MetaboLights
One of a pair of phellandrene cyclic monoterpene double-bond isomers in which one double bond is exocyclic (cf. alpha-phellandrene, where both of them are endoocyclic).
Identification
3-methylidene-6-(propan-2-yl)cyclohex-1-ene ,
p-mentha-1(7),2-diene
2-p-menthadiene
3-isopropyl-6-methylene-1-cyclohexene
3-methylene-6-(1-methylethyl)cyclohexene
4-isopropyl-1-methylene-2-cyclohexene
beta-Phellandren
beta-phellandrene
beta-phellandrene
Species
homo sapiens
NCBI:txid9606 24421258
NCBI:txid9606 17314143
Europe PubMed Central results
Conjugated dienes as prohaptens in contact allergy: in vivo and in vitro studies of structure-activity relationships, sensitizing capacity, and metabolic activation.
Author: Bergström MA, Luthman K, Nilsson JL, Karlberg AT.
Abstract: There is a great interest in developing in vitro/in silico methods for the prediction of contact allergenic activity. However, many proposed methods do not take the activation of prohaptens to sensitizers by skin metabolism into account. As a consequence, consumer products containing potent sensitizers could be marketed. To identify prohaptens, studies regarding their structure-activity relationships and the mechanisms of their activation must be conducted. In the present investigation, we have studied the structure-activity relationships for alkene prohaptens. A series of seven alkenes (1-7), all of the same basic structure but with variation in the number and position(s) of the double bond(s), were designed and screened for sensitizing capacity using the murine local lymph node assay. Compounds 1-7 were also incubated with liver microsomes in the presence of glutathione to trap and identify reactive metabolites. The metabolic conversion of three alkenes (9-11) to epoxides (12-15) was also studied along with comparison of their sensitizing capacity. Our results show that conjugated dienes in or in conjunction with a six-membered ring are prohaptens that can be metabolically activated to epoxides and conjugated with GSH. Related alkenes containing isolated double bonds and an acyclic conjugated diene were shown to be weak or nonsensitizers. For the first time, the naturally occurring monoterpenes alpha-phellandrene, beta-phellandrene, and alpha-terpinene were demonstrated to be prohaptens able to induce contact allergy. The difference in sensitizing capacity of conjugated dienes as compared to alkenes with isolated double bonds was found to be due to the high reactivity and sensitizing capacity of the allylic epoxides metabolically formed from conjugated dienes. We recommend that these structure-activity relationship rules are incorporated into in silico predictive databases and propose that the prediction of contact allergenic activity of suspected prohaptens is based on assessment of susceptibility to metabolic activation and chemical reactivity of potential metabolites.
DOI: 10.1021/tx060006n
Chemical composition and antimicrobial activity of essential oil of different parts of Seseli rigidum.
Author: Marcetić M, Bozić D, Milenković M, Lakusić B, Kovacević N.
Abstract: The chemical composition and antimicrobial activity of the essential oil of the Balkan endemic species Seseli rigidum Waldst. & Kit. (Apiaceae) was investigated. The monoterpene alpha-pinene was predominant in the volatile oil from aerial parts (57.4%) and fruit (23.3%). In the essential oil of the aerial parts limonene (6.7%), camphene (5.8%) and sabinene (5.5%) were also present in high amounts, and in the fruit oil, beta-phellandrene (17.4%) and sabinene (12.9%). On the contrary, the root essential oil was composed almost entirely of the polyacetylene falcarinol (88.8%). The antimicrobial activity of the root essential oil was significant against Staphylococcus aureus, S. epidermidis, Micrococcus luteus and Enterococcus faecalis (MICs 6.25-25.00 microg/mL). Volatile constituents from the root strongly inhibited the growth of methicillin-resistant strains of S. aureus (MICs 6.25-50.00 microg/mL). Anti-staphylococcal activity can be attributed to the main volatile constituent ofS. rigidum root, falcarinol.
Antimicrobial and antioxidant activities of Stachys lavandulifolia subsp. lavandulifolia essential oil and its infusion.
Author: Işcan G, Demirci B, Demirci F, Göger F, Kirimer N, Köse YB, Can Başer KH.
Abstract: Stachys lavandulifolia Vahl. subsp. lavandulifolia (Lamiaceae) is widely used in south Anatolia as a herbal tea. It is used for the treatment of gastrointestinal and respiratory disorders. Constituents of the essential oil obtained by hydrodistillation were analyzed both by GC-FID and GC/MS, simultaneously. Thirty-seven compounds representing 98.3% of the oil were characterized. Beta-Phellandrene (27%), alpha-pinene (18.5%) and germacrene-D (13%) were found as major components of the oil. Anticandidal, antibacterial and antioxidant properties of the oil and the prepared infusion were evaluated using several methods. The oil exhibited good inhibitory activity on Candida tropicalis (MIC 0.094 mg/mL). Staphylococcus aureus and Salmonella typhimurium growths were also inhibited by the oil at a concentration of 0.375 mg/mL. The prepared infusion of the flowering aerial parts showed weak antimicrobial effects against all the tested microorganisms, but demonstrated a remarkably radical scavenging activity (IC50: 3.9 microg/mL).
Chemical compositions of essential oils from Xyloselinum vietnamense and X. selinum leonidii.
Author: Tran HT, Nguyen SK, Nguyen TH, Tran MH, Nguyen TD.
Abstract: The chemical compositions of essential oils obtained by hydrodistillation from leaves and stems of Xyloselinum vietnamense and X. leonidii, two new species belonging to the family Apiaceae, were analyzed by GC-MS. The major components in both species were sabinene, alpha- and beta-pinene, myrcene, beta-phellandrene, (Z)-beta-ocimene, and terpinen-4-ol. The monoterpene sabinene was most abundant in the leaves of X. vietnamense (75.0%). These compounds might be considered as chemotaxonomic markers of Xyloselinum species. In the DPPH radical scavenging assay, all four essential oils showed moderate activity, while the water extracts exhibited stronger effects. The strong DPPH scavenging activity of the water residues of X. vietnamens and X. leonidii might be due to their phenolic components. This paper is the first report on the chemical compositions and antioxidant activity of X. vietnamens and X. leonidii.
Composition of the essential oils from Peucedanum cervaria and P. alsaticum growing wild in the urban area of Vienna (Austria).
Author: Chizzola R.
Abstract: The composition of the essential oil from the different above ground plant parts of Peucedanum cervaria and P. alsaticum (Apiaceae) collected in the urban area of Vienna has been studied. P. cervaria fruits and inflorescences had 1.5 and 1.8% essential oil, respectively. All the oils of P. cervaria were dominated by monoterpenes, with the main components being beta-pinene (7-58%), alpha-pinene (7-22%), sabinene (up to 22%), and beta-phellandrene with limonene (6-21%). P. alsaticum fruits afforded 0.3-0.4% essential oil. These oils were made up mainly by alpha-pinene (11-40%), sabinene (16-34%) and beta-phellandrene (12-31%). Stems and leaves produced only very small amounts of essential oil (< 0.05%). Besides monoterpenes, these oils contained also E-nerolidol (5-22%), spathulenol (up to 18%), dodecanal (up to 7.5%) and caryophyllene oxide (up to 7%).
Seasonal variations in the composition of the essential oils of rosemary (Rosmarinus officinalis, Lamiaceae).
Author: Lakusić D, Ristić M, Slavkovska V, Lakusić B.
Abstract: Seasonal variations in the composition of the essential oils obtained from rosemary plants of the same genotype cultivated in Belgrade were determined by GC and GC/MS. The main constituents were camphor (18.2 - 28.1%), 1,8-cineole (6.4-18.0%), alpha-pinene (9.7-13.5%), borneol (4.4-9.5%), camphene (5.1-8.7%), beta-pinene (2.1-8.1%), beta-phellandrene (4.6-6.5%), myrcene (3.4-5.9%) and bornyl acetate (0.2-7.9%). Cluster analysis showed that 16 samples that had been collected each month during the vegetative cycle can be separated into three main clades with different compositions of essential oils. In the shoots with fruits ('fruits' - Clade I) and shoots with developed leaves ('old shoots' - Clade III) camphor is dominant. In shoots with young and incompletely developed leaves ('young shoot' - Clade II) camphor and 1,8-cineole had almost the same concentration. The fact that the same genotype during the growing seasons can synthesize oils that are so different that they can be classified as different chemotypes confirms the opinion that the chemical composition of essential oils sometimes critically depends on the time of collection. Also, for the definition of chemotypes it is not enough to base this on a chemical analysis of an oil from one phenophase only.
Comparative study of the volatiles' composition of healthy and larvae-infested Artemisia ordosica.
Author: Zhang H, Zong S, Luo Y, Wang T, Wang J, Cao C.
Abstract: Volatiles emitted by healthy Artemisia ordosica (Asteraceae) and plants infested with larvae of Sphenoptera sp. (Coleoptera: Buprestidae) or Holcocerus artemisiae (Lepidoptera: Cossidae) were obtained using a dynamic headspace method and analysed by automatic thermal desorption/gas chromatography/mass spectrometry (ATD/GC/MS). Twenty-eight major compounds were identified, and qualitative and quantitative differences were compared. The novel green leaf volatiles 2-hexenal, (Z)-3-hexen-1-ol, 2-hexen-1-ol 1-hexanol, and (Z)-3-hexen-1-ol acetate, the terpenoids alpha-copaene, beta-cedrene, and (E,E)-alpha-farnesene, and the ester methyl salicylate were present in all infested plants. Volatiles from healthy plants were dominated by D-limonene (32.14%), beta-pinene (16.63%), beta-phellandrene (16.06%), and sabinene (12.88%). Volatiles from Sphenoptera sp. larvae-infested plants were dominated by D-limonene (24.74%), beta-pinene (21.05%), alpha-pinene (19.39%), and sabinene (11.64%), whereas volatiles from H. artemisiae larvae-infested plants were dominated by D-limonene (31.76%), sabinene (18.49%), ocimene (15.93%), and beta-phellandrene (10.59%). In addition to the qualitative variation, a larvae-induced quantitative change in the proportion of terpenoids in the blends was also a noticeable feature.
Essential oil composition and antimicrobial activity of aerial parts and ripe fruits of Echinophora spinosa (Apiaceae) from Italy.
Author: Fraternale D, Genovese S, Ricci D.
Abstract: The chemical composition and antimicrobial activity of the essential oils obtained from the flowering aerial parts and ripe fruits of Echinophora spinosa L. (Apiaceae) from central Italy were analyzed by GC/MS. The major constituents of the oil from the aerial parts were beta-phellandrene (34.7%), myristicin (16.5%), delta3-carene (12.6%), alpha-pinene (6.7%) and alpha-phellandrene (6.2%), and of the oil from the ripe fruits p-cymene (50.2%), myristicin (15.3%), alpha-pinene (15.1%) and alpha-phellandrene (8.1%). The two oils showed good antimicrobial activity against Clostridium difficile, C. perfringens, Enterococcus faecalis, Eubacterium limosum, Peptostreptococcus anaerobius and Candida albicans with MIC values respectively of 0.25, 0.25, 0.25, 0.25, 2.25, and 0.50%, v/v, and 0.13, 0.13, 0.13, 0.13, 2.25, 0.50%, v/v, for aerial parts and ripe fruits respectively. A less significant antimicrobial activity against bifidobacteria and lactobacilli, very important in the intestinal microflora, was also detected, with MIC values higher than 4.0%, v/v.
Essential oils composition of croton species from the Amazon.
Author: Turiel NA, Ribeiro AF, Carvalho EE, Domingos VD, Lucas FC, Carreira LM, Andrade EH, Maia JG.
Abstract: The essential oils of leaves and twigs from the Euphorbiaceous Croton draconoides, C. urucurana and Julocroton triqueter were obtained and analyzed by GC and GC-MS. In total, 101 volatile constituents were identified, comprising an average of 90% of the oil, mostly made up of mono- and sesquiterpenes. The monoterpene hydrocarbons varied from 1.2 to 40.2%, the sesquiterpene hydrocarbons from 34.0 to 49.6% and the oxygenated sesquiterpenes from 11.5 to 51.3%. The main compounds found in the oil of C. draconoides were beta-pinene (16.9%), alpha-pinene (16.5%), curzerene (12.8%), germacrene D (9.0%), gamma-elemene (4.7%), and elemol (4.4%). The oil of C. urucurana showed sesquicineole (23.0%), dehydro-sesquicineole (13.8%), beta-caryophyllene (7.9%), beta-bisabolol (5.0%), germacrene D (4.2%) and beta-elemene (4.1%) as the chief compounds. The oil of J. triqueter was dominated by beta-caryophyllene (16.3%), beta-phellandrene (10.2%), spathulenol (5.1%), caryophyllene oxide (5.0%), delta-cadinene (4.3%), (E)-nerolidol (4.3%), and alpha-copaene (4.1%).
Cytotoxic activity of essential oils of aerial parts and ripe fruits of Echinophora spinosa (Apiaceae).
Author: Fraternale D, Ricci D, Calcabrini C, Guescini M, Martinelli C, Sestili P.
Abstract: The cytotoxic effects of the essential oils obtained from the flowering aerial parts (APO) and ripe fruits (RFO) of Echinophora spinosa L. (Apiaceae) from central Italy toward human U937 promonocytoid cells were studied; the contribution of each of the major constituents to the whole cytotoxic activity of either APO or RFO was also characterized. The major components of APO were beta-phellandrene (34.7%), myristicin (16.5%), p-cymene (16.3%), delta3-carene (12.6%), alpha-pinene (6.7%) and alpha-phellandrene (6.2%); those of RFO p-cymene (50.2%), myristicin (15.3%), alpha-pinene (15.1%) and alpha-phellandrene (8.1%). Both oils tested were toxic to U937 cells, but RFO was much more cytotoxic: indeed, the IC50 values calculated from the linear regression curves of RFO and APO were 14.5 +/- 0.85 and 43.4 +/- 2.81 microg/mL, respectively. alpha-Pinene and alpha-phellandrene were identified as the most toxically relevant constituents: however, they did not completely account for the toxic effects of genuine APO and RFO. Interestingly, we found that p-cymene, although per se devoid of toxicity within the tested range of concentrations, was capable of significantly sensitizing U937 cells to the cytotoxic activity of alpha-pinene and alpha-phellandrene, and that specific mixtures of these three terpenes were as toxic as genuine APO and RFO.
Comparison of the volatile oil composition of three Atalantia species.
Author: Das AK, Swamy PS.
Abstract: The members of the genus Atalantia belonging to the family Rutaceae have many uses in traditional medicine. The aim of the present study was to investigate and compare the chemical composition of essential oils of three species of Atalantia namely Atalantia monophylla (Roxb.) DC., Atalantia racemosa Wight. and Atalantia wightii Tanaka. The extract percentage of the obtained essential oil was found to be 0.2, 0.17 and 0.31% in A. monophylla, A. racemosa and A. wightii respectively. The major compounds identified were alpha-Asarone (28.82%), Sabinene (13.19%), Eugenol methyl ether (12.71%), 1,2-Dimethoxy-4-(2-methoxyethenyl)benzene (11.63%) and beta-Pinene (5.3%) in the essential oil of A. monophylla. In A. racemosa, T-Cadinol (11.08%), Caryophyllene oxide (9.78%), beta-Caryophyllene (9.20%), Spathulenol (7.21%), beta-Phellandrene (5.67%) and Decanal (4.01%) and in A. wightii beta-Caryophyllene (16.37%), D-Limnonene (12.15%), Decanal (10.49%), beta-Myrcene (7.67%), Tetradecanal (6.99%), Caryophyllene oxide (6.29%) and Hexadecylene oxide (5.87%) were the main constituents. Sesquiterpenes were the major class of compounds in A. racemosa and A. wightii, while in A. monophylla the essential oil was predominated by ether compounds. The results showed that GC/MS analysis of essential oils is a significant step in the bio-chemical profiling and bio-prospecting of Atalantia species.
Chemical composition of Angelica pancicii essential oil determined by liquid and headspace GC-MS techniques.
Author: Simonović SR, Stankov-Jovanović VP, Mitić VD, Ilić MD, Petrović GM, Stojanović GS.
Abstract: The essential oil of the Balkan endemic species, Angelica pancicii, obtained by hydrodistillation, was analyzed by GC and GC-MS, applying the liquid injection mode. These results were compared with the chemical composition of volatiles achieved by the "headspace" injection mode, followed by GC and GC-MS (HS-GC-MS). A total of 40 compounds were identified in the essential oil (98.8% of the total oil) and 44 by HS-GC-MS (99.8% of the total oil). The most abundant class of compounds in both cases was monoterpenoids, which formed 92.7% of the essential oil (97.7% by HS-GC-MS) of total identified compounds. The major components in both cases were beta-phellandrene (54.9% and 60.1%, respectively), alpha-pinene (14.5% and 20.1%, respectively) and alpha-phellandrene (4.5% and 4.3%, respectively).
Seasonal variations in the composition of the essential oils of Lavandula angustifolia (Lamiacae).
Author: Lakusić B, Lakusić D, Ristić M, Marcetić M, Slavkovska V.
Abstract: Seasonal variations in the composition of the essential oils obtained from the same individual (of the same genotype) of Lavandula angustifolia cultivated in Belgrade were determined by GC and GC/MS. The main constituents were 1,8-cineole (7.1-48.4%), linalool (0.1-38.7%), bomeol (10.9-27.7%), beta-phellandrene (0.5-21.2%) and camphor (1.5-15.8%). Cluster analysis showed that the 21 samples collected each month during the vegetation cycle were separable into three main clades with different compositions of essential oils. In the shoots with flowers, inflorescences and fruits of clade I, linalool is dominant, in the young leaves before flowering and old leaves of clade II, 1,8-cineole is dominant. In the young and incompletely developed leaves of clade III, beta-phellandrene is dominant. The composition of the essential oils of lavender depended on the plant part and the stage of development.
Essential oils from Schinus species of northwest Argentina: Composition and antifungal activity.
Author: Sampietro DA, Belizana MM, Baptista ZP, Vattuone MA, Catalán CA.
Abstract: The composition of the essential oils from leaves (Sal) and fruits of S. areira (Saf), and fruits of S. fasciculatus (Sff) and S. gracilipes (Sgf) were analyzed by GC/MS. The major compounds identified were sabinene (26.0 +/- 0.5%), bicyclogermacrene (14.5 +/- 0.4%), and E-citral (6.7+/- 0.2%) in Sal oil, limonene (27.7 +/- 0.7%), sabinene (16.0+/- 0.5%), beta-phellandrene (14.6 +/- 0.8%) and bicyclogermacrene (8.1 +/- 0.2%) in Saf oil, sabinene (22.7 +/- 0.6%), alpha-phellandrene (18.7 +/- 0.3%), beta-phellandrene (15.7 +/- 0.4%), and bicyclogermacrene (8.1 +/- 0.2%) in Sff oil and beta-pinene (25.4 +/- 0.8%), alpha-pinene (24.7 +/- 0.7%), and sabinene (13.6 +/- 0.4%) in Sgf oil.The antifungal activity of the four oils was evaluated on strains of Fusarium verticillioides and F. graminearum, and the results compared with the effect of epoxyconazole, pyraclostrobin and thyme oil. The Sff oil had the highest antifungal activity among the Schinus oils tested, with MIC100 (F. graminearum) = 6 per thousand and MIC100 (F. verticillioides) = 12 per thousand. A principal component analysis suggests that 9 constituents (alpha-thujene, alpha-terpinene, p-cymene, gamma-terpinene, terpinolene, 1-terpineol, alpha-calacorene, alpha-phellandrene, and terpinen-4-ol) explain the higher antifungal effect of Sff. The MIC100s of Schinus oils were on average 30-60 and 8.5-17 fold lower than those obtained for thyme oil on F. verticillioides and F. graminearum, respectively. In the case of commercial fungicides, their MIC100s were three orders of magnitude lower than those of Schinus oils. The last ones showed an additive interaction when assayed in mixtures with the commecial fungicides and thyme oil. The results suggest that the doses of fungicides required for control of the Fusarium species can be reduced when they are assayed in mixtures with the Schinus oils.
The Benefit of Endovascular Thrombectomy for Stroke on Functional Outcome Is Sustained at 12 Months.
Author: Parameshwaran B, Cordato D, Parsons M, Cheung A, Manning N, Wenderoth J, Cappelen-Smith C.
Abstract: <h4>Background and purpose</h4>The short-term benefits of endovascular thrombectomy (EVT) for acute ischemic stroke (AIS) have been widely documented, yet there is limited evidence to show that this is sustained in the long term. We aimed to determine whether the benefit of EVT on functional outcome at 3 months is maintained at 12 months and the factors correlating with functional independence and quality of life.<h4>Methods</h4>Data for analysis came from a prospective registry of consecutive patients undergoing EVT at a single Comprehensive Stroke Center (Oct 2018-Sep 2019). A phone interview was conducted for 12-month patient outcomes. Functional outcome was assessed by the modified Rankin Scale (mRS). Quality of life was determined by return to usual place of residence, work, or driving and calculation of a health utility index using the European Quality of Life-5 Dimensions questionnaire (EQ-5D-3L).<h4>Results</h4>Of the 151 patients who underwent EVT during the study period, 12-month follow-up was available for 145 (96%). At 12 months, 44% (n = 64) of patients were functionally independent (mRS 0-2) compared to 48% at 3 months. Mortality at 12 months was 26% compared to 17% at 3 months. Significant predictors of functional independence at 12 months were younger age and lower baseline National Institutes of Health Stroke Scale. Better quality of life significantly correlated with return to usual place of residence and driving.<h4>Conclusion</h4>Three-month functional independence was sustained at 12 months, indicating that EVT remains beneficial for patients with AIS in the longer term.
DOI: 10.1159/000517929