Structural Characterization and Antimicrobial Evaluation of Atractyloside, Atractyligenin, and 15-Didehydroatractyligenin Methyl Ester

Brucoli, Federico; Borrello, María Teresa; Stapleton, Paul; Parkinson, Gary N.; Gibbons, Simon

doi:10.1021/np300080w

Cited by 20 publications

(18 citation statements)

References 20 publications

(38 reference statements)

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“…The physical and spectral data of compounds 1 were identical to those of pure samples previously isolated [17]. Compounds 2, 3 and 4 were prepared according to published procedures and their physical and spectroscopic data agreed with those reported in the literature [22].…”

Section: Synthetic Proceduressupporting

confidence: 56%

“…The crushed rhizome of A. gummifera was treated with an aqueous-acetone solution in order to isolate atractyloside 1 (ATR), according to published methods [22,23]. ATR was isolated in good yield and its NMR spectra and MS analysis were in accordance with the literature data [17]. The aqueous-acetone rhizome mixture was then extracted with chloroform and the organic fraction was concentrated and subjected to column chromatography over normal phase silica gel and semi-preparative HPLC to afford 2-furyl(phenyl)methanol 5 as a pale yellow amorphous solid.…”

Section: Chemistrymentioning

confidence: 85%

“…A total of 3.750 g of ATR 1 (0.85% yield) was recovered as a pale yellow solid, which was characterised by TLC (R f = 0.45, purple, TLC system 1), LC-MS and 1 H-NMR spectroscopy. NMR spectral data were identical to previously analysed pure sample of ATR [17].…”

Section: Extraction and Isolationmentioning

confidence: 99%

“…The A. gummifera rhizome contains atractyloside 1 (ATR), a glucoside consisting of the tetracyclic ent-kaurane diterpene atractyligenin 2 attached through a β-linkage to the anomeric carbon of a D-(+)-glucose residue ( Fig. 1) [17]. ATR exerts its biological activity by inhibiting the oxidative phosphorylation in the mitochondria of hepatocytes and proximal tubular epithelial cells, and has been extensively investigated for its pharmacological and chemical properties [18][19][20].…”

Section: Introductionmentioning

confidence: 99%

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2-furyl(phenyl)methanol isolated from Atractilis gummifera rhizome exhibits anti-leishmanial activity

et al. 2020

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We report for the first time the isolation of 2-furyl(phenyl)methanol (5) from the chloroform extracts of the Atractylis gummifera roots. A. gummifera is a thistle belonging to the Asteraceae family that produces the entkaurane diterpenoid glycoside atractyloside (ATR). ATR (1) was isolated and chemically modified to obtain its aglycone atractyligenin (2) and the methylated derivatives ATR-OMe (3) and genine-OMe (4). The compounds 1-5 were structurally characterised and evaluated against the intracellular amastigote, cultured within macrophages, and the extracellular promastigote of Leishmania donovani, the protozoan parasite responsible for the highly infective disease visceral leishmaniasis, which is fatal if untreated. The 2-furyl(phenyl)methanol 5 exhibited notable activity against the promastigote.

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Section: Synthetic Proceduressupporting

confidence: 56%

Section: Chemistrymentioning

confidence: 85%

Section: Extraction and Isolationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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2-furyl(phenyl)methanol isolated from Atractilis gummifera rhizome exhibits anti-leishmanial activity

et al. 2020

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“…ent -Kaurane diterpenoid derivatives with diverse unique chemical skeletons are generally quite complex, incorporating numbers of intricate ring systems and stereogenic centers, and exhibit promising biological activities [ 63 , 64 , 65 , 66 , 67 , 68 , 69 ]. The preparation of ent -kaurane diterpenoid libraries inevitably involved rather laborious and complex synthetic sequences, especially total synthesis [ 70 , 71 , 72 ].…”

Section: Oridonin As the Lead To Synthesize Ent mentioning

confidence: 99%

Oridonin, a Promising ent-Kaurane Diterpenoid Lead Compound

Han

Liao

et al. 2016

IJMS

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Oridonin belongs to ent-kaurane tetracyclic diterpenoid and was first isolated from Isodon species. It exhibits inhibitory activities against a variety of tumor cells, and pharmacological study shows that oridonin could inhibit cell proliferation, DNA, RNA and protein synthesis of cancer cells, induce apoptosis and exhibit an antimutagenic effect. In addition, the large amount of the commercially-available supply is also very important for the natural lead oridonin. Moreover, the good stability, suitable molecular weight and drug-like property guarantee its further generation of a natural-like compound library. Oridonin has become the hot molecule in recent years, and from the year 2010, more than 200 publications can be found. In this review, we summarize the synthetic medicinal chemistry work of oridonin from the first publication 40 years ago and share our research experience of oridonin for about 10 years, which may provide useful information to those who are interested in this research field.

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Structural characterization of carboxyatractyloside and acaricidal activity of natural ent-kaurene diterpenoids isolated from Chamaeleon gummifer against Tetranychus urticae

Badalamenti,

Bruno,

Pavela

et al. 2023

J Pest Sci

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Plant-borne secondary metabolites are attracting high interest for their potential use in agricultural applications, with special reference to the control of arthropod pests. In the present work, the structural elucidation of glycosylated diterpenoid carboxyatractyloside (2) isolated from the roots of Chamaeleon gummifer Cass. (Asteraceae) is reported by means of spectroscopic and spectrometric techniques. Complete identification occurred thanks to one- and two-dimensional NMR experiments, assigning the single protons and carbons, and the stereochemistry by the NOESY correlations. Carboxyatractyloside (2), together with two ent-kaurenes atractyloside (1) and atractyligenin (3), extracted from the roots of C. gummifer, have been tested for their acaricidal and oviposition inhibition activity against the two-spotted spider mite, Tetranychus urticae Koch (Acari: Tetranychidae) Notably, compounds 1–3 were toxic to T. urticae, leading to significant mortality, oviposition inhibition, reduced hatchability of eggs, and natality inhibition. However, at the lowest dose (12.5 µg cm−2) compound 2 was the most effective, leading to mortality > 60% after 5 days exposure, inhibiting oviposition by > 70% and egg hatching by 33%; it also reduced natality by 80%. Overall, these compounds represent valuable candidates to develop novel acaricides for crop protection. Further research on how to develop stable formulations for field use, as well as on non-target effects of these compounds on pollinators and mite biocontrol agents, is ongoing.

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Structural Characterization and Antimicrobial Evaluation of Atractyloside, Atractyligenin, and 15-Didehydroatractyligenin Methyl Ester

Cited by 20 publications

References 20 publications

2-furyl(phenyl)methanol isolated from Atractilis gummifera rhizome exhibits anti-leishmanial activity

2-furyl(phenyl)methanol isolated from Atractilis gummifera rhizome exhibits anti-leishmanial activity

Oridonin, a Promising ent-Kaurane Diterpenoid Lead Compound

Structural characterization of carboxyatractyloside and acaricidal activity of natural ent-kaurene diterpenoids isolated from Chamaeleon gummifer against Tetranychus urticae

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