(-)-Phyllocladene

beta-Selinene-Rich Essential Oils from the Parts of Callicarpa macrophylla and Their Antioxidant and Pharmacological Activities.[Pubmed:28930267]

Medicines (Basel). 2017 Jul 10;4(3). pii: medicines4030052.

Background:Callicarpa macrophylla (Varbenaceae) is a medicinal shrub and is traditionally used in India, China, and South Asia. Methods: The plant material was collected from lower Himalayan region of Uttarakhand in India. The essential oils from three different aerial parts were analyzed by GC-MS. Antioxidant activity, phenolic assay, and various pharmacological activities were determined by using existing methods which are generally practiced widely. Results: Over 51, 53, and 40 compounds were identified in C. macrophylla leaves essential oil (CMLEO), C. macrophylla pre mature seeds and fruits essential oil (CMEO-I) and C.macrophylla mature seeds and fruits essential oil (CMEO-II), respectively. These oils differ in relative contents of major compounds viz; beta-selinene (37.51% in CMLEO, 44.66% in CMEO-I and 57.01% in CMEO-II), (-)-Phyllocladene (9.76% in CMLEO, 5.80% in CMEO-I and 12.38% in CMEO-II), caryophelline oxide (7.34% in CMLEO, 8.74% in CMEO-I and 5.0% in CMEO-II), 9E-epi-caryophelline (6.23% in CMLEO, 1.27% in CMEO-I and 3.43% in CMEO-II), longipinocarvone (4.96% in CMLEO, 1.17% in CMEO-I and 2.0% in CMEO-II), and 1,8-cineole (2.23% in CMLEO, 3.10% in CMEO-I and 1.62% in CMEO-II). The oils exhibited good in vitro antioxidant activity. The maximum activity was found in CMEO-II with IC50 values 7.37 +/- 0.11, 11.49 +/- 0.87, 14.59 +/- 0.18, 15.66 +/- 0.03, and 17.49 +/- 0.13 microl/mL. The essential oils showed qualitative and quantitative diversity in the makeup of essential oils constituents. The oils were found to exhibit anti-inflammatory, analgesic, and antipyretic activity on swiss albino mice compared to the standard drugs, viz; ibuprofen, paracetamol and indomethacin. Conclusion: It is inferred from the study that the plant parts can be used scientifically in traditional systems as folk herbal medicine. Furthermore, we have generated a database for future reference and judicious exploitation of these oils from their natural setting.

Integrated Analysis of the Wood Oil from Xanthocyparis vietnamensis Farjon & Hiep. by Chromatographic and Spectroscopic Techniques.[Pubmed:27355937]

Molecules. 2016 Jun 27;21(7). pii: molecules21070840.

In order to get better knowledge about the volatiles produced by Xanthocyparis vietnamensis, a species recently discovered in Vietnam, its wood oil has been analyzed by a combination of chromatographic (GC, CC) and spectroscopic (GC-MS, (13)C-NMR) techniques. Forty components that accounted for 87.9% of the oil composition have been identified. The composition is dominated by nootkatene (20.7%), 11,12,13-tri-nor-eremophil-1(10)-en-7-one (17.2%), gamma-eudesmol (5.1%), nootkatone (4.7%), valencene (3.5%) and 13-nor-eremophil-1(10)-en-11-one (2.6%). The structure of two new compounds-10-epi-nor-gamma-eudesmen-11-one and 12-hydroxy-isodihydroagarofuran-has been elucidated, while 11,12,13-tri-nor-eremophil-1(10)-en-7-ol is reported as a natural product for the first time. The composition of X. vietnamensis wood oil varied drastically from those of leaf oils, dominated by hedycaryol (34.4%), (-)-Phyllocladene (37.8%) or by pimara-6(14)-15-diene (19.4%).

Electronic circular dichroism of chiral alkenes: B3LYP and CAM-B3LYP calculations.[Pubmed:25283773]

Chirality. 2015 Jan;27(1):23-31.

Time-dependent density functional theory (TDDFT) calculations of electronic circular dichroism (ECD) are widely used to determine absolute configurations (ACs) of chiral molecules. Two very popular DFT exchange-correlation functionals, one hybrid (B3LYP) and one long-range corrected (CAM-B3LYP), along with a hierarchical sequence of basis sets were investigated, and the ECD spectra predicted for eight alkenes and compared to gas-phase experimental spectra. Little variation in predicted ECD spectra was found with the basis set size enlargement, but the sensitivity to the functional is greater. Good agreement was obtained only with the CAM-B3LYP functional, leading to the conclusion that TDDFT calculations of ECD spectra can routinely provide reliable ACs if and only if an appropriate functional is used. For camphene, twistene, syn-(E)-bisfenchylidene, and (-)-Phyllocladene, solvent effects were estimated.

Essential oil composition of the different parts of Eryngium aquifolium from Spain.[Pubmed:20521555]

Nat Prod Commun. 2010 May;5(5):817-21.

The essential oils from the different parts [inflorescences (E.a.I), stems + leaves (E.a.SL) and roots (E.a.R)] of E. aquifolium Cav. gathered in Cadiz (Spain), have been extracted by steam distillation and analyzed by gas chromatography and gas chromatography coupled to mass spectrometry. Quantitative and qualitative differences have been found between the analyzed plant parts. A total of 107 compounds have been identified. The main constituents were germacrene D (30.3%) and sesquicineole (26.7%) for E.a.I fraction, germacrene D (46.0%) and myrcene (13.8%) in the E.a.SL, while E.a.R showed (-)-Phyllocladene isomer (63.6%) as a unique major compound. The percentage composition of the other constituents was lower than 5.5% in all the analyzed fractions. In agreement with other Eryngium species, no specific compound could be used as a marker for the chemotaxonomy of E. aquifolium. However, similarities in volatile composition were found between E. aquifolium and other species growing under similar environmental conditions. As far as we know, this is the first report on the essential oil of this species.

Essential oil composition of the different parts of Eryngium corniculatum Lam. (Apiaceae) from Spain.[Pubmed:18022631]

J Chromatogr A. 2007 Dec 21;1175(2):289-93.

The essential oil from the different parts (inflorescences, stems+leaves and roots) of E. corniculatum Lam. gathered in Guadalajara (Spain) has been extracted by steam distillation and analysed by gas chromatography and gas chromatography coupled to mass spectrometry. Quantitative and qualitative differences have been found between the analysed parts, although all of them contained the same principal compound, 2,4,6-trimethylbenzaldehyde, representing the 50.8%, 50.0%, and 29.8% of the total oil for inflorescences, stems+leaves and roots, respectively. Other representative constituents of the oil were similar in the different fractions: in the inflorescences compounds were found to be alpha-pinene (4.0%), chrysanthenyl acetate (4.0%), 2,4,5-trimethylbenzaldehyde (3.3%), (2Z,6E)-farnesol (2.0%), (E)-nerolidol (2.1%) and (Z)-beta-ocimene (2.1%), while the stems+leaves oil showed 2,4,5-trimethylbenzaldehyde (3.8%), alpha-pinene (3.4%), (E)-nerolidol (2.4%) and (2Z,6E)-farnesol (2.1%), and in the roots oil a (-)-Phyllocladene isomer (13.0%), (E)-nerolidol (9.4%), beta-eudesmol (4.1%) and (2Z,6E)-farnesol (2.1%) were found. The presence of C-10 compounds as the main fraction for an Eryngium species is worth mentioning. This is the first report on the chemical composition of this Mediterranean endemic species.

Analysis of the essential oil composition from the different parts of Eryngiumglaciale Boiss. from Spain.[Pubmed:16202420]

J Chromatogr A. 2005 Nov 11;1094(1-2):179-82.

The essential oil from the different parts (inflorescences, stems + leaves and roots) of Eryngium glaciale Boiss. gathered in Sierra Nevada (Spain) has been extracted by steam distillation and analysed by gas chromatography and gas chromatography coupled to mass spectrometry. Quantitative but not qualitative differences have been found between the analysed parts. The principal compounds from the inflorescences oil were found to be (-)-Phyllocladene isomer (43.5%), (E)-caryophyllene (15.2%) and valencene (11.5%), while the oil from stems and leaves only showed (-)-Phyllocladene isomer (41.3%) as main one. The oil from the roots presented (-)-Phyllocladene isomer (49.4%) and linalool (19.1%) as major constituents. This is the first report on the chemical composition of this species.

Essential oil composition of the different parts of Eryngium bourgatii Gouan from Spain.[Pubmed:15941061]

J Chromatogr A. 2005 May 13;1074(1-2):235-9.

The essential oil extracted from the different parts of Eryngium bourgatii Gouan: stems + leaves (E.b.SL), inflorescences (E.b.I) and roots (E.b.R), have been extracted by steam distillation and analysed by gas chromatography (GC) and gas chromatography coupled to mass spectrometry (GC-MS). Quantitative but not qualitative differences have been found between the analysed parts. The principal compounds from the inflorescences oil were found to be (-)-Phyllocladene (37.6%) and bicyclogermacrene (15.1%), while the oil from stems and leaves showed (-)-Phyllocladene (20.4%), gamma-muurolene (11.8%) and (E)-caryophyllene (10.1%) as main ones. The oil from the roots presented gamma-muurolene (15.4%) and (-)-Phyllocladene (15.0%) as major constituents. It is worth mentioning the presence of a diterpene, (-)-Phyllocladene, as main compound of the essential oil. This is the first report on the essential oil of this species.

Identification of (+)-phyllocladene, (--)-sandaracopimaradiene, and (+)-kaurene as new fungal metabolites from fusicoccin-producing Phomopsis amygdali F6.[Pubmed:15277764]

Biosci Biotechnol Biochem. 2004 Jul;68(7):1574-7.

A chemical analysis of the diterpene hydrocarbons produced by fusicoccin-producing fungus Phomopsis amygdali F6 identified five (-)-Phyllocladene-related tri- and tetracyclic diterpene hydrocarbons. The presence of (+)-phyllocladene, (--)-sandaracopimaradiene, (+)-isopimara-8,15-diene, and (+)-pimara-8(14),15-diene in the fungus was demonstrated by GC-MS, 1H-NMR, and [alpha]D measurements. (+)-Kaurene was also identified by GC-MS and chiral capillary GC. The possible biosynthetic relationship of these metabolites is discussed.

The steam volatile oil of Wollemia nobilis and its comparison with other members of the Araucariaceae (Agathis and Araucaria).[Pubmed:10793256]

Biochem Syst Ecol. 2000 Jul 1;28(6):563-578.

The leaf essential oil of Wollemia nobilis (Wollemi Pine) has been investigated and compared with other members of the family Araucariaceae. All araucaroids examined yielded steam volatile oils in low yields. The oil from Wollemia nobilis was composed mainly of (+)-16-kaurene (60%), together with alpha-pinene (9%) and germacrene-D (8%). Oils from Agathis species endemic to Australia were high in monoterpenes, in contrast to those isolated from extra-Australian species. The major constituents of A. atropurpurea oil were (-)-Phyllocladene (13%) and 16-kaurene (19%), followed by alpha-pinene (8%) and delta-cadinene (9%). A. microstachya yielded oil in which alpha-pinene (18%) was the major component; the only other components in excess of 5% were myrcene (7%), bicyclogermacrene (6%) and delta-cadinene (6%). A. robusta oil contained spathulenol (37%) and rimuene (6%). Approximately 40% of the oil was unidentified sesquiterpenes. A. australis oil contained 16-kaurene (37%), sclarene (5%) and an unidentified oxygenated diterpene K (12%) as major components; the only other compound in excess of 5% was germacrene-D (9%). 5,15-Rosadiene (60%), and 16-kaurene (7%) were the major constituents of A. macrophylla oil. A. moorei oil was rich in sesquiterpenes, but the only compounds in excess of 5% were allo-aromadendrene (6%), germacrene-D, delta-cadinene (10%), an unidentified sesquiterpene (12%) and 16-kaurene (6%). In A. ovata oil the most significant compounds were caryophyllene oxide (15%) and (-)-Phyllocladene (39%). Araucaria angustifolia contained germacrene-D (9%) and the diterpenes hibaene (30%) and (-)-Phyllocladene (20%) as major components of its essential oil. Oils of A. bidwillii, A. columnaris and A. cunninghamii were all low in mono- and sesquiterpenes and high in diterpenes. In the first, hibaene (76%) was the major constituent; the second contained hibaene (9%), sclarene (6%), luxuriadiene (13-epi-dolabradiene)(23%) and two unidentified diterpene hydrocarbons (B) (33%) and (E) (10%). In the last, 16-kaurene (53%) was the most significant component followed by hibaene (29%). A. heterophylla was unusual in that over half the oil was made up of the monoterpenoid alpha-pinene (52%), with (-)-Phyllocladene (32%) being the only other compound of significance. alpha-Pinene (18%) was a significant component of A. hunsteinii oil; sclarene (11%) and germacrene-D (5%) were the only other compounds present in concentrations of more than 5%. A. luxurians oil was composed of 5,15-rosadiene (20%) and luxuriadiene (13-epi-dolabradiene) (66%), previously unreported from natural sources. The major components of A. montana were (-)-Phyllocladene (61%) and 16-kaurene (23%). Sclarene (20%), luxuriadiene (19%) and the unidentified diterpene hydrocarbons (B) (25%) and (E) (10%) were the most important constituents of A. muelleri oil. A. scopulorum contained large amounts of 16-alpha-phyllocladanol (41%) as well as luxuridiene (10%) and delta-cadinene and alpha-copaene, both at 6%.