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UHPLC-MS/MS standardized extract of Vernonia amygdalina leaf inhibits CYP2C9 and CYP3A4 activities in hepatic cells of control and streptozotocin-induced diabetic rats

Sabbagh BA, Palanirajan VK, Chew YL, Chin JH, Ahmad M, Akowuah GA

Drug Metab Pers Ther, 2024 Dec 01;39(4):231-241.
PMID: 39658558 DOI: 10.1515/dmpt-2024-0005

OBJECTIVES: Vernonia amygdalina Del. is a perennial tropical shrub from Asteraceae. The fresh leaf of V. amygdalina is consumed as a vegetable due to its medicinal and nutritional properties. The present study focused on the quantification of bioactive compounds, luteolin-7-O-glucoside, luteolin-7-O-glucuronide, and 1,5-O-dicaffeoylquinic acid from aqueous leaf extract of V. amygdalina. The study also aims to investigate the effects of the aqueous leaf extract of V. amygdalina on cytochrome P450 2C9 (CYP2C9), and cytochrome P450 3A4 (CYP3A4) in hepatic cells of control and diabetic rats.
METHODS: The quantification of the bioactive compounds was conducted using ultra-high-performance liquid chromatography multiple reactions monitoring tandem mass spectrometry (UHPLC-MS/MS-MRM) technique. The effect of the extract on CYP2C9 and CYP3A4 activities was determined using a fluorometric screening kit according to the manufacturer's instructions.
RESULTS: The three bioactive compounds were detected and quantified in the aqueous leaf extract. Results showed that the content of luteolin-7-O-glucuronide (47 μg/mg) was the highest followed by luteolin-7-O-glucoside (3.5 μg/mg) and 1,5-O-dicaffeoylquinic acid (1.07 μg/mg). The extract showed an inhibitory effect on CYP3A4 and CYP2C9 enzyme activities in control and diabetic rats.
CONCLUSIONS: The UHPLC-MS/MS-MRM method is sensitive and reliable for the quality control of V. amygdalina leaf extract. The inhibitory effect of the extract suggests that concomitant use of V. amygdalina leaf preparations with conventional drugs metabolized and eliminated from the body by CYP3A4 and CYP2C9 enzymes may lead to possible interaction.

Matched MeSH terms: Glucosides/pharmacology; Glucosides/chemistry
Fulltext Some characteristics and functional properties of Chunma (Gastrodia Elata) as a food supplement: A short review

Jaswir, I., Octavianti, F., Lestari, W., Hendri, R., Ahmad, H.

International Food Research Journal, 2017;24(101):0-0.
MyJurnal

Gastrodin elata blume (Tianma in Chinese, Chunma in Korean) is a perennial parasitic herbaceous plant native to Korea, Japan and China (Chae et al., 2008). The plant has recently received very good attention, especially in Korea, due to its excellent health-promoting properties. This plant is reported to have excellent antioxidant, anticancer and anti-inflammatory properties. This paper briefly reviews some characteristics and functional properties of Chunma.

Matched MeSH terms: Glucosides
Fulltext A review on induced mutagenesis of Stevia rebaudiana Bertoni

Chiew, Miao Si, Lai, Kok Song, Sobri Hussein, Janna Ong Abdullah

The Pertanika Journal of Scholarly Research Reviews, 2016;2(3):77-85.
MyJurnal

Stevia rebaudiana Bertoni in the Asteraceae family is commercially valuable and cultivated throughout the world due to the great demand for its steviol glycosides (SGs) contents particularly rebaudioside A. Previous studies confirmed that maximal content of SGs in stevia was achieved at or just before flowering, and delayed flowering with long days provide longer duration for steviol glycosides accumulation. However, there is no suitable stevia variety to be cultivated in Malaysia due to her short day length. Mutation induction, including gamma irradiation, had been shown to be useful for generating genetic variations as well as developing new plant varieties from which desired mutants were successfully selected. The use of mutagens, both physical and chemical, has helped in creating mutants that expressed the selected desirable traits. This paper presents some selected essential data available in extant scientific studies on stevia with the focus on application of gamma irradiation on stevia. Both established achievements and recent publications of gamma radiation on stevia were reviewed. Emphasis is on the exceptional potential of stevia through induced mutation approach especially by using gamma rays.

Matched MeSH terms: Glucosides
Comparative secondary metabolites profiling and biological activities of aerial, stem and root parts of Salvadora oleoides decne (Salvadoraceae)

Saleem H, Ahmad I, Zengin G, Mahomoodally FM, Rehman Khan KU, Ahsan HM, et al.

Nat Prod Res, 2020 Dec;34(23):3373-3377.
PMID: 30678488 DOI: 10.1080/14786419.2018.1564299

In this study, different parts (aerial, stem and root) of Salvadora oleoides Decne were investigated in order to explore their phytochemical composition and biological potential. The bioactive contents were evaluated by conventional spectrophotometric methods. Additionally, the secondary metabolite compounds were identified by UHPLC-MS analysis. Biological potential was evaluated by determining antioxidant (DPPH, FRAP, and Phosphomolybdenum) and enzyme inhibitory (butrylcholinesterase and lipoxygenase) effects. Higher total bioactive contents were found in methanolic extracts which tend to correlate with higher radical scavenging and reducing potential of these extracts. LC/MS spectrum revealed the presence of 16 different secondary metabolites belonging to terpene, glucoside and sesquiterpenoid dervivatives. Glucocleomin and emotin A were the main compounds present in all three parts. The strongest butrylcholinesterase and lipoxygenase inhibitory activity was observed for root and stem DCM extracts. Demonstrated biological potential of S. oleoides plant can trace a new road map for developing newly designed bioactive pharmaceuticals.

Matched MeSH terms: Glucosides
Fulltext De novo transcriptome dataset of Stevia rebaudiana accession MS007

Samsulrizal NH, Khadzran KS, Shaarani SH, Noh AL, Sundram TC, Naim MA, et al.

Data Brief, 2020 Feb;28:104811.
PMID: 31871974 DOI: 10.1016/j.dib.2019.104811

Stevia rebaudiana (S. rebaudiana) is a herbaceous and perennial plant belonging to Asteraceae family. The genus stevia is well known as a natural producer of sweetener comprising non-caloric and non-carcinogenic steviol glycosides. In recent years, the capability in producing natural sweetner has increased the demand for S. rebaudiana as substitute of processed sugars. Flowering phase of S. rebaudiana has shown to affect the content of steviol glycosides in the leaves. Steviol glycosides level is the highest at the time of flower bud formation and lowest at time preceding and following flower bud formation. Therefore, sequencing and analysing the genes that are involved in flowering phase will provide platform for gene manipulation in increasing steviol glycosides content. The Stevia transcriptome data that include two stages of growth (before flowering and after flowering), were obtained using Illumina RNA-seq technology and can be accessed at NCBI Sequence Read Archive under Accession No. SRX6362785 and SRX6362784.

Matched MeSH terms: Glucosides
Fulltext Alterations in Herbage Yield, Antioxidant Activities, Phytochemical Contents, and Bioactive Compounds of Sabah Snake Grass (Clinacanthus Nutans L.) with Regards to Harvesting Age and Harvesting Frequency

Abd Samat NMA, Ahmad S, Awang Y, Bakar RAH, Hakiman M

Molecules, 2020 Jun 19;25(12).
PMID: 32575450 DOI: 10.3390/molecules25122833

Sabah snake grass or Clinacanthus nutans has drawn public interest having significant economic benefits attributable to the presence of phytochemicals and several interesting bioactive constituents that may differ according to harvesting age and harvesting frequency. The current study was aimed to evaluate the effect of harvesting age and harvesting frequency towards herbal yield, antioxidant activities, phytochemicals synthesis, and bioactive compounds of C. nutans. A factorial randomized completely block design with five replications was used to illustrate the relationship between herbal yield, DPPH (2, 2-diphenyl-1-picrylhydrazyl) and ferric reducing antioxidant power (FRAP) assays, total phenolic and flavonoid content affected by harvesting age (week 8, 12, and 16 after transplanting), and harvesting frequency (harvest 1, 2, and 3). The bioactive compounds by HPLC were also determined to describe the interaction effect between both harvesting age and harvesting frequency. The yield, antioxidant activities, and phytochemical contents were gradually increased as the plant grew, with the highest recorded during week 16. However, the synthesis and activities of phytochemicals were reduced in subsequent harvests despite the increment of the herbal yield. All bioactive compounds were found to be influenced insignificantly and significantly by harvesting age and harvesting frequency, respectively, specifically to shaftoside, iso-orientin, and orientin. Among all constituents, shaftoside was the main compound at various harvesting ages and harvesting frequencies. These results indicated that harvesting at week 16 with 1st harvest frequency might enhance the yield while sustaining the high synthesis of polyphenols and antioxidant activities of C. nutans.

Matched MeSH terms: Glucosides
Fulltext Textural and rheological properties of stevia ice cream

Pon, S.Y., Lee, W.J., Chong, G.H.

International Food Research Journal, 2015;22(4):1544-1549.
MyJurnal

Ice cream contains high sugar content and therefore it is in contradiction with the concept of healthy diet. The objective of this study is to determine the suitability of using stevia as an alternative natural sweetener in making ice cream. In- house ice cream formulation (as the control) and three different concentrations of stevia ice cream formulations of (A, B and C) were used. Physical properties of the ice cream such as the overrun, total soluble solid, meltdown rate, rheology, and textural properties were evaluated. All ice cream samples exhibited a nonNewtonian flow with pseudoplastic behavior. Stevia ice cream has a lower melting rate and has a higher sustainability. The power law also showed that apparent viscosities of stevia ice cream were higher. Therefore, stevia can be used as a natural sugar substitute in ice cream production.

Matched MeSH terms: Glucosides
A systematic review of the protective role of swertiamarin in cardiac and metabolic diseases

Leong XY, Thanikachalam PV, Pandey M, Ramamurthy S

Biomed Pharmacother, 2016 Dec;84:1051-1060.
PMID: 27780133 DOI: 10.1016/j.biopha.2016.10.044

BACKGROUND: Swertiamarin, is a secoiridoid glycoside found in genera of Enicostemma Species (Enicostemma littorale and Enicostemma axillare) belonging to the family of gentianaceae, which has been reported to cure many diseases such as diabetes, hypertension, atherosclerosis, arthritis, malaria and abdominal ulcers. However, to the best of our knowledge, till date systematic studies to understand the molecular basis of cardiac and metabolic disease preventing properties of swertiamarin has not been reported.
AIM OF THE REVIEW: The present review aims to compile an up-to-date information on the progress made in the protective role of swertiamarin in cardiac and metabolic diseases with the objective of providing a guide for future research on this bioactive molecule.
MATERIALS AND METHODS: Information on the swertiamarin was collected from major scientific databases (Pubmed, Springer, google scholar, and Web of Science) for publication between1974-2016. In this review, the protective role of swertiamarin on cardiac and metabolic diseases was discussed.
RESULTS: Swertiamarin reported to exhibit a wide range of biological activities such as anti-atherosclerotic, antidiabetic, anti-inflammatory and antioxidant effects. These activities were mainly due to its effect on various signaling pathways associated with cardiac remodeling events such as inhibition of NF-kB expression, LDL oxidation, apoptosis, inflammatory and lipid peroxidation markers and stimulation of antioxidant enzymes.
CONCLUSION: Sweriamarin exhibit a wide range of biological activities. This review presents evidence supporting the point of view that swertiamarin should be considered a potential therapeutic agent against cardiac and metabolic diseases, giving rise to novel applications in their prevention and treatment.

Matched MeSH terms: Iridoid Glucosides/adverse effects; Iridoid Glucosides/pharmacokinetics; Iridoid Glucosides/therapeutic use*
Gneyulins A and B, stilbene trimers, and noidesols A and B, dihydroflavonol-C-glucosides, from the bark of Gnetum gnemonoides

Shimokawa Y, Akao Y, Hirasawa Y, Awang K, Hadi AH, Sato S, et al.

J Nat Prod, 2010 Apr 23;73(4):763-7.
PMID: 20192242 DOI: 10.1021/np9007987

Gneyulins A (1) and B (2), two new stilbene trimers consisting of oxyresveratrol constituent units, and noidesols A (3) and B (4), two new dihydroflavonol-C-glucosides, were isolated from the bark of Gnetum gnemonoides. The structures and configurations of 1-4 were elucidated on the basis of 2D NMR correlations and X-ray analysis. Gneyulins A (1) and B (2) showed inhibition of Na(+)-glucose transporters (SGLT-1 and SGLT-2).

Matched MeSH terms: Glucosides/isolation & purification*; Glucosides/pharmacology; Glucosides/chemistry
A labdane diterpene glucoside from the rhizomes of Curcuma mangga

Abas F, Lajis NH, Shaari K, Israf DA, Stanslas J, Yusuf UK, et al.

J Nat Prod, 2005 Jul;68(7):1090-3.
PMID: 16038556

A new labdane diterpene glucoside, curcumanggoside (1), together with nine known compounds, including labda-8(17),12-diene-15,16-dial (2), calcaratarin A (3), zerumin B (4), scopoletin, demethoxycurcumin, bisdemethoxycurcumin, 1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one, curcumin, and p-hydroxycinnamic acid, have been isolated from the rhizomes of Curcuma mangga. Their structures were determined using a combination of 1D (1H NMR, 13C NMR, DEPT) and 2D (COSY, HSQC, HMBC) NMR techniques. All diarylheptanoids and scopoletin showed significant antioxidant activity. Zerumin B, demethoxycurcumin, bisdemethoxycurcumin, and curcumin also exhibited cytotoxic activity against a panel of five human tumor cell lines.

Matched MeSH terms: Glucosides/isolation & purification*; Glucosides/pharmacology; Glucosides/chemistry
Fulltext Optimization of Pluchea indica (L.) leaf extract using ultrasound-assisted extraction and its cytotoxicity on the HT-29 colorectal cancer cell line

Aishah Baharuddin S, Nadiah Abd Karim Shah N, Saiful Yazan L, Abd Rashed A, Kadota K, Al-Awaadh AM, et al.

Ultrason Sonochem, 2023 Dec;101:106702.
PMID: 38041881 DOI: 10.1016/j.ultsonch.2023.106702

Colorectal cancer (CRC) is the most common malignancy and the third primary cause of cancer-related mortalities caused by unhealthy diet, hectic lifestyle, and genetic damage. People aged ≥ 50 are more at risk for CRC. Nowadays, bioactive compounds from plants have been widely studied in preventing CRC because of their anticancer and antioxidant properties. Herein, ultrasound-assisted extraction (UAE) was used to extract the bioactive compounds of Pluchea indica (L.) leaves. The resultant total phenolic content (TPC) and total flavonoid content (TFC) of P. indica (L.) leaves were analyzed using a response surface methodology (RSM). The central composite design was implemented to evaluate the amplitude (10 %-70 %) and treatment time (2-10 min) on both responses, i.e., TPC and TFC of P. indica (L.) leaves. The optimum UAE conditions were observed 40 % amplitude and 6 min of treatment, where the TPC and TFC were 3.26 ± 0.00 mg GAE/g d.w. and 67.58 ± 1.46 mg QE/g d.w., respectively. The optimum P. indica (L.) leaf extract was then screened for its cytotoxicity on the HT-29 colorectal cancer cell line. This extract had strong cytotoxicity with a half-maximal inhibitory concentration value (IC50) of 12 µg/mL. The phytochemical screening of bioactive compounds revealed that the optimal P. indica (L.) leaf extract contains flavonoids, namely, kaempferol 3-[2''',3''',5'''-triacetyl]-alpha-L-arabinofuranosyl-(1->6)-glucoside, myricetin 3-glucoside-7-galactoside, quercetin 3-(3''-sulfatoglucoside), and kaempferol 7,4'-dimethyl ether 3-O-sulfate, which could be good sources for promising anticancer agents. This study employs the RSM approach to utilize UAE for bioactive compounds extraction of P. indica (L.) leaves, identified the specific compounds present in the optimized extract and revealed its potential in preventing CRC.

Matched MeSH terms: Glucosides
Fulltext Stachytarpheta jamaicensis (L.) Vahl: From Traditional Usage to Pharmacological Evidence

Liew PM, Yong YK

Evid Based Complement Alternat Med, 2016;2016:7842340.
PMID: 26925152 DOI: 10.1155/2016/7842340

Introduction. Stachytarpheta jamaicensis (L.) Vahl belongs to the family of Verbenaceae and is commonly known as Gervao, Brazilian tea, verbena cimarrona, rooter comb, or blue porter weed. It is one of the important plants with high medicinal and nutraceutical benefits. S. jamaicensis contains various medicinal properties in traditional and folk medicinal systems, with cures for several diseases. Objective. The objective of this review paper is to collect information concerning the morphology, distribution, traditional usage, phytochemical compositions, biological activities, and safety data of S. jamaicensis. Materials and Methods. The information was obtained from literature search through electronic databases such as PubMed and Google Scholar on S. jamaicensis. Results and Conclusion. The high medicinal properties of this plant, for instance, antimicrobial and antifungal effect as the main activities, but verbascoside as the main active chemical component, make it a valuable source of the medicinal compound. This review paper summarizes all information concerning the morphology, distribution, traditional usage, phytochemical compositions, pharmacological activities, and toxicological studies of S. jamaicensis.

Matched MeSH terms: Glucosides
Secondary metabolites from endemic species Iris adriatica Trinajstić ex Mitić (Iridaceae)

Bukvički D, Novaković M, Ab Ghani N, Marin PD, Asakawa Y

Nat Prod Res, 2018 Aug;32(15):1849-1852.
PMID: 29126369 DOI: 10.1080/14786419.2017.1402309

This manuscript describes the first detailed chemical investigation of endemic species Iris adriatica, including isolation and structure elucidation. Chemical analyses of the rhizome CH2Cl2/MeOH (2:1) extract revealed fourteen secondary metabolites, mainly isoflavonoids. Among isoflavonoids, two groups have been found: nigricin-type and tectorigenin-type. Dominant group of the isolated compounds has been nigricin-type isoflavones: nigricin, nigricin-4'-(1-O-β-D-glucopyranoside) and nigricin-4'-(1-O-β-D-glucopyranosyl (1-6)-β-D-glucopyranoside) with 2.5, 10 and 1% of the total extract, respectively. Irisxanthone - xanthone C-glucoside, β-sitosterol, benzophenone and one of its derivatives have also been found. Nigricin-type isoflavonoids and irisxanthone can be considered as possible chemotaxonomic markers for I. adriatica. 5,3',5'-Trimethoxy-6,7-methylenedioxyisoflavone-4'-(1-O-β-D-glucopyranoside) and benzophenone have been isolated from Iris species for the first time.

Matched MeSH terms: Glucosides/chemistry
Hydrogen bonds in galactopyranoside and glucopyranoside: a density functional theory study

Mosapour Kotena Z, Behjatmanesh-Ardakani R, Hashim R, Manickam Achari V

J Mol Model, 2013 Feb;19(2):589-99.
PMID: 22972691 DOI: 10.1007/s00894-012-1576-z

Density functional theory calculations on two glycosides, namely, n-octyl-β-D-glucopyranoside (C(8)O-β-Glc) and n-octyl-β-D-galactopyranoside (C(8)O-β-Gal) were performed for geometry optimization at the B3LYP/6-31G level. Both molecules are stereoisomers (epimers) differing only in the orientation of the hydroxyl group at the C4 position. Thus it is interesting to investigate electronically the effect of the direction (axial/equatorial) of the hydroxyl group at the C4 position. The structure parameters of X-H∙∙∙Y intramolecular hydrogen bonds were analyzed, while the nature of these bonds and the intramolecular interactions were considered using the atoms in molecules (AIM) approach. Natural bond orbital analysis (NBO) was used to determine bond orders, charge and lone pair electrons on each atom and effective non-bonding interactions. We have also reported electronic energy and dipole moment in gas and solution phases. Further, the electronic properties such as the highest occupied molecular orbital, lowest unoccupied molecular orbital, ionization energy, electron affinity, electronic chemical potential, chemical hardness, softness and electrophilicity index, are also presented here for both C(8)O-β-Glc and C(8)O-β-Gal. These results show that, while C(8)O-β-Glc possess- only one hydrogen bond, C(8)O-β-Gal has two intramolecular hydrogen bonds, which further confirms the anomalous stability of the latter in self-assembly phenomena.

Matched MeSH terms: Glucosides/chemistry*
Atomistic simulation studies of the α/β-glucoside and galactoside in anhydrous bilayers: effect of the anomeric and epimeric configurations

Ahmadi S, Manickam Achari V, Nguan H, Hashim R

J Mol Model, 2014 Mar;20(3):2165.
PMID: 24623320 DOI: 10.1007/s00894-014-2165-0

Fully atomistic molecular dynamics simulation studies of thermotropic bilayers were performed using a set of glycosides namely n-octyl-β-D-glucopyranoside (β-C8Glc), n-octyl-α-D-glucopyranoside (α-C8Glc), n-octyl-β-D-galactopyranoside (β-C8Gal), and n-octyl-α-D-galactopyranoside (α-C8Gal) to investigate the stereochemical relationship of the epimeric/anomeric quartet liner glycolipids with the same octyl chain group. The results showed that, the anomeric stereochemistry or the axial/equatorial orientation of C1-O1 (α/β) is an important factor controlling the area and d-spacing of glycolipid bilayer systems in the thermotropic phase. The head group tilt angle and the chain ordering properties are affected by the anomeric effect. In addition, the L(C) phase of β-C8Gal, is tilting less compared to those in the fluid L(α). The stereochemistry of the C4-epimeric (axial/equatorial) and anomeric (α/β) centers simultaneously influence the inter-molecular hydrogen bond. Thus, the trend in the values of the hydrogen bond for these glycosides is β-C8Gal > α-C8Glc > β-C8Glc > α-C8Gal. The four bilayer systems showed anomalous diffusion behavior with an observed trend for the diffusion coefficients; and this trend is β-C8Gal > β-C8Glc > α-C8Gal > α-C8Glc. The "bent" configuration of the α-anomer results in an increase of the hydrophobic area, chain vibration and chain disorganization. Since thermal energy is dispensed more entropically for the chain region, the overall molecular diffusion decreases.

Matched MeSH terms: Glucosides/chemistry*
Antiviral properties of ent-labdene diterpenes of Andrographis paniculata nees, inhibitors of herpes simplex virus type 1

Wiart C, Kumar K, Yusof MY, Hamimah H, Fauzi ZM, Sulaiman M

Phytother Res, 2005 Dec;19(12):1069-70.
PMID: 16372376

Andrographolide, neoandrographolide and 14-deoxy-11,12-didehydroandrographolide, ent-labdene diterpenes isolated from Andrographis paniculata showed viricidal activity against herpes simplex virus 1 (HSV-1). None of these compounds exhibited significant cytotoxicity at viricidal concentrations.

Matched MeSH terms: Glucosides/pharmacology
Molecular dynamics simulation of monoalkyl glycoside micelles in aqueous solution: influence of carbohydrate headgroup stereochemistry

Chong TT, Hashim R, Bryce RA

J Phys Chem B, 2006 Mar 16;110(10):4978-84.
PMID: 16526739

Comparative molecular dynamics simulations of n-octyl-beta-D-galactopyranoside (beta-C8Gal) and n-octyl-beta-D-glucopyranoside (beta-C8Glc) micelles in aqueous solution have been performed to explore the influence of carbohydrate stereochemistry on glycolipid properties at the atomic level. In particular, we explore the hypothesis that differences in T(m) and T(c) for beta-C8Gal and beta-C8Glc in lyotropic systems arise from a more extensive hydrogen bonding network between beta-C8Gal headgroups relative to beta-C8Glc, due to the axial 4-OH group in beta-C8Gal. Good agreement of the 13 ns micelle-water simulations with available experimental information is found. The micelles exhibit a similar shape, size, and degree of exposed alkyl chain surface area. We find net inter- and intra-headgroup hydrogen bonding is also similar for beta-C8Gal and beta-C8Glc, although n-octyl-beta-D-galactopyranoside micelles do exhibit a slightly greater degree of inter- and intra-headgroup hydrogen bonding. However, the main distinction in the calculated microscopic behavior of beta-C8Glc and beta-C8Gal micelles lies in solvent interactions, where beta-d-glucosyl headgroups are considerably more solvated (mainly at the equatorial O4 oxygen). These results agree with preceding theoretical and experimental studies of monosaccharides in aqueous solution. A number of long water residence times are found for solvent surrounding both micelle types, the largest of which are associated with surface protrusions involving headgroup clusters. Our simulations, therefore, predict differences in hydrogen bonding for the two headgroup stereochemistries, including a small difference in inter-headgroup interactions, which may contribute to the higher T(m) and T(c) values of beta-C8Gal surfactants relative to beta-C8Glc in lyotropic systems.

Matched MeSH terms: Glucosides/chemistry
Thermo-kinetics of lipase-catalyzed synthesis of 6-O-glucosyldecanoate

Gumel AM, Annuar MS, Heidelberg T, Chisti Y

Bioresour Technol, 2011 Oct;102(19):8727-32.
PMID: 21816608 DOI: 10.1016/j.biortech.2011.07.024

Lipase-catalyzed synthesis of 6-O-glucosyldecanoate from d-glucose and decanoic acid was performed in dimethyl sulfoxide (DMSO), a mixture of DMSO and tert-butanol and tert-butanol alone with a decreasing order of polarity. The highest conversion yield (> 65%) of decanoic acid was obtained in the blended solvent of intermediate polarity mainly because it could dissolve relatively large amounts of both the reactants. The reaction obeyed Michaelis-Menten type of kinetics. The affinity of the enzyme towards the limiting substrate (decanoic acid) was not affected by the polarity of the solvent, but increased significantly with temperature. The esterification reaction was endothermic with activation energy in the range of 60-67 kJ mol⁻¹. Based on the Gibbs energy values, in the solvent blend of DMSO and tert-butanol the position of the equilibrium was shifted more towards the products compared to the position in pure solvents. Monoester of glucose was the main product of the reaction.

Matched MeSH terms: Glucosides/chemical synthesis*
Fulltext Bioconversion of rebaudioside I from rebaudioside A

Prakash I, Bunders C, Devkota KP, Charan RD, Ramirez C, Snyder TM, et al.

Molecules, 2014 Oct 28;19(11):17345-55.
PMID: 25353385 DOI: 10.3390/molecules191117345

To supply the increasing demand of natural high potency sweeteners to reduce the calories in food and beverages, we have looked to steviol glycosides. In this work we report the bioconversion of rebaudioside A to rebaudioside I using a glucosyltransferase enzyme. This bioconversion reaction adds one sugar unit with a 1→3 linkage. We utilized 1D and 2D NMR spectroscopy (1H, 13C, COSY, HSQC-DEPT, HMBC, 1D TOCSY and NOESY) and mass spectral data to fully characterize rebaudioside I.

Matched MeSH terms: Glucosides/metabolism
Fulltext Analysis of the anticancer phytochemicals in Andrographis paniculata Nees. under salinity stress

Talei D, Valdiani A, Maziah M, Sagineedu SR, Saad MS

Biomed Res Int, 2013;2013:319047.
PMID: 24371819 DOI: 10.1155/2013/319047

Salinity causes the adverse effects in all physiological processes of plants. The present study aimed to investigate the potential of salt stress to enhance the accumulation of the anticancer phytochemicals in Andrographis paniculata accessions. For this purpose, 70-day-old plants were grown in different salinity levels (0.18, 4, 8, 12, and 16 dSm(-1)) on sand medium. After inducing a period of 30-day salinity stress and before flowering, all plants were harvested and the data on morphological traits, proline content and the three anticancer phytochemicals, including andrographolide (AG), neoandrographolide (NAG), and 14-deoxy-11,12-didehydroandrographolide (DDAG), were measured. The results indicated that salinity had a significant effect on the aforementioned three anticancer phytochemicals. In addition, the salt tolerance index (STI) was significantly decreased, while, except for DDAG, the content of proline, the AG, and NAG was significantly increased (P ≤ 0.01). Furthermore, it was revealed that significant differences among accessions could happen based on the total dry weight, STI, AG, and NAG. Finally, we noticed that the salinity at 12 dSm(-1) led to the maximum increase in the quantities of AG, NAG, and DDAG. In other words, under salinity stress, the tolerant accessions were capable of accumulating the higher amounts of proline, AG, and NAG than the sensitive accessions.

Matched MeSH terms: Glucosides/administration & dosage

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