Phebaclavin I, a novel 3-prenylated coumarin, and trichoclin acetate, a new natural furocoumarin, from the aerial parts of<i>Phebalium</i>aff.<i>tuberculosum</i>(Rutaceae)

Roux, Delphine Le; Muyard, Frédéric; Girard, Christian; Colombain, Michel; Tillequin, F.; Waterman, Peter G.; Bévalot, Françoise

doi:10.1080/14786410500087525

Cited by 5 publications

(5 citation statements)

References 30 publications

(30 reference statements)

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“…Commonly, coumarins with levorotatory activity have an S-configuration, while dextrorotatory activity is related to the R-configuration. 45 Therefore, the absolute stereochemistry of 4 was determined to be R due to its dextrorotatory activity of [α] D 23 +48 (c 0.05, MeOH). The chemical formula of corisis E (5) was deduced to be C 20 H 26 O 6 ([M + Na] + m/z 385.1619).…”

Section: Resultsmentioning

confidence: 99%

“…The stereochemistry of coumarins sharing similar chiral centers was determined by optical rotation. Commonly, coumarins with levorotatory activity have an S -configuration, while dextrorotatory activity is related to the R -configuration . Therefore, the absolute stereochemistry of 4 was determined to be R due to its dextrorotatory activity of [α] D 23 +48 ( c 0.05, MeOH).…”

Section: Resultsmentioning

confidence: 99%

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Isolating Antipathogenic Fungal Coumarins from Coriaria nepalensis and Determining Their Primary Mechanism In Vitro

Jian,

Fan,

Jin

et al. 2024

J. Agric. Food Chem.

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Through bioassay-guided isolation, eight undescribed coumarins (1−8), along with six reported coumarins (9−14), were obtained from Coriaria nepalensis. The new structures were determined by using IR, UV, NMR, HRESIMS, and ECD calculations. The results of the biological activity assays showed that compound 9 exhibited broad spectrum antifungal activities against all tested fungi in vitro and a significant inhibitory effect on Phytophthora nicotianae with an EC 50 value of 3.00 μg/mL. Notably, compound 9 demonstrated greater curative and protective effects against tobacco balack shank than those of osthol in vivo. Thus, 9 was structurally modified to obtain new promising antifungal agents, and the novel derivatives (17b, 17j, and 17k) exhibited better effects on Sclerotinia sclerotiorum than did lead compound 9. Preliminary mechanistic exploration illustrated that 9 could enhance cell membrane permeability, destroy the morphology and ultrastructure of cells, and reduce the exopolysaccharide content of P. nicotianae mycelia. Furthermore, the cytotoxicity results revealed that compound 9 exhibited relatively low cytotoxicity against HEK293 cell lines with an inhibition rate of 33.54% at 30 μg/mL. This research is promising for the discovery of new fungicides from natural coumarins with satisfactory ecological compatibility.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Isolating Antipathogenic Fungal Coumarins from Coriaria nepalensis and Determining Their Primary Mechanism In Vitro

Jian,

Fan,

Jin

et al. 2024

J. Agric. Food Chem.

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“…The second aim of the present study was to compare various natural coumarins, extracted from Rutaceous plants [9], [10], [11], [12] on UGT1A1-dependent bilirubin glucuronidation activity in cultured hepatocytes. We have chosen to measure Bili-UGT activity with these compounds, since chrysin did not induce PNP-UGT activity.…”

Section: Discussionmentioning

confidence: 99%

“…Coumarin (97 %) and chrysin (97 %) were purchased from Sigma-Aldrich. Umbelliferone, bergapten, imperatorin, avicennin and cis-avicennol were isolated from different Rutaceous species belonging to the genera Phebalium [9], [10], [11] and Philotheca [12] ( Fig. 1).…”

Section: Coumarins and Flavonoidsmentioning

confidence: 99%

“…But to our knowledge, coumarins have never been evaluated for their potential to modulate UGTs. In the present work, we examined the ability of a flavonoid, chrysin, and six natural coumarins, mainly isolated from different Rutaceous species, [9], [10], [11], [12] to modulate UGT1A6 and/or UGT1A1 activity, in cultured hepatocytes, from both rat and human origin.…”

Section: Introductionmentioning

confidence: 99%

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Effect of Chrysin and Natural Coumarins on UGT1A1 and 1A6 Activities in Rat and Human Hepatocytes in Primary Culture

Chlouchi¹,

Girard²,

Bonet³

et al. 2007

Planta Med

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Flavonoids and coumarins are naturally occurring compounds that are widely distributed in vegetables and have a broad pharmacological activity. Inducibility of UDP-glucuronosyltransferases (UGTs) by xenobiotics is well documented and can be considered beneficial for health. In particular, UGT1A1-dependent bilirubin conjugation plays a critical role in the detoxification of neurotoxic bilirubin and phenobarbital-mediated UGT1A1 induction therapy is commonly used in the treatment of unconjugated hyperbilirubinemic diseases such as Crigler-Najjar type II disease. In the present study, the effects of the flavone chrysin and six natural coumarins isolated from various Rutaceous plants on UGT1A6-dependent P-nitrophenol and/or UGT1A1-dependent bilirubin glucuronoconjugation activities were evaluated in cultured rat and human hepatocytes and compared to those of the prototypical UGT1A inducers beta-naphthoflavone, phenobarbital and clofibric acid. After 3 days of treatment at a concentration of 25 microM, the pyranocoumarins avicennin and CIS-avicennol, and the furocoumarins bergapten and imperatorin, increased by 2-fold UGT1A1-dependent activity, equivalent to the increases obtained with chrysin at 25 microM, whereas in the presence of the simple coumarins such as coumarin or umbelliferone, UGT1A1-dependent activity was not modified. In terms of structural requirements for UGT1A1 induction, the present study suggests that the B-ring (phenyl) for chrysin and the furan or pyran rings for coumarins are essential for the biological activity.

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Taxonomically significant coumarins from three Philotheca species (Rutaceae)

Chlouchi¹,

Girard²,

Bévalot³

et al. 2007

Biochemical Systematics and Ecology

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Phebaclavin I, a novel 3-prenylated coumarin, and trichoclin acetate, a new natural furocoumarin, from the aerial parts ofPhebaliumaff.tuberculosum(Rutaceae)

Cited by 5 publications

References 30 publications

Isolating Antipathogenic Fungal Coumarins from Coriaria nepalensis and Determining Their Primary Mechanism In Vitro

Isolating Antipathogenic Fungal Coumarins from Coriaria nepalensis and Determining Their Primary Mechanism In Vitro

Effect of Chrysin and Natural Coumarins on UGT1A1 and 1A6 Activities in Rat and Human Hepatocytes in Primary Culture

Taxonomically significant coumarins from three Philotheca species (Rutaceae)

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