Sesquiterpene lactones ofArtemisia pauciflora

Адекенов, С. М.; Кагарлицкий, А. Д.; Mukhametzhanov, M. N.; Kupriyanov, A. N.

doi:10.1007/bf00580577

Cited by 1 publication

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“…A similar shift in the lactone proton signal was also observed in the presence of a 1,10-epoxy ring in the guaianolide molecule, as in the case of arglabin, arborescine [ 2 ].…”

Section: Resultsmentioning

confidence: 57%

“…It is known that in the structure of most biologically active natural sesquiterpene γ-lactones, one of the characteristic functional groups is the epoxy group [ 2 ]. It is believed that the presence of this group affects the biological activity of the molecules of the compounds of this series.…”

Section: Resultsmentioning

confidence: 99%

“…Guaianolides constitute one of the largest and most widespread groups of natural sesquiterpene γ-lactones of plant origin. Most of them have pronounced biological activity [ 1 , 2 , 3 ]. Among the most accessible and promising sesquiterpene lactones of the guaiane type, estafiatin 1 has attracted attention ( Figure 1 ) and was first isolated from Artemisia mexicana Willd.…”

Section: Introductionmentioning

confidence: 99%

“…According to the literature data [ 2 , 4 , 15 ], it is known that a number of chemical transformations were carried out with the estafiatin molecule 1 : ozonolysis, catalytic hydrogenation, epoxidation, selective hydrogenation of the C11–C13 double bond, and nucleophilic addition according to the Michael reaction type. It was established that the course of the reactions mainly depends on the structural features of the given guaianolide molecule, i.e., with the presence of an exomethylene group conjugated with the carbonyl of γ-lactone, an exomethylene double bond at position C10=C14, an epoxy group.…”

Section: Introductionmentioning

confidence: 99%

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Syntheses Based on 3,4α-Epoxy-1,5,7α,6β(H)-guai-10(14),11(13)-dien-6,12-olide

Адекенов¹

2022

Molecules

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The sesquiterpene γ-lactone estafiatin 1, the molecule of which has a structure of 3,4α-epoxy-1,5,7α,6β(H)-guai-10(14),11(13)-dien-6,12-olide, is characteristic of plants of the genera Achillea L. and Artemisia L. of the Asteraceae family. This article presents the results of chemical modification for three reaction centers of the estafiatin molecule 1: epoxy cycle, exomethylene group conjugated with γ-lactone carbonyl, and exomethylene group in position С10=С14; and at the same time 33 new derivatives were synthesized, the structures of which were established based on physicochemical constants, spectral data (IR-, PMR-, 13C-NMR), and X-ray diffraction analysis. The stereo- and regiospecificity, as well as the chemoselectivity of the reaction based on estafiatin molecule 1, are discussed. The reactivity of the substrate is significantly influenced by the stereochemistry of its molecule, the nature of the reagent, and the reaction medium. Based on the results of in silico screening, derivatives of estafiatin with high binding energies for both DNA-topoisomerase I and DNA-topoisomerase II were identified. The values of the inhibitory dose of IC50 for estafiatin 1 and its derivatives were determined on cell lines of eight types of tumors. In vivo experiments of the samples made it possible to establish that estafiatin 1 and its derivatives have pronounced antitumor activity against Pliss lymphosarcoma, Walker’s carcinosarcoma, sarcoma 45, sarcoma-180, alveolar liver cancer PC-1, leukemia P-388 and L-1210, and sarcoma-45 resistant to 5-fluorouracil.

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“…A similar shift in the lactone proton signal was also observed in the presence of a 1,10-epoxy ring in the guaianolide molecule, as in the case of arglabin, arborescine [ 2 ].…”

Section: Resultsmentioning

confidence: 57%

Section: Resultsmentioning

confidence: 99%