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Title: Membrane Permeability of Terpenoids Explored with Molecular Simulation

Abstract

We report that terpenoids constitute a class of compounds with remarkable potential for pharmaceutical, fragrance, specialty chemical, and biofuel applications. However, their industrial production is limited by their rarity within their native plant hosts, creating considerable interest in microbial hosts capable of manufacturing terpenoids. To reduce production costs, nondestructive product recovery from these microbial hosts is preferred, and is achievable using a hydrophobic organic overlay. Our prior research has indicated that oxidized fatty acyl products may permeate faster through host membranes, increasing overall biorefinery productivity. To test this hypothesis for terpenoids, we computed membrane permeabilities of conventional terpenoid target products (e.g., limonene, bisabolene, farnesene) and related oxidized compounds through molecular dynamics simulations. These simulations indicate that terpenoid product permeabilities from cytosol to overlay are oxidation independent, as increases in membrane extraction efficiency due to product oxidation are proportionally offset by decreases in the membrane crossing rate if the membrane and organic phase are in close contact. However, if aqueous extraction is required, oxidation will accelerate the slow product extraction from the membrane. Experimental toxicity assays performed indicated that most terpenoids tested were tolerated by microbial hosts, although exposure to oxidized terpenes often retarded microbial growth compared with conventional terpenes. Finally,more » terpenoid oxidation is not expected to significantly increase or decrease the extraction productivity in an industrial setting where cells are in close contact, unlike the previously studied fatty acyl products.« less

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]
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  1. National Renewable Energy Laboratory (NREL), Golden, CO (United States)
Publication Date:
Research Org.:
National Renewable Energy Laboratory (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE)
OSTI Identifier:
1484588
Report Number(s):
NREL/JA-2700-72683
Journal ID: ISSN 1520-6106
Grant/Contract Number:  
AC36-08GO28308
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry
Additional Journal Information:
Journal Volume: 122; Journal Issue: 45; Journal ID: ISSN 1520-6106
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 59 BASIC BIOLOGICAL SCIENCES; terpene oxidation; molecular dynamics; membrane permeability

Citation Formats

Vermaas, Joshua V., Bentley, Gayle J., Beckham, Gregg T., and Crowley, Michael F. Membrane Permeability of Terpenoids Explored with Molecular Simulation. United States: N. p., 2018. Web. doi:10.1021/acs.jpcb.8b08688.
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Vermaas, Joshua V., Bentley, Gayle J., Beckham, Gregg T., & Crowley, Michael F. Membrane Permeability of Terpenoids Explored with Molecular Simulation. United States. https://doi.org/10.1021/acs.jpcb.8b08688
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Vermaas, Joshua V., Bentley, Gayle J., Beckham, Gregg T., and Crowley, Michael F. Tue . "Membrane Permeability of Terpenoids Explored with Molecular Simulation". United States. https://doi.org/10.1021/acs.jpcb.8b08688. https://www.osti.gov/servlets/purl/1484588.
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@article{osti_1484588,
title = {Membrane Permeability of Terpenoids Explored with Molecular Simulation},
author = {Vermaas, Joshua V. and Bentley, Gayle J. and Beckham, Gregg T. and Crowley, Michael F.},
abstractNote = {We report that terpenoids constitute a class of compounds with remarkable potential for pharmaceutical, fragrance, specialty chemical, and biofuel applications. However, their industrial production is limited by their rarity within their native plant hosts, creating considerable interest in microbial hosts capable of manufacturing terpenoids. To reduce production costs, nondestructive product recovery from these microbial hosts is preferred, and is achievable using a hydrophobic organic overlay. Our prior research has indicated that oxidized fatty acyl products may permeate faster through host membranes, increasing overall biorefinery productivity. To test this hypothesis for terpenoids, we computed membrane permeabilities of conventional terpenoid target products (e.g., limonene, bisabolene, farnesene) and related oxidized compounds through molecular dynamics simulations. These simulations indicate that terpenoid product permeabilities from cytosol to overlay are oxidation independent, as increases in membrane extraction efficiency due to product oxidation are proportionally offset by decreases in the membrane crossing rate if the membrane and organic phase are in close contact. However, if aqueous extraction is required, oxidation will accelerate the slow product extraction from the membrane. Experimental toxicity assays performed indicated that most terpenoids tested were tolerated by microbial hosts, although exposure to oxidized terpenes often retarded microbial growth compared with conventional terpenes. Finally, terpenoid oxidation is not expected to significantly increase or decrease the extraction productivity in an industrial setting where cells are in close contact, unlike the previously studied fatty acyl products.},
doi = {10.1021/acs.jpcb.8b08688},
journal = {Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry},
number = 45,
volume = 122,
place = {United States},
year = {Tue Oct 23 00:00:00 EDT 2018},
month = {Tue Oct 23 00:00:00 EDT 2018}
}
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Journal Article:
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Publisher's Version of Record
https://doi.org/10.1021/acs.jpcb.8b08688
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Cited by: 17 works
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Figures / Tables:

Figure 1 Figure 1: Terpenoid compounds and their oxidized equivalents considered in this study. The colored boundaries group together equivalent chemical functionalities, which are used consistently in other visualizations throughout the text. Red highlights bisabolene and its predominant oxidized form, bisabolol, blue highlights pinene and its derivatives verbenol and verbenone, green highlightsmore » limonene with derivatives terpineol and perillyl alcohol, and violet surrounds farnesene and its oxidation product farnesol.« less
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