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SM ISO690:2012 FULGA, Ala, GORINCIOI, Elena, BARBA, Alic, DRAGALIN, Ion, UNGUR, Nikon. Capitalization of the lavender wastes in solving tasks of ursolic acid chemistry. In: Ecological and environmental chemistry : - 2017, Ed. 6, 2-3 martie 2017, Chișinău. Chisinau, Republic of Moldova: Academy of Sciences of Moldova, 2017, Ediția 6, p. 157. |
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Ecological and environmental chemistry Ediția 6, 2017 |
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Conferința "Ecological and environmental chemistry 2017" 6, Chișinău, Moldova, 2-3 martie 2017 | ||||||
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Pag. 157-157 | ||||||
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Protection of the environment from toxic materials is an area of increasing concern. This communication describes some practical aspects of exploring the ursolic acid 1 chemistry, based on recycling the wastes of lavender Lavandula angustifolia Mill. The proposed by us sequence of synthetic manipulations solve the difficult and very important problem of separating ursolic acid 1 from its isomer – oleanolic acid 2. Both triterpenoids exhibit potent and very promising biological activities [1]. The environmentally preferable solvent, ethanol was employed for extracting the lavender straw by Soxhlet apparatus at room temperature. As a result, an inseparable mixture of ursolic 1 and oleanoic 2 acids was obtained. Then, the extracts were acetylated with acetic anhydride in pyridine and subsequently treated with diazomethane in ethyl ether. Composition of the obtained product was examined by GS-MS analysis that demonstrated the presence of 5 organic components in the reaction, from which compound 3 constituted 74.7 %, while its isomer, i.e. the corresponding ester of oleanolic acid constituted 23.5%. Further epoxidation of the product by the formate – hydrogen peroxide system lead to a mixture, from which ursolic derivative 3 was isolated in 58% yield. Further saponification with potassium hydroxide in ethanol finalized with a methoxy ester 4 in 61% yield. Ursolic acid 1 was obtained upon a subsequent saponification with potassium tert-butoxide in dimethylsulfoxide. Compounds 1, 3 and 4 were identified on the basis of their 1H and 13C NMR data. In conclusion, a convenient assay of isolation of the bioactive ursolic acid 1 by capitalizing the lavender wastes and developing of the environmentally friendly extraction with ethanol at room temperature was reported. The study is in progress of characterization of the fractions containing oleanane – type triterpenes. |
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