• 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

吡咯并吗啉螺缩酮天然产物抗氧化剂的家族级立体选择性合成及生物学评价

Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants.

作者信息

Verano Alyssa L, Tan Derek S

机构信息

Pharmacology Graduate Program , Weill Cornell Graduate School of Medical Sciences , Memorial Sloan Kettering Cancer Center , 1275 York Avenue, Box 422 , New York , NY 10065 , USA . Email:

Chemical Biology Program and Tri-Institutional Research Program , Memorial Sloan Kettering Cancer Center , 1275 York Avenue, Box 422 , New York , NY 10065 , USA.

出版信息

Chem Sci. 2017 May 1;8(5):3687-3693. doi: 10.1039/c6sc05505b. Epub 2017 Mar 15.

DOI:10.1039/c6sc05505b
PMID:28845229
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5571482/
Abstract

The pyranose spiroketal natural products pollenopyrroside A and shensongine A (also known as xylapyrroside A, -capparisine B) have been synthesized by stereoselective spirocyclizations of a common C1-functionalized glycal precursor. In conjunction with our previously reported syntheses of the corresponding furanose isomers, this provides a versatile family-level synthesis of the pyrrolomorpholine spiroketal natural products and analogues. In rat mesangial cells, hyperglycemia-induced production of reactive oxygen species, which is implicated in diabetic nephropathy, was inhibited by pollenopyrroside A and shensongine A with mid-μM IC values, while unnatural C2-hydroxy analogues exhibited more potent, sub-μM activity.

摘要

吡喃糖螺缩酮天然产物花粉吡咯糖苷A和参松碱A（也称为木糖吡咯糖苷A、-刺山柑碱B）已通过常见的C1-官能化糖烯前体的立体选择性螺环化反应合成。结合我们之前报道的相应呋喃糖异构体的合成方法，这为吡咯吗啉螺缩酮天然产物及其类似物提供了一种通用的家族级合成方法。在大鼠系膜细胞中，与糖尿病肾病相关的高血糖诱导的活性氧生成受到花粉吡咯糖苷A和参松碱A的抑制，其IC值在中μM范围内，而非天然的C2-羟基类似物表现出更强的亚μM活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/942b/5571482/3601626af0b2/c6sc05505b-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/942b/5571482/61fccf14b0c2/c6sc05505b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/942b/5571482/015d2ae54ef8/c6sc05505b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/942b/5571482/f8a5bb329589/c6sc05505b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/942b/5571482/0801cf28ba20/c6sc05505b-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/942b/5571482/e47b1978ceed/c6sc05505b-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/942b/5571482/3601626af0b2/c6sc05505b-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/942b/5571482/61fccf14b0c2/c6sc05505b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/942b/5571482/015d2ae54ef8/c6sc05505b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/942b/5571482/f8a5bb329589/c6sc05505b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/942b/5571482/0801cf28ba20/c6sc05505b-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/942b/5571482/e47b1978ceed/c6sc05505b-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/942b/5571482/3601626af0b2/c6sc05505b-f6.jpg

相似文献

1
Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants.吡咯并吗啉螺缩酮天然产物抗氧化剂的家族级立体选择性合成及生物学评价
Chem Sci. 2017 May 1;8(5):3687-3693. doi: 10.1039/c6sc05505b. Epub 2017 Mar 15.
2
Synthesis of the 2-formylpyrrole spiroketal pollenopyrroside A and structural elucidation of xylapyrroside A, shensongine A and capparisine B.2-甲酰基吡咯螺缩酮花粉吡咯苷 A 的合成及木蓝吡咯苷 A、桑辛素 A 和卡波林 B 的结构阐明。
Org Biomol Chem. 2016 Aug 10;14(32):7659-64. doi: 10.1039/c6ob01361a.
3
Synthetic approaches to access acortatarins, shensongines and pollenopyrroside; potent antioxidative spiro-alkaloids with a naturally rare morpholine moiety.合成方法获得阿考他丁、参松养心和花粉茄吡喃糖苷；具有天然罕见吗啉部分的强效抗氧化性螺环生物碱。
Fitoterapia. 2018 Sep;129:366-382. doi: 10.1016/j.fitote.2018.03.014. Epub 2018 Apr 1.
4
Stereoselective Synthesis of Spirolactone Analogues of Pyrrolomorpholine Alkaloids.吡咯吗啉生物碱螺内酯类似物的立体选择性合成
J Org Chem. 2024 Sep 6;89(17):12864-12870. doi: 10.1021/acs.joc.4c01608. Epub 2024 Aug 20.
5
Cephalostatin analogues--synthesis and biological activity.头霉素类似物——合成与生物活性
Fortschr Chem Org Naturst. 2004;87:1-80. doi: 10.1007/978-3-7091-0581-8_1.
6
Stereoselective synthesis of acortatarins A and B.阿科他他灵 A 和 B 的立体选择性合成。
Org Lett. 2012 Sep 7;14(17):4442-5. doi: 10.1021/ol3019456. Epub 2012 Aug 27.
7
4-Thiofuranoid Glycal: Versatile Glycosyl Donor for the Selective Synthesis of β-anomer of 4'-thionucleoside and its Biological Activities.4-噻吩糖醛苷：用于选择性合成 4'-硫代核苷β-异构体的多功能糖基供体及其生物活性。
Curr Med Chem. 2022;29(21):3684-3731. doi: 10.2174/0929867328666211115121434.
8
Combinatorial synthesis of natural product-like molecules using a first-generation spiroketal scaffold.使用第一代螺环缩酮支架进行类天然产物分子的组合合成。
J Comb Chem. 2002 Jan-Feb;4(1):56-72. doi: 10.1021/cc010047w.
9
Synthesis of the C(2)-C(13) fragment (the A-B spiroketal unit) of spongistatin 1 (altohyrtin A): use of a common intermediate for the synthesis of both spongistatin spiroketals.海绵他汀1（altohyrtin A）的C(2)-C(13)片段（A-B螺缩酮单元）的合成：使用共同中间体合成两种海绵他汀螺缩酮。
Org Lett. 2002 Oct 17;4(21):3723-5. doi: 10.1021/ol026688x.
10
Recent synthetic approaches toward non-anomeric spiroketals in natural products.近期天然产物中非端基螺旋缩酮的合成方法。
Molecules. 2008;13(10):2570-600. doi: 10.3390/molecules13102570.

引用本文的文献

1
Short Scalable Route to Bis-morpholine Spiroacetals and Oxazepane Analogues: Useful 3D-Scaffolds for Compound Library Assembly.双吗啉螺缩醛和氧杂氮杂环庚烷类似物的短程可扩展合成路线：用于化合物库组装的有用三维支架
J Org Chem. 2025 Feb 21;90(7):2652-2661. doi: 10.1021/acs.joc.4c02690. Epub 2025 Feb 10.
2
Pyrrole-2-carboxaldehydes: Origins and Physiological Activities.吡咯-2-甲醛：起源与生理活性。
Molecules. 2023 Mar 13;28(6):2599. doi: 10.3390/molecules28062599.
3
Spirocyclic derivatives as antioxidants: a review.螺环衍生物作为抗氧化剂：综述

本文引用的文献

1
Synthesis of the 2-formylpyrrole spiroketal pollenopyrroside A and structural elucidation of xylapyrroside A, shensongine A and capparisine B.2-甲酰基吡咯螺缩酮花粉吡咯苷 A 的合成及木蓝吡咯苷 A、桑辛素 A 和卡波林 B 的结构阐明。
Org Biomol Chem. 2016 Aug 10;14(32):7659-64. doi: 10.1039/c6ob01361a.
2
An Aggregation Advisor for Ligand Discovery.用于配体发现的聚集顾问程序。
J Med Chem. 2015 Sep 10;58(17):7076-87. doi: 10.1021/acs.jmedchem.5b01105. Epub 2015 Aug 28.
3
Spiroalkaloids from Shensong Yangxin capsule.参松养心胶囊中的螺环生物碱
RSC Adv. 2021 Jun 21;11(36):21926-21954. doi: 10.1039/d1ra01170g.
J Asian Nat Prod Res. 2015 May;17(5):559-66. doi: 10.1080/10286020.2015.1047354.
4
Cascade N-Alkylation/Hemiacetalization for Facile Construction of the Spiroketal Skeleton of Acortatarin Alkaloids with Therapeutic Potentiality in Diabetic Nephropathy.级联N-烷基化/半缩醛化反应用于简便构建在糖尿病肾病中具有治疗潜力的阿考他汀生物碱的螺缩酮骨架。
Nat Prod Bioprospect. 2014 Dec 16;5(1):37-45. doi: 10.1007/s13659-014-0049-8.
5
Solvent-dependent divergent functions of Sc(OTf)₃ in stereoselective epoxide-opening spiroketalizations.溶剂依赖性的 Sc(OTf)₃ 在立体选择性环氧化开环螺缩酮化反应中的不同功能。
Org Lett. 2014 May 2;16(9):2474-7. doi: 10.1021/ol500853q. Epub 2014 Apr 17.
6
Synthesis, structural characterization, aromatic characteristics, and metalation of neo-confused porphyrins, a newly discovered class of porphyrin isomers.新型-confused 卟啉的合成、结构特征、芳香性特征及金属化，这是一类新发现的卟啉异构体。
J Org Chem. 2014 May 2;79(9):4078-93. doi: 10.1021/jo500580e. Epub 2014 Apr 18.
7
Identification of bitter compounds in whole wheat bread.鉴定全麦面包中的苦味化合物。
Food Chem. 2013 Nov 15;141(2):1345-53. doi: 10.1016/j.foodchem.2013.03.021. Epub 2013 Mar 13.
8
Acortatarin A inhibits high glucose-induced extracellular matrix production in mesangial cells.阿考达亭 A 抑制高糖诱导的系膜细胞细胞外基质产生。
Chin Med J (Engl). 2013 Apr;126(7):1230-5.
9
Concise total synthesis of acortatarin A.阿考他丁A的简洁全合成
Biosci Biotechnol Biochem. 2013;77(3):676-8. doi: 10.1271/bbb.120862. Epub 2013 Mar 7.
10
Total synthesis of acortatarin A using a Pd(II)-catalyzed spiroketalization strategy.采用 Pd(II)催化的螺缩酮化策略全合成 acortatarin A。
J Org Chem. 2012 Oct 5;77(19):8410-6. doi: 10.1021/jo301835e. Epub 2012 Sep 25.