Membrane Permeability of Terpenoids Explored with Molecular Simulation

Joshua Vermaas, Gregg Beckham, Michael Crowley, Gayle Bentley

Research output: Contribution to journalArticlepeer-review

20 Scopus Citations


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. Thus, 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.

Original languageAmerican English
Pages (from-to)10349-10361
Number of pages13
JournalJournal of Physical Chemistry B
Issue number45
StatePublished - 2018

Bibliographical note

Publisher Copyright:
© Copyright 2018 American Chemical Society.

NREL Publication Number

  • NREL/JA-2700-72683


  • membrane permeability
  • molecular dynamics
  • terpene oxidation


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