A New Oleanane Type Saponin from the Aerial Parts of <i>Nigella sativa</i> with Anti-Oxidant and Anti-Diabetic Potential
Natural product studies explore potential and interesting new compounds to discover innovative drugs. <i>Nigella sativa</i> (<i>N. sativa)</i> (Ranunculaceae) is traditionally used to treat diabetes. Flavonoids and triterpenoid mostly show anti-diabetic activity. The current...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-05-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/25/9/2171 |
| _version_ | 1797568651504648192 |
|---|---|
| author | Amna Parveen Muhammad Asim Farooq Whang Wan Kyunn |
| author_facet | Amna Parveen Muhammad Asim Farooq Whang Wan Kyunn |
| author_sort | Amna Parveen |
| collection | DOAJ |
| description | Natural product studies explore potential and interesting new compounds to discover innovative drugs. <i>Nigella sativa</i> (<i>N. sativa)</i> (Ranunculaceae) is traditionally used to treat diabetes. Flavonoids and triterpenoid mostly show anti-diabetic activity. The current study aim to identify new compounds by a systematic study of the anti-oxidant and anti-diabetic activity of aerial parts of <i>N. sativa</i> concerning. Phytochemicals were isolated from the methanolic extract of aerial parts of the plant by column chromatography and identified by nuclear magnetic resonance spectroscopy and mass spectroscopy. A new triterpenoid saponin glycoside was isolated along with flavonoids. The anti-diabetic study was carried out by DPPH, ABTS, <inline-formula> <math display="inline"> <semantics> <mi mathvariant="sans-serif">α</mi> </semantics> </math> </inline-formula>-glucosidase, and protein tyrosine phosphatase 1B assays at doses of 12.5 to 250 µM. The isolated phytochemicals were identified as 3-O-(β-<span style="font-variant: small-caps;">d</span>-xylopyranosyl-(1-3)-α-<span style="font-variant: small-caps;">l</span>-rhamnopyrnaosyl-(1-2)-α-<span style="font-variant: small-caps;">l</span>-arabinopyranosyl]-28-O-(α-<span style="font-variant: small-caps;">l</span>-rhamno-pyranosyl-(1-4)-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl-(1-6)-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl] hederagenin (<b>1</b>), flaccidoside III (<b>2</b>), catechol (<b>3</b>), quercetin-3-gentiobiosides (<b>4</b>), magnoflorine (<b>5</b>), nigelflavonoside B (<b>6</b>), nigelloside (<b>7</b>), quercetin sphorotrioside (<b>8</b>), kaempferol-3, 7-diglucoside (<b>9</b>), kaempferol 3-O-rutinoside (<b>10</b>), rutin (<b>11</b>), 3-O-[α-<span style="font-variant: small-caps;">l</span>-rhamnopyranosyl-(1→2)-α-<span style="font-variant: small-caps;">l</span>-arabinopyranpsylhederagenin (<b>12</b>), 3β,23,28-trihydroxyolean-12-ene-3-O-α-<span style="font-variant: small-caps;">l</span>-arabinopyranoside(1→4)-a-rhamnopyranosyl,(1→4)-β-<span style="font-variant: small-caps;">d</span>-gluco-pyranoside (<b>13</b>), 3-O-α-<span style="font-variant: small-caps;">l</span>-rhamnopyranosyl-(1→2)-α-<span style="font-variant: small-caps;">l</span>-arabinopyranpsyl]-28-O-β-<span style="font-variant: small-caps;">d</span>-gluco-pyranosyl hederagenin (<b>14</b>), and α-hederin (<b>15</b>). These were isolated and are reported for the first time in this study. Compared <b>13</b> was identified as a new compound. Compound <b>2</b> was isolated for first time from the genus <i>Nigella</i>. Compound <b>6</b> was found to be the most active in the DPPH, and ABTS assays and compound <b>10</b> was found to be the most active in the α-glucosidase assay, with IC<sub>50</sub> 32.7 ± 0.1, 95.18 ± 0.9, 214.5 ± 0.0 µΜ, respectively. Compound <b>12</b>, at a dose of 125 µΜ, showed anti-diabetic activity in a PTP1B assay with IC<sub>50</sub> 91.30 <inline-formula> <math display="inline"> <semantics> <mrow> <mo>±</mo> </mrow> </semantics> </math> </inline-formula> 2.5 µΜ. In conclusion, the anti-diabetic activity of <i>N. sativa</i> is due to its flavonoids and TTSGs. Therefore, our studies suggest that the aerial parts of <i>N. sativa</i> are also a valuable and alternate source of valuable phytochemicals that could be used to develop anti-oxidant and anti-diabetic medicines. |
| first_indexed | 2024-03-10T20:00:00Z |
| format | Article |
| id | doaj.art-0d389976d0ea4617a4ba10d22c7e67a5 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T20:00:00Z |
| publishDate | 2020-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-0d389976d0ea4617a4ba10d22c7e67a52023-11-19T23:38:08ZengMDPI AGMolecules1420-30492020-05-01259217110.3390/molecules25092171A New Oleanane Type Saponin from the Aerial Parts of <i>Nigella sativa</i> with Anti-Oxidant and Anti-Diabetic PotentialAmna Parveen0Muhammad Asim Farooq1Whang Wan Kyunn2College of Pharmacy, Gachon University, Hambakmoero, Yeonsu-gu, Incheon 406-799, KoreaDepartment of Pharmaceutics, School of Pharmacy, China Pharmaceutical University, Nanjing 211198, ChinaCollege of Pharmacy, Chung-Ang University, Seoul 100-031, KoreaNatural product studies explore potential and interesting new compounds to discover innovative drugs. <i>Nigella sativa</i> (<i>N. sativa)</i> (Ranunculaceae) is traditionally used to treat diabetes. Flavonoids and triterpenoid mostly show anti-diabetic activity. The current study aim to identify new compounds by a systematic study of the anti-oxidant and anti-diabetic activity of aerial parts of <i>N. sativa</i> concerning. Phytochemicals were isolated from the methanolic extract of aerial parts of the plant by column chromatography and identified by nuclear magnetic resonance spectroscopy and mass spectroscopy. A new triterpenoid saponin glycoside was isolated along with flavonoids. The anti-diabetic study was carried out by DPPH, ABTS, <inline-formula> <math display="inline"> <semantics> <mi mathvariant="sans-serif">α</mi> </semantics> </math> </inline-formula>-glucosidase, and protein tyrosine phosphatase 1B assays at doses of 12.5 to 250 µM. The isolated phytochemicals were identified as 3-O-(β-<span style="font-variant: small-caps;">d</span>-xylopyranosyl-(1-3)-α-<span style="font-variant: small-caps;">l</span>-rhamnopyrnaosyl-(1-2)-α-<span style="font-variant: small-caps;">l</span>-arabinopyranosyl]-28-O-(α-<span style="font-variant: small-caps;">l</span>-rhamno-pyranosyl-(1-4)-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl-(1-6)-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl] hederagenin (<b>1</b>), flaccidoside III (<b>2</b>), catechol (<b>3</b>), quercetin-3-gentiobiosides (<b>4</b>), magnoflorine (<b>5</b>), nigelflavonoside B (<b>6</b>), nigelloside (<b>7</b>), quercetin sphorotrioside (<b>8</b>), kaempferol-3, 7-diglucoside (<b>9</b>), kaempferol 3-O-rutinoside (<b>10</b>), rutin (<b>11</b>), 3-O-[α-<span style="font-variant: small-caps;">l</span>-rhamnopyranosyl-(1→2)-α-<span style="font-variant: small-caps;">l</span>-arabinopyranpsylhederagenin (<b>12</b>), 3β,23,28-trihydroxyolean-12-ene-3-O-α-<span style="font-variant: small-caps;">l</span>-arabinopyranoside(1→4)-a-rhamnopyranosyl,(1→4)-β-<span style="font-variant: small-caps;">d</span>-gluco-pyranoside (<b>13</b>), 3-O-α-<span style="font-variant: small-caps;">l</span>-rhamnopyranosyl-(1→2)-α-<span style="font-variant: small-caps;">l</span>-arabinopyranpsyl]-28-O-β-<span style="font-variant: small-caps;">d</span>-gluco-pyranosyl hederagenin (<b>14</b>), and α-hederin (<b>15</b>). These were isolated and are reported for the first time in this study. Compared <b>13</b> was identified as a new compound. Compound <b>2</b> was isolated for first time from the genus <i>Nigella</i>. Compound <b>6</b> was found to be the most active in the DPPH, and ABTS assays and compound <b>10</b> was found to be the most active in the α-glucosidase assay, with IC<sub>50</sub> 32.7 ± 0.1, 95.18 ± 0.9, 214.5 ± 0.0 µΜ, respectively. Compound <b>12</b>, at a dose of 125 µΜ, showed anti-diabetic activity in a PTP1B assay with IC<sub>50</sub> 91.30 <inline-formula> <math display="inline"> <semantics> <mrow> <mo>±</mo> </mrow> </semantics> </math> </inline-formula> 2.5 µΜ. In conclusion, the anti-diabetic activity of <i>N. sativa</i> is due to its flavonoids and TTSGs. Therefore, our studies suggest that the aerial parts of <i>N. sativa</i> are also a valuable and alternate source of valuable phytochemicals that could be used to develop anti-oxidant and anti-diabetic medicines.https://www.mdpi.com/1420-3049/25/9/2171<i>Nigella sativa</i>antioxidantcolumn chromatographycharacterizationisolationtriterpenoid saponin derivatives |
| spellingShingle | Amna Parveen Muhammad Asim Farooq Whang Wan Kyunn A New Oleanane Type Saponin from the Aerial Parts of <i>Nigella sativa</i> with Anti-Oxidant and Anti-Diabetic Potential Molecules <i>Nigella sativa</i> antioxidant column chromatography characterization isolation triterpenoid saponin derivatives |
| title | A New Oleanane Type Saponin from the Aerial Parts of <i>Nigella sativa</i> with Anti-Oxidant and Anti-Diabetic Potential |
| title_full | A New Oleanane Type Saponin from the Aerial Parts of <i>Nigella sativa</i> with Anti-Oxidant and Anti-Diabetic Potential |
| title_fullStr | A New Oleanane Type Saponin from the Aerial Parts of <i>Nigella sativa</i> with Anti-Oxidant and Anti-Diabetic Potential |
| title_full_unstemmed | A New Oleanane Type Saponin from the Aerial Parts of <i>Nigella sativa</i> with Anti-Oxidant and Anti-Diabetic Potential |
| title_short | A New Oleanane Type Saponin from the Aerial Parts of <i>Nigella sativa</i> with Anti-Oxidant and Anti-Diabetic Potential |
| title_sort | new oleanane type saponin from the aerial parts of i nigella sativa i with anti oxidant and anti diabetic potential |
| topic | <i>Nigella sativa</i> antioxidant column chromatography characterization isolation triterpenoid saponin derivatives |
| url | https://www.mdpi.com/1420-3049/25/9/2171 |
| work_keys_str_mv | AT amnaparveen anewoleananetypesaponinfromtheaerialpartsofinigellasativaiwithantioxidantandantidiabeticpotential AT muhammadasimfarooq anewoleananetypesaponinfromtheaerialpartsofinigellasativaiwithantioxidantandantidiabeticpotential AT whangwankyunn anewoleananetypesaponinfromtheaerialpartsofinigellasativaiwithantioxidantandantidiabeticpotential AT amnaparveen newoleananetypesaponinfromtheaerialpartsofinigellasativaiwithantioxidantandantidiabeticpotential AT muhammadasimfarooq newoleananetypesaponinfromtheaerialpartsofinigellasativaiwithantioxidantandantidiabeticpotential AT whangwankyunn newoleananetypesaponinfromtheaerialpartsofinigellasativaiwithantioxidantandantidiabeticpotential |