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蛇床子素综述:化学性质与生物学特性

A review of nemorosone: Chemistry and biological properties.

作者信息

Cuesta-Rubio Osmany, Monzote Lianet, Fernández-Acosta Roberto, Pardo-Andreu Gilberto Lázaro, Rastrelli Luca

机构信息

Universidad Técnica de Machala, Facultad de Ciencias Químicas y de la Salud, Ave. Panamericana km 5½, 070101, Machala, Ecuador.

Departamento de Parasitología, Instituto de Medicina Tropical Pedro Kourí, Autopista Novia del Mediodía Km 6 1/2, 11400, La Habana, Cuba.

出版信息

Phytochemistry. 2023 Jun;210:113674. doi: 10.1016/j.phytochem.2023.113674. Epub 2023 Apr 10.

DOI:10.1016/j.phytochem.2023.113674
PMID:37044362
Abstract

Nemorosone is a bicyclic polyprenylated acylphloroglucinol derivative originally isolated from Clusia spp. and it can be obtained through chemical synthesis employing different synthetic strategies. Since its discovery, it has attracted great attention both from a biological and chemical viewpoint. In the present article, we attempted to review various chemical and biological topics around nemorosone, with an emphasis on its antiproliferative activities. For this purpose, relevant data was collected from different scientific databases including Google Scholar, PubMed, Scopus and ISI Web of Knowledge. This natural compound has shown activity against several types of malignancies such as leukemia, human colorectal, pancreatic, and breast cancer because it modulates multiple molecular pathways. Nemorosone has both cytostatic and cytotoxic activity and it also seems to induce apoptosis and ferroptosis. Additionally, it has antimicrobial capabilities against Gram-positive bacteria and parasites belonging to genus Leishmania. Its promising antiproliferative pre-clinical effects deserve further attention for anticancer and anti-parasitic drug development and translation to the clinic.

摘要

降香萜醇是一种双环多异戊烯基酰基间苯三酚衍生物,最初从藤黄属植物中分离得到,可通过采用不同合成策略的化学合成方法获得。自其被发现以来,它在生物学和化学方面都引起了极大关注。在本文中,我们试图综述围绕降香萜醇的各种化学和生物学主题,重点是其抗增殖活性。为此,从包括谷歌学术、PubMed、Scopus和ISI科学网在内的不同科学数据库中收集了相关数据。这种天然化合物已显示出对多种类型恶性肿瘤的活性,如白血病、人类结直肠癌、胰腺癌和乳腺癌,因为它能调节多种分子途径。降香萜醇具有细胞生长抑制和细胞毒性活性,似乎还能诱导细胞凋亡和铁死亡。此外,它对革兰氏阳性菌和属于利什曼原虫属的寄生虫具有抗菌能力。其有前景的临床前抗增殖作用在抗癌和抗寄生虫药物开发及转化至临床方面值得进一步关注。

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1
A review of nemorosone: Chemistry and biological properties.蛇床子素综述:化学性质与生物学特性
Phytochemistry. 2023 Jun;210:113674. doi: 10.1016/j.phytochem.2023.113674. Epub 2023 Apr 10.
2
Effects of nemorosone, isolated from the plant Clusia rosea, on the cell cycle and gene expression in MCF-7 BUS breast cancer cell lines.从玫瑰克鲁西亚木中分离出的nemorosone对MCF-7 BUS乳腺癌细胞系细胞周期和基因表达的影响。
Phytomedicine. 2015 Jan 15;22(1):153-7. doi: 10.1016/j.phymed.2014.11.007. Epub 2014 Nov 22.
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Cytotoxic activity of nemorosone in human MCF-7 breast cancer cells.尼莫柔斯酮对人 MCF-7 乳腺癌细胞的细胞毒性作用。
Can J Physiol Pharmacol. 2011 Jan;89(1):50-7. doi: 10.1139/y10-100.
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7-epi-nemorosone from Clusia rosea induces apoptosis, androgen receptor down-regulation and dysregulation of PSA levels in LNCaP prostate carcinoma cells.从变色满苏木中提取的 7-表-新莫罗斯酮可诱导 LNCaP 前列腺癌细胞凋亡、下调雄激素受体和 PSA 水平失调。
Phytomedicine. 2012 Nov 15;19(14):1298-306. doi: 10.1016/j.phymed.2012.08.004. Epub 2012 Sep 14.
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Comparison of the cytotoxic effects of enantiopure PPAPs, including nemorosone and clusianone.比较对映纯 PPAPs(包括 nemorosone 和 clusianone)的细胞毒性作用。
Bioorg Med Chem Lett. 2012 Oct 1;22(19):6144-7. doi: 10.1016/j.bmcl.2012.08.023. Epub 2012 Aug 11.
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Nemorosone blocks proliferation and induces apoptosis in leukemia cells.蛇床素可抑制白血病细胞增殖并诱导其凋亡。
Int J Clin Pharmacol Ther. 2008 Aug;46(8):428-39. doi: 10.5414/cpp46428.
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Microarray analysis of nemorosone-induced cytotoxic effects on pancreatic cancer cells reveals activation of the unfolded protein response (UPR).微阵列分析显示,云木香酮诱导的胰腺癌细胞毒性作用会激活未折叠蛋白反应(UPR)。
Br J Pharmacol. 2011 Mar;162(5):1045-59. doi: 10.1111/j.1476-5381.2010.01125.x.
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Chemosensitizing activity of Cuban propolis and nemorosone in doxorubicin resistant human colon carcinoma cells.古巴蜂胶和去甲泽拉木醛对阿霉素耐药人结肠癌细胞的增敏作用。
Fitoterapia. 2019 Jul;136:104173. doi: 10.1016/j.fitote.2019.104173. Epub 2019 May 11.
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The anti-cancer agent nemorosone is a new potent protonophoric mitochondrial uncoupler.抗癌剂尼莫佐酮是一种新型有效的质子载体线粒体解偶联剂。
Mitochondrion. 2011 Mar;11(2):255-63. doi: 10.1016/j.mito.2010.10.008. Epub 2010 Oct 31.
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Antimicrobial evaluation of the polyisoprenylated benzophenones nemorosone and guttiferone A.多异戊烯基二苯甲酮化合物 nemorosone 和 guttiferone A 的抗菌评估。
Phytother Res. 2011 Mar;25(3):458-62. doi: 10.1002/ptr.3401. Epub 2011 Jan 24.

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