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New Evidence Concerning the Structure, Composition, and Maturation of Class I (Polylabdanoid) Resinites

1995/05/05 by Ken B. Anderson · 2 citations
Chemistry · Pharmacology, Toxicology and Pharmaceutics · #Synthetic Organic Chemistry Methods #Radioactive element chemistry and processing #Plant-based Medicinal Research

paper · doi:10.1021/bk-1995-0617.ch006

openalex publication_date 1995/05/05 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/31

Abstract

Pyrolysis-Gas Chromatographic-Mass Spectrometric (Py-GC-MS) analysis of a range of Class I resinites indicates that the macromolecular structures of these resinites are typically derived from copolymers of labdanoid carboxylic acids, alcohols and hydrocarbons. Class Ia and Ib resinites are derived from copolymers of regular [1S, 4aR, 5S, 8aR] labdanoid diterpenes, especially communic acid, communol and/or biformenes. Class Ic resinites are based on structures derived from enantio [1S, 4aS, 5R, 8aS] labdanoids, especially ozic acid, ozol and/or enantio biformenes. The monomeric components of Class I resinites are readily determined in Py-GC-MS analyses by recognition of characteristic bicyclic products derived from the A/B ring system of the original labdanoid monomers. In addition to bicyclic products derived directly from the labdanoid A/B ring system, products derived by modification of this ring system are also observed in Py-GC-MS analyses of some Class I resinites. These include: bicyclic methyl ethers produced by pyrolytic hydrolysis/O-methylation of succinylated (esterified) communol monomers within the macromolecular structure of Class Ia resinites; and, in samples of moderate maturity, C 13 and C 14 bicyclic products derived from A-ring defunctionalized labdanoids. The existence of these A-ring defunctionalized products indicates the existence of a heretofore unrecognized maturation pathway in polylabdanoid resinites.

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