Biocatalytic and semisynthetic studies of the anticancer tobacco cembranoids

  title={Biocatalytic and semisynthetic studies of the anticancer tobacco cembranoids},
  author={Khalid A. El Sayed and Paul William Sylvester},
  journal={Expert Opinion on Investigational Drugs},
  pages={877 - 887}
Historically, tobacco use was primarily recreational and has been smoked in cigarettes, cigars and pipes, as well as smokeless forms of consumption, all of which are associated with adverse health effects. However, recent scientific investigations indicate that tobacco also contains several diverse secondary metabolites that may provide potential health benefits in the treatment of cancer and neurodegenerative diseases. Specifically, the leaf and flower of Nicotiana tabacum contain high amounts… 

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

This review is the first to provide a comprehensive summary of the chemical modifications and bioactivities of α- and β-CBD from their discovery to the present day; the review highlights their potential medicinal value for humans.

Semisynthetic and SAR Studies of Amide Derivatives of Neocrotocembraneic Acid as Potential Antitumor Agents

A series of novel amide derivatives of cembranoid neocrotocembraneic acid exhibited more potent antiproliferative activity than the reference drug etoposide against drug-resistant cell line K562/A02, indicating that it possessed a great potential for further development as a multidrug resistance modulator by structural modification.

Cytotoxic Plants: Potential Uses in Prevention and Treatment of Cancer

Being the rich sources of vitamins, minerals, and fiber without posing “any side effects” made fruits and vegetables the best choice to lowering cancer risk and also in maintaining good general health.

Incensole Acetate: A Novel Neuroprotective Agent Isolated from Boswellia Carterii

  • A. MoussaieffN. A. Shein E. Shohami
  • Biology
    Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism
  • 2008
It is shown that IA inhibits the production of inflammatory mediators in an in vitro model system of C6 glioma and human peripheral monocytes and suggests that they may serve as novel neuroprotective agents.

The Tobacco β-Cembrenediol: A Prostate Cancer Recurrence Suppressor Lead and Prospective Scaffold via Modulation of Indoleamine 2,3-Dioxygenase and Tryptophan Dioxygenase

β-CBT emerges as a promising PC recurrence suppressive lead by significantly suppressed IDO1, TDO2, and their final metabolite kynurenine levels in PC-3M cells.

Extraction, purification and anti-TMV effects of α (β)-2,7,11-cembratriene-4,6-diol from tobacco leaves

The α(β)-CBD mainly stimulates disease resistance of tobacco plants to resist TMV and it can be used as bioagents to control TMV in the future.



Anticancer and anti-inflammatory sulfur-containing semisynthetic derivatives of sarcophine.

The epoxide ring is targeted to generate sulfur-containing derivatives of sarcophine by reacting it with ammonium thiocyanate and Lawesson's reagent and the effect of these derivatives on highly malignant +SA mammary epithialial cell proliferation is reported.

Antiproliferative potential of sarcophine and its semisynthetic sulfur-containing derivatives against human mammary carcinoma cell lines

The preliminary results suggest that the sulfur-containing derivatives of sarcophine, especially 2 and 3, show potent and cell-specific antiproliferative activity.

Identification of cembratriene-4,6-diol as antitumor-promoting agent from cigarette smoke condensate.

The present data suggest that EBV-EA inhibition assay using Raji cells is effective for the first screening of inhibitors of tumor promotion, and provide evidence that CSC contains antitumor- Promoting agents in addition to carcinogenic and tumor-promoting agents already reported.

Biocatalytic and antimetastatic studies of the marine cembranoids sarcophine and 2-epi-16-deoxysarcophine.

Sarcophine, 2-epi-16-deoxysarcophines, and metabolites 5-9 revealed significant antimetastatic activity against the highly metastatic mouse melanoma cell line (B16B15b).

Semisynthesis of new sarcophine derivatives with chemopreventive activity.

In preliminary in vitro tests on inhibition of EBV-EA activation, compounds 10 and 12-15 have shown higher activity than the known chemopreventive agent sarcophytol A.


The residual DNA repair ability was almost completely abolished by manzamine A while sarcophine was ineffective and these compounds may be classified as potential genotoxic.

Tobacco Cembranoids

Abstract The discovery of the first diterpenoids of the cembrane type in tobacco dates back to the early 1960's. Since then some forty tobacco cembranoids have been encountered. Most of these have a

The effect of epigallocatechin galleate and sarcophytol A on DNA strand breakage induced by tobacco-specific nitrosamines and stimulated human phagocytes.

Both SaA and EGCG provided significant protection against the induction of genetic damage in these cells and may prove useful in the chemoprevention of tobacco-induced carcinogenesis.

Structurally Novel Bioconversion Products of the Marine Natural Product Sarcophine Effectively Inhibit JB6 Cell Transformation.

When evaluated for potential to inhibit TPA-induced JB6 cell transformation, several of the metabolites mediated inhibitory responses greater than sarcophytol A or sarcophine, most notably 7alpha-hydroxy-Delta(8(19))-deepoxysarcophine (6), which was comparable to 13-cis-retinoic acid.

Isolation and characterization of a monoamine oxidase B selective inhibitor from tobacco smoke.