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一种获取生物活性天然产物——二氢姜黄素/1,7 - 二芳基庚烷类化合物的简洁合成路线。

A concise synthesis route to access bioactive natural products-dihydrocurcumins/1,7-diarylheptanoids.

作者信息

Tripathi Datendra Nath, Rajendran Saravanakumar

机构信息

Chemistry Division, School of Advanced Sciences, Vellore Institute of Technology Chennai campus Vandalur-Kelambakkam Road Chennai - 600127 Tamil Nadu India

Anthem Biosciences Private Limited No 49, Canara Bank Road, Hosur Rd, Electronics City Phase 1, Bommasandra Industrial Area Bengaluru Karnataka 560099 India.

出版信息

RSC Adv. 2023 Sep 1;13(37):25871-25876. doi: 10.1039/d3ra05049a. eCollection 2023 Aug 29.

DOI:10.1039/d3ra05049a
PMID:37664191
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10472796/
Abstract

Dihydrocurcumin (DHCUR), a natural product and reductive metabolite of curcumin (CUR), is limitedly explored owing to its low bioavailability and limited accessibility due to lack of straightforward synthetic routes and poor yields with known methods. Herein, we report a concise and straightforward route to synthesize DHCUR and its analogs in excellent yields. Dihydroferuloylacetone is condensed with aldehydes to obtain desired DHCURs/1,7-diarylheptanoids in 81-90% yields. The developed protocol facilitates easy access to bioactive natural products, 1,7-diarylheptanoids and DHCUR, for therapeutic study.

摘要

二氢姜黄素（DHCUR）是姜黄素（CUR）的天然产物和还原代谢物，由于其生物利用度低，且由于缺乏直接的合成路线以及已知方法的产率低而难以获得，因此对其研究有限。在此，我们报道了一种简洁直接的路线，以优异的产率合成DHCUR及其类似物。二氢阿魏酰丙酮与醛缩合，以81-90%的产率获得所需的二氢姜黄素/1,7-二芳基庚烷类化合物。所开发的方法便于获得生物活性天然产物、1,7-二芳基庚烷类化合物和二氢姜黄素，用于治疗研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb32/10472796/87957b51947a/d3ra05049a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb32/10472796/117c14ff74b2/d3ra05049a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb32/10472796/cc281d8d1d16/d3ra05049a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb32/10472796/a643b9027b7a/d3ra05049a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb32/10472796/85f19f9d2c5c/d3ra05049a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb32/10472796/87957b51947a/d3ra05049a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb32/10472796/117c14ff74b2/d3ra05049a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb32/10472796/cc281d8d1d16/d3ra05049a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb32/10472796/a643b9027b7a/d3ra05049a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb32/10472796/85f19f9d2c5c/d3ra05049a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cb32/10472796/87957b51947a/d3ra05049a-f3.jpg

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Front Pharmacol. 2022 Mar 25;13:820806. doi: 10.3389/fphar.2022.820806. eCollection 2022.
2
Reductive metabolites of curcumin and their therapeutic effects.姜黄素的还原代谢产物及其治疗作用。
Heliyon. 2020 Nov 12;6(11):e05469. doi: 10.1016/j.heliyon.2020.e05469. eCollection 2020 Nov.
3
The molecular basis for the pharmacokinetics and pharmacodynamics of curcumin and its metabolites in relation to cancer.
姜黄素及其代谢物在癌症方面的药代动力学和药效学的分子基础。
Pharmacol Rev. 2013 Dec 24;66(1):222-307. doi: 10.1124/pr.110.004044. Print 2014.
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Formation of tetrahydrocurcumin by reduction of curcumin with cultured plant cells of Marchantia polymorpha.利用多歧藻的培养植物细胞还原姜黄素形成四氢姜黄素。
Nat Prod Commun. 2012 Apr;7(4):529-30.
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Molecular docking studies of curcumin analogs with phospholipase A2.姜黄素类似物与磷脂酶 A2 的分子对接研究。
Interdiscip Sci. 2011 Sep;3(3):189-97. doi: 10.1007/s12539-011-0090-9. Epub 2011 Sep 29.
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Feruloylacetone as the model compound of half-curcumin: synthesis and antioxidant properties.阿魏酰丙酮作为半姜黄素的模型化合物：合成与抗氧化性能。
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