Two‐dimensional NMR of sesquiterpenes. 8—complete assignment of 1H and 13C NMR spectra of seven sequiterpene alcohols from Neocallitropsis pancheri

Raharivelomanana, Phila; Bianchini, Jean‐Pierre; Cambon, A.; Azzaro, Maurizio; Faure, Robert

doi:10.1002/mrc.1260330315

Cited by 49 publications

(26 citation statements)

References 17 publications

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“…A sample of the oil obtained from heartwood (1g) was fractionated by silica gel medium pressure CC, using n-hexane and nhexane/diethyl ether mixtures as eluents. One of the fractions obtained (F54-66; 144.5 mg) was subjected to preparative RP-18 TLC and eluted successively with methanol/water (8:2), to obtain elemol and a mixture of the isomers epi-cubebol and cubebol, which were analyzed and characterized by 1 H NMR, 13 C NMR and GC-MS. NMR and MS data of elemol are in agreement with those of the literature [25]. Cubebol and epi-cubebol were also identified by comparison of the mass fragmentation patterns and 13 C NMR spectra described in the literature [26,27].…”

Section: Analysis Of Essential Oilssupporting

confidence: 85%

Essential Oil Characterization of Two Azorean Cryptomeria japonica Populations and Their Biological Evaluations

Moiteiro

Esteves

Ramalho

et al. 2013

Natural Product Communications

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Essential oils from foliage, bark and heartwood of Cryptomeria japonica D. Don from Azores Archipelago (Portugal) were analyzed by GC and GC-MS. Two populations, of black and reddish heartwood color, were studied. The main compounds found in the foliage of both populations were -pinene (9.6-29.5%), (+)-phyllocladene (3.5-26.5%), ent-kaur-16-ene (0.2-20.6%), sabinene (0.5-19.9%) and limonene (1.4-11.5%), with a large variation in individual compounds from each population. Heartwood oils were characterized by a high content of cubebol (2.8-39.9%) and epi-cubebol (4.1-26.9%) isomers, which were absent in the foliage. Elemol and eudesmol isomers were found in the foliage and heartwood oils, while (+)-phyllocladene was absent in heartwood. Black and reddish bark oils were composed of the diterpenes dehydroferruginol (1.9-5.1%) and ferruginol (2.6-11.5%), along with the sesquiterpenes -cadinene (10.4-15.9%), -muurolene (3.3-5.4%), epi-zonarene (4.0-5.0%), cubenol (9.3-14.0%), -muurolol (4.8-10.7%), -eudesmol (3.0-9.9%), eudesmol (1.9-7.0%) and hedycariol (1.4-6.2%). Azorean C. japonica oils exhibited significant chemical differences compared with native plants from Asia. The essential oils showed moderate antimicrobial activity against the pathogenic fungus Cryptococcus neoformans and human pathogenic bacteria (especially against multidrug-resistant Mycobacterium tuberculosis). The antimicrobial activity of the essential oils may be attributed to compounds such as ent-kaur-16ene, (+)-phyllocladene, ferruginol and elemol, which are present in different proportions within the complex oil mixture. These results suggest a potential use for C. japonica oils obtained from wood industry leftovers.

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Section: Analysis Of Essential Oilssupporting

confidence: 85%

Essential Oil Characterization of Two Azorean Cryptomeria japonica Populations and Their Biological Evaluations

Moiteiro

Esteves

Ramalho

et al. 2013

Natural Product Communications

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“…In our study, mixtures of α-, β-, and γ-eudesmol (2:2:1) were isolated from T. dolabrata var. hondai seeds; these compounds were identified by analyses of 1 H and 13 C NMR data, which agreed fully with those of Raharivelomanana and Bianchini (1995). However, the amount of eudesmols in the seeds was too low to be antifungal against the tested fungi, except for Mucor (4.95 μg seed -1 ).…”

Section: Discussionsupporting

confidence: 63%

The Antifungal Compound Totarol of Thujopsis dolabrata var. hondai Seeds Selects for Fungi on Seedling Root Surfaces

et al. 2007

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Hinoki-asunaro (Thujopsis dolabrata Sieb. et Zucc. var. hondai Makino) is a tree endemic in Japan whose seeds produce several terpenoids. We hypothesized that antifungal compounds in seeds might select for fungi on the root surfaces of T. dolabrata var. hondai seedlings. We examined seed and soil fungi, their sensitivity to methanol extracts of the seeds, the fungi on root surfaces of seedlings grown in Kanuma pumice (a model mineral soil) and nursery soil, and the frequency at which each fungus was detected on the seedling root surface. We calculated correlation coefficients between fungal detection frequency on root surfaces and fungal sensitivity to seed extracts. We also isolated from the seeds the antifungal compound totarol that selected for fungi on root surfaces. Species of Alternaria, Cladosporium, Pestalotiopsis, and Phomopsis were the most frequently isolated fungi from seeds. Mortierella and Mucor were the dominant fungi isolated from Kanuma pumice, whereas Umbelopsis and Trichoderma were the main fungi isolated from nursery soil. Alternaria, Cladosporium, Mortierella, Pestalotiopsis, and Phomopsis were the dominant fungi isolated from root surfaces of seedlings grown in Kanuma pumice, and Alternaria, Cladosporium, Pestalotiopsis, Phomopsis, and Trichoderma were the main root-surface fungi isolated from seedlings grown in nursery soil. The fungal detection frequencies on root surfaces in both soils were significantly and negatively correlated with fungal sensitivity to the seed extract. A similar correlation was found between the fungal detection frequency on root surfaces and fungal sensitivity to totarol. We conclude that totarol is one factor that selects for fungi on root surfaces of T. dolabrata var. hondai in the early growth stage.

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“…E-(-)-pinocamphone and (-)-caryophyllene oxide were obtained from fraction G, while purification of fraction J resulted in the isolation of (-)-guaiol and (+)-spathulenol. The isolated constituents were identified by comparing the MS and NMR data with literature reports (Coxon et al 1984, Raharivelomana et al 1995, Chaves and Santos 2002, Höld et al 2002, Bolzan 2007 …”

Section: Resultsmentioning

confidence: 99%

Anesthetic activity and bio-guided fractionation of the essential oil of Aloysia gratissima (Gillies & Hook.) Tronc. in silver catfish Rhamdia quelen

Benovit

Silva

Salbego

et al. 2015

An. Acad. Bras. Ciênc.

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This work aimed to determine the efficacy of the essential oil of A. gratissima as anesthetic for silver catfish, and to perform the bio-guided fractionation of essential oil aiming to isolate compounds responsible for the noted effects. Fish were submitted to anesthesia bath with essential oil, its fractions and isolated compounds to determine time of anesthetic induction and recovery. Eugenol (50 mg L -1 ) was used as positive control.Essential oil of A. gratissima was effective as an anesthetic at concentrations of 300 to 900 mg L -1 . Fish

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Two‐dimensional NMR of sesquiterpenes. 8—complete assignment of ¹H and ¹³C NMR spectra of seven sequiterpene alcohols from Neocallitropsis pancheri

Cited by 49 publications

References 17 publications

Essential Oil Characterization of Two Azorean Cryptomeria japonica Populations and Their Biological Evaluations

Essential Oil Characterization of Two Azorean Cryptomeria japonica Populations and Their Biological Evaluations

The Antifungal Compound Totarol of Thujopsis dolabrata var. hondai Seeds Selects for Fungi on Seedling Root Surfaces

Anesthetic activity and bio-guided fractionation of the essential oil of Aloysia gratissima (Gillies & Hook.) Tronc. in silver catfish Rhamdia quelen

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