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Why Terpenes Matter—The Entourage Effect
Published in Betty Wedman-St Louis, Cannabis as Medicine, 2019
α-Pinene is also found in pine needles, rosemary, basil, parsley, dill. Anti-inflammatory, bronchodilatory, antiMRSA, AChE inhibitorAlertness, memory
Use of Cannabinoids in Palliative Nutrition Care
Published in Victor R. Preedy, Handbook of Nutrition and Diet in Palliative Care, 2019
Terpenoids, which are the essential oil components of the cannabis plant that give it its characteristic aroma and flavor, have noted physiologic effects (Russo 2011). They are found in many different plants, including several used in and as foods, and have generally recognized as safe (GRAS) status in the United States (Russo 2011). Terpenoids found in cannabis include limonene, pinene, myrcene, linalool, ß-caryophyllene, caryophyllene oxide, nerolidol, and phytol (Russo 2011). Their documented pharmacologic activities include analgesia, anti-anxiety, anti-inflammatory, bronchodilation, sedative, anti-convulsant and anti-fungal to name a few (Russo 2011).
Monoterpenes-Based Pharmaceuticals: A Review of Applications In Human Health and Drug Delivery Systems
Published in Megh R. Goyal, Durgesh Nandini Chauhan, Plant- and Marine-Based Phytochemicals for Human Health, 2018
Irina Pereira, Aleksandra Zielińska, Francisco J. Veiga, Ana C. Santos, Izabela Nowak, Amélia M. Silva, Eliana B. Souto
There are two structural isomers of pinene found in nature: α-pinene (Fig. 4.1) and β-pinene (Fig. 4.2), which are main volatile components of the essential oil of turpentine—resulting product of pine tree resin hydrodistillation.37, 43, 88, 113 Beside α-pinene, β-pinene is also one of the most common terpenoids released by forest trees.44 Additionally, α-pinene can also be extracted from mandarin peel oil (Citrus reticulata, Rutaceae family).98
Biological activity of terpene compounds produced by biotechnological methods
Published in Pharmaceutical Biology, 2016
Roman Paduch, Mariusz Trytek, Sylwia K. Król, Joanna Kud, Maciej Frant, Martyna Kandefer-Szerszeń, Jan Fiedurek
(R)-(+)-Limonene and (1S)-(−)-α-pinene were used as terpene precursors. The following derivatives of (R)-(+)-limonene were tested: perillyl alcohol (obtained by biocatalytic oxidation in our laboratory) and carvone enantiomers, (R)-(−) and (S)-(+). (−)-α-Pinene derivatives were as follows: trans-verbenol (obtained by biocatalytic oxidation in our laboratory), (1S)-(−)-verbenone, and (1S)-(−)-linalool. Moreover, the set of material tested consisted of mixtures (MIX) of (R)-(+)-limonene derivatives: perillyl alcohol and (S)-(+) and (R)-(−)-carvone enantiomers (1:1:1 v/v/v), and (−)-α-pinene derivatives: linalool, trans-verbenol, and verbenone (1:1:1 v/v/v). Both initial terpenes and their derivatives were used for activity testing. The purpose of testing additional compounds was to analyse whether they express more advantageous biological activity against tumour cells than initial terpene.
Metabolic conversion of β-pinene to β-ionone in rats
Published in Xenobiotica, 2021
Lujain Aloum, Mohammad H. Semreen, Taleb H. Al-Tel, Hamza Al-Hroub, Muath Mousa, Richard L. Jayaraj, Eman Alefishat, Abdu Adem, Georg A Petroianu
Many studies demonstrated that α-pinene and β-pinene exert an array of pharmacological effects such as anticonvulsant (Zamyad et al. 2019), antitumor (Matsuo et al. 2011; Zhang et al. 2015), anticoagulative (Yang et al. 2011), antimicrobial (van Zyl et al. 2006; Rodrigues et al. 2015), anti-inflammatory (Rufino et al. 2014; Kim et al. 2015) and antioxidant (Türkez and Aydın 2016; Karthikeyan et al. 2018). Few studies addressed the pharmacokinetics and metabolic pathways of α-pinene and β-pinene (Salehi et al. 2019). Ishida et al. reported that the urinary metabolites of β-pinene in rabbits include (–)-trans-10-Pinanol (major), (–)-1-p-Menthene-7,8-diol (major), (+)-trans-Pinocarveol, (–)-α-terpineol and myrtenic acid while the urinary metabolites of α-pinene include (–)-trans-verbenol (major), myrtenol and myrtenic acid (Ishida et al. 1981). Similar metabolites were found in brushtail possum; α-pinene oral administration yielded trans-verbenol and myrtenic acid. The latter was isolated in brushtail possum fed with β-pinene (Southwell et al. 1980). In addition, verbenols, verbenone and 4-methyl-2-pentanol were produced in bark beetle exposed to α-pinene (Renwick et al. 1973; Hughes 1975; Renwick et al. 1976) while trans-pinocarveol and pinocarvone were present post treatment with β-pinene (Renwick et al. 1973). Monoterpenoid lactones were detected in the urine of koalas fed α- and β-pinene containing leaf (Southwell 1975). α-pinene urinary metabolites in humans post oral administration included myrtenol and cis- and trans-verbenol. According to the authors, GC–PCI-MS full scan of the urine also revealed three novel metabolites, where one appears to be myrtenic acid (Schmidt and Göen 2017).
The common indoor air pollutant α-pinene is metabolised to a genotoxic metabolite α-pinene oxide
Published in Xenobiotica, 2022
Suramya Waidyanatha, Sherry R. Black, Kristine L. Witt, Timothy R. Fennell, Carol Swartz, Leslie Recio, Scott L. Watson, Purvi Patel, Reshan A. Fernando, Cynthia V. Rider
While exposure to α-pinene in typical indoor air environments is frequent, it is also relatively low. For example, α-pinene was measured in 100% of indoor air samples from three cities in Michigan, with overall mean, median, and maximum concentrations of 9.04, 3.16, and 139.2 µg/m3 (0.0016, 0.00057, and 0.025 ppm), respectively (Jia et al. 2008). In a study of emissions from a newly manufactured house, α-pinene was found at 0.042 ppm (Hodgson et al. 2002). Concentrations of α-pinene inside taxis ranged from 0.2 to 1.8 µg/m3 (approximately 0.00004–0.00032 ppm) (Moreno et al. 2019). Contrastingly, occupational exposure to α-pinene can be quite high in the lumber industry. In a Canadian softwood lumber mill, α-pinene concentrations ranged from below the limit of detection (LOD; 0.3 µg/m3) to 5.1 mg/m3 (approximately 0.92 ppm) (Demers et al. 2000). Higher concentrations of α-pinene were measured in Finnish sawmills with arithmetic means in the range of 57–152 mg/m3 (approximately 10–27 ppm) and total monoterpenes (α-pinene, β-pinene, Δ3-carene, and limonene) reaching 326 mg/m3 (approximately 59 ppm) (Rosenberg et al. 2002). In addition to exposure via inhalation, oral exposure could occur through consumption of α-pinene-containing foods or dietary supplements (Tümen et al. 2018). Exposure to α-pinene via a normal diet is estimated at 317 μg/day (Adams et al. 2011). Many clinical trials have been conducted with dietary supplements made from concentrated pine bark extract (e.g. Pycnogenol®, Myrtol®, Oligopin®) provided in the range of 100–950 mg per day, but the α-pinene content is not reported (Matthys et al. 2011; Robertson et al. 2020). The most recent National Health and Nutrition Examination Survey (NHANES) reported blood concentration of α-pinene in the range 0.014–3.65 ng/mL (n = 1732, 87% detection) demonstrating exposure in the general population (NHANES 2022).