Literature DB >> 18222089

Biocatalytic and semisynthetic optimization of the anti-invasive tobacco (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol.

Khalid A El Sayed1, Surat Laphookhieo, Hany N Baraka, Muhammad Yousaf, Anne Hebert, Danielle Bagaley, Frederick A Rainey, A Muralidharan, Shibu Thomas, Girish V Shah.   

Abstract

Tobacco cembranoids were reported to inhibit tumorigenesis. Biocatalysis of (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol (1) using the symbiotic Bacillus sp. NC5, Bacillus sp. NK8, and Bacillus sp. NK7, isolated from the Red Sea sponge Negombata magnifica, afforded two new and four known hydroxylated metabolites 3-8. The use of symbiotic marine bacteria as biocatalysts for bioactive natural product scaffolds is very rare. Cembranoid 1 carbamate analogs 9-11 were prepared by its reaction with corresponding isocyanates. Cembranoid 1 and its bioconversion and carabamate products show anti-invasive activity against the human highly metastatic prostate PC-3M cancer cell line at 10-50 nM doses in Matrigel assay.

Entities:  

Mesh:

Substances:

Year:  2008        PMID: 18222089     DOI: 10.1016/j.bmc.2007.12.056

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  11 in total

1.  4R-cembranoid protects against diisopropylfluorophosphate-mediated neurodegeneration.

Authors:  P A Ferchmin; Myrna Andino; Rebeca Reyes Salaman; Janaina Alves; Joyce Velez-Roman; Brenda Cuadrado; Marimeé Carrasco; Wilmarie Torres-Rivera; Annabell Segarra; Antonio Henrique Martins; Jae Eun Lee; Vesna A Eterovic
Journal:  Neurotoxicology       Date:  2014-06-10       Impact factor: 4.294

2.  Induction of expression and functional activity of P-glycoprotein efflux transporter by bioactive plant natural products.

Authors:  Alaa H Abuznait; Hisham Qosa; Nicholas D O'Connell; Jessica Akbarian-Tefaghi; Paul W Sylvester; Khalid A El Sayed; Amal Kaddoumi
Journal:  Food Chem Toxicol       Date:  2011-08-10       Impact factor: 6.023

3.  In Vivo Evaluation of the Acute Systemic Toxicity of (1S,2E,4R,6R,7E,11E)-Cembratriene-4,6-diol (4R) in Sprague Dawley Rats.

Authors:  Nadezhda Sabeva; Oné R Pagán; Yancy Ferrer-Acosta; Vesna A Eterović; Peter A Ferchmin
Journal:  Nutraceuticals (Basel)       Date:  2022-04-09

Review 4.  Structural Modifications and Biological Activities of Natural α- and β-Cembrenediol: A Comprehensive Review.

Authors:  Kuo Xu; Xinying Du; Xia Ren; XiuXue Li; Hui Li; Xianjun Fu; Xiaoyi Wei
Journal:  Pharmaceuticals (Basel)       Date:  2022-05-13

5.  (1S,2E,4S,7E,11E)-2,7,11-Cembratriene-4,6-diol semisynthetic analogs as novel c-Met inhibitors for the control of c-Met-dependent breast malignancies.

Authors:  Hassan Y Ebrahim; Mohamed M Mohyeldin; Mohammad M Hailat; Khalid A El Sayed
Journal:  Bioorg Med Chem       Date:  2016-09-13       Impact factor: 3.641

6.  Protective activity of (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol analogues against diisopropylfluorophosphate neurotoxicity: preliminary structure-activity relationship and pharmacophore modeling.

Authors:  Vesna A Eterović; Angelie Del Valle-Rodriguez; Dinely Pérez; Marimée Carrasco; Mohammad A Khanfar; Khalid A El Sayed; Pedro A Ferchmin
Journal:  Bioorg Med Chem       Date:  2013-05-24       Impact factor: 3.641

7.  Pharmacokinetics and Metabolism of 4R-Cembranoid.

Authors:  Wanda Vélez-Carrasco; Carol E Green; Paul Catz; Anna Furimsky; Kathleen O'Loughlin; Vesna A Eterović; P A Ferchmin
Journal:  PLoS One       Date:  2015-03-26       Impact factor: 3.240

8.  4R-Cembranoid Improves Outcomes after 6-Hydroxydopamine Challenge in Both In vitro and In vivo Models of Parkinson's Disease.

Authors:  Jing Hu; P A Ferchmin; Ann M Hemmerle; Kim B Seroogy; Vesna A Eterovic; Jiukuan Hao
Journal:  Front Neurosci       Date:  2017-05-29       Impact factor: 4.677

Review 9.  A Review on Bioactivities of Tobacco Cembranoid Diterpenes.

Authors:  Ning Yan; Yongmei Du; Xinmin Liu; Hongbo Zhang; Yanhua Liu; Zhongfeng Zhang
Journal:  Biomolecules       Date:  2019-01-16

Review 10.  Applications of Marine-Derived Microorganisms and Their Enzymes in Biocatalysis and Biotransformation, the Underexplored Potentials.

Authors:  Willian G Birolli; Rafaely N Lima; André L M Porto
Journal:  Front Microbiol       Date:  2019-08-20       Impact factor: 5.640

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.