Anti-Inflammatory, Antidiabetic Properties and In Silico Modeling of Cucurbitane-Type Triterpene Glycosides from Fruits of an Indian Cultivar of <i>Momordica charantia</i> L.

Diabetes mellitus is a chronic disease and one of the fastest-growing health challenges of the last decades. Studies have shown that chronic low-grade inflammation and activation of the innate immune system are intimately involved in type 2 diabetes pathogenesis. <i>Momordica charantia</i&g...

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Main Authors: Wilmer H. Perera, Siddanagouda R. Shivanagoudra, Jose L. Pérez, Da Mi Kim, Yuxiang Sun, Guddadarangavvanahally K. Jayaprakasha, Bhimanagouda S. Patil
Format: Article
Language:English
Published: MDPI AG 2021-02-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/26/4/1038
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author Wilmer H. Perera
Siddanagouda R. Shivanagoudra
Jose L. Pérez
Da Mi Kim
Yuxiang Sun
Guddadarangavvanahally K. Jayaprakasha
Bhimanagouda S. Patil
author_facet Wilmer H. Perera
Siddanagouda R. Shivanagoudra
Jose L. Pérez
Da Mi Kim
Yuxiang Sun
Guddadarangavvanahally K. Jayaprakasha
Bhimanagouda S. Patil
author_sort Wilmer H. Perera
collection DOAJ
description Diabetes mellitus is a chronic disease and one of the fastest-growing health challenges of the last decades. Studies have shown that chronic low-grade inflammation and activation of the innate immune system are intimately involved in type 2 diabetes pathogenesis. <i>Momordica charantia</i> L. fruits are used in traditional medicine to manage diabetes. Herein, we report the purification of a new 23-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-allopyranosyl-5β,19-epoxycucurbitane-6,24-diene triterpene (charantoside XV, <b>6</b>) along with 25ξ-isopropenylchole-5(6)-ene-3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>1</b>), karaviloside VI (<b>2</b>), karaviloside VIII (<b>3</b>), momordicoside L (<b>4</b>), momordicoside A (<b>5</b>) and kuguaglycoside C (<b>7</b>) from an Indian cultivar of <i>Momordica charantia</i>. At 50 µM compounds, <b>2</b>–<b>6</b> differentially affected the expression of pro-inflammatory markers <i>IL-6</i>, <i>TNF-α</i>, and <i>iNOS</i>, and mitochondrial marker <i>COX-2</i>. Compounds tested for the inhibition of α-amylase and α-glucosidase enzymes at 0.87 mM and 1.33 mM, respectively. Compounds showed similar α-amylase inhibitory activity than acarbose (0.13 mM) of control (68.0–76.6%). Karaviloside VIII (56.5%) was the most active compound in the α-glucosidase assay, followed by karaviloside VI (40.3%), while momordicoside L (23.7%), A (33.5%), and charantoside XV (23.9%) were the least active compounds. To better understand the mode of binding of cucurbitane-triterpenes to these enzymes, in silico docking of the isolated compounds was evaluated with α-amylase and α-glucosidase.
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spelling doaj.art-7a8699cce59641b8a91321abbef60c922023-12-11T17:16:03ZengMDPI AGMolecules1420-30492021-02-01264103810.3390/molecules26041038Anti-Inflammatory, Antidiabetic Properties and In Silico Modeling of Cucurbitane-Type Triterpene Glycosides from Fruits of an Indian Cultivar of <i>Momordica charantia</i> L.Wilmer H. Perera0Siddanagouda R. Shivanagoudra1Jose L. Pérez2Da Mi Kim3Yuxiang Sun4Guddadarangavvanahally K. Jayaprakasha5Bhimanagouda S. Patil6Vegetable and Fruit Improvement Center, Department of Horticultural Sciences, Texas A&M University, 1500 Research Parkway, Suite A120, College Station, TX 77843, USAVegetable and Fruit Improvement Center, Department of Horticultural Sciences, Texas A&M University, 1500 Research Parkway, Suite A120, College Station, TX 77843, USAVegetable and Fruit Improvement Center, Department of Horticultural Sciences, Texas A&M University, 1500 Research Parkway, Suite A120, College Station, TX 77843, USADepartment of Nutrition, Texas A&M University, College Station, TX 77843, USADepartment of Nutrition, Texas A&M University, College Station, TX 77843, USAVegetable and Fruit Improvement Center, Department of Horticultural Sciences, Texas A&M University, 1500 Research Parkway, Suite A120, College Station, TX 77843, USAVegetable and Fruit Improvement Center, Department of Horticultural Sciences, Texas A&M University, 1500 Research Parkway, Suite A120, College Station, TX 77843, USADiabetes mellitus is a chronic disease and one of the fastest-growing health challenges of the last decades. Studies have shown that chronic low-grade inflammation and activation of the innate immune system are intimately involved in type 2 diabetes pathogenesis. <i>Momordica charantia</i> L. fruits are used in traditional medicine to manage diabetes. Herein, we report the purification of a new 23-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-allopyranosyl-5β,19-epoxycucurbitane-6,24-diene triterpene (charantoside XV, <b>6</b>) along with 25ξ-isopropenylchole-5(6)-ene-3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>1</b>), karaviloside VI (<b>2</b>), karaviloside VIII (<b>3</b>), momordicoside L (<b>4</b>), momordicoside A (<b>5</b>) and kuguaglycoside C (<b>7</b>) from an Indian cultivar of <i>Momordica charantia</i>. At 50 µM compounds, <b>2</b>–<b>6</b> differentially affected the expression of pro-inflammatory markers <i>IL-6</i>, <i>TNF-α</i>, and <i>iNOS</i>, and mitochondrial marker <i>COX-2</i>. Compounds tested for the inhibition of α-amylase and α-glucosidase enzymes at 0.87 mM and 1.33 mM, respectively. Compounds showed similar α-amylase inhibitory activity than acarbose (0.13 mM) of control (68.0–76.6%). Karaviloside VIII (56.5%) was the most active compound in the α-glucosidase assay, followed by karaviloside VI (40.3%), while momordicoside L (23.7%), A (33.5%), and charantoside XV (23.9%) were the least active compounds. To better understand the mode of binding of cucurbitane-triterpenes to these enzymes, in silico docking of the isolated compounds was evaluated with α-amylase and α-glucosidase.https://www.mdpi.com/1420-3049/26/4/1038<i>Momordica charantia</i>cucurbitane-type triterpene glycosidescharantoside XVα-amylaseα-glucosidaseanti-inflammatory activity
spellingShingle Wilmer H. Perera
Siddanagouda R. Shivanagoudra
Jose L. Pérez
Da Mi Kim
Yuxiang Sun
Guddadarangavvanahally K. Jayaprakasha
Bhimanagouda S. Patil
Anti-Inflammatory, Antidiabetic Properties and In Silico Modeling of Cucurbitane-Type Triterpene Glycosides from Fruits of an Indian Cultivar of <i>Momordica charantia</i> L.
Molecules
<i>Momordica charantia</i>
cucurbitane-type triterpene glycosides
charantoside XV
α-amylase
α-glucosidase
anti-inflammatory activity
title Anti-Inflammatory, Antidiabetic Properties and In Silico Modeling of Cucurbitane-Type Triterpene Glycosides from Fruits of an Indian Cultivar of <i>Momordica charantia</i> L.
title_full Anti-Inflammatory, Antidiabetic Properties and In Silico Modeling of Cucurbitane-Type Triterpene Glycosides from Fruits of an Indian Cultivar of <i>Momordica charantia</i> L.
title_fullStr Anti-Inflammatory, Antidiabetic Properties and In Silico Modeling of Cucurbitane-Type Triterpene Glycosides from Fruits of an Indian Cultivar of <i>Momordica charantia</i> L.
title_full_unstemmed Anti-Inflammatory, Antidiabetic Properties and In Silico Modeling of Cucurbitane-Type Triterpene Glycosides from Fruits of an Indian Cultivar of <i>Momordica charantia</i> L.
title_short Anti-Inflammatory, Antidiabetic Properties and In Silico Modeling of Cucurbitane-Type Triterpene Glycosides from Fruits of an Indian Cultivar of <i>Momordica charantia</i> L.
title_sort anti inflammatory antidiabetic properties and in silico modeling of cucurbitane type triterpene glycosides from fruits of an indian cultivar of i momordica charantia i l
topic <i>Momordica charantia</i>
cucurbitane-type triterpene glycosides
charantoside XV
α-amylase
α-glucosidase
anti-inflammatory activity
url https://www.mdpi.com/1420-3049/26/4/1038
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