Low-Volatile Lipophilic Compounds in Needles, Defoliated Twigs, and Outer Bark of <i>Pinus thunbergii</i>

Шпатов, А. В.; Попов, С. А.; Sal’nikova, O. I.; Khokhrina, E. A.; Shmidt, E. N.; Um, Byung-Hun

doi:10.1177/1934578x1300801227

Cited by 6 publications

(5 citation statements)

References 11 publications

(12 reference statements)

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“…Figure 3 shows the NMR spectra of the oleoresin sample collected in February (II) 2020. In this case, seven resin acids were detected: abietic (1), dehydroabietic (2), isopimaric (3), neoabietic (5), palustric (6), pimaric (7), and sandaracopimaric (8). By contrast to sample (IX), abietic was the main (57.8%), with pimaric (10.4%) being the second most abundant acid.…”

Section: Resultsmentioning

confidence: 86%

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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: 86%

“…The cones' extractives of Pinus halepensis, P. brutia, P. pinea, P. sylvestris, and P. nigra were analyzed by GC/ MS [3]. The same method was applied to nonvolatile compounds research of needles, trimmed saplings, and outer bark of P. densiflora [4] and P. thunbergii [5]. The resin of lodgepole pine (P. contorta) studied by GC [6].…”

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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“…Trans-communol (4) has also been isolated from various natural sources, such as Pinus thunbergii Lamb. [37], Chamaecyparis obtusa (Siebold and Zucc.) Endl.…”

Section: Resultsmentioning

confidence: 99%

Structural Elucidation of Malonylcommunol and 6β-Hydroxy-trans-communic Acid, Two Undescribed Diterpenes from Salvia cinnabarina. First Examples of Labdane Diterpenoids from a Mexican Salvia Species

et al. 2020

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The aerial parts of Salvia cinnabarina afforded two undescribed labdane diterpenoids 1 and 2 (malonylcommunol and 6β-hydroxy-trans-communic acid) along with two known labdane diterpenoids, trans-communic acid (3) and trans-communol (4). Additionally, seven known metabolites were also isolated; two isopimarane diterpenoids 5 and 6, two sesquiterpenoids identified as β-eudesmol (7) and cryptomeridiol (8), and three aromatic compounds identified as phthalic acid (9), a mixture of tyrosol fatty acid esters (10) and the flavone salvigenine (11). While compounds compounds 1-3 showed significant inhibition of yeast α-glucosidase, compounds 2, 3 and 7 had no anti-inflammatory activity in the edema model induced by TPA. This paper is not only the first report on a wild population of Salvia cinnabarina, but also of the presence of labdane-type diterpenoids in a Mexican Salvia sp.Molecules 2020, 25, 1808 2 of 17 spectroscopic and X-ray diffraction analysis [7,8]. Compound 12 has been tested in several in vitro and in vivo models and exhibits a wide array of biological activities, such as antispasmodic in the isolated guinea-pig ileum model, inhibition of urinary bladder contractility in rats [9] and intestinal motility in mice [10]. Hypotensive activity in a rat model [11], along with anxiolytic and anti-depressive effects in the elevated plus-maze and the forced swimming tests in mice have also been described [12]. Compound 12 showed antimutagenic activity in the Ames test on Salmonella typhimurium and Escherichia coli [13] and also had an anticlastogenic effect in human lymphocytes of its sodium salt [14]. It should be noted that, up to now, all the studies on S. cinnabarina, have been carried out solely on cultivated material from different Botanical Gardens.Continuing with our systematic study of the genus Salvia in Mexico, and ongoing investigation for biological activity diterpenes of chemosystematic importance [15], we report herein the first study on a wild population of S. cinnabarina collected in the State of Puebla (Mexico). Several diterpenoids of the labdane (1-4) and isopimarane (5-6) skeletons were isolated, as well as two eudesmane-type sesquiterpenoids (7-8), phtalic acid (9), tyrosol derivatives (10) and the flavone salvigenin (11). Compounds 1-2 proved to be undescribed labdane-type diterpenoids related to trans-communic acid (3) and trans-communol (4), also isolated from this plant, and their structures were established as malonylcommunol (1) and 6β-hydroxy-trans-communic acid (2). While compounds 1-3 showed significant inhibition of yeast α-glucosidase, compounds 2,3 and 7 showed no anti-inflammatory activity in the edema model induced by TPA. Results and DiscussionThe aerial parts of Salvia cinnabarina afforded 11 compounds (Figure 1) after extensive chromatographic separation and purification.Molecules 2020, 25, x FOR PEER REVIEW 2 of 17

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“…Acid compounds in the extract of Pinus thunbergii needles comprised mainly labdane-type diterpenoids (trans-communic acid) (Shpatov et al, 2013), while in the extracts of defoliated twigs and outer bark, the acids were represented predominantly by abietane-type compounds (neoabietic, dehydroabietic, abietic, levopimaric, and palustric acids; Figure 1.9). The major neutral components of the needle extract were 10-nonacosanol, labdanoids (18-hydroxy-13-epi-manoyl oxide and trans-communol), and beta-sitosterol.…”

Section: Diterpenementioning

confidence: 99%

Chemotaxonomy

Hao¹,

Gu²,

Xiao³

2015

Medicinal Plants

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Low-Volatile Lipophilic Compounds in Needles, Defoliated Twigs, and Outer Bark of Pinus thunbergii

Cited by 6 publications

References 11 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

Structural Elucidation of Malonylcommunol and 6β-Hydroxy-trans-communic Acid, Two Undescribed Diterpenes from Salvia cinnabarina. First Examples of Labdane Diterpenoids from a Mexican Salvia Species

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