Anti-Obesity Evaluation of <i>Averrhoa carambola</i> L. Leaves and Assessment of Its Polyphenols as Potential α-Glucosidase Inhibitors
<i>Averrhoa carambola</i> L. is reported for its anti-obese and anti-diabetic activities. The present study aimed to investigate its aqueous methanol leaf extract (CLL) in vivo anti-obese activity along with the isolation and identification of bioactive compounds and their in vitro α-glu...
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-08-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/16/5159 |
| _version_ | 1797408699678982144 |
|---|---|
| author | Nehal S. Ramadan Nabil H. El-Sayed Sayed A. El-Toumy Doha Abdou Mohamed Zeinab Abdel Aziz Mohamed Sobhy Marzouk Tuba Esatbeyoglu Mohamed A. Farag Kuniyoshi Shimizu |
| author_facet | Nehal S. Ramadan Nabil H. El-Sayed Sayed A. El-Toumy Doha Abdou Mohamed Zeinab Abdel Aziz Mohamed Sobhy Marzouk Tuba Esatbeyoglu Mohamed A. Farag Kuniyoshi Shimizu |
| author_sort | Nehal S. Ramadan |
| collection | DOAJ |
| description | <i>Averrhoa carambola</i> L. is reported for its anti-obese and anti-diabetic activities. The present study aimed to investigate its aqueous methanol leaf extract (CLL) in vivo anti-obese activity along with the isolation and identification of bioactive compounds and their in vitro α-glucosidase inhibition assessment. CLL improved all obesity complications and exhibited significant activity in an obese rat model. Fourteen compounds, including four flavone glycosides (<b>1</b>–<b>4</b>) and ten dihydrochalcone glycosides (<b>5</b>–<b>12</b>), were isolated and identified using spectroscopic techniques. New compounds identified in planta included (<b>1</b>) apigenin 6-<i>C</i>-(2-deoxy-<i>β</i>-D-galactopyranoside)-7-<i>O</i>-<i>β</i>-D-quinovopyranoside, (<b>8</b>) phloretin 3′-<i>C</i>-(2-<i>O</i>-(<i>E</i>)-cinnamoyl-3-<i>O</i>-<i>β</i>-D-fucopyranosyl-4-<i>O</i>-acetyl)-<i>β</i>-D-fucopyranosyl-6′-<i>O</i>-<i>β</i>-D fucopyranosyl-(1/2)-α-L arabinofuranoside, (<b>11a</b>) phloretin3′-<i>C</i>-(2-<i>O</i>-(<i>E</i>)-p-coumaroyl-3-<i>O</i>-<i>β-</i>D-fucosyl-4-<i>O</i>-acetyl)-<i>β</i>-D-fucosyl-6′-<i>O</i>-(2-<i>O</i>-<i>β</i>-D-fucosyl)-α-L-arabinofuranoside, (<b>11b</b>) phloretin3′-<i>C</i>-(2-O-<i>(Z)</i><i>-p</i>-coumaroyl-3-<i>O</i>-<i>β</i>-D-fucosyl-4-<i>O</i>-acetyl)-<i>β</i>-D-fucosyl-6′-<i>O</i>-(2-<i>O</i>-<i>β</i>-D-fucosyl)-α-L-arabinofuranoside. Carambolaside M (<b>5</b>), carambolaside Ia (<b>6</b>), carambolaside J (<b>7</b>), carambolaside I (<b>9</b>), carambolaside P (<b>10a</b>), carambolaside O (<b>10b</b>), and carambolaside Q (<b>12</b>), which are reported for the first time from <i>A. carambola</i> L. leaves, whereas luteolin 6-<i>C</i>-α-L-rhamnopyranosyl-(1-2)-<i>β</i>-D-fucopyranoside (<b>2</b>), apigenin 6-<i>C</i>-<i>β</i>-D-galactopyranoside (<b>3</b>), and apigenin 6-<i>C</i>-<i>α</i>-L-rhamnopyranosyl-(1-2)-<i>β</i>-L-fucopyranoside (<b>4</b>) are isolated for the first time from Family. Oxalidaceae. In vitro α-glucosidase inhibitory activity revealed the potential efficacy of flavone glycosides, viz., <b>1</b>, <b>2</b>, <b>3</b>, and <b>4</b> as antidiabetic agents. In contrast, dihydrochalcone glycosides (<b>5</b>–<b>11</b>) showed weak activity, except for compound <b>12</b>, which showed relatively strong activity. |
| first_indexed | 2024-03-09T04:02:16Z |
| format | Article |
| id | doaj.art-31d6ab062b434837b27b38eac63fdf10 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T04:02:16Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-31d6ab062b434837b27b38eac63fdf102023-12-03T14:11:15ZengMDPI AGMolecules1420-30492022-08-012716515910.3390/molecules27165159Anti-Obesity Evaluation of <i>Averrhoa carambola</i> L. Leaves and Assessment of Its Polyphenols as Potential α-Glucosidase InhibitorsNehal S. Ramadan0Nabil H. El-Sayed1Sayed A. El-Toumy2Doha Abdou Mohamed3Zeinab Abdel Aziz4Mohamed Sobhy Marzouk5Tuba Esatbeyoglu6Mohamed A. Farag7Kuniyoshi Shimizu8Chemistry of Tanning Materials and Leather Technology Department, National Research Centre, Dokki, Cairo 12622, EgyptChemistry of Tanning Materials and Leather Technology Department, National Research Centre, Dokki, Cairo 12622, EgyptChemistry of Tanning Materials and Leather Technology Department, National Research Centre, Dokki, Cairo 12622, EgyptNutrition and Food Sciences Department, National Research Centre, Dokki, Cairo 12622, EgyptPharmacognosy Department, College of Pharmacy, Cairo University, Kasr El Aini St., Cairo 11562, EgyptChemistry of Tanning Materials and Leather Technology Department, National Research Centre, Dokki, Cairo 12622, EgyptDepartment of Food Development and Food Quality, Institute of Food Science and Human Nutrition, Gottfried Wilhelm Leibniz University Hannover, Am Kleinen Felde 30, 30167 Hannover, GermanyPharmacognosy Department, College of Pharmacy, Cairo University, Kasr El Aini St., Cairo 11562, EgyptDepartment of Agro-Environmental Sciences, Graduate School of Bioresource and Bioenvironmental Sciences, Kyushu University, Fukuoka 819-0395, Japan<i>Averrhoa carambola</i> L. is reported for its anti-obese and anti-diabetic activities. The present study aimed to investigate its aqueous methanol leaf extract (CLL) in vivo anti-obese activity along with the isolation and identification of bioactive compounds and their in vitro α-glucosidase inhibition assessment. CLL improved all obesity complications and exhibited significant activity in an obese rat model. Fourteen compounds, including four flavone glycosides (<b>1</b>–<b>4</b>) and ten dihydrochalcone glycosides (<b>5</b>–<b>12</b>), were isolated and identified using spectroscopic techniques. New compounds identified in planta included (<b>1</b>) apigenin 6-<i>C</i>-(2-deoxy-<i>β</i>-D-galactopyranoside)-7-<i>O</i>-<i>β</i>-D-quinovopyranoside, (<b>8</b>) phloretin 3′-<i>C</i>-(2-<i>O</i>-(<i>E</i>)-cinnamoyl-3-<i>O</i>-<i>β</i>-D-fucopyranosyl-4-<i>O</i>-acetyl)-<i>β</i>-D-fucopyranosyl-6′-<i>O</i>-<i>β</i>-D fucopyranosyl-(1/2)-α-L arabinofuranoside, (<b>11a</b>) phloretin3′-<i>C</i>-(2-<i>O</i>-(<i>E</i>)-p-coumaroyl-3-<i>O</i>-<i>β-</i>D-fucosyl-4-<i>O</i>-acetyl)-<i>β</i>-D-fucosyl-6′-<i>O</i>-(2-<i>O</i>-<i>β</i>-D-fucosyl)-α-L-arabinofuranoside, (<b>11b</b>) phloretin3′-<i>C</i>-(2-O-<i>(Z)</i><i>-p</i>-coumaroyl-3-<i>O</i>-<i>β</i>-D-fucosyl-4-<i>O</i>-acetyl)-<i>β</i>-D-fucosyl-6′-<i>O</i>-(2-<i>O</i>-<i>β</i>-D-fucosyl)-α-L-arabinofuranoside. Carambolaside M (<b>5</b>), carambolaside Ia (<b>6</b>), carambolaside J (<b>7</b>), carambolaside I (<b>9</b>), carambolaside P (<b>10a</b>), carambolaside O (<b>10b</b>), and carambolaside Q (<b>12</b>), which are reported for the first time from <i>A. carambola</i> L. leaves, whereas luteolin 6-<i>C</i>-α-L-rhamnopyranosyl-(1-2)-<i>β</i>-D-fucopyranoside (<b>2</b>), apigenin 6-<i>C</i>-<i>β</i>-D-galactopyranoside (<b>3</b>), and apigenin 6-<i>C</i>-<i>α</i>-L-rhamnopyranosyl-(1-2)-<i>β</i>-L-fucopyranoside (<b>4</b>) are isolated for the first time from Family. Oxalidaceae. In vitro α-glucosidase inhibitory activity revealed the potential efficacy of flavone glycosides, viz., <b>1</b>, <b>2</b>, <b>3</b>, and <b>4</b> as antidiabetic agents. In contrast, dihydrochalcone glycosides (<b>5</b>–<b>11</b>) showed weak activity, except for compound <b>12</b>, which showed relatively strong activity.https://www.mdpi.com/1420-3049/27/16/5159antidiabetic<i>Averrhoa</i> <i>carambola</i> L.dihydrochalconeflavone glycosidesobesityOxalidaceae |
| spellingShingle | Nehal S. Ramadan Nabil H. El-Sayed Sayed A. El-Toumy Doha Abdou Mohamed Zeinab Abdel Aziz Mohamed Sobhy Marzouk Tuba Esatbeyoglu Mohamed A. Farag Kuniyoshi Shimizu Anti-Obesity Evaluation of <i>Averrhoa carambola</i> L. Leaves and Assessment of Its Polyphenols as Potential α-Glucosidase Inhibitors Molecules antidiabetic <i>Averrhoa</i> <i>carambola</i> L. dihydrochalcone flavone glycosides obesity Oxalidaceae |
| title | Anti-Obesity Evaluation of <i>Averrhoa carambola</i> L. Leaves and Assessment of Its Polyphenols as Potential α-Glucosidase Inhibitors |
| title_full | Anti-Obesity Evaluation of <i>Averrhoa carambola</i> L. Leaves and Assessment of Its Polyphenols as Potential α-Glucosidase Inhibitors |
| title_fullStr | Anti-Obesity Evaluation of <i>Averrhoa carambola</i> L. Leaves and Assessment of Its Polyphenols as Potential α-Glucosidase Inhibitors |
| title_full_unstemmed | Anti-Obesity Evaluation of <i>Averrhoa carambola</i> L. Leaves and Assessment of Its Polyphenols as Potential α-Glucosidase Inhibitors |
| title_short | Anti-Obesity Evaluation of <i>Averrhoa carambola</i> L. Leaves and Assessment of Its Polyphenols as Potential α-Glucosidase Inhibitors |
| title_sort | anti obesity evaluation of i averrhoa carambola i l leaves and assessment of its polyphenols as potential α glucosidase inhibitors |
| topic | antidiabetic <i>Averrhoa</i> <i>carambola</i> L. dihydrochalcone flavone glycosides obesity Oxalidaceae |
| url | https://www.mdpi.com/1420-3049/27/16/5159 |
| work_keys_str_mv | AT nehalsramadan antiobesityevaluationofiaverrhoacarambolailleavesandassessmentofitspolyphenolsaspotentialaglucosidaseinhibitors AT nabilhelsayed antiobesityevaluationofiaverrhoacarambolailleavesandassessmentofitspolyphenolsaspotentialaglucosidaseinhibitors AT sayedaeltoumy antiobesityevaluationofiaverrhoacarambolailleavesandassessmentofitspolyphenolsaspotentialaglucosidaseinhibitors AT dohaabdoumohamed antiobesityevaluationofiaverrhoacarambolailleavesandassessmentofitspolyphenolsaspotentialaglucosidaseinhibitors AT zeinababdelaziz antiobesityevaluationofiaverrhoacarambolailleavesandassessmentofitspolyphenolsaspotentialaglucosidaseinhibitors AT mohamedsobhymarzouk antiobesityevaluationofiaverrhoacarambolailleavesandassessmentofitspolyphenolsaspotentialaglucosidaseinhibitors AT tubaesatbeyoglu antiobesityevaluationofiaverrhoacarambolailleavesandassessmentofitspolyphenolsaspotentialaglucosidaseinhibitors AT mohamedafarag antiobesityevaluationofiaverrhoacarambolailleavesandassessmentofitspolyphenolsaspotentialaglucosidaseinhibitors AT kuniyoshishimizu antiobesityevaluationofiaverrhoacarambolailleavesandassessmentofitspolyphenolsaspotentialaglucosidaseinhibitors |