Identification and Quantitative Determination of Resin Acids from Corsican Pinus pinasterAiton Oleoresin Using ¹³C‐NMR Spectroscopy

Abstract

Twenty‐three resin samples have been obtained by tapping from individual Pinus pinaster adult trees grown in Corsica and submitted to acido‐basic partition. Identification and quantitative determination of resin acids has been carried out using 13C‐NMR spectroscopy following a method developed by our group. The main components were dehydroabietic acid (up to 37.6 %), levopimaric acid (up to 35.5 %) and abietic acid (up to 24.7 %). A lignan, pinoresinol, has been identified in some samples. Within the 23 compositions, submitted to k‐means analysis and Principal Component Analysis, two clusters have been perfectly differentiated, whose compositions were dominated by dehydroabietic acid (Group I, M=23.5 %, SD=6.3) and levopimaric acid (Group II, M=21.2 %; SD=6.2), respectively. Both compositions have been observed in the three locations of harvest.

Seasonal Changes in the Composition of Scots Pine (Pinus Syvestris L.) Oleoresin, Measured by the NMR Method

“…Figure 1 shows the NMR spectra of the solutions of the oleoresin samples collected in September (IX) 2019. Eight RA were detected, namely, abietic (1), dehydroabietic (2), isopimaric (3), levopimaric (4), neoabietic (5), palustric (6), pimaric (7), and sandaracopimaric (8) acids, as well as five MT, namely, camphene (9), limonene (10), α-pinene (12), β-pinene (13), and terpinolene (14). Also, myrcene (11) was present in some of the samples.…”

“…Quantitative determination of the RA from maritime pine (P. pinaster) oleoresin was carried out using 13 C NMR in CDCl 3 [10]. Abietane diterpenes were prepared and studied by NMR spectroscopy, and assignments for the 1 H and 13 C NMR peaks were obtained by means of correlation spectroscopy [11].…”

Rosin from Pinus pinaster Portuguese forests shows a regular profile of resin acids

“…The observed chemical profiles of P. pinaster rosin, where the prevalent resin acid is AA, closely followed by DHA and IPA, are consistent with those reported previously for related samples collected within Portugal ( Joye and Lawrence, 1967 ; Ghanmi et al., 2009 ; Simões et al., 2021 ; Alonso-Esteban et al., 2022 ; Rubini et al., 2022 ). Similar samples derived from the Corsica forest are rich in DHA and LEV instead ( Ottavioli et al., 2019 ). The prevalence of AA observed in the oleoresin samples is biotechnologically relevant since several fungal strains can modify AA structure, yielding derivatives with interesting pharmacological activities ( Özşen et al., 2017 ).…”

Microbial Conversion of Toxic Resin Acids

“…The abundance of RAs in the galipot is variable and also depends on the nature of the source. For example, the Siberian cedar ( P. sibirica ) galipot is characterized by a relatively uniform content of several (five or more) RAs, while DHA is the dominant component of galipots in most other pine and spruce trees (Table 1) [3,26].…”

“…Produced by coniferous plants of Pinaceae Lindl, resin acids (RAs) are one of the dominant groups of toxic compounds in liquid waste of pulp and paper mills (PPMs) [3]. Because of the shortcomings of the existing treatment systems and high chemical stability of RAs, they accumulate (up to 1500 mg/L) in nearby water bodies.…”