Pinuspalustrols A & B, Two Rare Dimeric Abietane-O-O-Abietane-Type Diterpenoids of Natural Colophony from Pinus palustris

AbdEl-Razek, Mohamed H; Soliman, Ahmed A.F.; Aboelmagd, Mohamed; El-Desoky, Ahmed H.

doi:10.21608/ejchem.2024.260239.9134

Pinuspalustrols A & B, Two Rare Dimeric Abietane-O-O-Abietane-Type Diterpenoids of Natural Colophony from Pinus palustris

Document Type : Original Article

Authors

¹ Chemistry of Natural Compounds Department, Institute of Pharmaceutical and Drug Industries Research, National Research Centre (NRC), 33 El-Behouth St., Dokki, Giza, P.O. 12622, Egypt

² Department of Pharmacognosy, Institute of Pharmaceutical and Drug Industries Research, National Research Centre (NRC), 33 El-Behouth St., Dokki, Giza, P.O. 12622, Egypt

10.21608/ejchem.2024.260239.9134

Abstract

Pinus palustris' natural colophony produced two novel secondary metabolites, pinuspalustrols A (1) & B (2), a unique pair of C-7 epimeric dimers based on abietane-type diterpenoids linked via C7-C12' peroxy conjunction system. Additionally, their biogenesis-related diterpenoid monomers were previously reported (3-10). Spectroscopic techniques, particularly 1D and 2D NMR together with HREIMS, were used to elucidate their planar structures, while their relative configurations were decided by NOESY spectra, together with comparison with NMR data of known analouges. Both pinuspalustrols A (1) and B (2) possess a skeleton of 12-Hydroxyabieta-8,11,13-trien-7-yl 6-Hydroxy-7-oxoabieta-8,11,13-trien-12-yl peroxide, but they are epimeric at position 7. It is noteworthy that chemical compounds 3-10 were first isolated from P. palustris.

Keywords