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Fulltext Identification of 5-Methoxy-2-(Diformylmethylidene)-3,3-Dimethylindole as an Anti-Influenza A Virus Agent

Tan MC, Wong WY, Ng WL, Yeo KS, Mohidin TB, Lim YY, et al.

PLoS One, 2017;12(1):e0170352.
PMID: 28114392 DOI: 10.1371/journal.pone.0170352

Influenza virus is estimated to cause 3-5 million severe complications and about 250-500 thousand deaths per year. Different kinds of anti-influenza virus drugs have been developed. However, the emergence of drug resistant strains has presented a big challenge for efficient antiviral therapy. Indole derivatives have been shown to exhibit both antiviral and anti-inflammatory activities. In this study, we adopted a cell-based system to screen for potential anti-IAV agents. Four indole derivatives (named 525A, 526A, 527A and 528A) were subjected to the antiviral screening, of which 526A was selected for further investigation. We reported that pre-treating cells with 526A protects cells from IAV infection. Furthermore, 526A inhibits IAV replication by inhibiting the expression of IAV genes. Interestingly, 526A suppresses the activation of IRF3 and STAT1 in host cells and thus represses the production of type I interferon response and cytokines in IAV-infected cells. Importantly, 526A also partially blocks the activation of RIG-I pathway. Taken together, these results suggest that 526A may be a potential anti-influenza A virus agent.
Structural approaches for the DNA binding motifs prediction in Bacillus thuringiensis sigma-E transcription factor (σETF)

Lim YY, Lim TS, Choong YS

J Mol Model, 2019 Sep 05;25(10):301.
PMID: 31486892 DOI: 10.1007/s00894-019-4192-3

The sigma-E transcription factor (σETF) can be found in most of the bacteria cells including Bacillus thuringiensis. However, the cellular regulatory mechanisms of these transcription factors in the mass production of δ-endotoxins during sporulation stage are yet to be revealed. In addition, the recognition of DNA towards σETF DNA binding motifs that led to the transcription activities is also being poorly studied. Therefore, this work studied the possible DNA binding motifs of σETF by utilising in silico approaches. The structure of σETF was first built via three different computational methods. A cognate DNA sequence was then docked to the predicted σETF DNA-binding motifs. The binding free energy calculated using molecular mechanics/Poisson-Boltzmann surface area (MM-PBSA) for triplicate 50 ns simulation of σETF-DNA complex revealed favourable binding energy of DNA to σETF (average ∆Gbind = -34.57 kcal/mol) mainly driven by non-polar interactions. This study revealed that σETF LYS131, ARG133, PHE138, TRP146, ARG222, LYS225 and ARG226 are most likely the key residues upon the binding and recognition of DNA prior to transcription actives. Since determination of genome-regulating protein which recognises specific DNA sequence is important to discriminate between the proteins preferences for different genes, this study might provide some understanding on the possible σETF-DNA recognition prior to transcription initiated for the δ-endotoxins production.
Extraction methods of butterfly pea (Clitoria ternatea) flower and biological activities of its phytochemicals

Jeyaraj EJ, Lim YY, Choo WS

J Food Sci Technol, 2021 Jun;58(6):2054-2067.
PMID: 33967304 DOI: 10.1007/s13197-020-04745-3

Clitoria ternatea or commonly known as 'Butterfly pea' has been used traditionally in Ayurvedic medicine in which various parts of the plants are used to treat health issues such as indigestion, constipation, arthritis, skin diseases, liver and intestinal problems. The flowers of C. ternatea are used worldwide as ornamental flowers and traditionally used as a food colorant. This paper reviews the recent advances in the extraction and biological activities of phytochemicals from C. ternatea flowers. The application of maceration or ultrasound assisted extraction greatly increased the yield (16-247% of increase) of phytochemicals from C. ternatea flowers. Various phytochemicals such as kaempferol, quercetin and myricetin glycosides as well as anthocyanins have been isolated from C. ternatea flowers. Clitoria ternatea flower extracts were found to possess antimicrobial, antioxidant, anti-inflammatory, cytotoxic and antidiabetic activities which are beneficial to human health. Clitoria ternatea flower is a promising candidate for functional food applications owing to its wide range of pharmacotherapeutic properties as well as its safety and effectiveness.
Enzymatic synthesis of quercetin oleate esters using Candida antarctica lipase B

Saik AY, Lim YY, Stanslas J, Choo WS

Biotechnol Lett, 2017 Feb;39(2):297-304.
PMID: 27812823 DOI: 10.1007/s10529-016-2246-5

OBJECTIVES: To investigate the lipase-catalyzed acylation of quercetin with oleic acid using Candida antarctica lipase B.
RESULTS: Three acylated analogues were produced: quercetin 4'-oleate (C33H42O8), quercetin 3',4'-dioleate (C51H74O9) and quercetin 7,3',4'-trioleate (C69H106O10). Their identities were confirmed with UPLC-ESI-MS and (1)H NMR analyses. The effects of temperature, duration and molar ratio of substrates on the bioconversion yields varied across conditions. The regioselectivity of the acylated quercetin analogues was affected by the molar ratio of substrates. TLC showed the acylated analogues had higher lipophilicity (152% increase) compared to quercetin. Partition coefficient (log P) of quercetin 4'-oleate was higher than those of quercetin and oleic acid. Quercetin 4'-oleate was also stable over 28 days of storage.
CONCLUSIONS: Quercetin oleate esters with enhanced lipophilicity can be produced via lipase-catalyzed reaction using C. antarctica lipase B to be used in topical applications.
Fulltext Antioxidant, cytotoxic, and antibacterial activities of Clitoria ternatea flower extracts and anthocyanin-rich fraction

Jeyaraj EJ, Lim YY, Choo WS

Sci Rep, 2022 09 01;12(1):14890.
PMID: 36050436 DOI: 10.1038/s41598-022-19146-z

Clitoria ternatea flower is a traditional medicinal herb that has been used as a natural food colourant. As there are limited studies on investigating the bioactivities of the anthocyanin-rich fraction of Clitoria ternatea flower, this study aimed to determine an efficient column chromatography method to obtain the anthocyanin-rich fraction from this flower and characterise its composition, antioxidant, antibacterial, and cytotoxic activities. Amberlite XAD-16 column chromatography was more efficient in enriching the total anthocyanin content (TAC) of the fraction with the highest TAC to total phenolic content (TPC) ratio of 1:6 than that using C18-OPN. A total of 11 ternatin anthocyanins were characterised in the anthocyanin-rich fraction by LC-MS analysis. The antioxidant activity of the anthocyanin-rich fraction was more potent in the chemical-based assay with an IC50 value of 0.86 ± 0.07 mg/mL using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay than cellular antioxidant assay using RAW 264.7 macrophages. In vitro cytotoxicity assay using human embryonic kidney HEK-293 cell line showed the anthocyanin-rich fraction to be more toxic than the crude extracts. The anthocyanin-rich fraction had more potent antibacterial activity than the crude extracts against Bacillus cereus, Bacillus subtilis, and Escherichia coli. The anthocyanin-rich fraction of C. ternatea has the potential to be used and developed as a functional food ingredient or nutraceutical agent.
Fulltext Sources and relative stabilities of acylated and nonacylated anthocyanins in beverage systems

Vidana Gamage GC, Lim YY, Choo WS

J Food Sci Technol, 2022 Mar;59(3):831-845.
PMID: 35185195 DOI: 10.1007/s13197-021-05054-z

Anthocyanins are considered as the largest group of water-soluble pigments found in the vacuole of plant cells, displaying range of colors from pink, orange, red, purple and blue. They belong to flavonoids, a polyphenolic subgroup. Application of anthocyanins in food systems as natural food colourants is limited due to the lack of stability under different environmental conditions such as light, pH, heat etc. Anthocyanins esterified with one or more acid groups are referred as acylated anthocyanins. Based on the presence or absence of acyl group, anthocyanins are categorized as acylated and nonacylated anthocyanins. Acylated anthocyanins are further classified as mono, di, tri, tetra acylated anthocyanins according to the number of acyl groups present in the anthocyanin. This review classifies common anthocyanin sources into non-acylated, mono-, di-, tri- and tetra-acylated anthocyanins based on the major anthocyanins present in these sources. The relative stabilities of these anthocyanins with respect to thermal, pH and photo stress in beverage systems are specifically discussed. Common anthocyanin sources such as elderberry, blackberry, and blackcurrant mainly contain nonacylated anthocyanins. Red radish, purple corn, black carrot also mainly contain mono acylated anthocyanins. Red cabbage and purple sweet potato have both mono and diacylated anthocyanins. Poly acylated anthocyanins show relatively higher stability compared with nonacylated and monoacylated anthocyanins. Several techniques such as addition of sweeteners, co-pigmentation and acylation techniques could enhance the stability of nonacylated anthocyanins. Flowers are main sources of polyacylated anthocyanins having higher stability, yet they have not been commercially exploited for their anthocyanins.
Fulltext Anthocyanins From Clitoria ternatea Flower: Biosynthesis, Extraction, Stability, Antioxidant Activity, and Applications

Vidana Gamage GC, Lim YY, Choo WS

Front Plant Sci, 2021;12:792303.
PMID: 34975979 DOI: 10.3389/fpls.2021.792303

Clitoria ternatea plant is commonly grown as an ornamental plant and possesses great medicinal value. Its flower is edible and also known as blue pea or butterfly pea flower. The unique feature of anthocyanins present in blue pea flowers is the high abundance of polyacylated anthocyanins known as ternatins. Ternatins are polyacylated derivatives of delphinidin 3,3',5'-triglucoside. This review covers the biosynthesis, extraction, stability, antioxidant activity, and applications of anthocyanins from Clitoria ternatea flower. Hot water extraction of dried or fresh petals of blue pea flower could be employed successfully to extract anthocyanins from blue pea flower for food application. Blue pea flower anthocyanins showed good thermal and storage stability, but less photostability. Blue pea flower anthocyanins also showed an intense blue colour in acidic pH between pH 3.2 to pH 5.2. Blue pea flower anthocyanin extracts demonstrate significant in vitro and cellular antioxidant activities. Blue pea flower anthocyanins could be used as a blue food colourant in acidic and neutral foods. The incorporation of blue pea flower anthocyanins in food increased the functional properties of food such as antioxidant and antimicrobial properties. Blue pea flower anthocyanins have also been used in intelligent packaging. A comparison of blue pea flower anthocyanins with two other natural blue colouring agents used in the food industry, spirulina or phycocyanin and genipin-derived pigments is also covered. Anthocyanins from blue pea flowers are promising natural blue food colouring agent.
Fulltext Antiproliferative activity of Vallaris glabra Kuntze (Apocynaceae)

Wong SK, Lim YY, Ling SK, Chiang Chan EW

Pharmacogn Mag, 2014 Apr;10(Suppl 2):S232-9.
PMID: 24991097 DOI: 10.4103/0973-1296.133238

Our earlier study on the antiproliferative (APF) activity of leaf extracts of ten Apocynaceae species showed that leaves of Vallaris glabra possessed strong and broad-spectrum properties.
Fulltext Caffeoylquinic acids in leaves of selected Apocynaceae species: Their isolation and content

Wong SK, Lim YY, Ling SK, Chan EW

Pharmacognosy Res, 2014 Jan;6(1):67-72.
PMID: 24497746 DOI: 10.4103/0974-8490.122921

Three compounds isolated from the methanol (MeOH) leaf extract of Vallaris glabra (Apocynaceae) were those of caffeoylquinic acids (CQAs). This prompted a quantitative analysis of their contents in leaves of V. glabra in comparison with those of five other Apocynaceae species (Alstonia angustiloba, Dyera costulata, Kopsia fruticosa, Nerium oleander, and Plumeria obtusa), including flowers of Lonicera japonica (Japanese honeysuckle), the commercial source of chlorogenic acid (CGA).