Structure of 22-deoxocucurbitacins isolated fromBryonia alba andEcbalium elaterium

Panosyan, A. G.; Никищенко, М. Н.; Avetisyan, Gayane

doi:10.1007/bf00579070

Cited by 6 publications

(6 citation statements)

References 18 publications

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“…Total assignments of carbons and protons were achieved by HMBC, HSQC, 1 H- 1 H COSY (Figures S6–S9 in supplementary information, respectively) and by comparison with a standard of cucurbitacin E. The stereostructure of cucurbitane skeleton in compound 1 was characterized by NOESY experiment (Figure 2 and Figure S10) and the comparison of key chemical shifts and coupling constants with literature. Thus, a coupling constant of 7.2 Hz for H-16 and H-17 is representative of β and α positions for H-16 and H-17, respectively [35,36]. The stereostructure of the C-20 position was deduced by comparison of the 13 C-NMR data (δ C 78.2 for C-20) with authentic glucocucurbitacin E and the literature’s NMR data for glucocucurbitacins I and E recorded in the same solvent (CDCl 3 [23]) and was deduced to be R oriented.…”

Section: Resultsmentioning

confidence: 99%

Cucurbitacins from the Leaves of Citrullus colocynthis (L.) Schrad

et al. 2015

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Abstract:Two new tetracyclic cucurbitane-type triterpene glycosides were isolated from an ethyl acetate extract of Citrullus colocynthis leaves together with four known cucurbitacins. Their structures were established on the basis of their spectroscopic data (mainly NMR and mass spectrometry). Evaluation of the in vitro cytotoxic activity of the isolated compounds against two human colon cancer cell lines (HT29 and Caco-2) and one normal rat intestine epithelial cell line (IEC6), revealed that one of the isolated compounds presented interesting specific cytotoxic activity towards colorectal cell lines.

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Section: Resultsmentioning

confidence: 99%

Cucurbitacins from the Leaves of Citrullus colocynthis (L.) Schrad

et al. 2015

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“…Although cucurbitacins are widespread in cucurbit plants, the major bitterness compounds of each species are different (Figure ). For instance, cucurbitacin C is only found in cucumber (Panosyan et al ., ), while cucurbitacins B and E are responsible for the bitterness of melon and watermelon, respectively (Da Costa and Jones, ; Shang et al ., ). A genetic study led to the characterization of the cytochrome P450s (CYPs) in conserved synthetic loci for the cucurbitacin core skeleton, while the loss of another CYP in melon and watermelon was found to be responsible for the species‐specific accumulation of cucurbitacin C (Zhou et al ., ).…”

Section: The Rise Of Metabolic Diversitymentioning

confidence: 99%

Metabolic GWAS‐based dissection of genetic bases underlying the diversity of plant metabolism

2018

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Plants have served as sources providing humans with metabolites for food and nutrition, biomaterials for living, and treatment for pain and disease. Plants produce a huge array of metabolites, with an immense diversity at both the population and individual levels. Dissection of the genetic bases for metabolic diversity has attracted increasing research attention. The concept of genome-wide association study (GWAS) was extended to studies on the diversity of plant metabolome that benefitted from the development of mass-spectrometry-based analytical systems and genome sequencing technologies. Metabolic genome-wide association study (mGWAS) is one of the most powerful tools for global identification of genetic determinants for diversity of plant metabolism. Recently, mGWAS has been performed for various species with continuous improvements, providing deeper insights into the genetic bases of metabolic diversity. In this review, we discuss fully the achievements to date and remaining challenges that are associated with both mGWAS and mGWAS-based multi-dimensional analysis. We begin with a summary of GWAS and its development based on statistical methods and populations. As variation in targeted traits is essential for GWAS, we review metabolic diversity and its rise at both the population and individual levels. Subsequently, the application of mGWAS for plants and its corresponding achievements are fully discussed. We address the current knowledge on mGWAS-based multi-dimensional analysis and emerging insights into the diversity of metabolism.

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“…20 Other congeners of cucurbitacin B, including dihydroisocucurbitacin B 3-glucoside (7) from Wilbrandia ebracteata (Cucurbitaceae), 21 23,24-dihydro-3-epiisocucurbitacin B (8), and the 23-epimeric pairs 9 and 10 from Bryonia verrucosa (Cucurbitaceae), were also reported. 23 23 …”

Section: Cucurbitacin Bmentioning

confidence: 99%

“…22 Compound 9 was subsequently shown to be identical to the aglycone of 22-deoxocucurbitosides A and B from B. alba. 23…”

Section: Cucurbitacin Bmentioning

confidence: 99%

Cucurbitacins and cucurbitane glycosides: structures and biological activities

et al. 2005

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The natural cucurbitacins constitute a group of triterpenoid substances which are well-known for their bitterness and toxicity. Structurally, they are characterized by the tetracyclic cucurbitane nucleus skeleton, namely, 19-(10-->9beta)-abeo-10alpha-lanost-5-ene (also known as 9beta-methyl-19-norlanosta-5-ene), with a variety of oxygen substitutions at different positions. According to the characteristics of their structures, cucurbitacins are divided into twelve categories. The biological effects of the cucurbitacins are also covered.

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Structure of 22-deoxocucurbitacins isolated fromBryonia alba andEcbalium elaterium

Cited by 6 publications

References 18 publications

Cucurbitacins from the Leaves of Citrullus colocynthis (L.) Schrad

Cucurbitacins from the Leaves of Citrullus colocynthis (L.) Schrad

Metabolic GWAS‐based dissection of genetic bases underlying the diversity of plant metabolism

Cucurbitacins and cucurbitane glycosides: structures and biological activities

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