of essential oil of Artemisia annua made by us, as well as the results of our own studies, including phytochemical studies allow characterizing the essential oil of Artemisia annua as a prospective source for the working out of new antimicrobial drugs.
About the Authors
D. A. KonovalovRussian Federation
Konovalov Dmitry Alexeevich – Doctor of Pharmaceutical Sciences, Professor
A. A. Khamilonov
Russian Federation
Khamilonov Artur Aleksandrovich – postgraduate student of the Chair of Pharmacognosy
References
1. Duke S.O., Vaughn K.C., Croom Jr. E.M., Elsohly H.N. Artemisinin, a constituent of annual wormwood (Artemisia annua), is a selective phytotoxin. Weed Science. 1987. Vol. 35. Is.4. P. 499-505.
2. Klayman D.L. Weeding out malaria. Natural History. 1989. no. 10. P. 18-26.
3. Bhakuni R. S., Jain D. C., Sharma R. P., Kumar S. Secondary metabolites of Artemisia annua and their biological activity. Current Science. 2001. Vol. 80. Is.1. P. 35-48.
4. Klayman D.L. Qinghaosu (artemisinin): an antimalarial drug from China. Science. 1985. Vol. 228, no. 4703. P. 10491055.
5. Li Y., Wu Y. L. How Chinese scientists discovered qinghaosu (artemisinin) and developed its derivatives? What are the future perspectives? Medecine tropicale: cale: revue du Corps de sante colonial. 1997. Vol. 58, no.3. Suppl. P. 9-12.
6. How ancient Chinese texts helped Tu Youyou to conquer malaria and win the Noble Prize; https://focus.ua/world/338396/.
7. Tan R. X., Zou W. X. Endophytes: a rich source of functional metabolites. Natural products reports. 2001. Vol.18. P. 448-459.
8. Toleva P.D., Ognyanov I.V., Karova E.A., Georgiev E.V. On tha Bulgarian essential oil of Artemisia annua Lin-naues. Riv. ital. essenze, profumi, piante offic., aroma, saponin cosmet., aerosol. 1975. Vol. 57, no. 10. P. 620-622.
9. Tsankova E., Ognyanov I. On the composition of the essential oil from Artemisia annua Linnaues. Riv. ital. essenze, profumi, piante offic., aroma, saponin cosmet., aerosol. 1976. Vol. 58, no. 10. P. 502-503.
10. Baghi G.D., Haider F., Dwivedi P.D., Singh A., Naqvi A.A. Essential oil constituents of Artemisia an-nua during different growth periods at monsoon conditions of subtropical north Indian plains. Journal of Essential Oil Research. 2003. Vol. 15. Is. 4. P. 248-250.
11. Woerdenbag H. J., Bos R., Salomons M. C., Hendriks H., Pras N., Malingre T. M. Volatile constituents of Artemisia annua L. (Asteraceae). Flavour and Fragrance Journal. 1993. Vol. 8. Is. 3. P. 131-137.
12. Mohammadreza V.-R. Variation in the essential oil composition of Arte-misia annua L. of different growth stages cultivated in Iran. Botany Research Journal. 2008. Vol.1. Is. 2. P. 33-35.
13. Goryaev M.I., Serkebaeva T.E., Kro-tova G.I., Dembitskiy A.D. Study for Substances which Compose Essential Oils. Plant resources. 1967. Vol.3, no. 1.P. 63-67.
14. Dembitskiy A.D., Krotova G.I., Ku-chukhidze N.M., Yakobashvili N.Z. Essential oil of Artemisia annua. Oil Industry. 1983. No. 3. Р. 31-34.
15. Khodakov G.V., Kotikov I.V. Component composition of the essential oil from Artemisia annua and A. scoparia. Chemistry of natural compounds. 2009. No. 6. P. 759-761.
16. Cafferata L.F.R., Gatti W.O., Mijailosky S. Secondary gaseous metabolites analyses of wild Artemisia annua L. Molecular Medicinal Chemistry. 2010. Vol. 21. P. 48-52.
17. Lawrence B. M. Progress in essential oils. Perfumer & flavorist. 1990. Vol. 15. P. 63-64.
18. Galambosi B. Results of cultural trials with Artemisia annua. Herba Hungarica. 1982. Vol. 21. Is.2/3. P. 119-125.
19. Georgiev E., Genov N., Christova N. Changes in the yield and quality of essential oil from wormwood during growth. Rasteniev Nauki. 1981. Vol. 18. Is. 7. P. 95-102.
20. Kapelev I.G. Brief results from the introduction of essential oil plants of the wormwood genus. Bulletin Gosudarst-vennogo Nikitskogo Botanicheskogo Sada. 1984. Vol. 54. P. 60-65.
21. Simon J.E., Charles D., Cebert E., Grant L., Janick J., Whipkey A. Artemisia an-nua L.: A promising aromatic and medicinal. Advances in new crops. 1990. P. 522-526.
22. Charles D.J., Simon J.E., Wood K.V., Heinstein P. Germplasm variation in artemisinin content of Artemism annua using an alternative method of artemis-inin analysis from crude plant extracts. Journal of natural products. 1990. Vol. 53. Is. 1. P. 157-160.
23. Kelsey R. G., Shafizadeh F. Glandular trichomes and sesquiterpene lactones of Artemisia nova (As-teraceae). Biochemical Systematics and Ecology. 1980. Vol. 8. Is. 4. P. 371-377.
24. Gupta S. K., Singh P., Bajpai P., Ram G., Singh D., Gupta M.M., Kumar S. Mor-phogenetic variation for artemisinin and volatile oil in Artemisia annua. Industrial crops and Products. 2002. Vol. 16. Is. 3. P. 217-224.
25. Kohlmunzer S. Poszukiwanie olejko-wich roslin cyneolowich we florre krajowej I obcej. Diss. pharm. et pharmacol. PAN. 1960. Vol.12, no. 2. P. 143-163.
26. Zhannan Y., Zhengwen Y., Chao Zh., Shiqiong L., Quancai P. Metabolic properties of composition of the essential oil from leaves of Artemisia annua L. in the micro-environment. Modern Pharmaceutical Research. 2008. Vol. 1. Is. 2. P. 14-19.
27. Chang Y.J., Song S.H., Park S.H., Kim S.U. Amorpha-4, 11-diene synthase of Artemisia annua: cDNA isolation and bacterial expression of a terpene syn-thase involved in artemisinin biosynthesis. Archives of Biochemistry and Biophysics. 2000. Vol. 383. Is. 2. P. 178-184.
28. Covello P. S., Teoh K. H., Polichuk D. R., Reed D. W., Nowak G. Functional ge-nomics and the biosynthesis of artemisi-nin. Phytochemistry. 2007. Vol. 68. Is. 14. P. 1864-1871.
29. Divya G., Vijender S., Mohammed A., Gopal Rao M., Sushil K. Essential oils of petal, leaf and stem of the antimalar-ial plant Artemisia annua. J. Nat. Med. 2007. Vol.61, no. 2. P. 187-191.
30. Charles D.J., Cebert E., Simon J.E. Characterization of the essential oil of Artemisia annua L. Journal of Essential Oil Research. 1991. Vol. 3. Is. 1. P. 33-39.
31. Woerdenbag H. J., Pras N., Chan N. G., Bang B. T., Bos R., van Uden W. Y6. Zhannan Y., Zhengwen Y., Chao Zh., Shiqiong L., Quancai P. Metabolic properties of composition of the essential oil from leaves of Artemisia annua L. in the micro-environment. Modern Pharmaceutical Research. 2008. Vol. 1. Is. 2. P.. P. V. Artemisinin, Related Sesquiterpenes, and Essential Oil in Artemisia annua During a Vegetation Period in Vietnam. Planta medica. 1994. Vol. 60. Is. 3. P. 272-275.
32. Hethelyi E.B., Cseko I.B., Grosz M., Mark G., Palinkas J.J. Chemical composition of the Artemisia annua essential oils from Hungary. Journal of essential oil research. 1995. Vol. 7. Is.1. P. 45-48.
33. Goel D., Goel R., Singh V., Ali M., Mal-lavarapu G. R., Kumar S. Composition of the essential oil from the root of Artemisia annua. J. Nat. Med. 2007. Vol. 61. P. 458-461.
34. Yao J., Zhao B. T., Wang J. L., Zang J. Study on the comparison of essential oil extracted with supercritical CO2 technology from Artemisia capillaries. Pratacult. Sci. 2009. Vol. 26. Is. 4. P. 37-42.
35. Polichuk D.R., Zhang Y., Reed D.W., Schmidt J.F., Covello P.S. A glandular trichome-specific monoterpene alcohol dehydrogenase from Artemisia annua. Phytochemistry. 2010. Vol. 71. Is. 11-12. P. 1264-1269.
36. Lu S., Xu R., Jia J.W., Pang J.H., Matsu-da S.P.T., Chen X.Y. Cloning and functional characterization of a beta-pinene synthase from Artemisia annua that shows a circadian pattern of expression. Plant Physiol. 2002. Vol. 130. P. 13351348.
37. Ahmad A., Mishra L.N. Terpenoids from Artemisia annua and constituents of its essential oil. Phytochemistry. 1994. Vol. 37. Is. 1. P. 183-186.
38. Chalchat J.C., Garry R.P. Influence of harvest time on yield and composition of Artemisia annua oil produced in France. J. Essent Oil Res. 1994. Vol. 6. P. 261268.
39. Holm Y., Laakso I., Hiltunen R., Galam-bosi B. Variations in the essential oil composition of Artemisia annua L. of Flav. Fragr. J. 1997. Vol. 12. P. 241-246.
40. Haider F., Dwivedi P., Singh S., Naqvi A. A., Bagchi G. Influence of transplanting time on essential oil yield and composition in Artemisia annua plants grown under the climatic conditions of sub-tropical north India. Flavour and fragrance journal. 2004. Vol. 19. Is. 1. P. 51-53.
41. Tzenkova R., Kamenarska Z., Draganov A.,AtanassovA. Composition ofArtemis-ia annua essential oil obtained from species growing wild in Bulgaria. Biotech-nol. Biotechnol. Eq. 2010. Vol. 24. Is.2. P. 1822-1835.
42. Ma Ch., Wang H., Lu X., Li H., Liu B., Xu G. Analysis of Artemisia annua L. volatile oil by comprehensive two-dimensional gas chromatography time-of-flight mass spectrometry. Journal of Chromatography A. 2007. Vol. 1150. P.50-53.
43. Xu X. J., Song H., Zhu X. R., Xue G. Q., An H. G., Wu D. Q. Analysis of Chemical Constituents of the Volatile Oil from Artemisia annua L. by GC/MS and Heuristic Evolving Latent Projection. J. Fine Chemicals. 2008. Vol. 12. P. 013.
44. Tellez M.R., Canel C., Rimando A.M., Duke S.O. Differential accumulation of isoprenoids in glanded and glandless Artemisia annua L. Phytochemistry. 1999. Vol. 52. Is. 6. P. 1035-1040.
45. Chaudhary V., Kapoor R., Bhatnagar A.K. Effectiveness of two arbuscular mycorrhizal fungi on concentrations of essential oil and artemisinin in three accessions of Artemisia annua L. Applied Soil Ecology. 2008. Vol. 40. Is. 1. P. 174-181.
46. Farooqi A. A., Shukla A., Shar-ma S., Khan A. Effect of Plant Age and GA3 on Artemisinin and Essential Oil Yield in Artemisia annua L. Journal of Herbs, Spices & Medicinal Plants. 1996. Vol. 4. Is. 1. P. 73-80.
47. Khangholil Sh., Rezaeinodehi A. Effect of Drying Temperature on Essential Oil Content and Composition of Sweet Wormwood (Artemisia annua) Growing Wild in Iran. Pakistan Journal of Biological Sciences. 2008. Vol.11, no. 6. P. 934-937.
48. State Pharmacopoeia of the USSR: issue 1. 11th edition. Moscow: Medicine, 1987. Р. 336.
49. Konovalov D.A., Vinyukov V.V. Artemisia annua and its medical value. Pyatigorsk: Pyatigorsk branch of Volgograd State University, 2013. Р. 153.
50. Toleva P., Tolev I. Possibilities for the application of the Artemisia oil in perfume industry and cosmetics with therapeutic action. IV International congress on essential oils. Tbilisi, 1968. Р. 91.
51. Juteau F., Masotti V., Bessiere J. M., Dherbomez M., Viano J. Antibacterial and antioxidant activities of Artemisia annua essential oil. Fitoterapia. 2002. Vol. 73. Is. 6. P. 532-535.
52. Soylu E. M., Tok F. M., Soylu S., Kaya A. D., Evrendilek G. A. Anti-fungal Activities of the Essential Oils on Post-harvest Disease Agent Pen-icillium digitatum. Pakistan Journal of Biological Sciences. 2005. Vol. 8. Is. 1. P. 25-29.
53. Soylu E. M., Yigitbas H., Tok F. M., Soylu S., Kurt S., Baysal O., Kaya A. D. Chemical composition and antifungal activity of the essential oil of Artemisia annua L. against foliar and soil-borne fungal pathogens. Journal of Plant Diseases and Protection. 2005. Vol. 112. Is.3. P. 229-239.
54. Shakil N.A., Prasad D., Saxena D.B., Gupta A.K. Nematicidal Activity of Essential Oils of Artemisia an-nua Against Root-knot and Reniform Nematodes. Annals of Plant Protection Sciences. 2004. Vol. 12. Is. 2. P. 397-402.
55. Khabriev R.U. Guidelines for experimental (preclinical) studies for new pharmacological substances. Moscow: Medicine, 2005. Vol. 7.
56. Perazzo F. F., Carvalho J. C. T., Carvalho J. E., Rehder V. L. G. Central properties of the essential oil and the crude ethanol extract from aerial parts of Artemisia an-nua L. Pharmacological Research. 2003. Vol. 48. Is. 5. P. 497-502.
Review
For citations:
Konovalov D.A., Khamilonov A.A. BIOLOGICALLY ACTIVE COMPOUNDS OF ARTEMISIA ANNUA. ESSENTIAL OIL. Pharmacy & Pharmacology. 2016;4(4):4-33. (In Russ.) https://doi.org/10.19163/2307-9266-2016-4-4-4-33