Rhapisterone D 20-acetate from the seeds ofLeuzea carthamoides

Borovikova, E. B.; Shangaraeva, G. S.; Baltaev, U. A.

doi:10.1007/bf02234931

Cited by 8 publications

(2 citation statements)

References 2 publications

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“…The phytochemicals isolated from the seeds of Rhaponticum carthamoides are phytosteroids and their derivates, such as 20-hydroxyecdysone, polypodine B, polypodine B-22- O -benzoate, makisterone A, 24(28)-dehydromakisterone A, rhapisterone, rhapisterone D 20-acetate, and carthamosterone A [ 53 , 54 , 56 , 90 , 91 , 92 , 93 ]. The average concentration of ecdysterone discovered in seeds is 0.57% [ 53 , 56 , 94 ].…”

Section: Resultsmentioning

confidence: 99%

Comparison between the Biological Active Compounds in Plants with Adaptogenic Properties (Rhaponticum carthamoides, Lepidium meyenii, Eleutherococcus senticosus and Panax ginseng)

Todorova

Ivanov

Ivanova

2021

Plants

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Background: In the 1960s, research into plant adaptogens began. Plants with adaptogenic properties have rich phytochemical compositions and have been used by humanity since ancient times. However, it is not still clear whether the adaptogenic properties are because of specific compounds or because of the whole plant extracts. The aim of this review is to compare the bioactive compounds in the different parts of these plants. Methods: The search strategy was based on studies related to the isolation of bioactive compounds from Rhaponticum carthamoides, Lepidium meyenii, Eleutherococcus senticosus, and Panax ginseng. The Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA) guidelines were followed. Results: This review includes data from 259 articles. The phytochemicals isolated from Rhaponticum carthamoides, Lepidium meyenii, Eleutherococcus senticosus, and Panax ginseng were described and classified in several categories. Conclusions: Plant species have always played an important role in drug discovery because their effectiveness is based on the hundreds of years of experience with folk medicine in different nations. In our view, there is great potential in the near future for some of the phytochemicals found in these plants species to become pharmaceutical agents.

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Section: Resultsmentioning

confidence: 99%

Comparison between the Biological Active Compounds in Plants with Adaptogenic Properties (Rhaponticum carthamoides, Lepidium meyenii, Eleutherococcus senticosus and Panax ginseng)

Todorova

Ivanov

Ivanova

2021

Plants

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“…The literature survey indicates that 50 new ecdysteroids have been reported from the Asteraceae family. These are inokosterone 20,22-acetonide ( 38 ), integristerone A-20,22-acetonide ( 39 ), 15-hydroxyponasterone A ( 40 ), 14- epi -ponasterone A 22- O - β - d -glucopyranoside ( 41 ), carthamoleusterone ( 42 ), 22-deoxy-28-hydroxymakisterone C ( 43 ), 26-hydroxymakisterone C ( 44 ) and 1 β -hydroxymakisterone C ( 45 ), isolated from the plant Leuzea carthamoides 56 , lesterone [5 β -cholest-7-en-2 α ,3 α ,11 β ,14 α ,20 R ,22 R ,25-heptahydroxy-6-one] ( 46 ), isolated from the plant L. carthamoides 57 , leuzeasterone ( 47 ) and (24 Z )-29-hydroxy-24(28)-dehydromakisterone C ( 48 ) isolated from the plant L. carthamoides 58 , coronatasterone (2-deoxy-3- epi -4 β ,20-dihydroxyecdysone) [(20 R ,22 R )-3 α ,4 β ,14 α ,20,22,25-hexahydroxy-5 β -cholest-7-en-6-one] ( 49 ), isolated from Serratula coronate 59 , 20-hydroxyecdysone-2- O - β - d -galactopyranoside ( 50 ), 3- O -acetyl-20-hydroxyecdysone-2- O - β - d -galactopyranoside ( 51 ), 3- O -acetyl-20-hydroxyecdysone-2- O - β - d -glucopyranoside ( 52 ), 24- O -acetyl- epi -abutasterone ( 53 ), 20-hydroxyecdysone-20,22-butylidene acetal ( 54 ), isolated from the plant Serratula chinensis 60 , 61 , rhapontisterone R 1 [2 β ,3 β ,11 α ,14 α ,20 ɛ ,22 ɛ -hexahydroxy-stigma-7,24(28)-dien-6-oxo-28,25-carbolactone] ( 55 ), isolated from Rhaponticum uniflorum 62 , turkesterone-2- O -cinnamate ( 56 ), isolated from R. uniflorum 63 , makisterone C-20,22-acetonide ( 57 ), isolated from R. uniflorum 64 , ajugasterone C-2,3,20,22-diacetonide ( 58 ) and 5-deoxykaladasterone-20,22-monoacetonide ( 59 ), isolated from R. uniflorum 65 , uniflorsterone ( 60 ), isolated from R. uniflorum 66 , rapisterone D 20-acetate ( 61 ), isolated from L. carthamoides 67 , 22- epi -ajugasterone C ( 62 ), isolated from Serratula cichoracea 68 , ajugasterone 11-acetate ( 63) 69 , 3- epi -20-hydroxyecdysone ( 64 ) 70 , ecdysone 22-acetate ( 65 ), (25 S )-inokosterone 26-acetate ( 66 ), 20,22- O -( R -ethylidene)-2...…”

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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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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Rhapisterone D 20-acetate from the seeds ofLeuzea carthamoides

Cited by 8 publications

References 2 publications

Comparison between the Biological Active Compounds in Plants with Adaptogenic Properties (Rhaponticum carthamoides, Lepidium meyenii, Eleutherococcus senticosus and Panax ginseng)

Comparison between the Biological Active Compounds in Plants with Adaptogenic Properties (Rhaponticum carthamoides, Lepidium meyenii, Eleutherococcus senticosus and Panax ginseng)

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

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

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