1H and 13C NMR spectral assignments of abietane diterpenes from <scp>Pinus heldreichii</scp> and <scp>Pinus nigra</scp> subsp. <scp>nigra</scp>

Koutsaviti, Aikaterini; Iοannou, Efstathia; Couladis, Maria; Τζακου, Ολγα; Roussis, Vassilios

doi:10.1002/mrc.4585

Cited by 11 publications

(5 citation statements)

References 34 publications

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“…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.…”

Section: Resultsmentioning

confidence: 99%

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

Skakovskii,

L.Yu.,

Gapan’kova

et al. 2023

Russ J Bioorg Chem

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Seasonal changes in the composition of Scots pine oleoresin were analyzed by 1 H and 13 C NMR spectroscopy. Due to favorable weather conditions (positive temperatures on the sampling dates throughout the year) samples for each of the 12 months were obtained and studied. Chloroform (CDCl 3 ) solutions of oleoresin were investigated. Eight resin acids: abietic, dehydroabietic, isopimaric, levopimaric, neoabietic, palustric, pimaric, and sandaracopimaric acids, as well as six monoterpenes: camphene, limonene, myrcene, α-pinene, β-pinene, and terpinolene, were identified and quantified. It was revealed that the amounts of the oleoresin released and its constituent α-pinene decreased at low temperatures. Other monoterpenes were not detected within the measurement accuracy in this period of time. It was supposed that monoterpenes, formed in smaller amounts during the period of pests' anabiosis, play the key role in the control of coniferous insect pests. The contents of dehydroabietic, isopimaric, neoabietic, pimaric, and sandaracopimaric acids were found to vary insignificantly throughout the year. An interrelation between the amounts of abietic, levopimaric, and palustric acids in the oleoresin composition was revealed. The observed interrelation was supposedly associated with low-temperature catalytic reactions of levopimaric acid isomerization leading to predominant formation of abietic acid. It was suggested that these processes should be taken into account to avoid errors in determining the contents of these acids in the oleoresin even in the case of statistical analysis.

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Section: Resultsmentioning

confidence: 99%

“…1 H and 13 C NMR spectral assignments of abietane diterpenes from Pinus heldreichii and Pinus nigra subsp. nigra was made in different solvents: CDCl 3 , C 6 D 6 , CD 3 OD, and (CD 3 ) 2 CO [9].…”

Section: Introductionmentioning

confidence: 99%

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

Skakovskii,

L.Yu.,

Gapan’kova

et al. 2023

Russ J Bioorg Chem

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“…Further signals were present at δ 5.67 δ 146.5 (C-15), and an olefinic methylene was also observable at δ 4.83–4.94 δ 111.4 (C-16). The presence of three quaternary methyl groups and the vinyl group suggested an abietane skeleton [ 25 , 28 ].…”

Section: Resultsmentioning

confidence: 99%

The Bark of Picea abies L., a Waste from Sawmill, as a Source of Valuable Compounds: Phytochemical Investigations and Isolation of a Novel Pimarane and a Stilbene Derivative

Sut

Baldan

Faggian³

et al. 2021

Plants

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In this work, the sawmill waste from Picea abies debarking was considered as source of valuable phytoconstituents. The extraction was performed using different ethanol/water mixtures, and characterization was obtained by LC-MSn. This latter revealed flavonoid glycosides, lignans, and procyanidins. Extraction with organic solvents (dichloromethane and methanol) and chromatographic separations of the obtained extracts by silica column followed by semi-preparative HPLC led to the isolation of polyphenols and terpenoids such as 21α-metoxy-serrat-14-en-3-one, 21α-hydroxy-serrat-14-en-3-one, pinoresinol, dehydroabietic acid, 15-hydroxy-dehydroabietic acid, 7-oxo-dehydroabietic acid, pimaric acid, 9β-pimara-7,15-dien-19-ol, 13-epi-manoyl oxide, taxifolin-3’-O-glucopyranoside, trans-astringin, and piceasides. Piceaside V and 9β-pimara-7-keto-19β-olide, two novel compounds identified for the first time in P. abies bark, were isolated, and their structures were elucidated using 1D and 2D NMR and MS techniques. The polyphenolic composition of the methanolic portion was also investigated using LC-MSn, and the piceaside content was estimated. To assess the antioxidant activity of main constituents, semi-preparative HPLC was performed on the methanolic extract, and the obtained fractions were assayed by using the DPPH test. Overall, this work shows the potential usefulness of P. abies bark as a source of valuable phytochemicals.

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“…Twenty-seven known compounds were identified as 13-oxo-8(14)-podocarpen-18-oic acid ( 6 ), 7,13-dioxo-8(14)-podocarpen-18-oic acid ( 7 ), 9,10-epoxy-9,10- seco -abieta-8,11,13-trien-18-oic acid ( 8) , 12α-methoxyabieta-7,13-diene-18-oic acid ( 9 ), 12-oxoabieta-7,13-dien-18-oic acid ( 10 ), 12-hydroxydehydroabietic acid ( 11 ), 12-hydroxy-7-oxoabieta-8,11,13-trien-18-oic acid ( 12 ), 7-oxoabieta-8,11,13-trien-18-oic acid ( 13 ), 7α-methoxydehydroabietic acid ( 14 ), 7α-hydroxydehydroabietic acid ( 15 ), 7β-hydroxydehydroabietic acid ( 16 ), 7β,15-dihydroxydehydroabietic acid ( 17 ), 7-oxo-15-hydroxydehydroabietic acid ( 18 ), 15-hydroxydehydroabietic acid ( 19 ), 15-methoxydehydroabietic acid ( 20 ), abiesadine E ( 21 ), 13-hydroxypodocarpa-8,11,13-trien-18-oic acid methyl ester ( 22 ), abieta-8,11,13,15-tetraen-18-oic acid ( 23 ), 7-oxoabieta-8(14),13(15)-dien-18-oic acid ( 24 ), isocupressic acid ( 25 ), agathadiol ( 26 ), 7-oxo-13β-methoxyabieta-8(14)-en-18-oic acid ( 27 ), ent -15,16-dihydroxypimar-8(14)-en-18-oic acid ( 28 ), pinyunin A ( 29 ), larikaempferic acid ( 30 ), 15-hydroxy-12-oxo-7,13-abietadien-18-oic acid ( 31 ), and 15-oxo-17-norabieta-8,11,13-trien-18-oic acid ( 32 ), by comparing their experimental and reported NMR data.…”

Section: Resultsmentioning

confidence: 99%

Diterpenoids from the Root Bark of Pinus massoniana and Evaluation of Their Phosphodiesterase Type 4D Inhibitory Activity

Ding

Zhang

et al. 2020

J. Nat. Prod.

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Thirty-two diterpenoids were obtained from the root bark of Pinus massoniana, and, among them, five compounds (pinmassins A–E) were identified as undescribed analogues. Spectroscopic methods, X-ray single-crystal diffraction analysis, and ECD calculations were applied to establish the structure of the new isolates. Pinmassin D (4) and abieta-8,11,13,15-tetraen-18-oic acid (23) showed moderate phosphodiesterase type 4D (PDE4D) inhibitory effects with IC50 values of 2.8 ± 0.18 and 3.3 ± 0.50 μM, respectively, and their binding modes were investigated by a molecular docking study.

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¹H and ¹³C NMR spectral assignments of abietane diterpenes from Pinus heldreichii and Pinus nigra subsp. nigra

Abstract: H. Shin et al.

Cited by 11 publications

References 34 publications

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

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

The Bark of Picea abies L., a Waste from Sawmill, as a Source of Valuable Compounds: Phytochemical Investigations and Isolation of a Novel Pimarane and a Stilbene Derivative

Diterpenoids from the Root Bark of Pinus massoniana and Evaluation of Their Phosphodiesterase Type 4D Inhibitory Activity

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1H and 13C NMR spectral assignments of abietane diterpenes from Pinus heldreichii and Pinus nigra subsp. nigra

Abstract: H. Shin et al.

Cited by 11 publications

References 34 publications

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

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

The Bark of Picea abies L., a Waste from Sawmill, as a Source of Valuable Compounds: Phytochemical Investigations and Isolation of a Novel Pimarane and a Stilbene Derivative

Diterpenoids from the Root Bark of Pinus massoniana and Evaluation of Their Phosphodiesterase Type 4D Inhibitory Activity

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¹H and ¹³C NMR spectral assignments of abietane diterpenes from Pinus heldreichii and Pinus nigra subsp. nigra