Sesquiterpenes of the Essential Oil of<i>Pinus sylvestris</i>

Chalchat, J. C.; Garry, Raymond-Philippe; Michet, A.

doi:10.1055/s-2007-969487

Cited by 25 publications

(25 citation statements)

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“…These data were similar to those reported for α-cadinol 16 . Except for the observed differences, especially for the carbon atoms at δ C 53.0 (C-7), 74.2 (C-11), 24.1 (C-12) and 32.1 (C-13), of 1 in respect to those of α-cadinol, what could be explained by the existence of an additional C-11 hydroxyl group in 1.…”

supporting

confidence: 91%

“…To the best of our knowledge, except for a publication in which the presence of eudesmol isomers from C. trichotoma wood 11 has been recorded, there have been no other reports of any similar chemical investigation in the literature. In this paper we describe the isolation and structure elucidation of the known compounds: β-sitosterol, sitosterol-β-D-glucoside 12 , oleanolic acid 13 , allantoin 14 , sucrose 15 , α-cadinol 16 , oncocalyxone A 8 , cordiachrome C 5 , and a new sesquiterpene, trichotomol (1). Although cordiachrome C (2) had been previously isolated from C. millenii, only the partial 1 H NMR data was provided but some doubt about its stereochemistry 5 has remained.…”

Section: Introductionmentioning

confidence: 99%

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Trichotomol, a New Cadinenediol from Cordia trichotoma

Menezes¹,

Lemos²,

Silveira³

et al. 2001

J. Braz. Chem. Soc.

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Um novo sesquiterpeno, nomeado trichotomol e compostos conhecidos como cordiacromo C, α-cadinol, ácido oleanólico, oncocalyxona A, β-sitosterol, glicosídeo do β-sitosterol, alantoína e sacarose foram isolados a partir do extrato etanólico do cerne de Cordia trichotoma. Suas estruturas foram determinadas por análises espectroscópicas e comparação com dados publicados para compostos estruturalmente relacionados.A new sesquiterpene, named trichotomol, and known compounds cordiachrome C, α-cadinol, oleanolic acid, oncocalyxone A, β-sitosterol, β-sitosterol-β-D-glucoside, allantoin and sucrose were isolated from the heart wood ethanol extract of Cordia trichotoma. Their structures were assigned unambiguously by spectroscopic analyses and comparison with the published data for structurally related compounds.

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supporting

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Trichotomol, a New Cadinenediol from Cordia trichotoma

Menezes¹,

Lemos²,

Silveira³

et al. 2001

J. Braz. Chem. Soc.

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“…The spectral data and our analysis compared satisfactorily with those reported in the literature. [9][10][11] …”

Section: Larvicidal Antimycobacterial and Antifungal Compounds From mentioning

confidence: 99%

“…1). 9,10) The 90% methanol fraction (25.5 g) was subjected to column chromatography (silica gel, 0.063-0.200 mm) using a hexane-chloroform-methanol gradient. Each fraction (F1-F9) was tested for antifungal activity in vitro.…”

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confidence: 99%

Larvicidal, Antimycobacterial and Antifungal Compounds from the Bark of the Peruvian Plant Swartzia polyphylla DC

Rojas

Bustamante

Ventosilla

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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Perú is a country with a large number of medicinal plants, many of which are used for the treatment of infectious diseases, 1) although only few studies have been conducted to prove their efficacy and safety. 2,3) Due to the emergence of micro-organism resistance to the common antibiotics 4) and its worldwide impact on health, our research aims to identify new natural products that may lead to the discovery of new antibacterial agents with higher efficiency and lower toxicity.As part of our continuing work on bioactive compounds from Peruvian medicinal plants, [5][6][7] the in vitro antimycobacterial activity of 102 ethanol extracts from 84 plants-used traditionally in Perú for the treatment of inflammatory or infectious disorders-was screened using a tetrazolium microplate assay (TEMA).8) In a separate screening, the antifungal and larvicidal activities of over 100 plants, including those previously tested for antimycobacterial activity, were bio-assayed.As a result of these screenings, Swartzia polyphylla DC (Fabaceae) was found to exhibit powerful antimycobacterial action against the sensitive H 37 Rv and multidrug-resistant Mycobacterium tuberculosis. It also inhibited the in vitro growth of the dermatophyte Trichophyton mentagrophytes, and was active against the larvae of the mosquito Culex quinquefasciatus. We are now pleased to report the isolation of the larvicidal, antimycobacterial and antifungal principles present in the crude extract of S. polyphylla.A solvent-partition of the 95% ethanol extract showed that the larvicidal and antimycobacterial activities were concentrated in the hexane fraction, while the 90% methanol fraction was active only in the antifungal assay. The hexane fraction (28 g) was chromatographed on a silica gel column using a hexane-chloroform-methanol gradient. Each fraction (F1-F7) was evaluated for larvicidal and antimycobacterial activity in vitro. The most active fraction (F6, 8.7 g) was purified by column chromatography using a hexanedichloromethane-ethanol gradient and then by MPLC (Lobar Lichroprep silica gel RP-8, 40-63 mm, 310ϫ25 mm, Merck) with acetonitrile-methanol-water (3 : 2 : 2) yielding the most active fraction F-6-4-2 (51.4 mg). This fraction was finally purified by HPLC (Waters Nova-pak H R silica 6 mm, 3.9ϫ300 mm, Waters Model 600E with Waters 2996 PDA detector) using hexane-chloroform gradient (0 to 70%) to obtain T-cadinol (1, 9 mg) (Fig. 1). 9,10) The 90% methanol fraction (25.5 g) was subjected to column chromatography (silica gel, 0.063-0.200 mm) using a hexane-chloroform-methanol gradient. Each fraction (F1-F9) was tested for antifungal activity in vitro. The most active fraction (F3) yielded fraction F3-7-5 (756 mg) after repeated column chromatography using hexane-ethylacetatemethanol as eluent. This fraction was finally purified by MPLC with methanol-water (6 : 4) to afford biochanin A (2, 15 mg) and dihydrobiochanin A (3, 59 mg) (Fig. 1). 11)The bark of S. polyphylla contains various flavonoids and isoflavones, some of them with strong activity against...

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“…have been published, [7][8][9][10][11][12][13][14][15] but no author has examined oil obtained from the female cones; furthermore, only one paper has compared the oils obtained from leaves of P. pinea, P. halepensis and P. nigra. 9 Chalchat et al 16 correlated the chemical composition and the antimicrobial activity of natural and oxygenated essential oils obtained from P. sylvestris, P. pinaster and other Pinaceae; the oxygenated oils gave the best results. Other researchers 17 have compared the antimicrobial activity of the essential oils of P. pinaster and Abies alba: the former was more effective.…”

Section: Introductionmentioning

confidence: 99%

Chemical composition of essential oils from needles, branches and cones of Pinus pinea, P. halepensis, P. pinaster and P. nigra from central ltaly

Macchioni

Cioni

Flamini

et al. 2003

Flavour & Fragrance J

145

113

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The composition of the essential oils from the needles, branches and female cones of four species of Pinaceae, Pinus pinea, P. halepensis, P. pinaster and P. nigra, has been analysed and comparative chemical evaluations were obtained. In P. pinea the major compound of the essential oils of all the three plant parts is limonene (58.9–62.5%), in P. halepensis α‐pinene (18.1%–53.6%) and myrcene (13.7–42.1%), in P. pinaster α‐pinene (24.7–40.4%) and β‐pinene (21.7–29.2%), and in P. nigra α‐pinene (28.4–61.7%). Copyright © 2003 John Wiley & Sons, Ltd.

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Sesquiterpenes of the Essential Oil ofPinus sylvestris

Cited by 25 publications

References 1 publication

Trichotomol, a New Cadinenediol from Cordia trichotoma

Trichotomol, a New Cadinenediol from Cordia trichotoma

Larvicidal, Antimycobacterial and Antifungal Compounds from the Bark of the Peruvian Plant Swartzia polyphylla DC

Chemical composition of essential oils from needles, branches and cones of Pinus pinea, P. halepensis, P. pinaster and P. nigra from central ltaly

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