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Fulltext Psoralen Derivatives: Recent Advances of Synthetic Strategy and Pharmacological Properties

Jamalis J, Yusof FSM, Chander S, Wahab RA, P Bhagwat D, Sankaranarayanan M, et al.

Antiinflamm Antiallergy Agents Med Chem, 2020;19(3):222-239.
PMID: 31241020 DOI: 10.2174/1871523018666190625170802

Psoralen or furocoumarin is a linear three ring heterocyclic compound. Psoralens are planar, tricyclic compounds, consisting of a furan ring fused to a coumarin moiety. Psoralen has been known for a wide spectrum of biological activities, spanning from cytotoxic, photosensitizing, insecticidal, antibacterial to antifungal effect. Thus, several structural changes were introduced to explore the role of specific positions with respect to the biological activity. Convenient approaches utilized for the synthesis of psoralen skeleton can be categorized into two parts: (i) the preparation of the tricyclic ring system from resorcinol, (ii) the exocyclic modification of the intact ring system. Furthermore, although psoralens have been used in diverse ways, we mainly focus in this work on their clinical utility for the treatment of psioraisis, vitiligo and skin-related disorder.

Matched MeSH terms: Furocoumarins/pharmacology*
Chalepin: isolated from Ruta angustifolia L. Pers induces mitochondrial mediated apoptosis in lung carcinoma cells

Richardson JS, Sethi G, Lee GS, Malek SN

BMC Complement Altern Med, 2016 Oct 12;16(1):389.
PMID: 27729078

Cancer has been one of the leading causes of mortality in this era. Ruta angustifolia L. Pers has been traditionally used as an abortifacient, antihelmintic, emmenagogue and ophthalmic. In Malaysia and Singapore, the local Chinese community used it for the treatment of cancer.

Matched MeSH terms: Furocoumarins/isolation & purification; Furocoumarins/pharmacology*; Furocoumarins/chemistry
Fulltext White Light Emission from a Simple Mixture of Fluorescent Organic Compounds

Muhamad Sarih N, Myers P, Slater A, Slater B, Abdullah Z, Tajuddin HA, et al.

Sci Rep, 2019 08 14;9(1):11834.
PMID: 31413269 DOI: 10.1038/s41598-019-47847-5

Three fluorescent organic compounds-furocoumarin (FC), dansyl aniline (DA), and 7-hydroxycoumarin-3-carboxylic acid (CC)-are mixed to produce almost pure white light emission (WLE). This novel mixture is immobilised in silica aerogel and applied as a coating to a UV LED to demonstrate its applicability as a low-cost, organic coating for WLE via simultaneous emission. In ethanol solution and when immobilised in silica aerogel, the mixture exhibits a Commission Internationale d'Eclairage (CIE) chromaticity index of (0.27, 0.33). It was observed that a broadband and simultaneous emission involving coumarin carboxylic acid, furocoumarin and dansyl aniline played a vital role in obtaining a CIE index close to that of pure white light.

Matched MeSH terms: Furocoumarins
Fulltext Cytochrome P450 induction properties of food and herbal-derived compounds using a novel multiplex RT-qPCR in vitro assay, a drug-food interaction prediction tool

Koe XF, Tengku Muhammad TS, Chong AS, Wahab HA, Tan ML

Food Sci Nutr, 2014 Sep;2(5):500-20.
PMID: 25473508 DOI: 10.1002/fsn3.122

A multiplex RT-qPCR was developed to examine CYP1A2, CYP2D6, and CYP3A4 induction properties of compounds from food and herbal sources. The induction of drug metabolizing enzymes is an important pharmacokinetic interaction with unique features in comparison with inhibition of metabolizing enzymes. Cytochrome induction can lead to serious drug-drug or drug-food interactions, especially if the coadministered drug plasma level is critical as it can reduce therapeutic effects and cause complications. Using this optimized multiplex RT-qPCR, cytochrome induction properties of andrographolide, curcumin, lycopene, bergamottin, and resveratrol were determined. Andrographolide, curcumin, and lycopene produced no significant induction effects on CYP1A2, CYP2D6, and CYP3A4. However, bergamottin appeared to be a significant in vitro CYP1A2 inducer starting from 5 to 50 μmol/L with induction ranging from 60 to 100-fold changes. On the other hand, resveratrol is a weak in vitro CYP1A2 inducer. Examining the cytochrome induction properties of food and herbal compounds help complement CYP inhibition studies and provide labeling and safety caution for such products.

Matched MeSH terms: Furocoumarins
Differentiation of Ficus deltoidea varieties and chemical marker determination by UHPLC-TOFMS metabolomics for establishing quality control criteria of this popular Malaysian medicinal herb

Afzan A, Kasim N, Ismail NH, Azmi N, Ali AM, Mat N, et al.

Metabolomics, 2019 Mar 04;15(3):35.
PMID: 30830457 DOI: 10.1007/s11306-019-1489-2

BACKGROUND: Ficus deltoidea Jack (Moraceae) is a plant used in Malaysia for various diseases including as a supplement in diabetes management. Morphology distinction of the 7 main varieties (var. angustifolia, var. bilobata, var. deltoidea, var. intermedia, var. kunstleri, var. motleyana and var. trengganuensis) is challenging due to the extreme leaf heterophylly and unclear varietal boundaries, making it difficult for quality control of F. deltoidea products.
OBJECTIVE: We aimed to compare the phytochemical composition of 7 varieties growing in different conditions at various geographical locations. We also aimed to establish the quality control markers for the authentication of these varieties.
METHODS: We applied untargeted UHPLC-TOFMS metabolomics to discriminate 100 leaf samples of F. deltoidea collected from 6 locations in Malaysia. A genetic analysis on 21 leaf samples was also performed to validate the chemotaxonomy differentiation.
RESULTS: The PCA and HCA analysis revealed the existence of 3 chemotypes based on the differentiation in the flavonoid content. The PLS-DA analysis identified 15 glycosylated flavone markers together with 1 furanocoumarin. These markers were always consistent for the respective varieties, regardless of the geographical locations and growing conditions. The chemotaxonomy differentiation was in agreement with the DNA sequencing. In particular, var. bilobata accession which showed divergent morphology was also differentiated by the chemical fingerprints and genotype.
CONCLUSION: Chemotype differentiation based on the flavonoid fingerprints along with the proposed markers provide a powerful identification tool to complement morphology and genetic analyses for the quality control of raw materials and products from F. deltoidea.

Matched MeSH terms: Furocoumarins
Comparative analysis of metabolites and antioxidant potentials from different plant parts of curcuma aeruginosa roxb.

Sanimah Simoh, Sew YS, Fazri Abd Rahim, Muhammad Aizuddin Ahmad, Alizah Zainal

Sains Malaysiana, 2018;47:3031-3041.

A comparative analysis of metabolites from different parts of Curcuma aeruginosa, i.e. leaves, stems, adventitious
roots and rhizomes was performed by GC-MS/MS coupled with multivariate statistical analysis. The GC-MS/MS analysis
confirmed the occurrence of 26 metabolites belonged to terpenoids in almost all the samples. The Principal Component
Analysis (PCA) indicated that there was a clear distinction between rhizomes and other plant parts, i.e. stems, leaves,
and adventitious roots that could be explained by relatively higher contents of terpenoids including curzerene, alphafarnesen, furanocoumarin, velleral, germacrone cineole, borneol, beta- and gamma- elemene and methenolone. The
results of Hierarchical Clustering Analyses (HCA) corresponded with the PCA results where many terpenoids found
abundantly high in rhizome were clustered together. This was supported by the Pearson correlation analysis that
showed a significantly good relationship between those terpenoids. The adventitious roots demonstrated the strongest
antioxidant activity as compared to the other plant parts which could be attributed to its highest Total Phenolic
Contents (TPC). Total phenolic contents of all the plant parts were positively correlated with their antioxidant activities
which indicate that phenolic compounds may play a role in the overall antioxidant activities of the plants. The results
of the study highlighted the potential of this underexploited Curcuma species which could serve as a new source of
important phytochemicals and natural antioxidant that could be incorporated in functional foods and nutraceuticals.
In addition, chemical and biological evidence shown in the present work has rationalised the different uses of various
plant parts of C. aeruginosa.

Matched MeSH terms: Furocoumarins
Induction of apoptosis by chalepin through phosphatidylserine externalisations and DNA fragmentation in breast cancer cells (MCF7)

Fakai MI, Abd Malek SN, Karsani SA

Life Sci, 2019 Mar 01;220:186-193.
PMID: 30682342 DOI: 10.1016/j.lfs.2019.01.029

AIMS: Chalepin, a naturally occurring compound isolated from Ruta angustifolia have been shown to exert a promising anticancer activity through various mechanisms. Hence, the need to investigate the apoptotic inducing ability of chalepin in MCF7 cells by various detection assays.
MATERIALS AND METHODS: Cytotoxicity screening of chalepin against MCF7 cells was conducted using SRB assay. Apoptosis induction was examined by established morphological and biochemical assays including phase contrast and Hoechst/PI staining fluorescence microscope. Similarly, Annexin-V/FITC and TUNEL assays were conducted using flow cytometry whereas caspase-3 activity was evaluated using microplate reader.
KEY FINDINGS: The result indicates remarkable cytotoxic activity against MCF7 cells, whereas it shows moderate cytotoxic activity against MDA-MB231 cells. Interestingly, chalepin did not present any toxicity against MRC5 normal cell line. Morphological examination using both phase contrast and fluorescence microscope displays typical apoptotic features such as membrane blebbing, DNA fragmentation, chromatin condensation and apoptotic bodies' formation following chalepin treatment against MCF7 cells at different concentration for 48 h. Apoptosis induction is significantly associated with externalisation of phosphatidylserine, and DNA fragmentation in MCF7 cells chalepin treated cells when compared with control. The protein expressions of caspase-8, 9 and cleaved PARP1 were upregulated which correlated well with increased caspase-3 activity.
SIGNIFICANCE: From our recent findings, chalepin was able to induced apoptosis in MCF7 cells and therefore, could be evaluated further as a potential source of anticancer agent for cancer treatment such as breast cancer.

Matched MeSH terms: Furocoumarins/pharmacology*
Evaluation of the antihyperlipidemic, anti-inflammatory, analgesic, and antipyretic activities of ethanolic extract of Ammi majus seeds in albino rats and mice

Koriem KM, Asaad GF, Megahed HA, Zahran H, Arbid MS

Int J Toxicol, 2012 Jun;31(3):294-300.
PMID: 22550046 DOI: 10.1177/1091581812440889

Pharmacological and biochemical studies on the Ammi majus seeds L. (family Umbelliferae) grown in Egypt are limited. Furocoumarins are the major constituents in the plant seeds. In the present study, the evaluation of the antihyperlipidemic, anti-inflammatory, analgesic, and antipyretic activities on albino rats and mice was done. After 2 months of administration, both the doses (50 and 100 mg/kg body weight [bwt], respectively) of the alcoholic extract of the A. majus seed result in a significant decrease in the concentrations of cholesterol, triglycerides, and low-density lipoprotein and increase in the concentration of high-density lipoprotein. The extract was found to inhibit the rat paw edema at both the doses, which means that it exerts a significant anti-inflammatory activity compared with control-untreated groups at the intervals of 30 and 60 minutes posttreatment. The antipyretic effect of the extract was quite obvious; it showed that 100 mg/kg bwt was more potent in lowering body temperature starting after 1 hour of treatment than the lower dose (50 mg/kg bwt). It is worth to mention that the A. majus extract with its coumarin contents as well as the tested biological activities of the plant was investigated for the first time in the current study. In conclusion, ethanolic extract of the A. majus seeds had antihyperlipidemic, anti-inflammatory, analgesic, and antipyretic activities that are dose dependant.

Matched MeSH terms: Furocoumarins/analysis; Furocoumarins/therapeutic use
Synthesis of furocoumarin-stilbene hybrids as potential multifunctional drugs against multiple biochemical targets associated with Alzheimer's disease

Agbo EN, Gildenhuys S, Choong YS, Mphahlele MJ, More GK

Bioorg Chem, 2020 08;101:103997.
PMID: 32554280 DOI: 10.1016/j.bioorg.2020.103997

A series of furocoumarin-stilbene hybrids has been synthesized and evaluated in vitro for inhibitory effect against acetylcholinesterase (AChE), butyrylcholinestarase (BChE), β-secretase, cyclooxygenase-2 (COX-2), and lipoxygenase-5 (LOX-5) activities including free radical-scavenging properties. Among these hybrids, 8-(3,5-dimethoxyphenyl)-4-(3,5-dimethoxystyryl)furochromen-2-one 4h exhibited significant anticholinesterase activity and inhibitory effect against β-secretase, COX-2 and LOX-5 activities. 2,2-Diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity and an in vitro cell-based antioxidant activity assay involving lipopolysaccharide induced reactive oxygen species production revealed that 4h has capability of scavenging free radicals. Molecular docking into AChE, BChE, β-secretase, COX-2 and LOX-5 active sites has also been performed.

Matched MeSH terms: Furocoumarins/chemistry*