Antimicrobial Triterpenoids and Ingol Diterpenes from Propolis of Semi-Arid Region of Morocco
The chemical composition and antimicrobial activity of propolis from a semi-arid region of Morocco were investigated. Fifteen compounds, including triterpenoids (<b>1</b>, <b>2</b>, <b>7</b>–<b>12</b>), macrocyclic diterpenes of ingol type (<b>3&...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-03-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/7/2206 |
| _version_ | 1827622988645662720 |
|---|---|
| author | Ralitsa Chimshirova Milena Popova Amina Chakir Violeta Valcheva Simeon Dimitrov Boryana Trusheva Abderrahmane Romane Vassya Bankova |
| author_facet | Ralitsa Chimshirova Milena Popova Amina Chakir Violeta Valcheva Simeon Dimitrov Boryana Trusheva Abderrahmane Romane Vassya Bankova |
| author_sort | Ralitsa Chimshirova |
| collection | DOAJ |
| description | The chemical composition and antimicrobial activity of propolis from a semi-arid region of Morocco were investigated. Fifteen compounds, including triterpenoids (<b>1</b>, <b>2</b>, <b>7</b>–<b>12</b>), macrocyclic diterpenes of ingol type (<b>3</b>–<b>6</b>) and aromatic derivatives (<b>13</b>–<b>15</b>), were isolated by various chromatographic methods. Their structures were elucidated by a combination of spectroscopic and chiroptical methods. Compounds <b>1</b> and <b>3</b> are new natural compounds, and <b>2</b>, <b>4</b>–<b>6</b>, and <b>9</b>–<b>11</b> are newly isolated from propolis. Moreover, the full nuclear magnetic resonance (NMR) assignments of three of the known compounds (<b>2</b>, <b>4</b> and <b>5</b>) were reported for the first time. Most of the compounds tested, especially the diterpenes <b>3</b>, <b>4</b>, and <b>6</b>, exhibited very good activity against different strains of bacteria and fungi. Compound <b>3</b> showed the strongest activity with minimum inhibitory concentrations (MICs) in the range of 4–64 µg/mL. The combination of isolated triterpenoids and ingol diterpenes was found to be characteristic for <i>Euphorbia</i> spp., and <i>Euphorbia officinarum</i> subsp. <i>echinus</i> could be suggested as a probable and new plant source of propolis. |
| first_indexed | 2024-03-09T11:36:54Z |
| format | Article |
| id | doaj.art-539d27e691b44a7a910ec6bb8b4b11da |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T11:36:54Z |
| publishDate | 2022-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-539d27e691b44a7a910ec6bb8b4b11da2023-11-30T23:41:02ZengMDPI AGMolecules1420-30492022-03-01277220610.3390/molecules27072206Antimicrobial Triterpenoids and Ingol Diterpenes from Propolis of Semi-Arid Region of MoroccoRalitsa Chimshirova0Milena Popova1Amina Chakir2Violeta Valcheva3Simeon Dimitrov4Boryana Trusheva5Abderrahmane Romane6Vassya Bankova7Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., Bl. 9, 1113 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., Bl. 9, 1113 Sofia, BulgariaLaboratory of Applied Chemistry, Faculty of Sciences Semlalia, Cadi Ayyad University, Boulevard Prince My Abdellah B.P. 2390, Marrakech 40000, MoroccoDepartment of Infectious Microbiology, The Stephan Angeloff Institute of Microbiology, Bulgarian Academy of Sciences, Acad. G. Bonchev St., Bl. 26, 1113 Sofia, BulgariaDepartment of Infectious Microbiology, The Stephan Angeloff Institute of Microbiology, Bulgarian Academy of Sciences, Acad. G. Bonchev St., Bl. 26, 1113 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., Bl. 9, 1113 Sofia, BulgariaLaboratory of Applied Chemistry, Faculty of Sciences Semlalia, Cadi Ayyad University, Boulevard Prince My Abdellah B.P. 2390, Marrakech 40000, MoroccoInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., Bl. 9, 1113 Sofia, BulgariaThe chemical composition and antimicrobial activity of propolis from a semi-arid region of Morocco were investigated. Fifteen compounds, including triterpenoids (<b>1</b>, <b>2</b>, <b>7</b>–<b>12</b>), macrocyclic diterpenes of ingol type (<b>3</b>–<b>6</b>) and aromatic derivatives (<b>13</b>–<b>15</b>), were isolated by various chromatographic methods. Their structures were elucidated by a combination of spectroscopic and chiroptical methods. Compounds <b>1</b> and <b>3</b> are new natural compounds, and <b>2</b>, <b>4</b>–<b>6</b>, and <b>9</b>–<b>11</b> are newly isolated from propolis. Moreover, the full nuclear magnetic resonance (NMR) assignments of three of the known compounds (<b>2</b>, <b>4</b> and <b>5</b>) were reported for the first time. Most of the compounds tested, especially the diterpenes <b>3</b>, <b>4</b>, and <b>6</b>, exhibited very good activity against different strains of bacteria and fungi. Compound <b>3</b> showed the strongest activity with minimum inhibitory concentrations (MICs) in the range of 4–64 µg/mL. The combination of isolated triterpenoids and ingol diterpenes was found to be characteristic for <i>Euphorbia</i> spp., and <i>Euphorbia officinarum</i> subsp. <i>echinus</i> could be suggested as a probable and new plant source of propolis.https://www.mdpi.com/1420-3049/27/7/2206propolistriterpenoidsingol diterpenesantimicrobial activity<i>Euphorbia</i> spp.Morocco |
| spellingShingle | Ralitsa Chimshirova Milena Popova Amina Chakir Violeta Valcheva Simeon Dimitrov Boryana Trusheva Abderrahmane Romane Vassya Bankova Antimicrobial Triterpenoids and Ingol Diterpenes from Propolis of Semi-Arid Region of Morocco Molecules propolis triterpenoids ingol diterpenes antimicrobial activity <i>Euphorbia</i> spp. Morocco |
| title | Antimicrobial Triterpenoids and Ingol Diterpenes from Propolis of Semi-Arid Region of Morocco |
| title_full | Antimicrobial Triterpenoids and Ingol Diterpenes from Propolis of Semi-Arid Region of Morocco |
| title_fullStr | Antimicrobial Triterpenoids and Ingol Diterpenes from Propolis of Semi-Arid Region of Morocco |
| title_full_unstemmed | Antimicrobial Triterpenoids and Ingol Diterpenes from Propolis of Semi-Arid Region of Morocco |
| title_short | Antimicrobial Triterpenoids and Ingol Diterpenes from Propolis of Semi-Arid Region of Morocco |
| title_sort | antimicrobial triterpenoids and ingol diterpenes from propolis of semi arid region of morocco |
| topic | propolis triterpenoids ingol diterpenes antimicrobial activity <i>Euphorbia</i> spp. Morocco |
| url | https://www.mdpi.com/1420-3049/27/7/2206 |
| work_keys_str_mv | AT ralitsachimshirova antimicrobialtriterpenoidsandingolditerpenesfrompropolisofsemiaridregionofmorocco AT milenapopova antimicrobialtriterpenoidsandingolditerpenesfrompropolisofsemiaridregionofmorocco AT aminachakir antimicrobialtriterpenoidsandingolditerpenesfrompropolisofsemiaridregionofmorocco AT violetavalcheva antimicrobialtriterpenoidsandingolditerpenesfrompropolisofsemiaridregionofmorocco AT simeondimitrov antimicrobialtriterpenoidsandingolditerpenesfrompropolisofsemiaridregionofmorocco AT boryanatrusheva antimicrobialtriterpenoidsandingolditerpenesfrompropolisofsemiaridregionofmorocco AT abderrahmaneromane antimicrobialtriterpenoidsandingolditerpenesfrompropolisofsemiaridregionofmorocco AT vassyabankova antimicrobialtriterpenoidsandingolditerpenesfrompropolisofsemiaridregionofmorocco |