• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

四氢呋喃基在海洋脂质和萜烯中的作用。

The Tetrahydrofuran Motif in Marine Lipids and Terpenes.

机构信息

Department of Organic Chemistry, Campus Miguel Delibes, University of Valladolid, 47011 Valladolid, Spain.

Departamento de Química Orgánica y Química Inorgánica, Facultad de Farmacia e Instituto de Investigación Química Andrés M. del Río (IQAR), Universidad de Alcalá, Ctra. Madrid-Barcelona, 28871 Madrid, Spain.

出版信息

Mar Drugs. 2022 Oct 15;20(10):642. doi: 10.3390/md20100642.

DOI:10.3390/md20100642
PMID:36286465
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9605582/
Abstract

Heterocycles are particularly common moieties within marine natural products. Specifically, tetrahydrofuranyl rings are present in a variety of compounds which present complex structures and interesting biological activities. Focusing on terpenoids, a high number of tetrahydrofuran-containing metabolites have been isolated during the last decades. They show promising biological activities, making them potential leads for novel antibiotics, antikinetoplastid drugs, amoebicidal substances, or anticancer drugs. Thus, they have attracted the attention of the synthetics community and numerous approaches to their total syntheses have appeared. Here, we offer the reader an overview of marine-derived terpenoids and related compounds, their isolation, structure determination, and a special focus on their total syntheses and biological profiles.

摘要

杂环化合物在海洋天然产物中尤为常见。具体来说,四氢呋喃环存在于各种具有复杂结构和有趣生物活性的化合物中。以萜类化合物为例,在过去几十年中已经分离出了大量含有四氢呋喃的代谢物。它们表现出有希望的生物活性,使它们成为新型抗生素、抗锥虫药物、杀阿米巴物质或抗癌药物的潜在先导化合物。因此,它们引起了合成化学家的关注,并且已经出现了许多针对它们的全合成方法。在这里,我们为读者提供了海洋衍生萜类化合物和相关化合物的概述,包括它们的分离、结构确定,以及特别关注它们的全合成和生物特征。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/3caddf3d6d57/marinedrugs-20-00642-sch016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/d47f413300ca/marinedrugs-20-00642-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/b3faed382d4f/marinedrugs-20-00642-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/ad803eca13a3/marinedrugs-20-00642-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/dae729e5eefc/marinedrugs-20-00642-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/d427d5290397/marinedrugs-20-00642-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/b56f2435086b/marinedrugs-20-00642-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/c2bf7c09907a/marinedrugs-20-00642-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/b8b08ba877aa/marinedrugs-20-00642-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/84f8dc6ab26c/marinedrugs-20-00642-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/86bde5d031db/marinedrugs-20-00642-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/8feec85ed89d/marinedrugs-20-00642-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/10c10a4ce9a0/marinedrugs-20-00642-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/508afeb08163/marinedrugs-20-00642-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/c8f7b0a916cb/marinedrugs-20-00642-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/673efc52578a/marinedrugs-20-00642-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/0bf2ff058986/marinedrugs-20-00642-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/b89de499d4e1/marinedrugs-20-00642-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/eb56d6f5edc9/marinedrugs-20-00642-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/a3b600b263f8/marinedrugs-20-00642-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/270143df2e77/marinedrugs-20-00642-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/23ec56ee1017/marinedrugs-20-00642-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/8411612ef9cd/marinedrugs-20-00642-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/d76ad274d2f2/marinedrugs-20-00642-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/3ffbd1056bdf/marinedrugs-20-00642-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/4d89b0a5d102/marinedrugs-20-00642-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/e09ab41a7ed1/marinedrugs-20-00642-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/de5a03591880/marinedrugs-20-00642-sch011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/938513706ffd/marinedrugs-20-00642-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/92be9f8949c1/marinedrugs-20-00642-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/933369d8117f/marinedrugs-20-00642-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/408e2382fd14/marinedrugs-20-00642-g020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/8989abba17df/marinedrugs-20-00642-sch012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/b3d9faed9231/marinedrugs-20-00642-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/098acced8f30/marinedrugs-20-00642-g022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/d3eeb9f5c235/marinedrugs-20-00642-g023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/8e37b0d2d27d/marinedrugs-20-00642-g024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/4bffdd1de346/marinedrugs-20-00642-g025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/27fc565e0ea1/marinedrugs-20-00642-g027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/0e483ec53d5c/marinedrugs-20-00642-g029.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/cd6a69039d5e/marinedrugs-20-00642-sch013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/581bc82a4bda/marinedrugs-20-00642-sch014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/3caddf3d6d57/marinedrugs-20-00642-sch016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/d47f413300ca/marinedrugs-20-00642-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/b3faed382d4f/marinedrugs-20-00642-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/ad803eca13a3/marinedrugs-20-00642-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/dae729e5eefc/marinedrugs-20-00642-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/d427d5290397/marinedrugs-20-00642-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/b56f2435086b/marinedrugs-20-00642-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/c2bf7c09907a/marinedrugs-20-00642-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/b8b08ba877aa/marinedrugs-20-00642-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/84f8dc6ab26c/marinedrugs-20-00642-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/86bde5d031db/marinedrugs-20-00642-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/8feec85ed89d/marinedrugs-20-00642-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/10c10a4ce9a0/marinedrugs-20-00642-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/508afeb08163/marinedrugs-20-00642-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/c8f7b0a916cb/marinedrugs-20-00642-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/673efc52578a/marinedrugs-20-00642-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/0bf2ff058986/marinedrugs-20-00642-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/b89de499d4e1/marinedrugs-20-00642-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/eb56d6f5edc9/marinedrugs-20-00642-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/a3b600b263f8/marinedrugs-20-00642-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/270143df2e77/marinedrugs-20-00642-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/23ec56ee1017/marinedrugs-20-00642-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/8411612ef9cd/marinedrugs-20-00642-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/d76ad274d2f2/marinedrugs-20-00642-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/3ffbd1056bdf/marinedrugs-20-00642-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/4d89b0a5d102/marinedrugs-20-00642-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/e09ab41a7ed1/marinedrugs-20-00642-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/de5a03591880/marinedrugs-20-00642-sch011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/938513706ffd/marinedrugs-20-00642-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/92be9f8949c1/marinedrugs-20-00642-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/933369d8117f/marinedrugs-20-00642-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/408e2382fd14/marinedrugs-20-00642-g020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/8989abba17df/marinedrugs-20-00642-sch012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/b3d9faed9231/marinedrugs-20-00642-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/098acced8f30/marinedrugs-20-00642-g022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/d3eeb9f5c235/marinedrugs-20-00642-g023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/8e37b0d2d27d/marinedrugs-20-00642-g024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/4bffdd1de346/marinedrugs-20-00642-g025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/27fc565e0ea1/marinedrugs-20-00642-g027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/0e483ec53d5c/marinedrugs-20-00642-g029.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/cd6a69039d5e/marinedrugs-20-00642-sch013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/581bc82a4bda/marinedrugs-20-00642-sch014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eec7/9605582/3caddf3d6d57/marinedrugs-20-00642-sch016.jpg

相似文献

1
The Tetrahydrofuran Motif in Marine Lipids and Terpenes.四氢呋喃基在海洋脂质和萜烯中的作用。
Mar Drugs. 2022 Oct 15;20(10):642. doi: 10.3390/md20100642.
2
The Tetrahydrofuran Motif in Polyketide Marine Drugs.四氢呋喃基在聚酮类海洋药物中的作用
Mar Drugs. 2022 Feb 3;20(2):120. doi: 10.3390/md20020120.
3
Molecular architecture and biomedical leads of terpenes from red sea marine invertebrates.红海海洋无脊椎动物中萜类化合物的分子结构与生物医学先导物
Mar Drugs. 2015 May 20;13(5):3154-81. doi: 10.3390/md13053154.
4
Terpenoids from Marine Soft Coral of the Genus : Chemistry and Biological Activities.海洋软珊瑚属萜类化合物:化学与生物活性。
Mar Drugs. 2018 Sep 9;16(9):320. doi: 10.3390/md16090320.
5
A Review of Terpenes from Marine-Derived Fungi: 2015-2019.海洋源真菌萜类化合物研究进展:2015-2019 年
Mar Drugs. 2020 Jun 18;18(6):321. doi: 10.3390/md18060321.
6
Natural peroxy anticancer agents.天然过氧抗癌剂。
Mini Rev Med Chem. 2007 Jun;7(6):571-89. doi: 10.2174/138955707780859396.
7
Syntheses and biological studies of marine terpenoids derived from inorganic cyanide.源自无机氰化物的海洋萜类化合物的合成及生物学研究
Nat Prod Rep. 2015 Apr;32(4):543-77. doi: 10.1039/c4np00109e.
8
Marine Natural Products as Models to Circumvent Multidrug Resistance.海洋天然产物作为克服多药耐药性的模型。
Molecules. 2016 Jul 8;21(7):892. doi: 10.3390/molecules21070892.
9
Chemistry, biosynthesis and biological activity of terpenoids and meroterpenoids in bacteria and fungi isolated from different marine habitats.从不同海洋生境中分离的细菌和真菌中的萜类和杂萜类的化学、生物合成和生物活性。
Eur J Med Chem. 2021 Jan 15;210:112957. doi: 10.1016/j.ejmech.2020.112957. Epub 2020 Oct 28.
10
Naturally occurring peroxides with biological activities.具有生物活性的天然过氧化物。
Mini Rev Med Chem. 2003 Mar;3(2):159-65. doi: 10.2174/1389557033405313.

引用本文的文献

1
Charge Relocation Enables a Modular and Diastereoselective Synthesis of cis-Substituted Tetrahydrofurans.电荷重排实现了顺式取代四氢呋喃的模块化和非对映选择性合成。
Angew Chem Int Ed Engl. 2025 Jul;64(29):e202503750. doi: 10.1002/anie.202503750. Epub 2025 Jun 4.
2
2-Butoxytetrahydrofuran, Isolated from , Attenuates Aggregative and Oxidative Properties of α-Synuclein and Alleviates Its Toxicity in a Transgenic Model of Parkinson's Disease.2-丁氧基四氢呋喃,从 中分离得到,可减弱 α-突触核蛋白的聚集和氧化特性,并减轻其在帕金森病转基因模型中的毒性。
ACS Chem Neurosci. 2024 Jun 5;15(11):2182-2197. doi: 10.1021/acschemneuro.4c00008. Epub 2024 May 10.
3

本文引用的文献

1
Proposal for structural revision of several monosubstituted tricycloalternarenes.提议对几种单取代三环[4.2.1.0~2,4]壬烯进行结构修订。
Phytochemistry. 2022 Jun;198:113141. doi: 10.1016/j.phytochem.2022.113141. Epub 2022 Mar 1.
2
The Tetrahydrofuran Motif in Polyketide Marine Drugs.四氢呋喃基在聚酮类海洋药物中的作用
Mar Drugs. 2022 Feb 3;20(2):120. doi: 10.3390/md20020120.
3
Catalytic Enantioconvergent Allenylation of Aldehydes with Propargyl Halides.催化对映选择性烯丙基化醛与丙炔卤化物。
Coral Lipids.
珊瑚脂质。
Mar Drugs. 2023 Oct 15;21(10):539. doi: 10.3390/md21100539.
4
Ligand-Enabled Double γ-C(sp )-H Functionalization of Aliphatic Acids: One-Step Synthesis of γ-Arylated γ-Lactones.配体促进的脂肪酸双γ-C(sp³)-H官能化:γ-芳基化γ-内酯的一步合成
Angew Chem Int Ed Engl. 2023 Dec 4;62(49):e202312331. doi: 10.1002/anie.202312331. Epub 2023 Oct 31.
5
Lipids and Terpenoids from the Deep-Sea Fungus R22 and Their Antagonism against Two Wheat Pathogens.深海真菌 R22 的脂类和萜类化合物及其对两种小麦病原菌的拮抗作用。
Molecules. 2023 Aug 24;28(17):6220. doi: 10.3390/molecules28176220.
Angew Chem Int Ed Engl. 2022 Mar 1;61(10):e202117114. doi: 10.1002/anie.202117114. Epub 2022 Jan 24.
4
Exploring Chemical Diversity of Sponges as a Source of Novel Lead Compounds in Drug Discovery.探索海绵的化学多样性,作为药物发现中新型先导化合物的来源。
Mar Drugs. 2021 Nov 26;19(12):667. doi: 10.3390/md19120667.
5
Asymmetric Total Syntheses, Stereostructures, and Cytotoxicities of Marine Bromotriterpenoids Aplysiol B (Laurenmariannol) and Saiyacenol A.海洋溴三萜烯 Aplysiol B(Laurenmariannol)和 Saiyacenol A 的不对称全合成、立体结构和细胞毒性。
Chem Asian J. 2022 Jan 3;17(1):e202101137. doi: 10.1002/asia.202101137. Epub 2021 Nov 16.
6
Isomalabaricane Triterpenes from the Marine Sponge sp.海洋海绵 sp. 中的异马烷三萜
Mar Drugs. 2021 Apr 6;19(4):206. doi: 10.3390/md19040206.
7
Marinoterpins A-C: Rare Linear Merosesterterpenoids from Marine-Derived Actinomycete Bacteria of the Family Streptomycetaceae.马林萜 A-C:来自海洋放线菌科链霉菌属海洋衍生放线菌的罕见线性单萜。
J Org Chem. 2021 Aug 20;86(16):11140-11148. doi: 10.1021/acs.joc.1c00262. Epub 2021 Apr 12.
8
Marine natural products.海洋天然产物。
Nat Prod Rep. 2021 Mar 4;38(2):362-413. doi: 10.1039/d0np00089b.
9
Structure and Computational Basis for Backbone Rearrangement in Marine Oxasqualenoids.海洋氧化鲨烯类化合物骨架重排的结构和计算基础。
J Org Chem. 2021 Feb 5;86(3):2437-2446. doi: 10.1021/acs.joc.0c02600. Epub 2020 Dec 28.
10
Isolation and Characterization of New Anti-Inflammatory and Antioxidant Components from Deep Marine-Derived Fungus SP. Bzo-l062.深海来源真菌 SP. Bzo-l062 新型抗炎抗氧化成分的分离与鉴定。
Mar Drugs. 2020 Nov 26;18(12):597. doi: 10.3390/md18120597.