Structure of ajugasterone C, a phytoecdysone with an 11-hydroxy-group

Imai, Sachihiko; Murata, E.; Fujioka, S.; Koreeda, Masato; Nakanishi, Koji

doi:10.1039/c29690000546

Cited by 40 publications

(10 citation statements)

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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 ).…”

Section: Resultsmentioning

confidence: 99%

“…The natural occurrence of 11α-hydroxy ecdysteroids in certain plant species (especially Ajuga spp. ; Imai et al, 1969 ; Canonica et al, 1973 ; Usmanov et al, 1975 ), provides precursors for the generation of 7,9(11)-dien-6-ones by dehydration ( Canonica et al, 1977 ; Qui and Nie, 1983 ). Here we report the simple synthesis in good yield of ecdysteroid 7,9(11)-dien-6-ones from the corresponding 11α-hydroxy ecdysteroid, demonstrate that the dienones retain high biological activity and provide indirect evidence that they are capable of covalently linking to ecdysteroid receptors in high yield on irradiation with long wavelength UV light (300 or 350 nm).…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

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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“…Spectroscopic analysis allowed us to readily identify compound 5 as the widespread ecdysterone; whereas sterol 6 was ajugasterone C, a rather uncommon ecdysone steroid first isolated from the leaves of Ajuga japonica in 1969. It was identified by comparison of its spectral properties with those reported in the literature.…”

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confidence: 99%

Novel Bromopyrrole Alkaloids from the Sponge Agelas dispar

1998

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Further investigation of the Caribbean marine sponge Agelas dispar for biologically active constituents has led to the isolation of the novel bromopyrrole alkaloids longamide B (1), and clathramides C (2) and D (3), whose structures have been determined by spectroscopic methods. Isolation of the known keramadine (4) and of the ecdysonic sterols ecdysterone (5) and ajugasterone C (6) is also reported. The antimicrobial activities of the isolated bromopyrrole alkaloids is summarized.

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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).…”

Section: Resultsmentioning

confidence: 99%

“…The natural occurrence of 11α-hydroxy ecdysteroids in certain plant species (especially Ajuga spp. ; Imai et al, 1969; Canonica et al, 1973; Usmanov et al, 1975), provides precursors for the generation of 7,9(11)-dien-6-ones by dehydration (Canonica et al, 1977; Qui and Nie, 1983). Here we report the simple synthesis in good yield of ecdysteroid 7,9(11)-dien-6-ones from the corresponding 11α-hydroxy ecdysteroid, demonstrate that the dienones retain high biological activity and provide indirect evidence that they are capable of covalently linking to ecdysteroid receptors in high yield on irradiation with long wavelength UV light (300 or 350 nm).…”

Section: Introductionmentioning

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

Structure of ajugasterone C, a phytoecdysone with an 11-hydroxy-group

Cited by 40 publications

References 0 publications

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

Novel Bromopyrrole Alkaloids from the Sponge Agelas dispar

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

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