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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。

Synthetic approaches to access acortatarins, shensongines and pollenopyrroside; potent antioxidative spiro-alkaloids with a naturally rare morpholine moiety.

机构信息

Department of Chemistry, Quaid-i-Azam University, 45320 Islamabad, Pakistan.

Department of Chemistry, Quaid-i-Azam University, 45320 Islamabad, Pakistan; Peter Grünberg Institute, PGI-6, Research Centre Jülich, D-52425 Jülich, Germany.

出版信息

Fitoterapia. 2018 Sep;129:366-382. doi: 10.1016/j.fitote.2018.03.014. Epub 2018 Apr 1.

DOI:10.1016/j.fitote.2018.03.014
PMID:29617626
Abstract

Pyrrole spiroketal alkaloids (PSAs) are a class of novel natural products that have been recently disclosed. Acortatarin A and acortatarin B, two potent antioxidative spiroalkaloids with a naturally rare morpholine moiety, are important members of this class. These spiroalkaloids are isolated from Acorus tatarinowii, Brassica campestris, Capparis spinose, bread crust, Xylaria nigripes and medicine Shensong Yangxin and could inhibit significantly the reactive oxygen species (ROS) production in high-glucose-induced mesangial cells in a time- and dose-dependent manner. Hence, these natural products are promising starting points for the formation of new therapeutics to medicate cardiovascular diseases, cancer, diabetic complications, and other diseases in which ROS are implicated. The impressive structure combined with an interesting pharmacological activity prompted synthetic chemists to construct an asymmetric synthetic strategy that could be used to access structural derivatives in addition to the larger quantities of natural products required for further biological investigations. This review summarizes the current state of the literature regarding with the synthesis of acortatarin A and B and its other family members viz. shensongine A, B and C, and pollenopyrroside A. The present review discusses the pros and cons of synthetic methodologies, which would be beneficial for further developments in the synthetic methodologies. Hopefully, this struggle pushes the reader's mind to consider new perspectives, think differently and forge new connections.

摘要

吡咯并螺缩酮生物碱(PSAs)是一类新型天然产物,最近已被披露。阿枯米定 A 和阿枯米定 B 是两种具有天然罕见吗啉部分的强效抗氧化螺缩酮生物碱,是该类的重要成员。这些螺缩酮生物碱从石菖蒲、白菜、杠柳、面包皮、黑炭菌和中药参松养心丸中分离得到,能够显著抑制高葡萄糖诱导的系膜细胞中活性氧(ROS)的产生,具有时间和剂量依赖性。因此,这些天然产物是形成新疗法治疗心血管疾病、癌症、糖尿病并发症和其他涉及 ROS 的疾病的有前途的起点。令人印象深刻的结构结合有趣的药理学活性促使合成化学家构建了一种不对称合成策略,除了需要进一步的生物学研究外,还可以用于构建结构衍生物。本文综述了关于阿枯米定 A 和 B 及其它家族成员如参松宁 A、B 和 C 以及花粉嘧啶 A 的合成研究现状。本文综述讨论了合成方法的优缺点,这将有助于进一步发展合成方法。希望这种努力能促使读者思考新的观点,以不同的方式思考问题,并建立新的联系。

相似文献

1
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.
2
Acortatarins A and B, two novel antioxidative spiroalkaloids with a naturally unusual morpholine motif from Acorus tatarinowii.菖蒲酮 A 和 B,两种新型具有天然不寻常吗啉基序的抗氧化性螺环生物碱来自菖蒲。
Org Lett. 2010 Apr 16;12(8):1844-7. doi: 10.1021/ol100451p.
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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.
4
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.
5
Total synthesis and stereochemical revision of acortatarins A and B.阿科他他汀 A 和 B 的全合成及立体化学修订。
Org Lett. 2011 Oct 21;13(20):5452-5. doi: 10.1021/ol202121k. Epub 2011 Sep 28.
6
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.
7
Spiroalkaloids from Shensong Yangxin capsule.参松养心胶囊中的螺环生物碱
J Asian Nat Prod Res. 2015 May;17(5):559-66. doi: 10.1080/10286020.2015.1047354.
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Recent progress in the isolation, bioactivity, biosynthesis, and total synthesis of natural spiroketals.天然螺缩酮的分离、生物活性、生物合成和全合成的最新进展。
Nat Prod Rep. 2018 Jan 25;35(1):75-104. doi: 10.1039/c7np00043j.
9
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.
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.

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