Ajugasterone C and 5-Deoxykaladasterone, an Ecdysteroid Artifact, from Leuzea carthamoides

Szendrei, K.; Varga, E.; Hajdú, Zoltán; Herke, Ibolya; Lafont, René; Girault, Jean‐Pierre

doi:10.1021/np50059a034

Cited by 17 publications

(10 citation statements)

References 3 publications

(6 reference statements)

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“…The plant is a rich source of phytoecdysteroids—a large class of steroid compounds [ 41 , 42 ]. Their structures are composed by 27–29 C-atoms, with a four-ring steroid skeleton [ 39 , 42 , 43 , 44 ] and contain polyhydroxyl groups (4–7 hydroxyl groups) [ 45 ]. Nowadays, more than 200 ecdysteroid compounds are described [ 41 , 46 ], 50 of which are isolated from Rhaponthicum carthamoides [ 13 ].…”

Section: Resultsmentioning

confidence: 99%

Comparison between the Biological Active Compounds in Plants with Adaptogenic Properties (Rhaponticum carthamoides, Lepidium meyenii, Eleutherococcus senticosus and Panax ginseng)

Todorova

Ivanov

Ivanova

2021

Plants

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Background: In the 1960s, research into plant adaptogens began. Plants with adaptogenic properties have rich phytochemical compositions and have been used by humanity since ancient times. However, it is not still clear whether the adaptogenic properties are because of specific compounds or because of the whole plant extracts. The aim of this review is to compare the bioactive compounds in the different parts of these plants. Methods: The search strategy was based on studies related to the isolation of bioactive compounds from Rhaponticum carthamoides, Lepidium meyenii, Eleutherococcus senticosus, and Panax ginseng. The Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA) guidelines were followed. Results: This review includes data from 259 articles. The phytochemicals isolated from Rhaponticum carthamoides, Lepidium meyenii, Eleutherococcus senticosus, and Panax ginseng were described and classified in several categories. Conclusions: Plant species have always played an important role in drug discovery because their effectiveness is based on the hundreds of years of experience with folk medicine in different nations. In our view, there is great potential in the near future for some of the phytochemicals found in these plants species to become pharmaceutical agents.

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Section: Resultsmentioning

confidence: 99%

Comparison between the Biological Active Compounds in Plants with Adaptogenic Properties (Rhaponticum carthamoides, Lepidium meyenii, Eleutherococcus senticosus and Panax ginseng)

Todorova

Ivanov

Ivanova

2021

Plants

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“…The three ecdysteroids used for the dehydration reaction ( 2 - 4 ) have all been isolated from plant sources ( Usmanov et al, 1975 ; Canonica et al, 1972 ; Imai et al, 1969 ), as have two of the intended dehydration products ( 5 [ Hou et al, 1982 ] and 6 [ Canonica et al, 1973 ]). Dacryhainansterone ( 5 ) has also been synthesised previously in a dehydration reaction from ajugasterone C ( Qui and Nie, 1983 ; Szendrei et al, 1988 ). Dehydration reactions were monitored by UV-spectrophotometry and a shift in the λ max from 242 nm to 300 nm indicated the formation of the conjugated dienone.…”

Section: Resultsmentioning

confidence: 99%

Ecdysteroid 7,9(11)-dien-6-ones as potential photoaffinity labels for ecdysteroid binding proteins

Bourne

Whiting

Dhadialla

et al. 2002

Journal of Insect Science

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Three ecdysteroid 7,9(11)-dien-7-ones (dacryhainansterone, 25-hydroxydacryhainansterone and kaladasterone) were prepared by dehydration of the corresponding 11a-hydroxy ecdysteroids (ajugasterone C, turkesterone and muristerone A, respectively). The biological activities of the dienones in the Drosophila melanogaster B II cell bioassay, which reflect the affinity for the ecdysteroid receptor complex, showed that the dienones retain high biological activity. Irradiation at 350 nm of the ecdysteroid dienones (100 nM) with bacterially-expressed dipteran and lepidopteran ecdysteroid receptor proteins (DmEcR/DmUSP or CfEcR/CfUSP), followed by loading with [ 3 H]ponasterone A revealed that irradiation of dacryhainansterone or kaladasterone resulted in blocking of >70% of the specific binding sites. Thus, ecdysteroid dienones show considerable potential as photoaffinity analogues for ecdysteroid binding proteins.

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“…Dacryhainansterone ( 5 ) has also been synthesised previously in a dehydration reaction from ajugasterone C (Qui and Nie, 1983; Szendrei et al, 1988). Dehydration reactions were monitored by UV-spectrophotometry and a shift in the λ max from 242 nm to 300 nm indicated the formation of the conjugated dienone.…”

Section: Resultsmentioning

confidence: 99%

Ecdysteroid 7,9(11)-dien-6-ones as potential photoaffinity labels for ecdysteroid binding proteins

Bourne

Whiting

Dhadialla

et al. 2002

Journal of Insect Science

View full text Add to dashboard Cite

Three ecdysteroid 7,9(11)-dien-7-ones (dacryhainansterone, 25-hydroxydacryhainansterone and kaladasterone) were prepared by dehydration of the corresponding 11a-hydroxy ecdysteroids (ajugasterone C, turkesterone and muristerone A, respectively). The biological activities of the dienones in the Drosophila melanogaster BII cell bioassay, which reflect the affinity for the ecdysteroid receptor complex, showed that the dienones retain high biological activity. Irradiation at 350 nm of the ecdysteroid dienones (100 nM) with bacterially-expressed dipteran and lepidopteran ecdysteroid receptor proteins (DmEcR/DmUSP or CfEcR/CfUSP), followed by loading with [3H]ponasterone A revealed that irradiation of dacryhainansterone or kaladasterone resulted in blocking of >70% of the specific binding sites. Thus, ecdysteroid dienones show considerable potential as photoaffinity analogues for ecdysteroid binding proteins.

show abstract

Ajugasterone C and 5-Deoxykaladasterone, an Ecdysteroid Artifact, from Leuzea carthamoides

Cited by 17 publications

References 3 publications

Comparison between the Biological Active Compounds in Plants with Adaptogenic Properties (Rhaponticum carthamoides, Lepidium meyenii, Eleutherococcus senticosus and Panax ginseng)

Comparison between the Biological Active Compounds in Plants with Adaptogenic Properties (Rhaponticum carthamoides, Lepidium meyenii, Eleutherococcus senticosus and Panax ginseng)

Ecdysteroid 7,9(11)-dien-6-ones as potential photoaffinity labels for ecdysteroid binding proteins

Ecdysteroid 7,9(11)-dien-6-ones as potential photoaffinity labels for ecdysteroid binding proteins

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