The minor ecdysteroids from <i>Ajuga turkestanica</i>

Guibout, Louis; Mamadalieva, Nilufar Z.; Balducci, Christine; Girault, Jean‐Pierre; Lafont, René

doi:10.1002/pca.2563

Cited by 28 publications

(19 citation statements)

References 27 publications

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“…Ajuga Linn., a member of the Labiatae family, comprises approximately 50 species that are primarily dispersed in temperate regions of Eurasia . Several Ajuga species have been employed to treat inflammation and infectious diseases. − Previous phytochemical investigations of this genus of plants resulted in the isolation of diterpenoids, − particularly neo -clerodane diterpenoids, steroids, ,− and iridoids, ,, which displayed extensive biological effects, − such as antibacterial, insect antifeedant, cytotoxic, and vasoconstrictor activities.…”

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confidence: 99%

Anti-inflammatory neo-Clerodane Diterpenoids from Ajuga pantantha

et al. 2020

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Eight new neo-clerodane diterpenoids (1–8) were acquired from the aerial parts of Ajuga pantantha. Spectroscopic data analysis permitted the definition of their structures, and experimental and calculated electronic circular dichroism data were used to define their absolute configurations. Compounds 2 and 4–8 were found to have NO inhibitory effects with IC50 values of 20.2, 45.5, 34.0, 27.0, 45.0, and 25.8 μM, respectively. The more potent compounds 2, 6, and 8 were analyzed to establish their anti-inflammatory mechanism, including regulation of the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins as well as their binding interactions with the two proteins.

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confidence: 99%

Anti-inflammatory neo-Clerodane Diterpenoids from Ajuga pantantha

et al. 2020

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“…It seems that the optimal method for ecdysteroid analysis should involve multidimensional and multistage separation (by HPLC or UPLC) due to enhanced efficiency and resolution of such approach . In addition, application of gradient elution in 2D‐HPLC mode improves separation of ecdysteroid‐rich extracts due to higher efficiency and selectivity in comparison to isocratic elutions.…”

Section: Discussionmentioning

confidence: 99%

Chromatographic separation, determination and identification of ecdysteroids: Focus on Maral root (Rhaponticum carthamoides, Leuzea carthamoides)

Głazowska

Kamiński

2018

J of Separation Science

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The review presents general principles for choosing optimal conditions for ecdysteroid separation, identification, and isolation using HPLC/TLC techniques in RP, NP‐HILIC or NP modes. Analytics of ecdyteroids pose a still insufficiently resolved problem. Plant‐derived ecdysteroids are a point of interest of pharmaceutical industry and sport medicine due to their postulated adaptogenic and anabolic properties. In insects, ecdysteroids regulate larval transformation. Maral root (Rhaponticum carthamoides, Leuzea carthamoides), traditional Siberian folk‐medicine plant used as stimulant to boost overall health and fitness, is a particularly rich source of a wide variety of phytoecdysteroids. The similarity of molecular structures of ecdysteroids present in its extracts together with high content of unrelated compounds of similar chromatographic characteristics makes optimization of separation, identification and isolation of ecdysteroids a difficult analytical task. In that respect, two‐dimensional separations, two‐dimensional separations, 2D HPLC or 2D TLC, could be of use. For identification, the hyphenated techniques are particularly important. Thus, comprehensive overview of MS spectral parameters of ecdysteroids is provided. Described principles could easily be applied for separation of ecdysteroids in extracts from other sources. They are also useful for development of separation procedures for isolation of ecysteroids in preparative‐scale applications.

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“…These are 28- epi -cyasterone [(22 R ,24 S ,25 S ,28 S ) 5 β -stigmast-7-ene-26-oic acid, 2 β ,3 β ,14,20,22,28-hexahydroxy-6-oxo- γ -lactone] ( 152 ), isolated from Eriophyton wallchii 115 , ajugalide-E ( 153 ) from Ajuga taiwanensis 116 , breviflorasterone ( 154 ), ajugacetalsterone C ( 155 ), ajugacetalsterone D ( 156 ) from Ajuga macrosperma var. breviflora 117 , decumbesterone A ( 157 ) 118 and ajugacetalsterone E ( 158 ) 119 isolated from Ajuga decumbens , 22-dehydrocyasterone-2-glucoside ( 159 ), ajugacetalsterone A ( 160 ) and ajugacetalsterone B ( 161 ), isolated from Ajuga nipponensis 120 , 25-hydroxy-atrotosterone A ( 162 ), 11-hydroxy-cyasterone ( 163 ), 11-hydroxy-sidisterone ( 164 ), turkesterone 22-acetate ( 165 ), 22 oxo-turkesterone ( 166 ), 11-hydroxy-Δ24-capitasterone ( 167 ) and turkesterone 20,22-acetonide ( 168 ), isolated from Ajuga turkestanica 121 , reptanslactone A ( 169 ), reptanslactone B ( 170 ) and sendreisterone ( 171 ), isolated from Ajuga reptans var. reptans 122 , 21-hydroxyshidasterone ( 172 ), 11 β -hydroxy-20-deoxyshidasterone ( 173 ) and 2,3-acetonide-24-hydroxyecdysone ( 174 ), isolated from Vitex doniana 123 , 24- epi -pinnatasterone ( 175 ) 124 and scabrasterone ( 176 ) 124 , isolated from Vitex scabra , 26-hydroxypinnatasterone ( 177 ), isolated from Vitex cymosa 125 , (24 R )-11 α ,20,24-trihydroxyecdysone ( 178 ) 126 , and 11 α ,20,26-trihydroxyecdysone ( 179 ) 126 and 24-methylshidasterone ( 180 ) 127 , isolated from Vitex canescens .…”

Section: New Naturally Occurring Phytoecdysteroids Reported Since 1999mentioning

confidence: 99%

The phytochemical, biological, and medicinal attributes of phytoecdysteroids: An updated review

Das¹,

Mishra

Bishayee³

et al. 2021

Acta Pharmaceutica Sinica B

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The phytoecdysteroids (PEs) comprise a large group of biologically-active plant steroids, which have structures similar to those of insect-molting hormones. PEs are distributed in plants as secondary metabolites that offer protection against phytophagus (plant-eating) insects. When insects consume the plants containing these chemicals, they promptly molt and undergo metabolic destruction; the insects eventually die. Chemically, ecdysteroids are a group of polyhydroxylated ketosteroids that are structurally similar to androgens. The carbon skeleton of ecdysteroids is termed as cyclopentanoperhydro-phenanthrene with a β -side chain at carbon-17. The essential characteristics of ecdysteroids are a cis -(5 β -H) junction of rings A and B, a 7-en-6-one chromophore, and a trans -(14 α -OH) junction of rings C and D. Plants only synthesize PEs from mevalonic acid in the mevalonate pathway of the plant cell using acetyl-CoA as a precursor; the most common PE is 20-hydroxyecdysone. So far, over 400 PEs have been identified and reported, and a compilation of 166 PEs originating from 1998 has been previously reviewed. In the present review, we have summarized 212 new PEs reported between 1999 and 2019. We have also critically analyzed the biological, pharmacological, and medicinal properties of PEs to understand the full impact of these phytoconstituents in health and disease.

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The minor ecdysteroids from Ajuga turkestanica

Cited by 28 publications

References 27 publications

Anti-inflammatory neo-Clerodane Diterpenoids from Ajuga pantantha

Anti-inflammatory neo-Clerodane Diterpenoids from Ajuga pantantha

Chromatographic separation, determination and identification of ecdysteroids: Focus on Maral root (Rhaponticum carthamoides, Leuzea carthamoides)

The phytochemical, biological, and medicinal attributes of phytoecdysteroids: An updated review

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