Related Experiment Video
Updated: Jul 8, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Semisynthetic and biotransformation studies of (1S,2E,4S,6R,7E,11E)-2,7,11-cembratriene-4,6-diol
Khalid A El Sayed1, Surat Laphookhieo, Muhammad Yousaf
1Department of Basic Pharmaceutical Sciences, College of Pharmacy, University of Louisiana at Monroe 71209, USA. elsayed@ulm.edu
Abstract:
Tobacco-derived (1 S,2 E,4 S,6 R,7 E,11 E)-2,7,11-cembratriene-4,6-diol (1) and (1 S,2 E,4 R,6 R,7 E,11 E)-2,7,11-cembratriene-4,6-diol (2) were first shown to display potential antitumor-promoting activity in the mid-1980s. However, very little is currently understood regarding the structural activity relationships of tobacco cembranoids. The aim of this present study was to explore antiproliferative activity of various derivatives of (1 S,2 E,4 S,6 R,7 E,11 E)-2,7,11-cembratriene-4,6-diol (1) using semisynthetic and biotransformation approaches. Derivatives of 1 include esterified, oxidized, halogenated, and nitrogen- and sulfur-containing compounds (3-17). Biotransformation of 1 using Mucor ramannianus ATCC 9628 and Cunninghamella elegans ATCC 7929 afforded the known 10 S,11 S-epoxy analogue of 1 (4) as the main metabolite. Biotransformation of the 6-O-acetyl analogue (3) using the marine symbiotic Bacillus megaterium strain MO31 afforded (1 S,2 E,4 S,6 R,7 E,11 E,10 R)-2,7,11-cembratriene-4,6,10-triol (18). (1 S,2 E,4 S,6 R,7 E,11 E,13 R)-2,7,11-Cembratriene-4,6,13-triol-6-O-acetate (6), (1 S,2 E,4 S,6 R,7 E,11 E,13 S)-2,7,11-cembratriene-4,6,13-triol-6-O-acetate (7), the rearranged alpha-ketol (1 S,2 E,4 S,7 Z,11 E)-2,7,11-cembratrien-4-ol-6-one (11), and the secocembranoid 12 showed antiproliferative activity against highly malignant +SA mammary epithelial cells with an IC50 range of 15-30 microM.
Related Concept Videos
Stability of Conjugated Dienes
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
