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

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Polypunctosides E-K: seven new steroidal saponins from Polygonatum punctatum Royle ex Kunth and their nitric oxide production inhibitory activities
Journal of Natural Medicines ( IF 2.5 ) Pub Date : 2022-11-19 , DOI: 10.1007/s11418-022-01663-w
Tran Thi Thu Ha _{1,

2} , Nguyen Tien Dung ₂ , Bui Huu Tai _{3,

4} , Phan Van Kiem _{3,

4}

Affiliation

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 (1–4) and three furospirostans (5–7). 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 1–7 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.

Graphical Abstract

中文翻译：

Polypunctosides EK：Polygonatum punctatum Royle ex Kunth 的七种新甾体皂苷及其一氧化氮产生抑制活性

Polygonatum punctatum Royle ex Kunth 是一种在古老的天然森林中发现的高价值药用植物。对这种植物的根部进行的植物化学研究导致分离出七种新的甾体皂苷，包括四种呋喃糖醇 ( 1 – 4 ) 和三种呋喃螺糖醇 ( 5 – 7 )。它们的结构被阐明为 (25 R )-26 -O- ( β - d- glucopyranosyl)-furost-5-ene-3 β ,17 α ,22 α ,26-tetraol 3 -O-α - l -arabinopyranosyl- (1 → 2)- β - d-吡喃葡萄糖基-(1 → 4)- β - d-半乳糖苷 ( 1 ), (25 R )-26 -O- ( β - d-吡喃葡萄糖基)-furost-5-ene-3 β ,14 α ,17 α ,22 α ,26-五醇 3 -O-α - l -阿拉伯吡喃糖基-(1 → 2)- β - d-吡喃葡萄糖基-(1 → 4)- β - d -吡喃半乳糖苷 ( 2 ), (25 R )-26 -O - ( β - d -glucopyranosyl)-furost-5-ene-22 α-methoxy-3 β ,17 α ,26-triol 3 -O-α - l -arabinopyranosyl-(1 → 2)- β - d -glucopyranosyl-(1 → 4)- β - d -galactopyranoside ( 3 ), ( 25 R )-26 -O- ( β - d -glucopyranosyl)-furost-5-ene-22 α -methoxy -3 β ,17 α ,26-triol 3 -O- [ α - l -arabinopyranosyl-(1 → 2)- β - d -吡喃葡萄糖基-(1 → 4)]-[乙酰氧基-(→ 6)]- β -d -吡喃半乳糖苷 ( 4 ), 26 -O- ( β - d -吡喃葡萄糖基)-14 α, 17 α -dihydroxynuatigenin 3 -O-α - l -arabinopyranosyl-(1 → 2)- β - d -glucopyranosyl-(1 → 4)- β - d -吡喃半乳糖苷 ( 5 ), 26 -O- ( β - d -glucopyranosyl)-17 α -hydroxynuatigenin 3 -O-α - l -arabinopyranosyl-(1 → 2)- β - d -glucopyranosyl -(1 → 4)- β- d -吡喃半乳糖苷 ( 6 ), 和 26 -O- ( β - d -吡喃葡萄糖基)-14 α -hydroxynuatigenin 3 -O-α - l -arabinopyranosyl-(1 → 2)- β - d -glucopyranosyl-(1 → 4)- β - d -吡喃半乳糖苷 ( 7 ) 通过广泛的光谱分析，包括红外、高分辨率电喷雾电离质谱以及一维和二维核磁共振光谱。化合物1 – 7用 IC 抑制脂多糖激活的 RAW264.7 细胞中一氧化氮的产生_{50 个}值范围从 41.5 ± 3.2 到 62.2 ± 3.7 µM，而阳性对照化合物l -NMMA 的值为 33.8 ± 2.6 µM。

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更新日期：2022-11-19

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