Distribution of phytoecdysteroids in plants of Uzbekistan and the possibility of using drugs based on them in neurological practice

Saatov, Z.; Agzamkhodzhaeva, D. A.; Сыров, В. Н.

doi:10.1007/bf02234932

Cited by 18 publications

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“…Additional functionalities included the signal of an olefinic proton at d 6.21 (br s) as well as nine methine protons and seven methylene groups and an acetyl methyl group also supported the basic skeleton of phytoecdysteroid. As shown in Table 1 the 1 H-and 13 C-NMR spectra for compound 1 showed a high analogy with those of 22-acetylcasterone with a cis fused A/B ring junction and 14a-hydroxy-7-ene-6-one skeleton 19) Results of two-dimensional correlation spectroscopy (2D-COSY) and the long-range 13 C-1 H correlation in heteronuclear multiple bond correlation (HMBC) experiments also confirmed that the planar structure of 1 was the same as 22-acetylcasterone (2). But the differences in the chemical shifts and the multiplicities of A-ring protons suggesting that the new compound might be one epimer at C-2 and/or C-3.…”

Section: Resultsmentioning

confidence: 81%

“…The known compounds, 22-acetylcasterone (2), 19) A new phytoecdysteroid, namely ajugalide-E (1), together with twenty five known compounds were isolated from Ajuga taiwanensis collected from Tainan, Taiwan. Their structures were determined by spectral analysis including high resolution one-and two-dimensional NMR spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

“…The known compounds, 22-acetylcasterone (2), 19) ajugalactone (3), 20) cyasterone (4), 21) isocyasterone (5), 21) ajugamacrin B (6), 22) ajugapantin A (7), 23) ajugamarin C1 (8), 15) ajugalide-A (9), 24) -B (10), 24) -C (11), 24) -D (12), 24) pheophytin-a (13), 25) 14) harpagide (18), 26) galiridoside (19), 14) teuhircoside (20), 27) b-sitosterol (21), 28) stigmasterol (22), 28) b-sitosteryl-D-glucoside (23), 28) vanillic acid (24), 28) kaempferol (25) 29) and nicotinic acid (26) 30) were also isolated from Ajuga taiwanensis. Their structures were identified by comparison of their spectroscopic data (UV, IR, NMR and mass spectrometry) with values in the literature.…”

Section: Resultsmentioning

confidence: 99%

“…The NOEs between H-2 and H-5 and between H-3 and H-9 showed the hydroxyl groups at C-2 and C-3 to be quasiequatorial, respectively, with trans geometry. On the basis of these results, the structure of ajugalide-E was elucidated as 1.The known compounds, 22-acetylcasterone (2), 19) A new phytoecdysteroid, namely ajugalide-E (1), together with twenty five known compounds were isolated from Ajuga taiwanensis collected from Tainan, Taiwan. Their structures were determined by spectral analysis including high resolution one-and two-dimensional NMR spectroscopy.…”

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A New Phytoecdysteroid from Ajuga taiwanensis

Chan

Kuoh

et al. 2005

Chem. Pharm. Bull.

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Many plants contain ecdysteroids, polyhydroxysteroids with a cis-fused A/B ring junction and 14a-hydroxy-7-ene-6-one system, structurally related with ecdysone, the biosynthetic precursor of the insect moulting hormone.1) These compounds exhibit interesting physiological activities such as regulation of moulting in insects, hormonal functions involve regeneration, metamorphosis, reproduction and differentiation in all arthropods, and antiulcer, antirheumatic, insulin regulation and diuretic or tonic effects in mammals. 2)Among the numerous plants containing phytoecdysteroids, those pertaining to Ajuga genus are unique for the great variety of such compounds produced.3) Species belonging to genus Ajuga have been used as folk medicinal plants as anthelmintic against intestinal disorders, antifungal, hypoglycaemic, antitumor and antimicrobial agents. 4,5) Furthermore, it has also been reported that some species of this genus were especially used as diuretic agents, as a remedy for fever, toothache, dysentery and hypertension. 6) Earlier chemical investigations have led to the isolation of clerodane diterpenoids, 7-9) ecdysteroids, 3,5,10,11) flavonoids, 12) iridoids [13][14][15] and triglycerides.16) The compounds isolated from the genus Ajuga, exert a broad spectrum of biological and pharmacological actions such as cytotoxic, anti-mitotic, anti-bacterial, cardiotonic, vasorelaxing, antifungal and antifeedant and insect growth-inhibitions. These facts encouraged us to investigate the chemical constituents of an Ajuga species A. taiwanensis NAKAI ex MURATA (Labiatae) mainly distributed in the Taiwan, Philippines and Ryukyus which has been often used for the treatment of hepatitis and hepatoma in Taiwanese folk medicine.17) The isolation of ajugalide A to D from title plant has recently been reported from our laboratories. In this paper, we now describe the isolation and structural elucidation of one new phytoecdysteroid, ajugalide-E (1) and twenty five known compounds. Results and DiscussionAjugalide-E (1) was isolated as an optically active, white amorphous solid, mp 210-212°C. The high-resolution fastatom bombardment mass spectrum (HR-FAB-MS) of 1 showed a pseudo molecular ion peak ([MϩH] . These data were consistent with the occurrence of characteristic side chain with g-lactone by similitude with 22-acetylcasterone signals. Additional functionalities included the signal of an olefinic proton at d 6.21 (br s) as well as nine methine protons and seven methylene groups and an acetyl methyl group also supported the basic skeleton of phytoecdysteroid. As shown in Table 1 the 1 H-and 13 C-NMR spectra for compound 1 showed a high analogy with those of 22-acetylcasterone with a cis fused A/B ring junction and 14a-hydroxy-7-ene-6-one skeleton 19) Results of two-dimensional correlation spectroscopy (2D-COSY) and the long-range 13 C-1 H correlation in heteronuclear multiple bond correlation (HMBC) experiments also confirmed that the planar structure of 1 was the same as 22-acetylcasterone (2). But the differences in...

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Section: Resultsmentioning

confidence: 81%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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A New Phytoecdysteroid from Ajuga taiwanensis

Chan

Kuoh

et al. 2005

Chem. Pharm. Bull.

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“…Ecdysteroids have also been found in some species of the genera Dianthus and Melandrium [1,2]. To the best of our knowledge, there are no data on ecdysteroids produced by the genus Comastoma tenella Rottb.…”

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confidence: 99%

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Berkenov

2017

IJGP

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АbstractAim: Design a new pharmaceutical technology for isolation novel ecdysteroid 3α,14α,22R, 25-tetrahydroxy-5α (Н)-cholest-7-en-6-one from the epigeal organs of ComastomatenellaRottb. Research NMR spectrscopy and biological activity. Material and Methods: The isolation procedure involved extraction with aqueous ethanol, partitioning(petroleum ether-ethyl acetate) of the obtained extract to remove non-polar impurities, extraction of the water layer with isobutyl alcohol, and subsequent purification by aluminum oxide column chromatography. According to NMR spectroscopy, mass spectrometry, and microanalysis, the structure of 3α,14α,22R,25-tetrahydroxy-5α(Н)-cholest-7-en-6-one (1). Results and Discussion: During the study of plants ComastomatenellaRottb was isolated new phytoecdysteroid.According to NMR spectroscopy, mass spectrometry, and microanalysis, the structure of 3α,14α,22R,25-tetrahydroxy-5α(Н)-cholest-7-en-6-one.Isolated object was examined for anti-inflammatory activity of the compound.Thus, the present study established high anti-inflammatory activity of 3α,14α,22R,25-tetrahydroxy-5α(Н)-cholest-7-en-6-one1 in the dose of 50 mg/kg in an experimental model of an acute exudative reaction. Conclusion: From the results of the study on the anti-inflammatory activity, it became clear that object potently and significantly reduced the number of abdominal writhings as compared to the control animals.

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The phytoecdysteroid profiles of 7 species of Silene (Caryophyllaceae)

Zibareva

Yeriomina

Munkhjargal

et al. 2009

Arch Insect Biochem Physiol

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The phytoecdysteroid profiles of extracts of aerial parts of flowering plants of 7 ecdysteroid-containing species in the genus Silene (Caryophyllaceae; S. fridvaldszkyana Hampe, S. gigantea L., S. graminifolia Otth, S. mellifera Boiss. & Reuter, S. repens Patr., S. schmuckeri Wettst., and S. sendtneri Boiss.) have been examined and identified by HPLC and, in the case of two new compounds, by mass spectrometry and NMR. S. frivaldszkyana was found to contain predominantly 20-hydroxyecdysone (20E), with smaller amounts of 2-deoxyecdysone (2dE), 2-deoxy-20-hydroxyecdysone (2d20E), polypodine B (polB), integristerone A (IntA), 26-hydroxypolypodine B (26polB), and 20,26-dihydroxyecdysone (20,26E). Additionally, a new minor ecdysteroid, 26-hydroxyintegristerone A, has been identified from this species. S. gigantea contains 3 major ecdysteroids (2dE, 2d20E, and 20E) and much smaller amounts of intA and 2-deoxy-20-hydroxyecdysone 25-beta-D-glucoside, which is a new ecdysteroid. Ecdysteroids in the other 5 species have been identified by co-chromatography with reference compounds on RP- and NP-HPLC systems. There is considerable variability with regard to ecdysteroid profiles within the genus Silene. The chemotaxonomic value of ecdysteroid profiles within the genus Silene is discussed.

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Distribution of phytoecdysteroids in plants of Uzbekistan and the possibility of using drugs based on them in neurological practice

Cited by 18 publications

References 0 publications

A New Phytoecdysteroid from Ajuga taiwanensis

A New Phytoecdysteroid from Ajuga taiwanensis

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The phytoecdysteroid profiles of 7 species of Silene (Caryophyllaceae)

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