Вестник БГУ. Медицина и фармация
Библиографическое описание:
, , , , , , , ХАМАЗУЛЕН И ЕГО СОДЕРЖАНИЕ В ЗАВИСИМОСТИ ОТ ГЕНЕТИЧЕСКИХ И ВНЕШНИХ УСЛОВИЙ ПРОИЗРАСТАНИЯ В РАСТЕНИЯХ РОДА ПОЛЫНЬ // Вестник БГУ. Медицина и фармация. - 2025. №1. . - С. 45-56.
Заглавие:
ХАМАЗУЛЕН И ЕГО СОДЕРЖАНИЕ В ЗАВИСИМОСТИ ОТ ГЕНЕТИЧЕСКИХ И ВНЕШНИХ УСЛОВИЙ ПРОИЗРАСТАНИЯ В РАСТЕНИЯХ РОДА ПОЛЫНЬ
Финансирование:
Исследование выполнено при поддержке прикладных научных исследований Министерства образования и науки Республики Бурятия «Разработка инноваци- онных лекарственных средств ранозаживляющего и антимикробного действия на основе природного сырья».
Коды:
Аннотация:
Хамазулен — это сесквитерпен, обнаруженный в растениях рода Artemisia L., обладающий антиоксидантной, противовоспалительной, антимикробной и другими свойствами. Содержание хамазулена зависит от генетических особенностей вида и факторов внешней среды, таких как климат, почва и методы культивации. Азулен — это «артефакт», как таковой в «чистом» виде практически не встречается в природных источниках. Его много содержится в эфирных маслах, которые получают перегонкой растительного сырья с водяным паром, но здесь он образуется в процессе перегонки из проазуленов. Проазуленами в растениях являются сесквитерпеновые лактоны и спирты, из которых в растениях синтезируются многочисленные производные азулена. Биосинтез хамазулена включает два основных пути: мевалонатный и метилэритритолфосфатный. Понимание механизмов биосинтеза хамазулена и факторов, влияющих на его содержание, необходимо для эффективного использования этого вещества в медицинской и фармацевтической практике, данному аспекту посвящен указанный обзор. В статье рассматриваются виды полыни, содержащие хамазулен, с указанием географического распространения и фармакологической активности, а также влияние различных факторов на накопление хамазулена.
Ключевые слова:
хамазулен, биологически активные вещества, эфирные масла, полынь Сиверса, фармакологическая активность.
Список литературы:
Valles J., García S., Hidalgo O. et al. Biology, genome evolution, biotechnologi- cal issues and research including applied perspectives in Artemisia. Advances in Botan- ical Research. 2011; 60: 349–419.
Bora K. S., & Sharma A. The Genus Artemisia: A Comprehensive Review. Pharmaceutical Biology. 2010; 49(1): 101–109.
Abad M. J. Bedoya L. M., Apaza L., Bermejo P. The Artemisia L. Genus: A Review of Bioactive Essential Oils. Molecules. 2012; 17: 2542–2566.
Ramadan M., Goeters S., Watzer B. et al. Chamazulene Carboxylic Acid and Matricin: A Natural Profen and Its Natural Prodrug, Identified Through Similarity to Synthetic Drug Substances. Journal of Natural Products. 2006; 69: 1041–1045.
Jaimand K., Rezaee M. B., Mozaffarian V. Chemical constituents of the leaf and flower oils from Achillea millefolium ssp. elbursensis Hub.-Mor. from Iran rich in chamazulene. Journal of Essential Oil Research. 2006; 18: 293–295.
Arnold H. J., Arnold N., Bellomaria B., Valentini G. Etude chimique de l'huile essentielle d'Artemisia arborescens L. de l'ile de Karpathos (Dodecanese). Plantes Medicinales et Phytotherapie. 1993; 26: 135–142.
Goldstein J. L., Brown M. S. Regulation of the mevalonate pathway. Nature. 1990; 343: 425–430.
Bochar D. A., Friesen, J. A., Stauffacher, C. V., Rodwell, V. W. Role of mevalo- nate pyrophosphate decarboxylase in terpenoid biosynthesis. The Journal of Biological Chemistry. 1999; 274(1): 15–44.
Qureshi N., Porter J. W. Conversion of mevalonic acid to isopentenyl pyrophos- phate in mammalian systems. The Journal of Biological Chemistry. 1981; 256(2): 677–682.
Poulter C. D., Rilling H. C. The prenyltransfer reaction. Comprehensive Bio- chemistry. 1981; 15: 45–89.
Sprenger G. A., Schörken U., Wiegert T. et al. Identification of a thiamine- dependent synthase in E. coli required for DXP synthesis. Proceedings of the National Academy of Sciences. 1997; 94(22): 12102–12107.
Kuzuyama T., Takagi M., Kaneda K. et al. The nonmevalonate pathway for terpenoid biosynthesis in bacteria and plastids. Annual Review of Microbiology. 2000; 54. P. 309–336.
Rohmer M. The discovery of a mevalonate-independent pathway for isopre- noid biosynthesis in bacteria, algae, and higher plants. Natural Product Reports. 1999. 16(5): 565–574.
Lichtenthaler, H. K. The 1-deoxy-D-xylulose-5-phosphate pathway of isopre- noid biosynthesis in plants. Annual Review of Plant Biology. 1999; 50: 47–65.
Croteau R., Kutchan T. M. Natural products (secondary metabolites). Biochemistry and Molecular Biology of Plants. 2005: 1250–1318.
Bohlmann J., Keeling C. I. Terpenoid biosynthesis in conifers — gene cloning and molecular characterization. Phytochemistry. 2008; 69(10): 241–266.
Gonzalez-Coloma A., Reina M., Diaz C. E. et al. Chemical and biological pro- files of essential oils from Artemisia absinthium and Artemisia pontica. Phytochemis- try. 2006; 67(14): 151–157.
Capuzzo A., Occhipinti A., Maffei M. E. Antioxidant and radical scavenging activities of chamazulene. Natural Products Research. 2014; 28: 2321–2323.
Rekka E. A., Kourounakis A. P., Kourounakis P. N. Investigation of the effect of chamazulene on lipid peroxidation and free radical processes. Research Communications in Molecular Pathology and Pharmacology. 1996; 92: 361–364.
Ornano L., Venditti A., Ballero M. Chemopreventive and Antioxidant Activity of the Chamazulene-Rich Essential Oil Obtained from Artemisia arborescens L. Grow- ing on the Isle of La Maddalena, Sardinia, Italy. Chem Bio Chem, 2013; 10(8): 1464– 1470.
Petretto G. L., Chessa M., Piana A. Chemical and biological study on the es- sential oil of Artemisia caerulescens L. ssp. densiflora (Viv.). Natural Product Research. 2012; 27(19): 1709–1715.
Presti M. Lo., Crupi M. L., Zellner B. d’A. et al. Characterization of Artemisia arborescens L. (Asteraceae) leaf-derived essential oil from Southern Italy. Journal of Essential Oil Research. 2007; 19(3): 218–224.
Russo A., Bruno M., Avola R. et al. Chamazulene-Rich Artemisia arbo- rescens Essential Oils Affect the Cell Growth of Human Melanoma Cells. Plants. 2020; 9: 1000.
Militello M., Settanni L., Aleo A. Chemical composition and antibacterial po- tential of Artemisia arborescens L. essential oil. Curr. Microbiol. 2010; 62: 1274–1281.
Militello M., Carrubba A., & Blázquez M. A. Artemisia arborescens L.: essen- tial oil composition and effects of plant growth stage in some genotypes from Sicily. Journal of Essential Oil Research. 2012; 24(3): 229–235.
Michelakis E. C., Evergetis E., Koulocheri S. D., Haroutounian S. A. Exploita- tion of Artemisia arborescens as a renewable source of chamazulene: Seasonal varia- tion and distillation conditions. Nat. Prod. Commun. 2016; 11: 1513–1516.
March J. Advanced Organic Chemistry: Reactions, Mechanisms, and Struc- ture. 3rd Edition. John Willey & Sons, Inc., New York, USA, 1985.
Said Mel-A., Militello M., Saia S. Artemisia arborescens Essential Oil Compo- sition, Enantiomeric Distribution, and Antimicrobial Activity from Different Wild Pop- ulations from the Mediterranean Area. Chem Biodivers. 2016 Aug; 13(8): 1095–102.
Marongiu B., Piras A., & Porcedda S. Comparative analysis of the oil and su- percritical CO2 extract of Artemisia arborescens L. and Helichrysum splen- didum (Thunb.) Less. Natural Product Research. 2006; 20(5): 421–428.
Pappas R., Sheppard-Hanger S. Artemisia arborescens — essential oil of the Pacific Northwest: a high-chamazulene, low-thujone essential oil with potential skin- care applications. Aromather. J. 2000; 10: 30–33.
Janackovic P., Novaković J., Soković M. et al. Composition and antimicrobial activity of essential oils of Artemisia judaica, A. herba-alba and A. arborescens from Libya. Archives of Biological Sciences. 2015; 67: 455– 466.
Bouzenna H., & Krichen L. Pelargonium graveolens L’Her. and Artemisia ar- borescens L. essential oils: Chemical composition, antifungal activity against Rhi- zoctonia solani and insecticidal activity against Rhysopertha dominica. Natural Product Research. 2012. 27(9): 841–846.
Abderrahim A., Belhamel K., Chalcat J. C., Figuérédo G. Chemical composi- tion of the essential oil from Artemisia arborescens L. growing wild in Algeria. Rec- ords of Natural Products. 2010; 4: 87–90.
K. Younes S. Merghache N. Djabou D. et al. Chemical composition, antibacte- rial and antioxydant activitiées of a new essential oil chemotype of algerian Artemesia arborescens L. Afr J Pharm Pharmaco. 2012; 6(42): 2912–2921.
Janackovic P.; Rajcevic N. Gavrilovic M et al. Essential oil composition of five Artemisia (Compositae) species in regards to chemophenetics. Biochem. Syst. Ecol. 2019; 87: 103960.
Riahi L., Chograni H., Masmoudi A. S., & Cherif A. Genetic resources of Tu- nisian Artemisia arborescens L. (Asteraceae), pattern of volatile metabolites concentra- tion and bioactivity and implication for conservation. Biochemical Systematics and Ecology. 2019; 87: 103952.
Riahi L., Chograni H., Ben Rejeb F. et al. Efficient in vitro regeneration of the endangered species Artemisia arborescens L. through direct organogenesis and impact on secondary metabolites production. Hortic. Environ. Biotechnol. 2022; 63: 439–450.
Politeo O., Cajic I., Simic A. et al. Comparative Study of Chemical Composi- tion and Cholinesterase Inhibition Potential of Essential Oils Isolated from Artemisia Plants from Croatia. Separations. 2023; 10: 546.
Plescia F., Venturella F., Lauricella M. et al. Chemical composition, cytotoxic effects, antimicrobial and antibiofilm activity of Artemisia arborescens (Vaill.)
growing wild in the province of Agrigento, Sicily, Italy. Plant Biosystems - An In- ternational Journal Dealing with All Aspects of Plant Biology. 2022. 156(6): 1336– 1345.
Costa R., Ragusa S., Russo M. et al. Phytochemical screening of Artemisia ar- borescens L. by means of advanced chromatographic techniques for identification of health-promoting compounds. J Pharm Biomed Anal. 2016. Jan 5; 117: 499–509.
Соктоева Т. Э. Фармакогностическое исследование Artemisia annua L. и Artemisia sieversiana Willd. флоры Бурятии: диссертация на соискание ученой степени кандидата фармацевтических наук. Улан-Удэ, 2011. 172 с. Текст: непо- средственный.
Сравнительный анализ состава эфирных масел, полученных гидродистилляцией, и эфирномасличной фракции СО₂-экстракта Artemisia sieversiana Willd. и Artemisia annua L. / Т. Э. Рандалова, Г. Л. Рыжова, К. А. Дычко [и др.] // Химия растительного сырья. 2014. № 4. С. 61–64. Текст: непосредственный.
Рэнцэнбямбаа С. Фармакогностическая характеристика Artemisia adamsii Вess. и Artemisia macrocephala Jaque. ex Bess. флоры Бурятии и Монголии и раз- работка лекарственных средств на их основе: диссертация на соискание ученой степени кандидата фармацевтических наук. Улан-Удэ, 2020. 194 с. Текст: непо- средственный.
Дыленова Е. П. Фармакогностическая характеристика Artemisia frigida Willd. и Artemisia jacutica Drob. и разработка лекарственных средств на их основе: диссертация на соискание ученой степени кандидата фармацевтических наук. Улан-Удэ, 2019. 226 с. Текст: непосредственный.
Bora K. S., & Sharma A. The Genus Artemisia: A Comprehensive Review. Pharmaceutical Biology. 2010; 49(1): 101–109.
Abad M. J. Bedoya L. M., Apaza L., Bermejo P. The Artemisia L. Genus: A Review of Bioactive Essential Oils. Molecules. 2012; 17: 2542–2566.
Ramadan M., Goeters S., Watzer B. et al. Chamazulene Carboxylic Acid and Matricin: A Natural Profen and Its Natural Prodrug, Identified Through Similarity to Synthetic Drug Substances. Journal of Natural Products. 2006; 69: 1041–1045.
Jaimand K., Rezaee M. B., Mozaffarian V. Chemical constituents of the leaf and flower oils from Achillea millefolium ssp. elbursensis Hub.-Mor. from Iran rich in chamazulene. Journal of Essential Oil Research. 2006; 18: 293–295.
Arnold H. J., Arnold N., Bellomaria B., Valentini G. Etude chimique de l'huile essentielle d'Artemisia arborescens L. de l'ile de Karpathos (Dodecanese). Plantes Medicinales et Phytotherapie. 1993; 26: 135–142.
Goldstein J. L., Brown M. S. Regulation of the mevalonate pathway. Nature. 1990; 343: 425–430.
Bochar D. A., Friesen, J. A., Stauffacher, C. V., Rodwell, V. W. Role of mevalo- nate pyrophosphate decarboxylase in terpenoid biosynthesis. The Journal of Biological Chemistry. 1999; 274(1): 15–44.
Qureshi N., Porter J. W. Conversion of mevalonic acid to isopentenyl pyrophos- phate in mammalian systems. The Journal of Biological Chemistry. 1981; 256(2): 677–682.
Poulter C. D., Rilling H. C. The prenyltransfer reaction. Comprehensive Bio- chemistry. 1981; 15: 45–89.
Sprenger G. A., Schörken U., Wiegert T. et al. Identification of a thiamine- dependent synthase in E. coli required for DXP synthesis. Proceedings of the National Academy of Sciences. 1997; 94(22): 12102–12107.
Kuzuyama T., Takagi M., Kaneda K. et al. The nonmevalonate pathway for terpenoid biosynthesis in bacteria and plastids. Annual Review of Microbiology. 2000; 54. P. 309–336.
Rohmer M. The discovery of a mevalonate-independent pathway for isopre- noid biosynthesis in bacteria, algae, and higher plants. Natural Product Reports. 1999. 16(5): 565–574.
Lichtenthaler, H. K. The 1-deoxy-D-xylulose-5-phosphate pathway of isopre- noid biosynthesis in plants. Annual Review of Plant Biology. 1999; 50: 47–65.
Croteau R., Kutchan T. M. Natural products (secondary metabolites). Biochemistry and Molecular Biology of Plants. 2005: 1250–1318.
Bohlmann J., Keeling C. I. Terpenoid biosynthesis in conifers — gene cloning and molecular characterization. Phytochemistry. 2008; 69(10): 241–266.
Gonzalez-Coloma A., Reina M., Diaz C. E. et al. Chemical and biological pro- files of essential oils from Artemisia absinthium and Artemisia pontica. Phytochemis- try. 2006; 67(14): 151–157.
Capuzzo A., Occhipinti A., Maffei M. E. Antioxidant and radical scavenging activities of chamazulene. Natural Products Research. 2014; 28: 2321–2323.
Rekka E. A., Kourounakis A. P., Kourounakis P. N. Investigation of the effect of chamazulene on lipid peroxidation and free radical processes. Research Communications in Molecular Pathology and Pharmacology. 1996; 92: 361–364.
Ornano L., Venditti A., Ballero M. Chemopreventive and Antioxidant Activity of the Chamazulene-Rich Essential Oil Obtained from Artemisia arborescens L. Grow- ing on the Isle of La Maddalena, Sardinia, Italy. Chem Bio Chem, 2013; 10(8): 1464– 1470.
Petretto G. L., Chessa M., Piana A. Chemical and biological study on the es- sential oil of Artemisia caerulescens L. ssp. densiflora (Viv.). Natural Product Research. 2012; 27(19): 1709–1715.
Presti M. Lo., Crupi M. L., Zellner B. d’A. et al. Characterization of Artemisia arborescens L. (Asteraceae) leaf-derived essential oil from Southern Italy. Journal of Essential Oil Research. 2007; 19(3): 218–224.
Russo A., Bruno M., Avola R. et al. Chamazulene-Rich Artemisia arbo- rescens Essential Oils Affect the Cell Growth of Human Melanoma Cells. Plants. 2020; 9: 1000.
Militello M., Settanni L., Aleo A. Chemical composition and antibacterial po- tential of Artemisia arborescens L. essential oil. Curr. Microbiol. 2010; 62: 1274–1281.
Militello M., Carrubba A., & Blázquez M. A. Artemisia arborescens L.: essen- tial oil composition and effects of plant growth stage in some genotypes from Sicily. Journal of Essential Oil Research. 2012; 24(3): 229–235.
Michelakis E. C., Evergetis E., Koulocheri S. D., Haroutounian S. A. Exploita- tion of Artemisia arborescens as a renewable source of chamazulene: Seasonal varia- tion and distillation conditions. Nat. Prod. Commun. 2016; 11: 1513–1516.
March J. Advanced Organic Chemistry: Reactions, Mechanisms, and Struc- ture. 3rd Edition. John Willey & Sons, Inc., New York, USA, 1985.
Said Mel-A., Militello M., Saia S. Artemisia arborescens Essential Oil Compo- sition, Enantiomeric Distribution, and Antimicrobial Activity from Different Wild Pop- ulations from the Mediterranean Area. Chem Biodivers. 2016 Aug; 13(8): 1095–102.
Marongiu B., Piras A., & Porcedda S. Comparative analysis of the oil and su- percritical CO2 extract of Artemisia arborescens L. and Helichrysum splen- didum (Thunb.) Less. Natural Product Research. 2006; 20(5): 421–428.
Pappas R., Sheppard-Hanger S. Artemisia arborescens — essential oil of the Pacific Northwest: a high-chamazulene, low-thujone essential oil with potential skin- care applications. Aromather. J. 2000; 10: 30–33.
Janackovic P., Novaković J., Soković M. et al. Composition and antimicrobial activity of essential oils of Artemisia judaica, A. herba-alba and A. arborescens from Libya. Archives of Biological Sciences. 2015; 67: 455– 466.
Bouzenna H., & Krichen L. Pelargonium graveolens L’Her. and Artemisia ar- borescens L. essential oils: Chemical composition, antifungal activity against Rhi- zoctonia solani and insecticidal activity against Rhysopertha dominica. Natural Product Research. 2012. 27(9): 841–846.
Abderrahim A., Belhamel K., Chalcat J. C., Figuérédo G. Chemical composi- tion of the essential oil from Artemisia arborescens L. growing wild in Algeria. Rec- ords of Natural Products. 2010; 4: 87–90.
K. Younes S. Merghache N. Djabou D. et al. Chemical composition, antibacte- rial and antioxydant activitiées of a new essential oil chemotype of algerian Artemesia arborescens L. Afr J Pharm Pharmaco. 2012; 6(42): 2912–2921.
Janackovic P.; Rajcevic N. Gavrilovic M et al. Essential oil composition of five Artemisia (Compositae) species in regards to chemophenetics. Biochem. Syst. Ecol. 2019; 87: 103960.
Riahi L., Chograni H., Masmoudi A. S., & Cherif A. Genetic resources of Tu- nisian Artemisia arborescens L. (Asteraceae), pattern of volatile metabolites concentra- tion and bioactivity and implication for conservation. Biochemical Systematics and Ecology. 2019; 87: 103952.
Riahi L., Chograni H., Ben Rejeb F. et al. Efficient in vitro regeneration of the endangered species Artemisia arborescens L. through direct organogenesis and impact on secondary metabolites production. Hortic. Environ. Biotechnol. 2022; 63: 439–450.
Politeo O., Cajic I., Simic A. et al. Comparative Study of Chemical Composi- tion and Cholinesterase Inhibition Potential of Essential Oils Isolated from Artemisia Plants from Croatia. Separations. 2023; 10: 546.
Plescia F., Venturella F., Lauricella M. et al. Chemical composition, cytotoxic effects, antimicrobial and antibiofilm activity of Artemisia arborescens (Vaill.)
growing wild in the province of Agrigento, Sicily, Italy. Plant Biosystems - An In- ternational Journal Dealing with All Aspects of Plant Biology. 2022. 156(6): 1336– 1345.
Costa R., Ragusa S., Russo M. et al. Phytochemical screening of Artemisia ar- borescens L. by means of advanced chromatographic techniques for identification of health-promoting compounds. J Pharm Biomed Anal. 2016. Jan 5; 117: 499–509.
Соктоева Т. Э. Фармакогностическое исследование Artemisia annua L. и Artemisia sieversiana Willd. флоры Бурятии: диссертация на соискание ученой степени кандидата фармацевтических наук. Улан-Удэ, 2011. 172 с. Текст: непо- средственный.
Сравнительный анализ состава эфирных масел, полученных гидродистилляцией, и эфирномасличной фракции СО₂-экстракта Artemisia sieversiana Willd. и Artemisia annua L. / Т. Э. Рандалова, Г. Л. Рыжова, К. А. Дычко [и др.] // Химия растительного сырья. 2014. № 4. С. 61–64. Текст: непосредственный.
Рэнцэнбямбаа С. Фармакогностическая характеристика Artemisia adamsii Вess. и Artemisia macrocephala Jaque. ex Bess. флоры Бурятии и Монголии и раз- работка лекарственных средств на их основе: диссертация на соискание ученой степени кандидата фармацевтических наук. Улан-Удэ, 2020. 194 с. Текст: непо- средственный.
Дыленова Е. П. Фармакогностическая характеристика Artemisia frigida Willd. и Artemisia jacutica Drob. и разработка лекарственных средств на их основе: диссертация на соискание ученой степени кандидата фармацевтических наук. Улан-Удэ, 2019. 226 с. Текст: непосредственный.
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