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Composition of the essential oil of White sage, Salvia apiana
Abstract
The essential oil of white sage, Salvia apiana, was obtained by steam distillation and analysed by GC-MS. A total of 13 components were identified, accounting for >99.9% of the oil. The primary component was 1,8-cineole, accounting for 71.6% of the oil.
... However, essential oil isolated from in vitro shoots had a greater percentage (11.75%) of sesquiterpene hydrocarbons than the one obtained from raw material (1.49%). The results of GC analysis are in good agreement with the data presented by other researchers [37][38][39][40] . The observed differences in essential oil content of different biomasses may be due to the fact that the raw material did not originate from the parent plant from which the culture was initiated. ...
... After this time, the production of essential oil dropped and achieved a stable level www.nature.com/scientificreports/ of 0.85-0.86% (days [35][36][37][38][39][40][41][42]. The concentrations of the main constituents of essential oil were stable throughout the cultivation period in RITA bioreactors ( Fig. 3; Table 1). ...
Microshoot cultures of the North American endemic Salvia apiana were established for the first time and evaluated for essential oil production. Stationary cultures, grown on Schenk-Hildebrandt (SH) medium, supplemented with 0.22 mg/L thidiazuron (TDZ), 2.0 mg/L 6-benzylaminopurine and 3.0% (w/v) sucrose, accumulated 1.27% (v/m dry weight) essential oil, consisting mostly of 1,8-cineole, β-pinene, α-pinene, β-myrcene and camphor. The microshoots were adapted to agitated culture, showing biomass yields up to ca. 19 g/L. Scale-up studies demonstrated that S. spiana microshoots grow well in temporary immersion systems (TIS). In the RITA bioreactor, up to 19.27 g/L dry biomass was obtained, containing 1.1% oil with up to ca. 42% cineole content. The other systems employed, i.e. Plantform (TIS) and a custom made spray bioreactor (SGB), yielded ca. 18 and 19 g/L dry weight, respectively. The essential oil content of Plantform and SGB-grown microshoots was comparable to RITA bioreactor, however, the content of cineole was substantially higher (ca. 55%). Oil samples isolated from in vitro material proved to be active in acetylcholinesterase (up to 60.0% inhibition recorded for Plantform-grown microshoots), as well as hyaluronidase and tyrosinase-inhibitory assays (up to 45.8 and 64.5% inhibition observed in the case of the SGB culture).
... Some of the species possess antimicrobial, antimalarial, antioxidant and antiproliferative activities (Loizzo et al. 2014;Russo et al. 2015;Jassbi et al. 2016;Moridi Farimani & Abbas-Mohammadi 2016). Salvia apiana, commonly known as white sage, can be found scattered throughout southwestern North America, with the highest concentration in Southern California (Borek et al. 2006). Natives to the Southern California region have been known to use the leaves in traditional Chumash healing involves prayer, relaxation and natural plant-based remedies to cure a variety of ailments (Takeoka et al. 2010). ...
... The plant is used for diaphoretic and diuretic effects (Dentali & Hoffmann 1990). Previous to our research, several compounds including flavonoids, mono-, sesqui-, di-and tri terpenes, have been already identified and/or isolated from S. apiana (Pettit et al. 1966;González et al. 1992;Luis, Lahlou, Andrés, Sood, et al. 1996;Dentali & Hoffmann 1990;Borek et al. 2006;Abreu et al. 2008;Takeoka et al. 2010). However, this plant has not been studied for cannabinoid or opioid receptors activity. ...
Salvia apiana (white sage, Lamiaceae family) plant is native to southern California and parts of Mexico. Some Native American tribes local to this region consider S. apiana to be sacred and burn the leaves as incense for purification ceremonies. The plant has been used to treat sore throats, coughs, chest colds, upper respiratory infections and poison oak rashes. The aqueous ethanolic extract of S. apiana showed moderate CB1 activity (58.3% displacement). Chromatographic purification of the ethanolic extract on silica gel column led to isolation of nine compounds: rosmadial (I), carnosol (II), 16-hydroxycarnosol (III), sageone (IV), cirsimaritin (V), salvigenin (VI), oleanolic acid (VII), 3β,28-dihydroxy-urs-12-ene (VIII), and ursolic acid (IX). The structures of the isolated compounds were determined by their 1D, 2D NMR and MS spectral data. All the fractions and isolated compounds were tested for cannabinoid and opioid receptor binding.
... Some of the species possess antimicrobial, antimalarial, antioxidant and antiproliferative activities (Loizzo et al. 2014;Russo et al. 2015;Jassbi et al. 2016;Moridi Farimani & Abbas-Mohammadi 2016). Salvia apiana, commonly known as white sage, can be found scattered throughout southwestern North America, with the highest concentration in Southern California (Borek et al. 2006). Natives to the Southern California region have been known to use the leaves in traditional Chumash healing involves prayer, relaxation and natural plant-based remedies to cure a variety of ailments (Takeoka et al. 2010 practice, white sage is infused into water in order to relax the patient (Luis, Lahlou, Andrés, Sood, et al. 1996). ...
... The plant is used for diaphoretic and diuretic effects (Dentali & Hoffmann 1990). Previous to our research, several compounds including flavonoids, mono-, sesqui-, di-and tri terpenes, have been already identified and/or isolated from S. apiana (Pettit et al. 1966;González et al. 1992;Luis, Lahlou, Andrés, Sood, et al. 1996;Dentali & Hoffmann 1990;Borek et al. 2006;Abreu et al. 2008;Takeoka et al. 2010). However, this plant has not been studied for cannabinoid or opioid receptors activity. ...
Salvia apiana (white sage, Lamiaceae family) plant is native to California. Indian tribes consider S. apiana to be sacred and burn the leaves as incense for purification ceremonies [1]. The plant has been used to treat sore throats, coughs, chest colds, upper respiratory infections, systemic poison oak rashes and acute candidal vaginitis. Native Americans widely used this plant in traditional Chumash healing [2]. Infusion of the leaves is used as a diaphoretic or diuretic [3]. The aqueous ethanolic extract of S. apiana showed moderate CB1 activity (58.3% displacement). The extract was fractionated on silica gel column chromatography using hexanes-acetone gradient to yield 15 fractions. Repeated column chromatography led to isolation of ten compounds, which were identified to be four diterpenes: rosmadial (I), carnosol (II), 16-hydroxycarnosol (III) & sageone (IV), two flavonoids: cirsimaritin (V), & salvigenin (VI), three triterpenes: oleanolic acid, erythrodiol, ursolic acid and a fatty acid: montanic acid. All the fractions and isolated compounds were submitted for biological studies to check for cannabinoid and opioid receptor binding. Acknowledgements: The project was supported by Award Number P20GM104932 from the National Institute of General Medical Sciences and in part by NCNPR. References: [1] Ali A, et al. (2015) Journal of Agriculture and Food Chemistry, 63: 447 – 456. [2]. Takeoka GR, et al. (2010) Journal of Essential Oil Research. 22: 241 – 244. [3]. Luis JG, et al. (1996) Tetrahedron Letters, 37: 4213 – 4216,
... It is very common that they contain additives such as alcohols, some other terpenes, and/or other fragrance compounds. However, the use of monoterpene-rich essential oils or cosmetic products with such essential oils, e.g., fir needle oil mainly composed of β-pinene (35-48%) (Régimbal and Collin 1994), orange oil mainly composed of limonene (77-95%) (Verzera et al. 2004;Tao et al. 2009), geranium oil rich in citronellol (37.5%) (Sharopov et al. 2014), or sage oil rich in 8-cineole (71.6%) (Borek et al. 2006), results in the dominant percentage share of terpenes in the investigated air samples. Geranium oil additionally contains a large fraction of alcohols in its composition (50-60%) (Babu and Kaul 2005), which also significantly influences collected air sample composition (see Fig. 5, spa 2 sampling day 07 March 2019). ...
Due to excessive application of essential oils and scented products in spa salons during aromatherapy and massage sessions, the elevated concentration of total volatile organic compounds (TVOCs), particularly terpenes, which are known as secondary organic aerosol (SOA) precursors, is expected there. This study was aimed at determination of VOCs with a particular regard to terpenes in air samples collected in selected spa salons located in Northern Poland. Active air sampling was conducted before and after treatments. Samples were analyzed with the use of thermal desorption gas chromatography coupled with flame-ionization detector (TD-GC-FID) and mass spectrometer (TD-GC-MS). Obtained results allowed to characterize chemical composition of indoor air of spa salons and also to relate the dependence between applied essential oil and indoor air chemical composition. It has been proved that (i) spa salons are characterized by TVOC concentrations exceeding recommended values of 300–400 μg m−3 in most of examined cases, reaching up to several thousand of micrograms per cubic meter, (ii) TVOC concentration is strictly related to salon characteristics and carried out treatments, (iii) terpenes constitute a significant part of TVOCs present in spa indoor air, from 22 up to 86%, (iv) most commonly investigated terpenes in the literature (d-limonene, α-pinene, camphene, and linalool) were also determined at the highest concentration levels in this study and (v) VOC chemical composition is strictly dependent on the type of applied essential oils. On the basis of obtained results, it may be stated that extensive application of essential oils rich in terpenes can significantly alter indoor air chemistry of spa salons, thereby influencing health and well-being of employees working there.
Graphical abstract
... Small flowers of white sage can be purple or white with long anthers (Adams and Garcia 2005). This species can be found scattered throughout southwestern North America, with the highest abundance in Southern California (Borek et al. 2006). Salvia divinorum, commonly known as diviner's sage, is a medicinal plant native to Mexico and traditionally used by the Mazatec peoples for spiritual practices due to its hallucinogenic properties. ...
Sage is medicinal plant, known for its antioxidant and anti-inflammatory effects. Eight extract samples were tested in this study: extract from Salvia officinalis L. varieties from two different geographical localities (Jaslovské Bohunice and Pobedim, Slovakia), Salvia officinalis L., variety “bicolor”, Salvia officinalis L., variety “purpurescens”, Salvia apiana , Salvia divinorum , and two callus cultures of Salvia sclarea L. and Salvia aethiopis L. The highest values for composite parameters were observed for extract from Salvia apiana . It can be concluded that prepared sage extract samples are rich on polyphenolic acids (2 950±265 μg.mL ⁻¹ GAeq.) and amines (197±5.50 μg.mL ⁻¹ TRPeq.). HPLC analysis confirmed the dominant content of rosmarinic acid in the extracts; the highest content was detected in the Salvia apiana extract (1 120±15 μg.mL ⁻¹ ). Extract from Salvia apiana expressed too the highest antioxidant activity (1 710 – 4 669 μg.mL ⁻¹ TEAC). Similarly, the highest inhibition activity was observed for this extract on thrombin (57±3.3 %) and on other proteinases (over 80 %). Spearman correlation analysis and PCA analyses revealed a coherence between antioxidant activity of samples and their content of rosmarinic acid as well as inhibitory activity towards particular proteases, and revealed the significance of thiol based secondary metabolites. Cluster analysis demonstrates the differences of Salvia apiana extract from extracts of S. officinalis L., the group of S. divinorum extract and from callus cultures.
... Although lowly exploited, S. apiana has been previously studied regarding its essential oils composition, which are known to contain high amounts of terpenes and terpene derivatives, particularly β-pinene, α-pinene, borneol, 1,8-cineole, campholenic acid, and β-caryophyllene [13,16]. Moreover, phytochemical analysis of hydroethanolic or acetone extracts of this species have allowed the identification of distinct diterpenes and triterpenes, as well as the flavonoids cirsimaritin and salvigenin [17,18]. ...
Salvia apiana and Salvia farinacea var. Victoria Blue decoctions were screened for diverse bioactivities, including the ability to counteract oxidative and inflammatory events, as well as to act as cytotoxic and antimicrobial agents. Both extracts showed good activities and that of S. apiana origin was particularly effective regarding the ability to prevent lipid peroxidation and to prevent nitric oxide (NO●) production in lipopolysaccharide (LPS)-activated murine macrophage RAW 264.7 cell line (EC50 = 50 μg/mL). Moreover, it displayed high cytotoxic capacity against hepatocellular carcinoma HepG2, cervical carcinoma HeLa, and breast carcinoma cells MCF-7, but comparatively low effects in porcine liver primary cells, which highlights its selectivity (GI50 = 41–60 μg/mL vs. 362 μg/mL, respectively). Further, it exhibited inhibitory and lethal potential against a panel of Gram-positive and Gram-negative bacteria. It is possible that the bioactive properties of the two Salvia extracts are associated to their phenolic components and, in the particular case of S. apiana, to its richness in phenolic terpenes, namely in rosmanol, hydroxycarnosic acid and a derivative of sageone, which were found in the extract.
... The primary components observed in Salvia apiana were 1,8-cineole (71.6%), b-pinene (9.1%) and a-pinene (9.0%), accounting for 89.7% of the oil. Most of Salvia species except for S. fruticosa (22-64% 1,8-cineole) and S. tomentosa (17% 1,8-cineole) do not show high levels of 1,8-cineole (Borek et al., 2006). Chemical composition and biological activities of essential oils of sage Salvia officinalis and S.lavandulifolia from Spain were investigated by Santana et al. (2012) and 61 compounds were identified, 23 of which represented >1% of the essential oil. ...
... The analysis of the essential oil composition of Salvia species indicated that essential oils of these species showed significant variations in the concentration of compounds (Flamini et al., 2007;Liang et al., 2009;Ozer et al., 2007;Oztürk et al., 2009;Pitarokili et al., 2006;Salehi et al., 2008). Although, 1.8-cineole was found to be the major compound in the essential oil of some species such as S. fruticosa (Sivropoulou et al., 1997), S. tomentosa (Haznedaroglu et al., 2001), S. aramiensis (Demirci et al., 2002), S. apiana (Borek et al., 2006), S. aucheri (Özcan et al., 2003). ...
Salvia apiana, commonly known as white sage, is an aromatic evergreen subshrub of the chaparral, commonly found in coastal plains in California and Baja California. It has been traditionally used by the Chumash people as a ritual and medicinal plant and used as a calmative, a diuretic, and a remedy for the common cold. However, until recently, relatively little has been known about the composition and biological activity of white sage. Phytochemical studies on S. apiana revealed the presence of substantial amounts of essential oil, accompanied by a variety of triterpenes, C23 terpenoids, diterpenes, and flavonoids. Extracts of the plant have been shown to exhibit antioxidative, antimicrobial, and cytotoxic effects. The influence of white sage constituents on the nervous system, including GABA, opioid, and cannabinoid receptors, has also been documented. The review aimed to compile information on the taxonomy, botany, chemical composition, and biological activities of S. apiana. White sage was compared with other representatives of the genus in terms of chemical composition. The differences and similarities between S. apiana and other sage species were noted and discussed in the context of their therapeutic applications. Reports on ethnomedicinal uses of white sage were confronted with reports on chemistry, bioactivity, and bioavailability of S. apiana constituents. Finally, a critical assessment of the available data was made and perspectives for the use of white sage preparations in modern phytomedicine were discussed.
Chemical composition of essential oils obtained from four species of genus Salvia were analyzed by gas chromatography (GC) and gas chromatography mass spectrometry (GC-MS). Main compounds identified from Salvia species essential oils were as follows: 1,8-cineole (71.7%), -pinene (5.1%), camphor (4.4%) and -pinene (3.8%) in S. apiana; borneol (17.4%), -eudesmol (10.4%), bornyl acetate (5%) and guaiol (4.8%) in S. elegans; bornyl acetate (11.4%), -caryophyllene (6.5%), caryophyllene oxide (13.5%) and spathulenol (7.0%) in S. leucantha; -thujene (25.8%), viridiflorol (20.4%), -thujene (5.7%) and camphor (6.4%) in S. officinalis. In biting deterrent bioassays, essential oil of S. leucantha and S. elegans at 10 µg/cm2 showed activity similar to DEET (97%, N, N-diethyl-meta-toluamide) in both the species of mosquitoes whereas activity of S. officinalis and S. apiana was lower than the other oils or DEET. Pure compounds β-eudesmol and guaiol showed biting deterrent activity similar to DEET at 25 nmol/cm2 whereas activity of 13-epi-manool, caryophyllene oxide, borneol, bornyl acetate and β-caryophyllene was significantly lower than β-eudesmol, guaiol or DEET. All essential oils showed larvicidal activity except S. apiana which was inactive at the highest dose of 125 ppm against both mosquito species. Based on 95% CIs, all the essential oils showed higher toxicity in Anopheles quadrimaculatus than Aedes aegypti. Essential oil of S. leucantha with LC50 value of 6.2 ppm showed highest toxicity in An. quadrimaculatus.
Volatile constituents of the aerial parts of fresh white sage (Salvia apiana Jepson) were isolated by extraction with diethyl ether followed by high vacuum distillation with a solvent assisted flavor evaporation (SAFE) apparatus. The isolated volatiles were analyzed by GC and GC/MS. A total of 84 constituents were identified (constituting 95.1% of the total area), 11 of which were tentatively identified. The volatiles were characterized by a high content of hydrocarbon and oxygenated monoterpenes. The major constituents identified were 1,8-cineole (34.5%), camphor (21.7%), β-pinene (7.4%), α-pinene (6.4%), delta-3-carene (6.4%), camphene (3.9%), limonene (3.5%), myrcene (3.2%), and terpinolene (1.3%).
The essential oil content and composition of Salvia fruticosa (Greek sage) plants growing wild in 20 localities scattered on the island of Crete are studied. The results of our analyses have shown a noticeable variation in the essential oil content (ranging from 1.1 up to 5.1%) and the amount of the four main oil components: 1,8-cineole (22.7-64.2% of total oil), α-thujone (1.0-19.2%) β-thujone (0.9-25.6%) and camphor (0.8-30.3%). Discriminant analysis revealed that the variation pattern of the essential oil content and the amount of the four main oil components is geographically related, following a W → E direction. Plants grown in Western Crete show a lower essential oil content and their oils are characterised by the predominance of 1,8-cineole. On the other hand, those collected from Eastern Crete exhibit higher values in essential oil content and their oils, besides 1,8-cineole, are rich in α- and β-thujone or camphor. Our findings are further discussed in relation to literature data.
The new natural diterpenes, 6,7-didehydroferruginol, 6,7-didehydrosempervirol, 16-hydroxy-6,7-didehydroferruginol, 11,12,16-trihydroxy-20(10 → 5)abeo-abieta-1(10),6,8,11,13-pentaene, the diterpene quinones, 16-hydroxyroyleanone and 6-deoxo-5,6-didehydrolanugon Q plus the known compounds ferruginol, miltiodiol, cryptotanshinone, lanugon Q and salvicanol were isolated from the roots of Salvia apiana. Their structures were established by spectrometry. The co-occurrence of so many abietane diterpenes with different degrees of oxidation and modified skeletons is in accordance with the biosynthetic route previously proposed for these compounds.
The pentacyclic triterpene composition of a southern California variety of Salvia apiana (fam. Labiatae) has been assessed. The presence of α-amyrin, oleanolic acid and ursolic acid has been established. Separation of α-amyrin from a closely related impurity believed to be β-amyrin was accomplished by subjecting the mixture to selenium dioxide oxidation and isolating α-amyrin by preparative thin-layer chromatography on silver nitrate-silica gel. Evidence for the presence of isomeric mixtures of two dihydroxy triterpenes and two triterpene aldehydes representing intermediate stages of oxidation from α- and β-amyrin to ursolic and oleanolic acids was presented. Isolation of ursolic acid from a Mexican variety of Salvia karwinskii was also reported.
A new C23 terpenoid, 13, 14-dioxo-11-hydroxy-7-methoxy-hassane-8, 11, 15-trien-(22,6)-olide 2 was isolated from the aerial part of Salvia apiana Jeps. This new C23 terpenoid has a new basic skeleton 1 for wich we propose the name of hassanane. The structure of 2 was established from its spectroscopic data. A possible common biosynthetic origin of 2 and the previously reported apiananes is also discussed.
The genus Salvia (Lamiaceae) is represented in Turkey by 89 species, of which 45 are endemic. The essential oils obtained by hydrodistillation from different Salvia spp. were analysed by GC–MS. Enantiomeric separation of some constituents in these oils were determined by MD-GC–MS. -Pinene, β-pinene, camphor, limonene, linalool and borneol, mainly contained in Salvia oils, were investigated for their enantiomeric distributions. Copyright © 2001 John Wiley & Sons, Ltd.
Abstract
The essential oil of Salvia argentea L., collected from south-eastern Serbia, was analysed by GC–MS. Forty-seven constituents were identified. The oil was characterized by a high content of sesquiterpenes. The major constituents were viridiflorol (32.4%), manool (14.6%) and α-humulene (10.7%). Copyright © 2001 John Wiley & Sons, Ltd.
Recent studies have shown a high degree of variability in quantity and composition of essential oils among different clones of Salvia fruticosa found in the island of Crete. Forty-eight clones representing three different populations were analysed for their essential oils and for their genetic profiles using RAPD markers. The current study aims to assess the level of genetic diversity of Salvia fruticosa in Crete and its relation to the essential oil profiles.
The essential oil of Salvia tomentosa aerial parts, consisting of 1,8-cineol (17%), beta-caryophyllene (11%), cyclofenchene (10%) and delta-cadinene (6%), was screened for its antimicrobial activity. The essential oil remarkably inhibited the growth of tested Gram-positive and Gram-negative bacteria except for Pseudomonas aeruginosa.