Ecdysteroids of the root bark of Vitex canescens

Suksamrarn, Apichart; Promrangsan, Nart; Chitkul, Bordin; Homvisasevongsa, Sureeporn; Sirikate, Achara

doi:10.1016/s0031-9422(97)00102-7

Cited by 17 publications

(12 citation statements)

References 13 publications

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“…-An extensive literature search was undertaken to identify studies on ecdysteroids in works such as periodicals, data banks such as NAPRALERT (Natural Products Alert) and that at the University of Illinois, Chicago, Chemical (24) [ 2 ] 24-Epimakisterone A (8) [ 8 ] Calonysterone (9) [8] [10] Turkesterone (2) [ 8 ] [ 9 ] 24-Epiabutasterone (11) [ 8 ] Shidasterone (5) [ 8 ] 20,26-Dihydroxyecdysone (19) [11] (24R )-11a,20,24-Trihydroxyecdysone (17) [12] 11a,20,26-Trihydroxyecdysone (15) [12] Canescensterone (4) [ (13) [24] Calonysterone (9) [24] Pterosterone (22) [24] 24-Epimakisterone A (8) [24] 20-Hydroxyecdysone (1) [24] Polypodine B (23) [24] Ajugasterone C (6) [24] Pinnatasterone (3)…”

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confidence: 99%

Ecdysteroids from Vitex Species: Distribution and Compilation of Their ¹³C‐NMR Spectral Data

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Duringer

Maia

et al. 2008

Chemistry & Biodiversity

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Iridoids and ecdysteroids are found in some genera of the family Verbenaceae. In such cases, they are used as chemotaxonomic markers for the difficult task of taxonomic identification by using morphological characteristics of plants belonging to this family. The present work describes the distribution of ecdysteroids in plants from the genus Vitex from a review of previous work on seventeen Vitex species. In addition, (13)C-NMR data of the main ecdysteroids found in this genus are described. This study attempted to summarize previous research on ecdysteroids distribution in Vitex species with the addition of (13)C-NMR analysis to further refine the characterization of these compounds in the Verbenaceae family.

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confidence: 99%

Ecdysteroids from Vitex Species: Distribution and Compilation of Their ¹³C‐NMR Spectral Data

Filho

Duringer

Maia

et al. 2008

Chemistry & Biodiversity

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“…2) proved the presence of OR (R≠H) and a five-membered ring unit in the side chain [19]. Further support of this structure was achieved from the comparison of its spectral data with those of shidasterone [16,18] Assuming the structure of compound 2, the methyl doublet could possibly exist at C-21, implying 20-deoxyshidasterone. C-11 has been observed to be a biosynthetically labile hydroxylation point in ecdysteroids [19][20][21], with cyclisation of the side chain to the tetrahydrofuran; attachment of a hydroxyl group at C-11 was the other possible difference between the two compounds.…”

Section: Resultsmentioning

confidence: 89%

“…In the course of this study, the entire partitioned fractions from the methanol extracts of V. doniana stem bark exhibited comparable reduction in carrageenan-induced paw oedema formation in rats, suggesting similar bioactive components in the fractions. As an effort to identify the bioactive substances, chromatographic separation and purifications resulted in the isolation of three new ecdysteroids, 21hydroxyshidasterone (1), 11-hydroxy-20-deoxyshidasterone (2), and 2,3-acetonide-24-hydroxyecdysone (3) together with four known ecdysteroids identified as shidasterone (4) [16], ajugasterone C (5) [1], 24-hydroxyecdysone (6) [17], and 11β,24-dihydroxyecdysone (7) [1] based on their spectral data (MS and NMR) that corresponded to the previously published data (l " Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Phytoecdysteroids from the Stem Bark of Vitex doniana and Their Anti-Inflammatory Effects

et al. 2012

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A number of Vitex species have been investigated as a source of potential bioactive compounds such as ecdysteroids [1], diterpenoids [2], iridoids [3], flavonoids, and phenolic compounds [4] demonstrating antioxidant, anti-inflammatory, antimicrobial, hepatoprotective, analgesic, antihistaminic, anti-implantation, and antiasthmatic activities [5,6]. Generally, ecdysteroids and iridoids have been explored as chemotaxonomic markers for the plants in the family Lamiaceae including Vitex species [7]. Vitex doniana Sweet (Lamiaceae) is a small to medium sized tree growing up to 25 m tall with no phytochemical report in spite of the available ethnopharmacological significance among different African communities [8], including use of water decoctions of different parts for treatment of stomach and rheumatic pains as well as inflammatory disorders [9,10]. Antidepressant effects and potentiation of sodium thiopental sleeping time, muscle relaxant [11], anti-inflammatory, and analgesic activities [8] of V. doniana leaf extracts have been reported as well as antihypertensive effects on normative and hypertensive rats, trypanocidal and antidiarrheal activities of the stem bark [12]. Recent indication of anti-inflammatory, anticonvulsant, and antipyretic properties of ethanol extracts [13] of V. doniana stem bark prompted a phytochemical analysis of the plantʼs stem bark for potential anti-inflammatory compounds. As a result of this study, isolation of three new phytoecdysteroids [21-hydroxyshidasterone (1), 11β-hydroxy-20-deoxyshidasterone (2), and 2,3-acetonide-24-hydroxyecdysone (3)] and four known phytoecdysteroids [shidasterone (4), ajugasterone C (5), 24-hydroxyecdysone (6), and 11β,24-dihydroxyecdysone (7)] with comparable anti-inflammatory activities as diclofenac are reported. Abstract !With reference to the ethnopharmacological significance of Vitex doniana Sweet (Lamiaceae) leaves in the treatment of stomach and rheumatic pains as well as inflammatory disorders, biological studies on its stem bark extracts have also reported anti-inflammatory and analgesic activities, with no attempt to identify the active components. Chromatographic and spectroscopic procedures identified three new phytoecdysteroids: 21-hydroxyshidasterone (1), 11β-hydroxy-20-deoxyshidasterone (2), and 2,3-acetonide-24-hydroxyecdysone (3) from the stem bark methanol extracts along with known ecdysteroids shidasterone (4), ajugasterone C (5), 24-hydroxyecdysone (6), and 11β,24-hydroxyecdysone (7). The compounds (1-7) showed significant (p ≤ 0.05) inhibitory effect at 100 mg/kg dose on rat paw oedema development due to carrageenan-induced inflammation in Sprague Dawley rats. These results suggest a possible contribution of ecdysteroids to the anti-inflammatory effect of some V. doniana stem bark extracts. Abbreviations

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“…102 Finally, 24-epiabutasterone 41 was isolated from the root bark of Vitex canescens (Verbenaceae), along with five known ecdysteroids. 103 …”

Section: Phytoecdysteroidsmentioning

confidence: 99%

Recent advances in chemical ecology

Harborne¹

1999

Nat. Prod. Rep.

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Ecdysteroids of the root bark of Vitex canescens

Cited by 17 publications

References 13 publications

Ecdysteroids from Vitex Species: Distribution and Compilation of Their ¹³C‐NMR Spectral Data

Ecdysteroids from Vitex Species: Distribution and Compilation of Their ¹³C‐NMR Spectral Data

Phytoecdysteroids from the Stem Bark of Vitex doniana and Their Anti-Inflammatory Effects

Recent advances in chemical ecology

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Ecdysteroids of the root bark of Vitex canescens

Cited by 17 publications

References 13 publications

Ecdysteroids from Vitex Species: Distribution and Compilation of Their 13C‐NMR Spectral Data

Ecdysteroids from Vitex Species: Distribution and Compilation of Their 13C‐NMR Spectral Data

Phytoecdysteroids from the Stem Bark of Vitex doniana and Their Anti-Inflammatory Effects

Recent advances in chemical ecology

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Ecdysteroids from Vitex Species: Distribution and Compilation of Their ¹³C‐NMR Spectral Data

Ecdysteroids from Vitex Species: Distribution and Compilation of Their ¹³C‐NMR Spectral Data