Stereochemical determination of NMR chemical shifts in marine terpenoids, antheliol and sangiangol B, using DFT calculations

Novriyandi Hanif; Fabians Faisal Dinelsa; Henny Dwi Yanti; Anggia Murni; Junichi Tanaka

doi:10.1080/14786419.2022.2147171

Stereochemical determination of NMR chemical shifts in marine terpenoids, antheliol and sangiangol B, using DFT calculations

Nat Prod Res. 2023 Aug-Sep;37(18):3170-3176. doi: 10.1080/14786419.2022.2147171. Epub 2022 Nov 17.

Authors

Novriyandi Hanif¹, Fabians Faisal Dinelsa¹, Henny Dwi Yanti², Anggia Murni², Junichi Tanaka³

Affiliations

¹ Department of Chemistry, IPB University, Bogor, Indonesia.
² Tropical Biopharmaca Research Center, IPB University, Bogor, Indonesia.
³ Department of Chemistry, Biology and Marine Science, University of the Ryukyus, Okinawa, Japan.

PMID: 36395185
DOI: 10.1080/14786419.2022.2147171

Abstract

Stereochemical determination of the flexible trinor-guaiane sesquiterpenoid, antheliol (1a) and the flexible diterpenoid, sangiangol B (2a), isolated from a marine soft coral, Anthelia sp., was supported by quantum chemical calculations of NMR chemical shifts at DFT levels. The relative configuration of antheliol is now revealed, as 1S*, 4S*, 7S*, 10R* as in 1b, whereas sangiangol B (2c) has complete stereochemistry as 1S*, 7R*, 8R*, 10R*, 11R*, 12S*.

Keywords: DFT calculations; flexible natural products; stereochemistry; structure determination.