Simultaneous Determination of Six Coumarins in Rat Plasma and Metabolites Identification of Bergapten <i>in Vitro</i> and <i>in Vivo</i>

Liao, Man; Song, Guohe; Cheng, Xiaoye; Diao, Xingxing; Sun, Yupeng; Zhang, Lantong

doi:10.1021/acs.jafc.7b05637

Cited by 15 publications

(9 citation statements)

References 28 publications

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“…Bergapten (BP) (C 12 H 8 O 4 ) or 5-methoxypsoralen (5-MOP) ( Figure 1 ) is a psoralen compound (also known as furocoumarin) found in bergamot essential oil, other citrus essential oils, and grapefruit juice [ 1 , 2 ]. This furanocoumarin derivate is also found in a wide variety of medicinal plants, in particular, plants of the Rutaceae and Umbelliferae family as figs, parsley, celery, and anise [ 3 – 5 ]. Furanocoumarins derived from herbal and citrus extracts have been reported to exert many biological activities including antibacterial, antioxidant, immunomodulator, apoptotic, and anticancer agents [ 6 ].…”

Section: Introductionmentioning

confidence: 99%

Pharmacological Properties of Bergapten: Mechanistic and Therapeutic Aspects

Quetglas-Llabrés

Quispe

Herrera‐Bravo

et al. 2022

Oxidative Medicine and Cellular Longevity

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Bergapten (BP) or 5-methoxypsoralen (5-MOP) is a furocoumarin compound mainly found in bergamot essential oil but also in other citrus essential oils and grapefruit juice. This compound presents antibacterial, anti-inflammatory, hypolipemic, and anticancer effects and is successfully used as a photosensitizing agent. The present review focuses on the research evidence related to the therapeutic properties of bergapten collected in recent years. Many preclinical and in vitro studies have been evidenced the therapeutic action of BP; however, few clinical trials have been carried out to evaluate its efficacy. These clinical trials with BP are mainly focused on patients suffering from skin disorders such as psoriasis or vitiligo. In these trials, the administration of BP (oral or topical) combined with UV irradiation induces relevant lesion clearance rates. In addition, beneficial effects of bergamot extract were also observed in patients with altered serum lipid profiles and in people with nonalcoholic fatty liver. On the contrary, there are no clinical trials that investigate the possible effects on cancer. Although the bioavailability of BP is lower than that of its 8-methoxypsoralen (8-MOP) isomer, it has fewer side effects allowing higher concentrations to be administered. In conclusion, although the use of BP has therapeutic applications on skin disorders as a sensitizing agent and as components of bergamot extract as hypolipemic therapy, more trials are necessary to define the doses and treatment guidelines and its usefulness against other pathologies such as cancer or bacterial infections.

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Section: Introductionmentioning

confidence: 99%

Pharmacological Properties of Bergapten: Mechanistic and Therapeutic Aspects

Quetglas-Llabrés

Quispe

Herrera‐Bravo

et al. 2022

Oxidative Medicine and Cellular Longevity

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“…1), 1 was not assessed for its larvicidal activity owing to insufficient sample quantity. This compound belongs to the coumarin class which is very common in plant secondary metabolites and widely distributed in species showing antibacterial, antileishmanial, anti‐inflammatory and anticancer properties 35 . It is important to highlight that 1 corresponds to a natural 3‐arylcoumarin and is not reported in the literature.…”

Section: Discussionmentioning

confidence: 99%

“…This compound belongs to the coumarin class which is very common in plant secondary metabolites and widely distributed in species showing antibacterial, antileishmanial, anti-inflammatory and anticancer properties. 35 It is important to highlight that 1 corresponds to a natural 3-arylcoumarin and is not reported in the literature. Full structural elucidation and MS analysis determined its exact chemical structure as 2H-1-Benzopyran-2-one, 7-hydroxy-3-(5 0 -methoxyphenyl).…”

Section: Discussionmentioning

confidence: 99%

Machaerium acutifolium compounds with larvicidal activity against Aedes aegypti

Melo

Sousa

Sá

et al. 2020

Pest Management Science

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BACKGROUND Plant extracts and isolated compounds are known for their insecticidal activity. The Aedes aegypti mosquito has a significant medical impact as it transmits a number of arboviruses and is able to develop resistance to the commercially available insecticides. This study investigates larvicidal compounds isolated from Machaerium acutifolium, designated by the Brazilian Forest Service as a sustainable species. RESULTS A M. acutifolium trunk ethyl acetate extract was fractionated using chromatographic methods with full structural elucidation by mass spectrometry (MS), nuclear magnetic resonance and specific rotation analyses revealing: one new 3‐arylcoumarin derivative 1; two flavonoids 2 and 3; a trans‐stilbene 4, and an unprecedented natural indene 5. The larvicidal activity against Ae. aegypti after 24 h exposure was: crude extract (median lethal dose, LC50 205 mg L–1), fraction C (LC50 27 mg L–1) and 5 (LC50 24 mg L–1). CONCLUSION A M. acutifolium extract showed larvicidal activity, which increased with prolonged exposure, demonstrating LC50 75 mg L–1 after 72 h. Although the flavonoids 2 and 3 and trans‐stilbene 4 were deemed inactive according to the adopted mortality limit, additional tests revealed their ability to cause 65% Ae. aegypti larvae mortality, suggesting they could contribute to the larvicidal activity. Compound 5, identified by liquid chromatography‐MS, was over eight‐fold more toxic to larvae than the crude extract after 24 h. Therefore, 5 constitutes a structural model for new prototypes to control Ae. aegypti. These data reinforce the potential of natural products as a source of commercial alternatives for vector control strategies, respecting both sustainability and eco‐friendly principles. © 2020 Society of Chemical Industry

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“…There are 24 metabolites detected, and the metabolic pathways mainly include oxidation, hydrogenation, hydrolysis, methylation, demethylation, oxidative hydrolysis, glucoside formation, and sulfate formation. Among them, metabolites hydrolyzed by mono‐oxide esters and demethylated metabolites are considered to be important metabolites that can be found in all biological samples (Liao et al, 2018). Induction or inhibition of CYP enzymes is a major mechanism that underlies drug–drug interactions (Manikandan & Nagini, 2018).…”

Section: Pharmacokinetics Effects Of Bergaptenmentioning

confidence: 99%

Bergapten: A review of its pharmacology, pharmacokinetics, and toxicity

Liang

Xie

et al. 2021

Phytotherapy Research

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Bergapten is a natural furocoumarin, also known as 5-methoxypsoralen, and its medicinal value has been paid more and more attention. By sorting out the pharmacological literature of bergapten, we found that bergapten has a wide range of pharmacological effects, including neuroprotection, organ protection, anticancer, antiinflammatory, antimicrobial, and antidiabetes effects. However，bergapten has complex impacts on the hepatic metabolic enzyme. Moreover, pharmacokinetic studies showed that bergapten has higher absolute bioavailability and can cross the blood-brain barrier and has a great potential for treating brain disease, but the mechanism needs further clarification to make greater use of its ability to treat brain diseases. Furthermore, the phototoxicity of bergapten combined with ultraviolet light has always been mentioned. In view of its wide range of pharmacological activities, bergapten is expected to be a potential drug candidate for the treatment of diabetes and diabetes-induced osteoporosis, epilepsy, Alzheimer's disease, depression, and cancer. However, further studies are needed to elucidate its molecular mechanisms and targets. The phototoxicity of bergapten as a side effect should be further avoided. On the other hand, the photoactivation of bergapten in the anticancer aspect can be better utilized.

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Simultaneous Determination of Six Coumarins in Rat Plasma and Metabolites Identification of Bergapten in Vitro and in Vivo

Cited by 15 publications

References 28 publications

Pharmacological Properties of Bergapten: Mechanistic and Therapeutic Aspects

Pharmacological Properties of Bergapten: Mechanistic and Therapeutic Aspects

Machaerium acutifolium compounds with larvicidal activity against Aedes aegypti

Bergapten: A review of its pharmacology, pharmacokinetics, and toxicity

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