利用系统发育学和质谱评估相结合的方法从海洋蓝细菌中发现靶向天然产物。
Targeted natural products discovery from marine cyanobacteria using combined phylogenetic and mass spectrometric evaluation.
作者信息
Salvador-Reyes Lilibeth A, Engene Niclas, Paul Valerie J, Luesch Hendrik
机构信息
†Department of Medicinal Chemistry, University of Florida, 1345 Center Drive, Gainesville, Florida 32610, United States.
‡Marine Science Institute, College of Science, University of the Philippines, Diliman, Velasquez Street, Quezon City 1101, Philippines.
出版信息
J Nat Prod. 2015 Mar 27;78(3):486-92. doi: 10.1021/np500931q. Epub 2015 Jan 30.
Abstract
Combined phylogenetic and HPLC-MS-based natural products dereplication methods aimed at identifying cyanobacterial collections containing the potent cytotoxins largazole, dolastatin 10, and symplostatin 1 were developed. The profiling of the phylogeny, chemical space, and antiproliferative activity of cyanobacterial collections served to streamline the prioritization of samples for the discovery of new secondary metabolites. The dereplication methods highlighted the biosynthetic potential and combinatorial pharmacology employed by marine cyanobacteria. We found that largazole was always coproduced with dolastatin 10 or with symplostatin 1 and consequently tested combinations of these agents against colon cancer cells. Combinatorial regimens of largazole and dolastatin 10 aimed at curbing the growth of HCT116 cancer cells showed cooperative activity.
摘要
我们开发了基于系统发育和高效液相色谱-质谱联用的天然产物去重复方法，旨在鉴定含有强效细胞毒素拉加唑、多拉司他汀10和共生菌素1的蓝藻菌株。对蓝藻菌株的系统发育、化学空间和抗增殖活性进行分析，有助于简化发现新的次生代谢产物的样品优先级排序。去重复方法突出了海洋蓝藻所采用的生物合成潜力和组合药理学。我们发现拉加唑总是与多拉司他汀10或共生菌素1共同产生，因此测试了这些药物组合对结肠癌细胞的作用。旨在抑制HCT116癌细胞生长的拉加唑和多拉司他汀10联合方案显示出协同活性。
相似文献
1
Targeted natural products discovery from marine cyanobacteria using combined phylogenetic and mass spectrometric evaluation.利用系统发育学和质谱评估相结合的方法从海洋蓝细菌中发现靶向天然产物。
J Nat Prod. 2015 Mar 27;78(3):486-92. doi: 10.1021/np500931q. Epub 2015 Jan 30.
2
Combinatorial strategies by marine cyanobacteria: symplostatin 4, an antimitotic natural dolastatin 10/15 hybrid that synergizes with the coproduced HDAC inhibitor largazole.海洋蓝细菌的组合策略：symplostatin 4，一种抗有丝分裂的天然多拉司他汀10/15杂合物，可与共同产生的组蛋白去乙酰化酶抑制剂拉戈唑协同作用。
Chembiochem. 2009 Jul 6;10(10):1634-9. doi: 10.1002/cbic.200900192.
3
Largazole: from discovery to broad-spectrum therapy.拉罗塞拉：从发现到广谱治疗。
Nat Prod Rep. 2012 Apr;29(4):449-56. doi: 10.1039/c2np00066k. Epub 2012 Feb 14.
4
Isolation of dolastatin 10 from the marine cyanobacterium Symploca species VP642 and total stereochemistry and biological evaluation of its analogue symplostatin 1.从海洋蓝藻Symploca属VP642中分离多拉司他汀10及其类似物symplostatin 1的全立体化学和生物学评价
J Nat Prod. 2001 Jul;64(7):907-10. doi: 10.1021/np010049y.
5
Carriebowlinol, an antimicrobial tetrahydroquinolinol from an assemblage of marine cyanobacteria containing a novel taxon.卡里鲍利诺，一种从含有新分类单元的海洋蓝细菌组合中提取的抗菌四氢喹啉醇。
J Nat Prod. 2015 Mar 27;78(3):534-8. doi: 10.1021/np500598x. Epub 2014 Dec 23.
6
Apratoxin H and apratoxin A sulfoxide from the Red Sea cyanobacterium Moorea producens.来源于红海蓝藻 Moorea producens 的阿普拉毒素 H 和阿普拉毒素 A 亚砜。
J Nat Prod. 2013 Sep 27;76(9):1781-8. doi: 10.1021/np4004992. Epub 2013 Sep 9.
7
Symplostatin 3, a new dolastatin 10 analogue from the marine cyanobacterium Symploca sp. VP452.Symplostatin 3，一种来自海洋蓝藻Symploca sp. VP452的新型多拉司他汀10类似物。
J Nat Prod. 2002 Jan;65(1):16-20. doi: 10.1021/np010317s.
8
Applying a Chemogeographic Strategy for Natural Product Discovery from the Marine Cyanobacterium .应用化学生态策略从海洋蓝细菌中发现天然产物
Mar Drugs. 2020 Oct 14;18(10):515. doi: 10.3390/md18100515.
9
Heterologous production of 4-O-demethylbarbamide, a marine cyanobacterial natural product.海洋蓝细菌天然产物 4-O-去甲巴卡亭 III 的异源生物合成。
Org Lett. 2012 Dec 7;14(23):5824-7. doi: 10.1021/ol302575h. Epub 2012 Nov 13.
10
Isolation and structure of the cytotoxin lyngbyabellin B and absolute configuration of lyngbyapeptin A from the marine cyanobacterium Lyngbya majuscula.从海洋蓝藻巨大鞘丝藻中分离细胞毒素灵比环肽B及其结构，以及灵比环肽A的绝对构型
J Nat Prod. 2000 Oct;63(10):1437-9. doi: 10.1021/np000104n.
引用本文的文献
1
Progress in the discovery and development of anticancer agents from marine cyanobacteria.从海洋蓝细菌中发现和开发抗癌药物的进展。
Nat Prod Rep. 2025 Feb 19;42(2):208-256. doi: 10.1039/d4np00019f.
2
Unveiling the Bioprospecting Efficacy and Textile Dyeing of a Novel Endophytic Mycobial Red Pigment.揭示一种新型内生真菌红色素的生物勘探功效及纺织染色性能
Indian J Microbiol. 2024 Jun;64(2):618-634. doi: 10.1007/s12088-024-01211-y. Epub 2024 Feb 27.
3
Biosynthesis of Dolastatin 10 in Marine Cyanobacteria, a Prototype for Multiple Approved Cancer Drugs.海洋蓝细菌中 Dolastatin 10 的生物合成，多种已批准癌症药物的原型。
Org Lett. 2024 Feb 23;26(7):1321-1325. doi: 10.1021/acs.orglett.3c04083. Epub 2024 Feb 8.
4
Process Development and Scale-up Total Synthesis of Largazole, a Potent Class I Histone Deacetylase Inhibitor.强效I类组蛋白去乙酰化酶抑制剂拉加唑的工艺开发与放大全合成
Org Process Res Dev. 2018 Feb 16;22(2):190-199. doi: 10.1021/acs.oprd.7b00352. Epub 2018 Jan 30.
5
Natural products and drug discovery.天然产物与药物发现
Natl Sci Rev. 2022 Sep 29;9(11):nwac206. doi: 10.1093/nsr/nwac206. eCollection 2022 Nov.
6
Natural Products of Marine Origin for the Treatment of Colorectal and Pancreatic Cancers: Mechanisms and Potential.海洋源天然产物治疗结直肠癌和胰腺癌的作用机制及潜力
Int J Mol Sci. 2022 Jul 21;23(14):8048. doi: 10.3390/ijms23148048.
7
Biotechnological Innovations from Ocean: Transpiring Role of Marine Drugs in Management of Chronic Disorders.海洋生物技术创新：海洋药物在慢性疾病管理中的作用。
Molecules. 2022 Feb 24;27(5):1539. doi: 10.3390/molecules27051539.
8
Possible Functional Roles of Patellamides in the Ascidian- Symbiosis.可能的功能角色的 Patellamides 在共生关系。
Mar Drugs. 2022 Feb 2;20(2):119. doi: 10.3390/md20020119.
9
A review of research progress of antitumor drugs based on tubulin targets.基于微管蛋白靶点的抗肿瘤药物研究进展综述
Transl Cancer Res. 2020 Jun;9(6):4020-4027. doi: 10.21037/tcr-20-682.
10
Largazole Inhibits Ocular Angiogenesis by Modulating the Expression of VEGFR2 and p21.拉帕替尼通过调节 VEGFR2 和 p21 的表达抑制眼血管生成。
Mar Drugs. 2021 Aug 22;19(8):471. doi: 10.3390/md19080471.
本文引用的文献
1
Five chemically rich species of tropical marine cyanobacteria of the genus Okeania gen. nov. (Oscillatoriales, Cyanoprokaryota).新属奥克尼亚属（Okeania gen. nov.）（颤藻目，蓝原核生物）的五种富含化学物质的热带海洋蓝细菌。
J Phycol. 2013 Dec;49(6):1095-106. doi: 10.1111/jpy.12115. Epub 2013 Oct 21.
2
Biological targets and mechanisms of action of natural products from marine cyanobacteria.来自海洋蓝藻细菌的天然产物的生物学靶点及作用机制
Nat Prod Rep. 2015 Mar;32(3):478-503. doi: 10.1039/c4np00104d.
3
Potent elastase inhibitors from cyanobacteria: structural basis and mechanisms mediating cytoprotective and anti-inflammatory effects in bronchial epithelial cells.蓝藻中强效的弹性蛋白酶抑制剂：在支气管上皮细胞中发挥细胞保护和抗炎作用的结构基础和介导机制。
J Med Chem. 2013 Feb 14;56(3):1276-90. doi: 10.1021/jm3017305. Epub 2013 Jan 28.
4
Phylogenetic inferences reveal a large extent of novel biodiversity in chemically rich tropical marine cyanobacteria.系统发育推断揭示了富含化学物质的热带海洋蓝细菌中大量新的生物多样性。
Appl Environ Microbiol. 2013 Mar;79(6):1882-8. doi: 10.1128/AEM.03793-12. Epub 2013 Jan 11.
5
The discovery and development of brentuximab vedotin for use in relapsed Hodgkin lymphoma and systemic anaplastic large cell lymphoma.本妥昔单抗维迪昔单抗在复发型霍奇金淋巴瘤和系统性间变性大细胞淋巴瘤中的发现和发展。
Nat Biotechnol. 2012 Jul 10;30(7):631-7. doi: 10.1038/nbt.2289.
6
MEGA5: molecular evolutionary genetics analysis using maximum likelihood, evolutionary distance, and maximum parsimony methods.MEGA5：用于最大似然法、进化距离法和最大简约法的分子进化遗传学分析。
Mol Biol Evol. 2011 Oct;28(10):2731-9. doi: 10.1093/molbev/msr121. Epub 2011 May 4.
7
Underestimated biodiversity as a major explanation for the perceived rich secondary metabolite capacity of the cyanobacterial genus Lyngbya.低估了生物多样性是解释为什么人们认为蓝藻属 Lyngbya 具有丰富的次生代谢产物的主要原因。
Environ Microbiol. 2011 Jun;13(6):1601-10. doi: 10.1111/j.1462-2920.2011.02472.x. Epub 2011 Apr 7.
8
Veraguamides A-G, cyclic hexadepsipeptides from a dolastatin 16-producing cyanobacterium Symploca cf. hydnoides from Guam.瓦拉瓜米德 A-G，来自关岛产海兔素 16 的蓝细菌 Symploca cf. hydnoides 的环状六肽。
J Nat Prod. 2011 May 27;74(5):917-27. doi: 10.1021/np200076t. Epub 2011 Mar 29.
9
Caylobolide B, a macrolactone from symplostatin 1-producing marine cyanobacteria Phormidium spp. from Florida.卡洛夫内酯 B，一种来自佛罗里达产 symplostatin 1 的海洋蓝细菌属 Phormidium spp. 的大环内酯。
J Nat Prod. 2010 Sep 24;73(9):1606-9. doi: 10.1021/np100467d.
10
Dereplication and de novo sequencing of nonribosomal peptides.非核糖体肽的去重复和从头测序
Nat Methods. 2009 Aug;6(8):596-9. doi: 10.1038/nmeth.1350. Epub 2009 Jul 13.
Zotero 插件