Acylated glucosylflavones as α-glucosidase inhibitors from Tinospora crispa leaf

Chang, Cheng Fu; Ho, Sheau Ling; Lee, Shoei‐Sheng

doi:10.1016/j.bmc.2015.04.053

Cited by 27 publications

(24 citation statements)

References 39 publications

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“…crispa leaf led to four acylated glycosylflavonoids. Among the isolated compounds, isovitexin 2′′-( E )- p -coumarate ( 206 ) showed the best activity against α -glucosidase with an IC 50 value of 4.3 ± 1.4 μ M [ 146 ].…”

Section: Chemical Constituentsmentioning

confidence: 99%

Genus Tinospora: Ethnopharmacology, Phytochemistry, and Pharmacology

Chi

She

Han

et al. 2016

Evidence-Based Complementary and Alternative Medicine

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The genus Tinospora includes 34 species, in which several herbs were used as traditional medicines by indigenous groups throughout the tropical and subtropical parts of Asia, Africa, and Australia. The extensive literature survey revealed Tinospora species to be a group of important medicinal plants used for the ethnomedical treatment of colds, headaches, pharyngitis, fever, diarrhea, oral ulcer, diabetes, digestive disorder, and rheumatoid arthritis. Indian ethnopharmacological data points to the therapeutic potential of the T. cordifolia for the treatment of diabetic conditions. While Tinospora species are confusing in individual ingredients and their mechanisms of action, the ethnopharmacological history of those plants indicated that they exhibit antidiabetic, antioxidation, antitumor, anti-inflammation, antimicrobial, antiosteoporosis, and immunostimulation activities. While the clinical applications in modern medicine are lacking convincing evidence and support, this review is aimed at summarizing the current knowledge of the traditional uses, phytochemistry, biological activities, and toxicities of the genus Tinospora to reveal its therapeutic potentials and gaps, offering opportunities for future researches.

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Section: Chemical Constituentsmentioning

confidence: 99%

Genus Tinospora: Ethnopharmacology, Phytochemistry, and Pharmacology

Chi

She

Han

et al. 2016

Evidence-Based Complementary and Alternative Medicine

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“…Recently, some potent α-glucosidase inhibitors, such as oxindoles [5] and biscoumarins [6], have been developed. Our study found that isovitexin 2''-(E)-p-coumarate among 17 flavonoids isolated from Tinospora crispa leaf showed the best activity against α-glucosidase with an IC 50 value of 4.3 ± 1.4 µM [7]. The 3′-hydroxylated derivative, however, was much less active (IC 50 35.7 µM).…”

Section: Introductionmentioning

confidence: 71%

“…The 3′-hydroxylated derivative, however, was much less active (IC 50 35.7 µM). Such significant difference was rationalized by molecular dynamic (MD) simulation study on constructed α-glucosidase (AG) model [7]. The good correlation between in vitro assay and MD simulation encouraged us to investigate whether the anti-α-glucosidase proanthocyanidins (Figure 1), isolated from Machilus philippinensis leaf [8], follow such relationship.…”

Section: Introductionmentioning

confidence: 99%

In Silico Docking Analysis of A-type Proanthocyanidins to <i>α</i>-Glucosidase Constructed by Correlation with in Vitro Bioassay

Ho¹,

Lin²,

Tsai³

et al. 2019

JDDMC

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The type A proanthocyanidins (2−8) with (2β→O→7, 4β→8) interflavane linkage, isolated from Machilus philippinensis, have been found to possess inhibitory activity against α-glucosidase (EC 3.2.1.20 from Bacillus stearothermophilus). To rationalize such activity, computer assisted docking of these compounds and the positive control, acarbose, on the conformation model of α-glucosidase (AG), built by using human intestinal maltase glucoamylase as a template, was undertaken in this study. The result showed good correlation between IC 50 values and docking scores, expressed as binding energy (∆G), obtained from London (trimatch)-refinement (forcefield Affinity∆G) mode. Among these isolates, the most potent aesculitannin B (2) (IC 50 3.5 µM) showed the best docking score (∆G-21.48 kcal/mol). Being interested in clarification of structure and activity relationship, virtual screening on the related compounds, including the de-unit III homologs of 2−8 (i.e., nor-series) and additional 13 stereoisomers of the trimeric 2 at the C-2 and C-3 positions of units II and III, was further carried out. This docking study indicated the de-unit III homologs of 2−8 did not have better binding energies than 2. As for the trimers, 3-entC, 3C-entE, 3ent-C, 3C, and 3ent, showed comparable docking score to 2. The verification of this virtual screening was partially done by evaluating the inhibitory activity of the dimeric 2-nor-ent, 3-nor, 3-nor-ent, and iso-2-nor-ent, isolated from peanut skins, against α-glucosidase. Of these, iso-2-nor-ent, the only proanthocyanidin with (2β→O→7, 4β→6) interflavane linkage, showed the best activity (IC 50 9.72 µM). Their simulation profiles of docking score also displayed a reasonable qualitative consistency with the overall trend of the bioassay results. This study demonstrates that virtual screening using this built model to search α-glucosidase inhibitors is facile and feasible and peanut skin might be used as a hypoglycemic food.

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“…It is widely known as Brotowali in Indonesia. It is widely distributed over tropical and subtropical Asia including India, Thailand, Vietnam, Philippines, Indonesia, and Malaysia (Chang et al, 2015). This plant is commonly used as traditional medicine, especially its stem.…”

Section: Introductionmentioning

confidence: 99%

Antituberculosis Activity of Brotowali (Tinospora crispa) Extract and Fractions against Mycobacterium tuberculosis using Microplate Alamar Blue Assay Method

et al. 2017

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Tuberculosis (TB), in which caused by pathogenic bacteria, Mycobacterium tuberculosis, has become the major causes of death among all of infectious diseases. The increasing incidence of multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB ABSTRAK Tuberkulosis (TB) adalah penyakit yang disebabkan oleh infeksi Mycobacterium tuberculosis dan menjadi penyakit infeksi yang menyebabkan paling banyak kematian di dunia. Daruratnya penyakit TB dan meningkatnya kasus multidrug-resistant tuberculosis (MDR-TB) dan XDR-TB ini mendorong dilakukannya

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Acylated glucosylflavones as α-glucosidase inhibitors from Tinospora crispa leaf

Cited by 27 publications

References 39 publications

Genus Tinospora: Ethnopharmacology, Phytochemistry, and Pharmacology

Genus Tinospora: Ethnopharmacology, Phytochemistry, and Pharmacology

In Silico Docking Analysis of A-type Proanthocyanidins to <i>α</i>-Glucosidase Constructed by Correlation with in Vitro Bioassay

Antituberculosis Activity of Brotowali (Tinospora crispa) Extract and Fractions against Mycobacterium tuberculosis using Microplate Alamar Blue Assay Method

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Acylated glucosylflavones as α-glucosidase inhibitors from Tinospora crispa leaf

Cited by 27 publications

References 39 publications

Genus Tinospora: Ethnopharmacology, Phytochemistry, and Pharmacology

Genus Tinospora: Ethnopharmacology, Phytochemistry, and Pharmacology

In Silico Docking Analysis of A-type Proanthocyanidins to &lt;i&gt;α&lt;/i&gt;-Glucosidase Constructed by Correlation with in Vitro Bioassay

Antituberculosis Activity of Brotowali (Tinospora crispa) Extract and Fractions against Mycobacterium tuberculosis using Microplate Alamar Blue Assay Method

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In Silico Docking Analysis of A-type Proanthocyanidins to <i>α</i>-Glucosidase Constructed by Correlation with in Vitro Bioassay