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The roots of Salvia rhytidea: a rich source of biologically active diterpenoids

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Natural Product Research
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Abstract

Sahandinone (1), 12-deoxysalvipisone (2), miltirone (3), 7α-acetoxyroyleanone (4), and labda-7,14-dien-13-ol (5) were isolated from the roots of Salvia rhytidea Benth. (Lamiaceae). Their structures were elucidated by a combination of spectroscopic analyses including EIMS and NMR. The 13C NMR spectroscopic data were revised for the quaternary carbons of both 1 and 3 with the help of HMBC spectra in respect to the spectral data previously reported in the literature. Compounds 1 and 3, two very potent anticancer agents, were isolated in high yields from the roots of the plant. The biological activities of the plants’ constituents were reported in the literature as antimicrobial, cytotoxic and antimalarial are discussed in this article.The major anticancer agents from Salvia rhytidea.

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... There are 61 Salvia species naturally growing in Iran, seventeen of them are endemic (Jamzad, 2012). Several species of Salvia are pharmacologically active and have been widely used in folk medicine (Wu et al., 2013;Firuzi et al., 2013;Jassbi et al., 2017). Bioassay-guided purification of chemical constituents of Salvia species has resulted in the isolation of many bioactive phytochemicals such as flavonoids, phenolics, terpenoids and steroids (Jassbi et al., 2017). ...
... Several species of Salvia are pharmacologically active and have been widely used in folk medicine (Wu et al., 2013;Firuzi et al., 2013;Jassbi et al., 2017). Bioassay-guided purification of chemical constituents of Salvia species has resulted in the isolation of many bioactive phytochemicals such as flavonoids, phenolics, terpenoids and steroids (Jassbi et al., 2017). Among them, more than 550 diterpenoids have been reported from different Salvia species (Kabouche and Kabouche, 2008), most of which have shown a broad spectrum of interesting biological activities and ecological roles, that include antimicrobial, anticancer, antiviral, antioxidant and anti-inflammatory activities (González, 2015;Jassbi et al., 2017). ...
... Bioassay-guided purification of chemical constituents of Salvia species has resulted in the isolation of many bioactive phytochemicals such as flavonoids, phenolics, terpenoids and steroids (Jassbi et al., 2017). Among them, more than 550 diterpenoids have been reported from different Salvia species (Kabouche and Kabouche, 2008), most of which have shown a broad spectrum of interesting biological activities and ecological roles, that include antimicrobial, anticancer, antiviral, antioxidant and anti-inflammatory activities (González, 2015;Jassbi et al., 2017). Among different classes of anticancer drugs, natural products remain a main source of potential drugs to treat human tumors. ...
Article
Salvia lachnocalyx Hedge, Lamiaceae, is an endemic sage which grows naturally in the Fars Province of Iran. The phytochemical analyses of the roots of S. lachnocalyx led to the isolation of five known diterpenoids: ferruginol (1), taxodione (2), sahandinone (3), 4-dehydrosalvilimbinol (4) and labda-7,14-dien-13-ol (5). Their chemical structures were elucidated using one (¹H and ¹³C) and two dimensional (COSY, HSQC and HMBC) NMR spectroscopic data as well as electron impact mass spectra. The cytotoxicity of the purified compounds was evaluated against three human cancer cell lines; MOLT-4 (acute lymphoblastic leukemia), HT-29 (colorectal adenocarcinoma) and MCF7 (breast adenocarcinoma) and all of the isolated compounds showed considerable cytotoxic activity against these cell lines. Compounds 2 and 3 (IC50 range: 0.41–3.87μg/ml) with endocyclic α,β-unsaturated carbonyl functional group, exhibited the highest cytotoxic activities compared to the other compounds (IC50 range: 6.85–17.23μg/ml). In conclusion, compounds 2 and 3 are presented as compounds that deserve further investigation of their biological activities.
... 7α-acetoxyroyleanone extracted from the root of Salvia rhytidea, because of cytotoxic activities, is used in many natural anticancer agents [16][17][18]. Salvia rhytidea Benth (Lamiaceae) is one of the wild species of medicinal plants that grow in the eastern regions of Iran and is native to this region. This plant is a species of sage [19]. ...
... This plant is a species of sage [19]. Many species of sages have attracted the attention of researchers to discover their secondary compounds because they have been used as medicinal plants for various purposes in many parts of the world [18]. Curzerene is an aromatic terpenoid used in various studies as a toxic element in removing mosquitoes and other larvivorous organisms [14,20]. ...
Article
Background Since the COVID-19 outbreak in early 2020, researchers and studies are continuing to find drugs and/or vaccines against the disease. As shown before, medicinal plants can be very good sources against viruses because of their secondary compounds which may cure diseases and help in survival of patients. There is a growing trend in the filed patents in this field. Aims In the present study, we test and suggest the inhibitory potential of five herbal based extracts including 7α-acetoxyroyleanone, Curzerene, Incensole, Harmaline, and Cannabidiol with antivirus activity on the models of the significant antiviral targets for COVID-19 like spike glycoprotein, Papain-like protease (PLpro), non-structural protein 15 (NSP15), RNA-dependent RNA polymerase and core protease by molecular docking study. Methods The Salvia rythida root was extracted, dried, and pulverized by a milling machine. The aqueous phase and the dichloromethane phase of the root extractive were separated by two-phase extraction using a separatory funnel. The separation was performed using the column chromatography method. The model of the important antivirus drug target of COVID-19 was obtained from the Protein Data Bank (PDB) and modified. TO study the binding difference between the studied molecules, the docking study was performed. Result These herbal compounds are extracted from Salvia rhytidea, Curcuma zeodaria, Frankincense, Peganum harmala, and Cannabis herbs, respectively. The binding energies of all compounds on COVID-19 main targets are located in the limited area of 2.22-5.30 kcal/mol. This range of binding energies can support our hypothesis for the presence of the inhibitory effects of the secondary metabolites of mentioned structures on COVID-19. Generally, among the investigated herbal structures, Cannabidiol and 7α- acetoxyroyleanone compounds with the highest binding energy have the most inhibitory potential. The least inhibitory effects are related to the Curzerene and Incensole structures by the lowest binding affinity. Conclusion The general arrangement of the basis of the potential barrier of binding energies is in the order below: Cannabidiol > 7α-acetoxyroyleanone > Harmaline> Incensole > Curzerene. Finally, the range of docking scores for investigated herbal compounds on the mentioned targets indicates that the probably inhibitory effects on these targets obey the following order: main protease> RNA-dependent RNA polymerase> PLpro> NSP15> spike glycoprotein.
... Punica granatum [135] Pomegranate Lythraceae Africa, Asia Whole plant Flavonoids, anthocyanins 139 Quassia amara [136] Bitter ash wood Simaroubaceae Africa Leaves Quassinoids 140 ...
... Salvia rhytidea [139] Persian sage Lamiaceae Iran, Afghanistan ...
... Royleanones 1 to 3 and 7 have been isolated from different genera of the Lamiaceae family, 4-6 while 2 has also been described from species of the Taxodiaceae family. 7,8 Some of these compounds exhibit antibacterial, [9][10][11] cytotoxic, 12 antiviral, 13 gastroprotective, 14 and antiparasitic 15,16 activities. ...
... H-2β, H-6β, and Me-18, respectively. The H-5α signal at δ1. 16 showed correlation with that at δ 0.92 thereby assigning Me-19. Some coupling constant values which can directly be extracted from the spectra are given in Table 3. ...
... Royleanones 1 to 3 and 7 have been isolated from different genera of the Lamiaceae family, 4-6 while 2 has also been described from species of the Taxodiaceae family. 7,8 Some of these compounds exhibit antibacterial, [9][10][11] cytotoxic, 12 antiviral, 13 gastroprotective, 14 and antiparasitic 15,16 activities. ...
... H-2β, H-6β, and Me-18, respectively. The H-5α signal at δ1. 16 showed correlation with that at δ 0.92 thereby assigning Me-19. Some coupling constant values which can directly be extracted from the spectra are given in Table 3. ...
Article
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The known diterpenoids horminone (1) and taxoquinone (2) as a mixture, and pure 6,7-dehydroroyleanone (7) were isolated from the aerial parts of not yet studied Salvia concolor Lamb. Although 1 and 2 are known, the ¹ H Nuclear Magnetic Resonance (NMR) data of their acetyl derivatives 4 to 6 are only partially described. Moreover, the ¹³ C NMR data assignments for 4 and 6 show some inconsistencies and reveal better agreement with those we obtained for diastereoisomeric 3 and 5. Since stereochemical aspects were in doubt, it was considered as mandatory to unambiguously determine the absolute configuration of 3 to 6 using vibrational circular dichroism spectroscopy, which then allowed the complete ¹ H and ¹³ C NMR chemical shift assignments of 4 to 6.
... Most of the Salvia species are pharmacologically active and have been widely used in folk medicine for more than 60 different ailments ranging from aches to epilepsy. Target treatments include colds, bronchitis, tuberculosis, obesity, diabetes, depression, dementia and menstrual disorders [4][5][6][7]. Salvia species are renowned for their abundance of flavonoids, phenolics, terpenoids and steroids, most of which have a broad spectrum of biological activity including antimicrobial, antioxidant, antiinflammatory, anticancer and antiviral activities [7][8][9]. ...
... Target treatments include colds, bronchitis, tuberculosis, obesity, diabetes, depression, dementia and menstrual disorders [4][5][6][7]. Salvia species are renowned for their abundance of flavonoids, phenolics, terpenoids and steroids, most of which have a broad spectrum of biological activity including antimicrobial, antioxidant, antiinflammatory, anticancer and antiviral activities [7][8][9]. ...
Article
Diterpenoids salvimulticanol (1) and salvimulticaoic acid (2) together with known diterpenoid (3-6) were isolated from Salvia multicaulis. Structures were elucidated by spectroscopic techniques including HRESIMS as well as 1D-, and 2D-NMR. In-vitro cytotoxicity was assayed against human cancer cell lines. As several metabolites exhibited activity against drug-resistance lines, compounds were screened against a panel of human drug-sensitive and multidrug-resistant cancer lines. A proposed biosynthetic pathway for these new diterpenoids (1-2) as well as the cytotoxic structure-activity relationship of all identified compounds were discussed. Compound 1 and 6 showed the most potent cytotoxicity with IC50 11.58 and 4.13 towards leukemia cell lines CCRF-CEM and CEM-ADR5000, respectively.
... This genus includes nearly 1000 species which are widely distributed all over the world. Genus Salvia is a rich source of essential oils, flavonoids and terpenoids (Al-Aboudi et al. 2015;Hussain et al. 2016;Jassbi et al. 2016;Salimikia et al. 2016;Tabatabaei et al. 2017). This genus is reported for antioxidant, antimicrobial and antiviral activities (Jassbi et al. 2016;Moridi Farimani & Abbas-Mohammadi 2016). ...
... Genus Salvia is a rich source of essential oils, flavonoids and terpenoids (Al-Aboudi et al. 2015;Hussain et al. 2016;Jassbi et al. 2016;Salimikia et al. 2016;Tabatabaei et al. 2017). This genus is reported for antioxidant, antimicrobial and antiviral activities (Jassbi et al. 2016;Moridi Farimani & Abbas-Mohammadi 2016). Plants belonging to genus Salvia are well known in folk medicine to treat epilepsy, aches, colds, bronchitis and menstrual disorders (Velickovic et al. 2002;Tajbakhsh et al. 2007;Güllüce et al. 2006). ...
Article
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Salvia aethiopis is a perennial plant native to Eurasia and known by the common names Mediterranean sage or African sage. This plant has been used in Iranian medicine as a carminative and tonic. The ethanolic extract of aerial part of S. aethiopis exhibited moderate to weak activity towards delta and kappa opioid receptors (46.3 and 45.3% displacement, respectively). Chromatographic purification of the ethanolic extract on silica gel column led to isolation of one new: 3α-hydroxy-8α-acetoxy-13,14,15,16-tetranorlabdan-12-oic acid (I) and three known compounds: sesquiterpene spathulenol (II), β-sitosterol (III) and β-sitosterol-3-O-glucoside (IV). The structures of all isolated compounds were elucidated by their NMR (1D and 2D) and MS spectral data. All the fractions and isolated compounds were tested for cannabinoid and opioid receptor binding assays.
... Los productos naturales como aceites esenciales, compuestos fenólicos, saponinas, compuestos flavonoides, terpenoides, esteroides, ácidos grasos, alcaloides y otros aislados de plantas medicinales y aromáticas, tienen una larga historia por su bioactividad frente a ciertos patógenos (Hernández-Diaz et al., 2001;Nostro & Papalia, 2012). Se han reportado más de 550 diterpenoides de diferentes especies de Salvia (Kabouche & Kabouche, 2008), la mayoría de los cuales han mostrado un amplio espectro de actividades biológicas interesantes y desempeñan roles ecológicos, que incluyen funciones antimicrobianas, anticancerígenas, antivirales, antioxidantes y antiinflamatorias (Jassbi et al., 2017;González-Chávez et al., 2018). La utilización de productos botánicos obtenidos de Salvia amarissima han sido ampliamente estudiados debido a sus moléculas bioactivas farmacológicamente como flavonoides, fenoles, terpenoides y esteroides (Jassbi et al., 2006;2016). ...
Article
El chancro bacteriano causado por Clavibacter michiganensis subsp. michiganensis (Cmm), representa una de las amenazas más devastadoras para el cultivo de tomate. En este estudio se investigó la eficacia antimicrobiana de la fracción de acetato de etilo obtenida a partir del extracto soluble en acetona de hojas y flores de Salvia amarissima (EC-SA), así como de los diterpenoides amarissinina A (STJ-3) y amarissinina C (STJ-1), como posibles tratamientos biorracionales para el control de Cmm, comparándolos con un control químico tradicional. Mediante ensayos de inhibición in vitro, se observó que el diterpenoide STJ-1 de Salvia amarissima mostró la mayor actividad antimicrobiana de todos los tratamientos, a una concentración de 25 μg/mL. En condiciones de invernadero, el tratamiento con 25 μg/mL de STJ-1 de S. amarissima redujo en un 30% la incidencia y un 42% el índice promedio de la severidad del cáncer bacteriano en plantas de tomate respecto al testigo positivo. Los resultados indican que los extractos de S. amarissima, en particular el diterpenoide STJ-1, representan una alternativa biorracional prometedora para el control de Cmm en los cultivos de tomate. Estos extractos exhiben una eficacia superior a la proporcionada por los productos químicos tradicionales, ofreciendo una solución sostenible y efectiva en la lucha contra esta enfermedad.
... Among the abietane diterpenoids, those with orthoor paraquinone-quinol functionality at C-11/C12 or C-11/C-14 constitute a very important type of terpenoids in the roots of Salvia species (Bisio et al. 2019). Phytochemical and biological investigation on the roots of S. sahendica, S. rhytidea, S. lachnocalyx and S. hydrangea resulted in isolation of several abietane and rearranged abietane or abeo-abietane diterpenoids with antimicrobial, antileishmanial and cytotoxic activities (Jassbi et al. 2006;Hadavand Mirzaei et al. 2017;Jassbi et al. 2017). We report here the occurrence of ferruginol (1) and five quinone abietanes diterpenoids; taxodione (2), 12-deoxy-6-hydroxy-6,7-dehydroroyleanone (3), 14-deoxycoleon U (4), 15-deoxyfuerstione (5) and taxodone (6) in the roots of S. spinosa for the first time and provide cytotoxicity data of the identified compounds. ...
Article
The roots of Salvia spinosa L. (Lamiaceae) were extracted with hexane, dichloromethane (DCM) and ethyl acetate. The DCM extract exhibited cytotoxic activity (IC50 32.7 µg/mL) against MFC-7 breast cancer cell line in MTT colorimetric bioassay. Ferruginol (1), taxodione (2), 12-deoxy-6-hydroxy-6,7-dehydroroyleanone (3), 14-deoxycoleon U (4), 15-deoxyfuerstione (5) and taxodone (6) were isolated from the DCM roots extract. Their structures were elucidated by a combination of spectroscopic analyses including EIMS and 1H- and 13C NMR spectra. The cytotoxicity of compound 3 was determined against MCF-7 and K562 cell lines and compared with the other compounds. A pharmacophore model was built based on potent input compounds to resolve important pharmacophore features responsible for cytotoxic activity of the isolated compounds.
... The biological activities of the plants' constituents were reported in the literature as antimicrobial, cytotoxic and antimalarial. [40] Also the methanolic extract of S. rhytidea Benth. was rich in flavonoids and tannins. ...
... Leriifoliol (63), leriifolione (64), salvialeriicone (65), salvialeriol (66) were identified in root of S. leriifolia (Choudhary et al., 2013;Farimani et al., 2018;Hussain et al., 2016). Additionally, sahandinone (67), 12-deoxysalvipisone (68), miltirone (69), 7α-acetoxyroyleanone (70), and 1-deoxo aurocadiol (71) were isolated from root of S. rhytidea (Eghtesadi et al., 2016;Jassbi et al., 2017). The aerial parts and roots of S. multicaulis was reported to contain salvimulticanol (72), salvimulticaoic acid (73), 3-oxo-12-methoxy-14-hydroxyabieta-8,11,13-triene (74), 6-oxo-12-peroxyabieta-8,11,13-triene (75), multicaulin (76), 12-demethylmulticauline (77), multiorthoquinone (78) and 12-demethylmultiorthoquinone (79) (Hegazy et al., 2018;Ulubelen et al., 1997bUlubelen et al., , 1998. ...
Article
Salvia is the largest genus of the Lamiaceae family, with over 900 species in the world which about 60 species are distributed in Iran, 17 of them are endemic. In Iran, Salvia species have been used to treat various diseases with a wide spectrum of pharmacological activity in vitro and in vivo. The present review summarizes the phytochemistry and pharmacology of medicinal Iranian Salvia species in order to describe their therapeutic potential for a range of diseases. . Phytochemical investigations reveal that the Iranian Salvia has a varied range of metabolites including terpenoids, flavonoids and phenolic acids. The most important pharmacological activities are antidiabetic, antioxidant, antimicrobial, cytotoxic and anti-inflammatory. Iranian Salvia traditionally used as carminatives, analgesics, digestive aids, antiseptics, sedative, anxiolytic, hypnotic, pain reduction and antidiabetic. Among the endemic species, the most interesting for human health are treating a variety of diseases.
... [34], S. rhytidea Benth. [35] and S. reuterana Boiss [36] which grow in Europe or the Middle East. This is the first time that labdane type diterpenoids have been isolated from a sage of the subgenus Calospahce. ...
Article
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The aerial parts of Salvia cinnabarina afforded two undescribed labdane diterpenoids 1 and 2 (malonylcommunol and 6β-hydroxy-trans-communic acid) along with two known labdane diterpenoids, trans-communic acid (3) and trans-communol (4). Additionally, seven known metabolites were also isolated; two isopimarane diterpenoids 5 and 6, two sesquiterpenoids identified as β-eudesmol (7) and cryptomeridiol (8), and three aromatic compounds identified as phthalic acid (9), a mixture of tyrosol fatty acid esters (10) and the flavone salvigenine (11). While compounds compounds 1–3 showed significant inhibition of yeast α-glucosidase, compounds 2, 3 and 7 had no anti-inflammatory activity in the edema model induced by TPA. This paper is not only the first report on a wild population of Salvia cinnabarina, but also of the presence of labdane-type diterpenoids in a Mexican Salvia sp.
... In addition, S. sahendica is used in Iranian folk medicine as an antibacterial and antifungal herb, and also for the treatment of dyspepsia (Esmaeili et al., 2009). Salvia species are rich in triterpenoids (Ballesta-Acosta et al., 2002), polyphenols (Lu and Foo, 2000), and diterpenoids (Xu et al., 2006;Fan et al., 2017;Venditti et al., 2017) exerting a variety of biological activities, such as antioxidant (Kabouche et al., 2007), antifeedant (Fraga et al., 2005), antibacterial (Kawahara et al., 2004), antimutagenic (Amaro-Luis et al., 1998), anti-inflammatory (Baricevic et al., 2001), cytotoxic (Guerrero et al., 2006;Jassbi et al., 2017;Beladjila et al., 2018), anti-HIV (Zhang et al., 2008), lipase inhibitory (Marrelli et al., 2019), and antiplatelet aggregation activities (Liu et al., 2011). ...
Article
Ten undescribed neo-clerodane diterpenoids, named hispanins A-J, together with six known ones, were isolated from the aerial parts of Salvia hispanica L. Their structures were established by extensive spectroscopic analysis. The absolute configurations of the undescribed compounds were determined by the ECD data and single crystal X-ray diffraction analysis. Hispanins B and C represented the first neo-clerodane diterpenoids with a unique oxygen bridge between C-19 and C-20. All isolated compounds were evaluated for their protective effects against H2O2-induced cardiomyocyte injury. Five of these compounds showed significant cardioprotective effects.
... Salvipisone (132), a 11,14-p-12-hydroxyquinone diterpene, obtained from the roots of S. aethiopis L., collected in Spain, was one of the first isolated compounds belonging to 4,5-seco-5,l0-friedo-abietane group ( Rodríguez et al. 1984). Its 12-deoxy derivative (133) was obtained from the aerial parts of S. rytidea Benth. in 2016 ( Jassbi et al. 2017). The roots of S. sclarea yielded a new acetyl derivative of salvipisone (134) ( Ulubelen et al. 1997a). ...
Article
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A total of 175 abietane quinone diterpenes with ortho- or para-quinone chromophore, namely 11,12-ortho-quinone abietane, 11,14-para-quinone abietane, seco-abietane and abeo-abietanes quinones were surveyed from 130 species of Salvia of central Asia/Mediterranean area, eastern Asia, and Central and South America. An organized information on the phytochemistry and the biological activities, i.e. anti-cancer, antioxidant, anxiolytic and antidepressant, anti-obesity, antinflammatory, as well as antimicrobial and toxicological aspects of these compounds was provided. Due to the many nomenclatural mistakes caused by the abundance of data, and the need to provide the plant knowledge for further chemotaxonomic studies, the results about the botany and the taxonomy of the plant source of these compounds were also summarized.
... In our ongoing search for the bioactive phytochemicals from Iranian sage species (Farjam et al., 2013;Jassbi et al., 2012Jassbi et al., , 2017Jassbi et al., 2006;Mirzaei et al., 2017), we report here on the analysis of the constituents of S. ceratophylla roots. ...
Article
Two previously undescribed rearranged abietanes, ceratol (1) and ceratodiol (2), and three known abietane-diterpenoids, including 1-ketoaethiopinone (3), ferruginol (4) and 12-deoxysalvipisone (5), were isolated from roots of Salvia ceratophylla. The structures of the purified compounds (1–5) were characterized based on analyses of their spectroscopic data, including 1D and 2D NMR and high-resolution electrospray mass spectra. The analytical data were then compared with those reported in the literature. Cytotoxicity of the isolated compounds was examined against two human cancer cell lines, MOLT-4 (human lymphoblastic leukemia) and MCF-7 (human breast adenocarcinoma), using the MTT reduction assay. Whereas compound 2 showed cytotoxicity against both cancer cells, 1 showed weak toxicity against MOLT-4 cells and no toxicity against MCF-7 cells. Compound 3 and compound 5, both of which had an α, β-unsaturated carbonyl function, showed the highest cytotoxic activities among the tested compounds.
... Salvia species have been used extensively in Turkey for herbal tea. Owing to the secretion of varied secondary metabolites, many Salvia species display a large variety of biological activities, such as anticancer (Jassbi et al. 2017;Ulubelen et al. 1999), anti-inflammatory, cardioprotective (Kolak et al. 2001;Ulubelen et al. 2002). The phytochemical investigation on Salvia cryptantha mainly based on extract activity such as antiviral (Civra et al. 2017), antitumor ( € Ozer et al. 2013). ...
Article
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Salvia absconditiflora Greuter & Burdet (Synonym Salvia cryptantha Montbret & Aucher ex Benth) has been used extensively for traditional medicine. The aerial of plant material was boiled in water then filtrated. The filtrate was partitioned with ethyl acetate and n-butanol sequentially to yield the ethyl acetate and n-butanol extract. A sample of water was lyophilized to yield the water extract. Ethyl acetate extract revealed the highest antioxidant activity and included the most phenolic compounds among the extracts. Hence, ethyl acetate extract was subjected to chromatographic techniques. Ursolic acid (1), crismaritin (2), luteolin (3), rosmarinic acid methyl ester (4), 3,4-dihydroxyl benzaldehyde (protocatechuic aldehyde) (5), caffeic acid (6), apigenin-7-O-β-glucoside (7), rosmarinic acid (8) and luteolin-7-O-β-glucoside (9) were isolated and the structures were elucidated by spectroscopic methods including 1D, 2D NMR, and LC-TOF/MS. Cirsimaritin (2), luteolin (3), rosmarinic acid methyl ester (4), rosmarinic acid (8), luteolin-7-O-β-glucoside (9) displayed the considerable antioxidant activity.
... Salvia genus is also a source of anti-cancer compounds. There are several reports on the isolation of cytotoxic and genotoxic metabolites from Salvia species (Akaberi et al., 2015;Jassbi et al., 2016;Topçu, 2006;Zhang et al., 2012). ...
... Further purification by a combination of silica gel CC, and preparative and semipreparative RP-HPLC afforded 17 abietane, icetexane, and isopimarane diterpenoids. Fourteen of them were identified as known compounds, including 12-hydroxy-20-norabieta-8,11,13-triene (1) [21], carnosol (3) [22], 7α-ethoxyrosmanol (4) [23], miltirone (5) [24], Δ 9 -dehydro-ferruginol (7) [25], ferruginol (8) [26], miltiodiol (10), 1-oxomiltirone (11) [27], barbatusol (12) [28], 11,12-dihydroxy-20-norabieta-5(10),8,11,13-tetraen-1-one (13) [29], ent-isopimara-8,15-diene-18-ol (14) [30], rosmanol (15), epi-rosmanol (16) [22], and galdosol (17) [23] (▶ Fig. 1). Compounds 3 and 15 have been reported from the aerial parts [31] of P. abrotanoides, while 11 has been previously isolated from the roots [2]. ...
Article
As part of a screening for new antiparasitic natural products from Iranian plants, n-hexane and ethyl acetate extracts from the aerial parts of Perovskia abrotanoides were found to exhibit strong inhibitory activity against Trypanosoma brucei rhodesiense and Leishmania donovani. The activity was tracked by high-performance liquid chromatography (HPLC)-based activity profiling. Preparative isolation by a combination of silica gel column chromatography and HPLC afforded 17 diterpenoids (1–17), including 14 abietane-, two icetexane-, and one isopimarane-type derivatives. Among these, (5R,10S)-11-hydroxy-12-methoxy-20-norabieta-8,11,13-triene (2), 12-hydroxy-norabieta-1(10),8,11,13-tetraene-1,11-furan (6), and 12-methoxybarbatusol (9) were new compounds, the structure of which was established by comprehensive spectroscopic data analysis (one- and two-dimensional nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, electronic circular dichroism). The antiprotozoal activity of the isolated compounds was evaluated against T. b. rhodesiense, Trypanosoma cruzi, L. donovani, and Plasmodium falciparum. Selectivity indexes (SI) were calculated in comparison to cytotoxicity on rat myoblast (L6) cells. Particularly active were 7α-ethoxyrosmanol (4) with an IC50 of 0.8 µM against T. b. rhodesiense (SI 14.9) and an IC50 of 1.8 µM (SI 6.9) against L. donovani, ferruginol (8) with an IC50 of 2.9 µM (SI 19.2) against P. falciparum, and miltiodiol (10) with an IC50 of 0.5 µM (SI 10.5) against T. b. rhodesiense. None of the compounds exhibited selective toxicity against T. cruzi (SI ≤ 1.6).
... It is represented in the Iranian flora by 58 species, of which 17 are endemic (Mozaffarian 2010). Some of these species have been used as medicinal, aromatic and ornamental plants (Habibi et al. 2000;Naghibi et al. 2010;Al-Aboudi et al. 2015;Hussain et al. 2016;Jassbi et al. 2016;Moridi Farimani & Abbas-Mohammadi 2016;Salimikia et al. 2016). A broad spectrum of biological activities has been reported for Salvia species, such as antioxidant, antimicrobial, anti-inflammatory, cytotoxic and antiplasmodial properties (Kamatou et al. 2008). ...
Article
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Phytochemical investigation of n-hexane extract of Salvia sahendica by normal phase column chromatography resulted in the isolation of six compounds. Structures were established by 1D and 2D NMR spectroscopy, and HRMS, as a new norditerpene 1, and known terpenoids, sclareol (2), oleanolic acid (3), β-sitosterol (4), salvigenin (5) and 3α-hydroxy-11α,12α-epoxyoleanan-28,13β-olide (6). The absolute configuration of 1 was confirmed by a combination of X-ray single crystal analysis and electronic circular dichroism spectroscopy. In vitro cytotoxic activity on breast cancer cell line (MDA-MB-231) and also the antimicrobial activity of the pure compounds were tested against Staphylococcus aureus, Bacilus cereus and Escherichia coli.
... practices (Walker et al. 2004). 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). ...
Article
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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.
... The genus Salvia L. (Lamiaceae) contains more than 1000 species of herbs, subshrubs and shrubs with many of the species commonly used in cosmetics and in local folk medical practices (Walker et al. 2004). 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). ...
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A new diterpenoid quinone has been isolated and characterized on the basis of the chemical and spectroscopic properties.
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The essential oils of eight Salvia species collected from different localities in Iran were analyzed by gas chromatography/mass spectrometry (GC/MS). The analytical results were compared with those previously published for related Iranian sage species in order to identify chemical markers for these species. Salvia eremophila, S. hypoleuca, and S. reuteriana are endemic, while S. atropatana, S. chloroleuca, S. santolinifolia, S. aegyptiaca, and S. macrosiphon also grow wild in neighboring countries. We categorized the Iranian Salvia species into four main chemotypes according to their essential-oil constituents: those which are dominated by 1) monoterpenes, 2) mono- and sesquiterpenes, or 3) sesquiterpenes as the major constituents, and 4) those containing low-molecular-weight acids, aldehydes, and esters, and green-leaf volatiles (GLVs). Likely due to the chemical diversity of different Salvia chemotypes, this categorization was supported by principal component analysis (PCA) for the group sampled here, but not for the values reported in the literature. We identified the following chemical markers: α-pinene, β-pinene, 1,8-cineol, linalool, and borneol in monoterpene-rich species, or β-caryophyllene, germacrene D, bicyclogermacrene, spathulenol, and caryophyllene oxide in sesquiterpene-rich species. Among these, α-pinene, β-caryophyllene, and germacrene D are the most common and abundant in the Salvia species investigated. In accordance with their close biological taxonomy, the chemical similarity of the essential oils of S. santolinifolia and S. eremophila is so high that we may consider them chemically identical.
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A new diterpene, named rosmariquinone, was isolated from the leaves ofRosmarinus officinalis L. The leaves were first extracted using methanol and, upon further purification, this extract yielded rosmariquinone. Structure elucidation of the antioxidant was done using IR, MS,1H-NMR and13C-NMR.
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Phytochemical investigations of the n-hexane extract from the roots of Peltodon longipes (Lamiaceae) resulted in the isolation of 12 known abietane diterpenes (1-12). Structures were established on the basis of one and two dimensional nuclear magnetic resonance spectroscopic data ((1)H and (13)C, COSY, HSQC and HMBC), electron ionization mass spectrometric analysis (EIMS) as well as comparison with data from literature. These compounds, as well as eight known diterpenes (13-19) from Salvia miltiorrhiza, and two from Salvia sahendica (20 and 21) were evaluated for their cytotoxic effects in human pancreatic (MIAPaCa-2) and melanoma (MV-3) tumor cell lines using the MTT assay. Tanshinone IIa (13), 7α-acetoxyroyleanone (1), 1,2-dihydrotanshinone (16) and cryptotanshinone (14) had the highest cytotoxic effects in MIAPaCa-2, displaying IC(50) of 1.9, 4.7, 5.6, and 5.8 μM, respectively. Structure-activity relationships of abietane diterpenoid quinones are discussed.
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Two naphthoquinone diterpenoids, 1 and 2, one tricyclic, and one tetracyclic rearranged abietane ('4,5-seco-10,5-friedo-abietane') diterpenoids, 3 and 4, respectively, together with horminone (5) have been isolated from the roots of Salvia sahendica. Compounds 2 and 3 are new, and the 13C-NMR assignment for compound 4 was modified using ' Heteronuclear Multiple-Bond Correlation' (HMBC) spectroscopic data. The structures of the compounds have been established by using different spectral data including 1D- and 2D-NMR, IR, UV, and MS. The elemental composition for the major peaks of 3 and 4 were determined by ' High-Resolution Electron Impact Mass Spectrometry' (HR-EI-MS). The relative configurations of the new compounds were determined by 1H-NMR and 'Rotating-Frame NOES' (ROESY) spectroscopy. Compounds 1, 2, and 5 showed antifungal activities when tested on Blakeslea trispora. Lapachol, a prelynated naphthoquinone, was used as a positive control. The biological activities of the related naphthoquinones and abietane diterpenoids were discussed.
Constituents of roots of Salvia deserta SCHANG. (Xinjiang-Danshen)
  • Y Tezuka
  • R Kasimu
  • J X Li
  • P Basnet
  • K Tanaka
  • T Namba
  • S Kadota