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Polypunctosides E-K: seven new steroidal saponins from Polygonatum punctatum Royle ex Kunth and their nitric oxide production inhibitory activities

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Abstract

Polygonatum punctatum Royle ex Kunth is a high-value medicinal plant found in old natural forests. A phytochemical study on the roots of this plant led to the isolation of seven new steroidal saponins including four furostans (14) and three furospirostans (57). Their structures were elucidated as (25R)-26-O-(β-d-glucopyranosyl)-furost-5-ene-3β,17α,22α,26-tetraol 3-O-α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (1), (25R)-26-O-(β-d-glucopyranosyl)-furost-5-ene-3β,14α,17α,22α,26-pentaol 3-O-α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (2), (25R)-26-O-(β-d-glucopyranosyl)-furost-5-ene-22α-methoxy-3β,17α,26-triol 3-O-α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (3), (25R)-26-O-(β-d-glucopyranosyl)-furost-5-ene-22α-methoxy-3β,17α,26-triol 3-O-[α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)]-[acetoxy-(→ 6)]-β-d-galactopyranoside (4), 26-O-(β-d-glucopyranosyl)-14α,17α-dihydroxynuatigenin 3-O-α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (5), 26-O-(β-d-glucopyranosyl)-17α-hydroxynuatigenin 3-O-α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (6), and 26-O-(β-d-glucopyranosyl)-14α-hydroxynuatigenin 3-O-α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (7) by extensive spectroscopic analyses, including infrared, high-resolution electrospray ionization mass spectrometry, and one- and two-dimensional nuclear magnetic resonance spectroscopy. Compounds 17 inhibited nitric oxide production in lipopolysaccharide activated RAW264.7 cells with IC50 values ranging from 41.5 ± 3.2 to 62.2 ± 3.7 µM, compared to 33.8 ± 2.6 µM for the positive control compound l-NMMA.

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Acknowledgements

This work is financial supported from the project “Study on genetic diversity and medicinal active ingredient of Polygonatum punctatum Royle ex Knuth in Vietnam”, under the KOVALEVSKAYA FRIZE 2019 for outstanding achievements in science by an individual female scientist (Prof. Dr. Tran Thi Thu Ha).

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Ha, T.T.T., Dung, N.T., Tai, B.H. et al. Polypunctosides E-K: seven new steroidal saponins from Polygonatum punctatum Royle ex Kunth and their nitric oxide production inhibitory activities. J Nat Med 77, 238–249 (2023). https://doi.org/10.1007/s11418-022-01663-w

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