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从黄花海绵中分离得到的去甲骆驼蓬碱及其通过抑制 iNOS 和 NF-κB 发挥体外抗炎活性的潜在作用。

Norlignan glucosides from Hypoxis hemerocallidea and their potential in vitro anti-inflammatory activity via inhibition of iNOS and NF-κB.

机构信息

National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, 38677, United States.

National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, 38677, United States; Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, MS, 38677, United States.

出版信息

Phytochemistry. 2020 Apr;172:112273. doi: 10.1016/j.phytochem.2020.112273. Epub 2020 Jan 23.

DOI:10.1016/j.phytochem.2020.112273
PMID:31981957
Abstract

Eleven diarylpentanoid/norlignan glucosides, along with five other specialized metabolites, were isolated and characterized from the hydro-alcoholic extract of Hypoxis hemerocallidea corms. Hypoxhemerolosides A-F were found to be undescribed compounds. Curcapicycloside was isolated and identified for the first time in its original form, previously it was reported as a methylated derivative. In addition, (1S,2R)-1-(3,4-dihydroxyphenyl)-5-(4-β-D-glucopyranoxy-3-hydroxyphenyl)-1-methoxypent-4-yn-2-ol and (1S,2R)-1-(3,4-dihydroxyphenyl)-1-ethoxy-5-(4-β-D-glucopyranoxy-3-hydroxyphenyl)pent-4-yn-2-ol were isolated and characterized as artifacts, generated during extraction/isolation procedures from possible 1-(3,4-dihydroxyphenyl)-5-(4-β-D-glucopyranoxy-3-hydroxyphenyl)pent-4-yne-1,2-diol. Structure elucidation was mainly achieved by the interpretation of 1D and 2D NMR and HRESIMS data. The isolated compounds were screened for anti-inflammatory activity in terms of iNOS and NF-κB inhibition as well as for cytotoxicity. Hypoxhemerolosides C-E and obtuside A moderately inhibited nitric oxide production in LPS-stimulated mouse macrophages (RAW 264.7).

摘要

从黄花洼皮鳞茎的水醇提取物中分离并鉴定了 11 种 diarylpentanoid/norlignan 葡萄糖苷和另外 5 种特殊代谢产物。Hypoxhemerolosides A-F 被发现是未描述的化合物。首次以其原始形式分离并鉴定了 Curcapicycloside,以前曾报道为甲基化衍生物。此外,(1S,2R)-1-(3,4-二羟基苯基)-5-(4-β-D-吡喃葡萄糖氧基-3-羟基苯基)-1-甲氧基戊-4-炔-2-醇和(1S,2R)-1-(3,4-二羟基苯基)-1-乙氧基-5-(4-β-D-吡喃葡萄糖氧基-3-羟基苯基)戊-4-炔-2-醇被分离并鉴定为伪物,是在提取/分离过程中由可能的 1-(3,4-二羟基苯基)-5-(4-β-D-吡喃葡萄糖氧基-3-羟基苯基)戊-4-炔-1,2-二醇生成的。结构阐明主要通过 1D 和 2D NMR 和 HRESIMS 数据的解释来实现。对分离得到的化合物进行了抗炎活性筛选,包括 iNOS 和 NF-κB 抑制作用以及细胞毒性。Hypoxhemerolosides C-E 和 obtuside A 适度抑制 LPS 刺激的小鼠巨噬细胞(RAW 264.7)中一氧化氮的产生。

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