5,6-Dihydro-α-pyrones from the leaves of Cryptocarya pulchinervia (Lauraceae)

Juliawaty, Lia Dewi; Ra'idah, Pramukti N; Abdurrahman, Syawal; Hermawati, Elvira; Alni, Anita; Tan, Marselina Irasonia; Ishikawa, Hayato; Syah, Yana Maolana

doi:10.1007/s11418-020-01397-7

Cited by 18 publications

(13 citation statements)

References 19 publications

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“…In conclusion, our work, entirely consistent with other observations, attests that the cryptoconcatone and pironetin scaffolds can be further exploited to design anticancer agents. There exists a variety of 5,6-dihydro-α-pyrones in plants, such as monticolides [ 49 ], pulchrinervialactone [ 50 ], cryptorigidifoliols [ 51 ], cryptomoscatones [ 36 ] and others. All these compounds should be tested as modulators of microtubule dynamics.…”

Section: Discussionmentioning

confidence: 99%

Molecular Docking of Cryptoconcatones to α-Tubulin and Related Pironetin Analogues

Vergoten

Bailly

2023

Plants

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Cryptoconcatones A-L represent a series of 12 dihydropyrone derivatives isolated from the evergreen tree Cryptocarya concinna Hance, which is well distributed in southeast Asia. The lead compound in the series, cryptoconcatone L, has revealed antiproliferative activity against cultured cancer cells but its mechanism of action remains unknown. Based on a structural analogy with the anticancer natural product pironetin, which is well known for binding covalently to α-tubulin and for functioning as a microtubule polymerization inhibitor, we investigated the interaction of cryptoconcatones with tubulin dimers using molecular docking. The α-tubulin binding capacity of each compound was quantified (through calculation of the empirical energy of interaction ΔE) and structure–binding relationships were delineated. Two compounds were found to interact with α-tubulin much more potently than pironetin: cryptoconcatones F and L. In both cases, the facile formation of a covalent bond with Cys316 was evidenced, as observed with the parent compound pironetin. A few other pironetin analogues were investigated, including spicigerolide, which is an analogue of another known α-tubulin binder. Altogether, this study points to the identification of a series of 5,6-dihydro-α-pyrones as α-tubulin-binding agents. The study contributes to a better understanding of the mechanism of action of cryptoconcatones and should help the design of analogues targeting the pironetin site of α-tubulin.

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Section: Discussionmentioning

confidence: 99%

Molecular Docking of Cryptoconcatones to α-Tubulin and Related Pironetin Analogues

Vergoten

Bailly

2023

Plants

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“…A hair growth activity test was carried out using the ethyl acetate extract of M. peltata leaves at concentrations of 10%, 20%, and 30%. The method of [ 14 ] used in this test is one of the methods for determining hair growth activity by shaving; the back of the rabbit's hair is shaved clean and then divided into six 2 × 2 cm squares. The test used six healthy male rabbits (number calculated by the rule of [ 15 ] aged 4–5 months, with no anatomical defects.…”

Section: Methodsmentioning

confidence: 99%

Active Antialopecia Chemical Identification of Merremia peltata Leaves and Computational Study toward Androgen Receptor Using Molecular Docking and Molecular Dynamic Simulation

Abdurrahman

Ruslin

Hasanah

et al. 2022

The Scientific World Journal

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Alopecia is a health condition in which the hair loses its function in some or all of the body. Alopecia occurs due to various genetic, environmental, and nutritional factors. One of the methods developed to treat alopecia is through inhibition of the enzyme 5-α-reductase, which converts testosterone into its more potent metabolite, dihydrotestosterone (DHT). In ethnomedicine, the leaves of Merremia peltata are used by the people of Sulawesi as a remedy for baldness. Therefore, in this study, an in vivo study was conducted on rabbits to investigate the antialopecia activity of the ethanolic extract of M. peltata leaves. The purified M. peltata leaf extract was fractionated using vacuum liquid chromatography with several solvents to produce fractions F1–F5. Each fraction was then retested in vivo in rabbits, and its content was then analyzed by LC-MS. An in silico study was then carried out using minoxidil as a comparison ligand; 17 compounds derived from M. peltata leaves were identified as antialopecia compounds through prediction of molecular interactions and molecular dynamics simulation and prediction of absorption, distribution, metabolism, excretion, and toxicology (ADME-Tox). The assay results showed that fractions F2 and F3 had a better effect on hair growth compared to the positive control, and the test compound obtained from the LC-MS analysis, bufotalinin, had a strong binding energy to the receptor in the molecular docking interaction study: −5.99 kcal/mol compared to −4.8 kcal/mol for minoxidil. Molecular dynamics simulation analysis with complex stability parameters based on solvent-accessible surface area (SASA), principal component analysis (PCA), root mean square deviation (RMSD), and root mean square fluctuation (RMSF) showed that bufotalinin has good affinity for androgen receptors. ADME-Tox prediction for bufotalinin showed good results for the parameters of skin permeability, absorption, and distribution. Therefore, bufotalinin, a steroid compound, is a potential androgen receptor antagonist and could be useful in the treatment of alopecia.

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“…The ethyl acetate phase was concentrated with a Rotary Vacuum Evaporator so that 40 grams of ethyl acetate extract was obtained. Furthermore, the extract was analyzed using thin-layer chromatography (TLC) to determine the separation pattern of each fraction that was separated using n-hexane eluent: ethyl acetate (1:1) [15].…”

Section: Purified Extractmentioning

confidence: 99%

Potential Antidiabetic Activities of Fractions From Purified Extract of Lawsonia Inermis Leaves in Alloxan–induced Diabetic Mice

et al. 2021

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Objective: This research was conducted to determine the potential antidiabetic activity fractions of purified extract Lawsonia inermis leaves in mice (Mus musculus) and identification of the compound. Methods: The method included maceration, purification using ethanol and distilled water was followed by liquid-liquid extraction using ethyl acetate and magnesium sulfate as drying agents. Furthermore, the extract was analyzed using thin layer chromatography (TLC) for testing the purified extract. Fractionation using vacuum liquid chromatography, antidiabetic activity test of fractions at dose 100 mg/kgBW with alloxan induced and compound identification by Liquid Chromatography-Mass Spectrometry (LC-MS/MS) using HPLC connected to a Q-TOF spectrometer equipped with an ESI source, with Phenomenon column C8, and methanol with 0.3% formic acid as solvent. Results: The results showed that from the purification step of L. inermis leaves by vacuum liquid chromatography method, 7 fractions were obtained, i.e. A-G fractions. While the antidiabetic activity of fractions shown by decreasing blood sugar level in mice on the 15th day were 64, 75, 73, 73, 57, 45 and 67%, respectively. The identified compounds from each fraction were the ester groups namely 12-hydroxy-methyl abietate, 9,12-octadecadienoic acid (Z,Z)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl ester, dehydromorroniaglycone, and (E)-hexadecyl-ferulate; the steroid group namely siraitic acid E; phenylpropanoid groups namely umbelliferone and bletilol C, and the alkaloid groups namely moupinamide and valine. Conclusion: L. inermis leaves had activity in lowering blood sugar levels. LC-MS/MS analysis revealed the presence of ester groups, steroid groups, phenylpropanoid groups and alkaloid groups. The presence of these compounds mostly contribute to antidiabetic activity.

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5,6-Dihydro-α-pyrones from the leaves of Cryptocarya pulchinervia (Lauraceae)

Cited by 18 publications

References 19 publications

Molecular Docking of Cryptoconcatones to α-Tubulin and Related Pironetin Analogues

Molecular Docking of Cryptoconcatones to α-Tubulin and Related Pironetin Analogues

Active Antialopecia Chemical Identification of Merremia peltata Leaves and Computational Study toward Androgen Receptor Using Molecular Docking and Molecular Dynamic Simulation

Potential Antidiabetic Activities of Fractions From Purified Extract of Lawsonia Inermis Leaves in Alloxan–induced Diabetic Mice

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