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来自鱼腥草种子的具有抗炎活性的新木脂素和二芳基壬烷类衍生物。

Neolignans and Diarylnonanoid Derivatives with Anti-inflammatory Activity from Houtt. Seeds.

作者信息

Le Tam Thi, Kim Jonghwan, Kang Tae Kyeom, Lee Wook-Bin, Kim Myungsuk, Kim Chung Sub, Jung Sang Hoon

机构信息

Natural Product Research Center, Korea Institute of Science and Technology (KIST), Gangneung 25451, Republic of Korea.

Department of Biopharmaceutical Convergence, Sungkyunkwan University, Suwon 16419, Republic of Korea.

出版信息

ACS Omega. 2024 Jul 30;9(32):35170-35181. doi: 10.1021/acsomega.4c05649. eCollection 2024 Aug 13.

DOI:10.1021/acsomega.4c05649
PMID:39157106
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11325528/
Abstract

Houtt. is rich in lignans, neolignans, and diarylnonanoids, with well-documented anti-inflammatory properties. However, there is limited research on the conjugated forms of diarylnonanoids, neolignans, monoterpenes, and others and their anti-inflammatory effects. Our study isolated 33 new compounds (--, and -), including two neolignans, alongside various neolignan-diarylnonanoid, propenylbenzene-diarylnonanoid, 2,3-dimethylbutane-type lignan-diarylnonanoid, and monoterpene-diarylnonanoid conjugates, along with previously reported compounds (, , and -). Their chemical structures were determined via spectroscopic analyses. Compounds , , , , , , , and exhibited potent inhibition of NF-κB/AP1 and IRF signaling induced by TLR agonists. Notably, stereoisomers showed distinct behavior, while 10,11-isomers induced cytotoxicity, and 10,11-isomers produced contrasting effects, especially within group-I compounds.

摘要

鱼腥草富含木脂素、新木脂素和二芳基壬烷类化合物,具有充分记载的抗炎特性。然而,关于二芳基壬烷类、新木脂素、单萜类及其他化合物的共轭形式及其抗炎作用的研究有限。我们的研究分离出33种新化合物(——,以及——),包括两种新木脂素,以及各种新木脂素 - 二芳基壬烷类、丙烯基苯 - 二芳基壬烷类、2,3 - 二甲基丁烷型木脂素 - 二芳基壬烷类和单萜 - 二芳基壬烷类共轭物,还有先前报道的化合物(——,——,以及——)。通过光谱分析确定了它们的化学结构。化合物——,——,——,——,——,——,——和——对TLR激动剂诱导的NF - κB/AP1和IRF信号传导表现出强效抑制作用。值得注意的是,立体异构体表现出不同的行为,10,11 - 异构体诱导细胞毒性,而10,11 - 异构体产生相反的效果[此处原文有误,推测是前后两个10,11 - 异构体表述反了,暂按推测翻译,实际翻译时建议结合正确原文修改],特别是在I组化合物中。

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本文引用的文献

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J Enzyme Inhib Med Chem. 2023 Dec;38(1):2251099. doi: 10.1080/14756366.2023.2251099.
2
Malabaricone C derived from nutmeg inhibits arachidonate 5-lipoxygenase activity and ameliorates psoriasis-like skin inflammation in mice.荜茇宁 C 来源于肉豆蔻,可抑制花生四烯酸 5-脂氧合酶的活性,并改善小鼠类似银屑病的皮肤炎症。
Free Radic Biol Med. 2022 Nov 20;193(Pt 1):1-8. doi: 10.1016/j.freeradbiomed.2022.09.028. Epub 2022 Sep 29.
3
New Monoterpene-Conjugated Phenolic Constituents from Nutmeg and Their Autophagy Modulating Activities.
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J Agric Food Chem. 2022 Aug 10;70(31):9684-9693. doi: 10.1021/acs.jafc.2c03370. Epub 2022 Jul 29.
4
Phytochemical and pharmacological properties of Myristica fragrans Houtt.: an updated review.肉豆蔻的植物化学和药理学特性:最新综述。
Arch Pharm Res. 2020 Nov;43(11):1067-1092. doi: 10.1007/s12272-020-01285-4. Epub 2020 Nov 18.
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