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Conformational analysis of macrocyclic frankincense (Boswellia) diterpenoids

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Abstract

Frankincense oleoresin has been used in traditional medicine for more than 5000 years. The phytochemistry of frankincense (Boswellia spp.) resins includes triterpenoids (including boswellic acids and their derivatives), diterpenoids (cembrenoids and cneorubenoids), and essential oils. The macrocyclic cembrene diterpenoids may play a part in the biological activities of frankincense resin, but neither the biological targets nor the modes of interaction with the targets are currently known. How these macrocycles interact with biological macromolecules likely depends on what conformation(s) are energetically available to them. In this work, a conformational analysis of 15 Boswellia cembrene diterpenoids and 1 verticillane diterpenoid was carried out at the B3LYP/6-31G* and M06-2X/6-31G* levels of theory, including the SM8 aqueous solvation model. The lowest-energy conformations of boscartin B and incensole oxide were the same as the previously reported X-ray crystal structures, while the lowest-energy conformations of boscartins A and C were very similar to the crystal structures. Boscartins D-H and isoincensole oxide showed only one low-energy conformation for each compound and are predicted to be conformationally locked. Incensole, isoincensolol, and serratol are predicted to be conformationally mobile with several low-energy forms. The conformational mobility of Boswellia cembrenoid diterpenoids depends largely on the degree of epoxidation, either oxirane or tetrahydrofuran rings.

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Acknowledgments

This work was carried out as part of the activities of the Aromatic Plant Research Center (APRC, https://aromaticplant.org/). The author is grateful to dōTERRA International (https://www.doterra.com/US/en) for financial support of the APRC.

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Authors and Affiliations

  1. Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL, 35899, USA

    William N. Setzer

  2. Aromatic Plant Research Center, 615 St. George Square Court, Suite 300, Winston-Salem, NC, 27103, USA

    William N. Setzer

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  1. William N. Setzer
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Correspondence to William N. Setzer.

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The author declares no conflicts of interest. The funding sponsor, dōTERRA International, played no role in the design of the study; in the collection, analysis, or interpretation of the data; conclusions of the study; or in the decision to publish the results.

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Setzer, W.N. Conformational analysis of macrocyclic frankincense (Boswellia) diterpenoids. J Mol Model 24, 74 (2018). https://doi.org/10.1007/s00894-018-3625-8

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  • DOI: https://doi.org/10.1007/s00894-018-3625-8

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