Additional minor ecdysteroid components of Leuzea carthamoides

Budêšínský, Miloś; Vokáč, Karel; Harmatha, Juraj; Cvačka, Josef

doi:10.1016/j.steroids.2007.12.021

Cited by 50 publications

(26 citation statements)

References 31 publications

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“…The EtOAc-and nBuOH-soluble fractions were subjected to repeated column chromatography over silica gel and ODS, followed by preparative HPLC, and afforded five new compounds (1)(2)(3)(4)(5) along with the known phytoecdysteroids, ponasteroside A (6) (Takemoto et al, 1968;Fang et al, 2008), ponasterone A (7) (Nakanishi et al, 1966;Vokáč et al, 1998), and 20-hydroxyecdysone (8) (Vokáč et al, 1998;Buděšínský et al, 2008). The structures of known compounds were determined by interpretation of their spectroscopic data as well as by comparison with reported data.…”

Section: Resultsmentioning

confidence: 99%

Phytoecdysteroids from the rhizomes of Brainea insignis

Xie

Tao

et al. 2010

Phytochemistry

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Section: Resultsmentioning

confidence: 99%

Phytoecdysteroids from the rhizomes of Brainea insignis

Xie

Tao

et al. 2010

Phytochemistry

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“…For example, large scale isolation of ecdysteroids from 1000 kg of Leuzea carthamoides yielded 1 kg of pure 20E, while further chromatographic purification of a selected crude fraction (still containing ca. 30% of 20E) gave minor compounds in 4–125 mg amounts5. Accordingly, it is not surprising that 20E is by far the most deeply studied ecdysteroid, and much less is known about the (supposedly, but not necessarily similar) bioactivities and safety of its less widespread derivatives.…”

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Ecdysteroid-containing food supplements from Cyanotis arachnoidea on the European market: evidence for spinach product counterfeiting

Hunyadi

Herke

Lengyel

et al. 2016

Sci Rep

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Phytoecdysteroids like 20-hydroxyecdysone (“ecdysterone”) can exert a mild, non-hormonal anabolic/adaptogenic activity in mammals, and as such, are frequently used in food supplements. Spinach is well-known for its relatively low ecdysteroid content. Cyanotis arachnoidea, a plant native in China, is among the richest sources of phytoecdysteroids, and extracts of this plant are marketed in tons per year amounts via the internet at highly competitive prices. Here we report the investigation of a series of food supplements produced in Germany and claimed to contain spinach extracts. Twelve ecdysteroids including two new compounds were isolated and utilized as marker compounds. A comparative analysis of the products with Cyanotis and spinach extracts provides evidence that they were manufactured from Cyanotis extracts instead of spinach as stated. Based on the chromatographic fingerprints, 20-hydroxyecdysone 2- and 3-acetate are suggested as diagnostic markers for related quality control. This case appears to represent an unusual type of dietary supplement counterfeiting: undeclared extracts from alternative plants would supposedly ‘guarantee’ product efficacy.

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“…This extract was successively subjected to Diaion HP20, silica gel, and Chromatorex octadecyl silica (ODS) column chromatography as well as HPLC using ODS to yield 13 compounds (1-13).Compounds 5-13 were identified as reptoside (5), 12) harpagide (6), 12) 6-epi-acetyl harpagide (7), 13) acetyl harpagide (8), 12) ajugaside A (9), 15) ajugalactone (11), 9) 20-hydroxyecdysone (12), 16) and 20-hydroxyecdysone 3-acetate (13), 16) respectively, based on their physical and spectral data ( Fig. 1).…”

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“…Compounds 5-13 were identified as reptoside (5), 12) harpagide (6), 12) 6-epi-acetyl harpagide (7), 13) acetyl harpagide (8), 12) ajugaside A (9), 14) 1-octen-3-ol 3-O-glucopyranosyl-(1→2)-[O-arabinopyranosyl-(1→6)]-glucopyranoside (10), 15) ajugalactone (11), 9) 20-hydroxyecdysone (12), 16) and 20-hydroxyecdysone 3-acetate (13), 16) respectively, based on their physical and spectral data (Fig. 1).…”

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confidence: 99%

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Four New Iridoid Glucosides from Ajuga reptans

Ono

Furusawa

Ozono

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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NoteAjuga reptans L. (Labiatae) is native to Europe, and has been used as a traditional vulnerary.1) This plant has been reported to contain iridoids, 1,2) diterpenoids, [3][4][5][6][7] ecdysteroids, [8][9][10] and anthocyanins.11) The present paper describes the isolation and structural elucidation of four new iridoid glucosides (1-4) along with four known iridoid glucosides (5-8), one known diterpenoid glycoside (9), one known aliphatic alcohol glycoside (10), and three known ecdysteroids (11-13), as well as the antioxidative activities of 9.Dried whole plants of A. reptans were extracted with methanol (MeOH). This extract was successively subjected to Diaion HP20, silica gel, and Chromatorex octadecyl silica (ODS) column chromatography as well as HPLC using ODS to yield 13 compounds (1-13).Compounds 5-13 were identified as reptoside (5), 12) harpagide (6), 12) 6-epi-acetyl harpagide (7), 13) acetyl harpagide (8), 12) ajugaside A (9), 15) ajugalactone (11), 9) 20-hydroxyecdysone (12), 16) and 20-hydroxyecdysone 3-acetate (13), 16) respectively, based on their physical and spectral data ( Fig. 1).Compound 1, tentatively named ajureptaside A, was obtained as a syrup, and exhibited an [MϩNa] ϩ ion peak at m/z 477 in the positive-ion FAB-MS. (d 99.9, 74.6, 78.0, 71.8, 77.8, 63.0). These 1 H-and 13 C-NMR signals (Tables 1 and 2, respectively) were assigned with the aid of 1 H-1 H correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond correlation (HMBC) spectra. The planar structure of 1, which was an iridoid glucopyranoside whose aglycone moiety (Agl) possessed three hydroxyl groups at C-4, C-5, and C-6, one methoxy group at C-3, and one acetoxy group at C-8, could be determined as illustrated in Fig. 2. The relative configurations at C-1, C-3, C-4, C-5, C-6, C-8, and C-9 of Agl were concluded to be S*, R*, R*, S*, R*, S*, and S*, respectively, on the basis of the nuclear Overhauser and exchange spectroscopy (NOESY) spectrum, in which key correlations were observed between H-1 of Agl and H 3 -10 of Agl; H-4 of Agl and H-6 of Agl; and H-4 of Agl and H 3 -10 of Agl, as shown in Fig. 3, and by analysis of the coupling constants (J H-1-H-9 0 Hz; J H-3-H-4 8.0 Hz) between H-1 and H-9; and H-3 and H-4 in the 1 H-NMR spectrum. Acidic hydrolysis of 1 gave D-glucose, which was confirmed by optical rotation using chiral detection in HPLC analysis, and the coupling constant of the signal due to the anomeric proton [d 4.73 (d, Jϭ8.0 Hz)] indicated the mode of glycosidic linkage of the glucopyranosyl group to be b. Consequently, the structure of 1 was concluded to be 8-Oacetyl-4b-hydroxy-3a-methoxy-dihydroharpagide. Four new iridoid glucosides were isolated from the whole plant of Ajuga reptans L. (Labiatae) along with four known iridoid glucosides, one known diterpenoid glycoside, one known aliphatic alcohol glycoside, and three known ecdysteroids. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence. The diterpenoid gl...

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Additional minor ecdysteroid components of Leuzea carthamoides

Cited by 50 publications

References 31 publications

Phytoecdysteroids from the rhizomes of Brainea insignis

Phytoecdysteroids from the rhizomes of Brainea insignis

Ecdysteroid-containing food supplements from Cyanotis arachnoidea on the European market: evidence for spinach product counterfeiting

Four New Iridoid Glucosides from Ajuga reptans

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