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Article

A New Oleanane Type Saponin from the Aerial Parts of Nigella sativa with Anti-Oxidant and Anti-Diabetic Potential

1
College of Pharmacy, Gachon University, Hambakmoero, Yeonsu-gu, Incheon 406-799, Korea
2
Department of Pharmaceutics, School of Pharmacy, China Pharmaceutical University, Nanjing 211198, China
3
College of Pharmacy, Chung-Ang University, Seoul 100-031, Korea
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(9), 2171; https://doi.org/10.3390/molecules25092171
Received: 23 March 2020 / Revised: 27 April 2020 / Accepted: 29 April 2020 / Published: 6 May 2020
(This article belongs to the Section Natural Products Chemistry)
Natural product studies explore potential and interesting new compounds to discover innovative drugs. Nigella sativa (N. sativa) (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 N. sativa 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, α -glucosidase, and protein tyrosine phosphatase 1B assays at doses of 12.5 to 250 µM. The isolated phytochemicals were identified as 3-O-(β-d-xylopyranosyl-(1-3)-α-l-rhamnopyrnaosyl-(1-2)-α-l-arabinopyranosyl]-28-O-(α-l-rhamno-pyranosyl-(1-4)-β-d-glucopyranosyl-(1-6)-β-d-glucopyranosyl] hederagenin (1), flaccidoside III (2), catechol (3), quercetin-3-gentiobiosides (4), magnoflorine (5), nigelflavonoside B (6), nigelloside (7), quercetin sphorotrioside (8), kaempferol-3, 7-diglucoside (9), kaempferol 3-O-rutinoside (10), rutin (11), 3-O-[α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranpsylhederagenin (12), 3β,23,28-trihydroxyolean-12-ene-3-O-α-l-arabinopyranoside(1→4)-a-rhamnopyranosyl,(1→4)-β-d-gluco-pyranoside (13), 3-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranpsyl]-28-O-β-d-gluco-pyranosyl hederagenin (14), and α-hederin (15). These were isolated and are reported for the first time in this study. Compared 13 was identified as a new compound. Compound 2 was isolated for first time from the genus Nigella. Compound 6 was found to be the most active in the DPPH, and ABTS assays and compound 10 was found to be the most active in the α-glucosidase assay, with IC50 32.7 ± 0.1, 95.18 ± 0.9, 214.5 ± 0.0 µΜ, respectively. Compound 12, at a dose of 125 µΜ, showed anti-diabetic activity in a PTP1B assay with IC50 91.30 ± 2.5 µΜ. In conclusion, the anti-diabetic activity of N. sativa is due to its flavonoids and TTSGs. Therefore, our studies suggest that the aerial parts of N. sativa are also a valuable and alternate source of valuable phytochemicals that could be used to develop anti-oxidant and anti-diabetic medicines. View Full-Text
Keywords: Nigella sativa; antioxidant; column chromatography; characterization; isolation; triterpenoid saponin derivatives; flavonoids Nigella sativa; antioxidant; column chromatography; characterization; isolation; triterpenoid saponin derivatives; flavonoids
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MDPI and ACS Style

Parveen, A.; Farooq, M.A.; Kyunn, W.W. A New Oleanane Type Saponin from the Aerial Parts of Nigella sativa with Anti-Oxidant and Anti-Diabetic Potential. Molecules 2020, 25, 2171. https://doi.org/10.3390/molecules25092171

AMA Style

Parveen A, Farooq MA, Kyunn WW. A New Oleanane Type Saponin from the Aerial Parts of Nigella sativa with Anti-Oxidant and Anti-Diabetic Potential. Molecules. 2020; 25(9):2171. https://doi.org/10.3390/molecules25092171

Chicago/Turabian Style

Parveen, Amna, Muhammad Asim Farooq, and Whang Wan Kyunn. 2020. "A New Oleanane Type Saponin from the Aerial Parts of Nigella sativa with Anti-Oxidant and Anti-Diabetic Potential" Molecules 25, no. 9: 2171. https://doi.org/10.3390/molecules25092171

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