A new 26-norlanostane from <i>Phlogacanthus turgidus</i> growing in Vietnam

Tri, Mai Dinh; Phat, Nguyen Tan; Trung, Nguyễn Tiến; Phan, Cam-Tu Dang; Minh, Phan Ngoc; Thanh, Mai; Nguyen, Thi-Phuong; Dang, Chi-Hien; Truong, Le Van; Pham, Nguyen Kim Tuyen; Ngoc, Tran Thi Bich; Duong, Thuc‐Huy

doi:10.1080/10286020.2021.1913125

Cited by 3 publications

(4 citation statements)

References 21 publications

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“…Compared to acarbose, BA displayed superior inhibition against α-glucosidase in very low concentrations, with IC 50 value of 16.83 ± 1.16 µM, which was approximately 50-fold stronger than acarbose (841.3 ± 29.6 µM). Previous research had reported BA inhibited α-glucosidase in vitro with IC 50 value from 10.6 to 83.6 µM, which was in accordance with our result [7,29,30]. Combined with previous papers [7,29,30,[32][33][34], it was found that the different substitutions at C-3 and C-28 positions of BA could have influence on the inhibition activity.…”

Section: Inhibitory Effect Of Ba Against α-Glucosidasesupporting

confidence: 92%

“…Previous research had reported BA inhibited α-glucosidase in vitro with IC 50 value from 10.6 to 83.6 µM, which was in accordance with our result [7,29,30]. Combined with previous papers [7,29,30,[32][33][34], it was found that the different substitutions at C-3 and C-28 positions of BA could have influence on the inhibition activity. Additional polar interactions formed at C-3 and C-28 of BA would improve the inhibitory potency.…”

Section: Inhibitory Effect Of Ba Against α-Glucosidasesupporting

confidence: 92%

“…Several studies have reported its regulatory effects on glucose absorption and uptake [23,24], insulin resistance [25], glucose production and glycogen synthesis [17,[26][27][28]. BA was also found to inhibit α-glucosidase activity in vitro [7,[29][30][31] and its inhibition mechanism was investigated by spectroscopic analysis and molecular docking [7]; however, the binding mechanism as well as the alleviated effect on postprandial hyperglycemia was still unclear. In the present study, we firstly verified the inhibitory effect of BA and investigated its synergy with acarbose on α-glucosidase.…”

Section: Introductionmentioning

confidence: 99%

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Binding Interaction of Betulinic Acid to α-Glucosidase and Its Alleviation on Postprandial Hyperglycemia

Chen

et al. 2022

Molecules

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Inhibiting the intestinal α-glucosidase can effectively control postprandial hyperglycemia for type 2 diabetes mellitus (T2DM) treatment. In the present study, we reported the binding interaction of betulinic acid (BA), a pentacyclic triterpene widely distributed in nature, on α-glucosidase and its alleviation on postprandial hyperglycemia. BA was verified to exhibit a strong inhibitory effect against α-glucosidase with an IC50 value of 16.83 ± 1.16 μM. More importantly, it showed a synergistically inhibitory effect with acarbose. The underlying inhibitory mechanism was investigated by kinetics analysis, surface plasmon resonance (SPR) detection, molecular docking, molecular dynamics (MD) simulation and binding free energy calculation. BA showed a non-competitive inhibition on α-glucosidase. SPR revealed that it had a strong and fast affinity to α-glucosidase with an equilibrium dissociation constant (KD) value of 5.529 × 10−5 M and a slow dissociation. Molecular docking and MD simulation revealed that BA bound to the active site of α-glucosidase mainly due to the van der Waals force and hydrogen bond, and then changed the micro-environment and secondary structure of α-glucosidase. Free energy decomposition indicated amino acid residues such as PHE155, PHE175, HIE277, PHE298, GLU302, TRY311 and ASP347 of α-glucosidase at the binding pocket had strong interactions with BA, while LYS153, ARG210, ARG310, ARG354 and ARG437 showed a negative contribution to binding affinity between BA and α-glucosidase. Significantly, oral administration of BA alleviated the postprandial blood glucose fluctuations in mice. This work may provide new insights into the utilization of BA as a functional food and natural medicine for the control of postprandial hyperglycemia.

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Section: Inhibitory Effect Of Ba Against α-Glucosidasesupporting

confidence: 92%

Section: Inhibitory Effect Of Ba Against α-Glucosidasesupporting

confidence: 92%

Section: Introductionmentioning

confidence: 99%

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Binding Interaction of Betulinic Acid to α-Glucosidase and Its Alleviation on Postprandial Hyperglycemia

Chen

et al. 2022

Molecules

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“…The chemical components of other Phlogacanthus plants have been reported by previous studies. For instance, turgidol, a new compound, together with 5 known triterpenoids such as lupenone, lupeol, betulin, taraxer and betulinic acid were obtained from the chloroform extract of Phlogacanthus turgidus (9). Similarly, 6 chemical components of P. turgidus was identified in the ethyl acetate extract, including one derivative of phenylethanoid glycosides (martynoside), one lignan ((+)-syringaresinol), 2 steroids (bsitosterol and daucosterol) and two norisoprenoids ((+)-dehydrovomifoliol and (3S,5R,6R,7E,9S)megastiman-7-ene-3,5,6,9-tetrol) (10).…”

Section: Chemical Compositions Of Acetone Extract Of P Cornutusmentioning

confidence: 99%

Phlogacanthus cornutus: chemical profiles and antioxidant effects

et al. 2022

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Phlogacanthus cornutus is a rare species and the chemical profiles and the bioactivities of this plant are unknown. In present study, the chemical components of the acetone extract as well as the antioxidant activity of acetone extract and its fractions such as n-hexane, chloroform and ethyl acetate of P. cornutus were firstly reported. A total of 33 constituents were identify in the acetone extract of this plant using Gas Chromatography/Mass Spectrometry assay, in which trans-cinnamic acid (21.26%), neophytadiene (6.36%), linolenic acid (5.86%), dihydroagathic acid (5.71%), n-hexadecanoic acid (5.53%), phytol (4.14%) and cis-cinnamic acid (3.23%) were the major compounds. The acetone extract and its fractions such as n-hexane, chloroform and ethyl acetate of P. cornutus showed DPPH radical scavenging activity with IC50 value of 234.31, 185.95, 758.65 and 458.52 µg/mL respectively.

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