Abietane and nor-abitane diterpenoids from the roots of Salvia rhytidea
© The Author(s) 2016
Received: 1 May 2016
Accepted: 22 June 2016
Published: 13 July 2016
The genus Salvia is a rich source of structurally diverse terpenoids. Different species of the Salvia have been used in folk medicine of Iran and therefore attracted the attention of researchers for exploring their chemical constituents. In a project directed at structurally interesting bioactive metabolites from Iranian Lamiaceae, we studied Salvia rhytidea.
Fractionation of the petroleum ether extract of the root of S. rhytidea led to the isolation of a new 20-nor-abietane diterpenoid (1), together with seven known compounds, comprising five abietane diterpenoids (2–6), and two rearranged abietanes (7, 8). Their structures were established by a combination of 1D and 2D NMR.
Our results showed that the root of S. rhytidea could be considered as a new and rich source of different types of abietane and rearranged abietane diterpenoids.
KeywordsSalvia rhytidea Diterpenoid Abietane Solvent extraction Column chromatography Structure elucidation
The genus Salvia is a rich source of structurally diverse terpenoids (Kintzios 2000; Moridi Farimani et al. 2013). Among these, numerous diterpenoids with promising bioactivities, such as antileishmanial, antitumor, antimicrobial, antifungal properties, have been reported from Salvia species (Ebrahimi et al. 2013; Tan et al. 2002; Akaberi et al. 2015; Moridi Farimani and Miran 2014; Ulubelen 2003; Jassbi et al. 2006). The most abundant diterpenoids in the genus are abietanes and rearranged abietanes (Wu et al. 2012). The genus Salvia is represented in the Iranian flora by 61 species, of which 17 are endemic (Jamzad et al. 2012). Salvia rhytidea Benth is an endemic species that grows widely in the eastern parts of Iran (Rechinger 1987). In our efforts to discover new and potentially bioactive secondary metabolites from Iranian Salvia species (Moridi Farimani and Mazarei 2014; Ebrahimi et al. 2014; Moridi Farimani et al. 2012; Bahadori et al. 2015; Moridi Farimani et al. 2008), we investigated the petroleum ether extract of the root of S. rhytidea. Here we report the isolation and structure elucidation of 1-deoxo aurocadiol (1), as a new 20-nor-abietane diterpenoid. In addition, the abietane diterpenoids ferruginol (2), taxodione (3), arucadiol (4), deoxyneocryptotanshinone (5), and 7α- Ethoxyroyleanone (6), and rearranged abietanes microstegiol (7) and 12-hydroxysapriparaquinone (8) were isolated and are described here for S. rhytidea for the first time.
Results and discussion
Ferruginol (2) is a well known abietane diterpenoid which was isolated from different Salvia species such as S. syriaca and S. sclarea (Ulubelen et al. 2000, 1994). Antileishmanial (Tan et al. 2002), antimicrobial (Ulubelen et al. 1999), cytotoxic (Moujir et al. 1996; Fronza et al. 2011), antihypertensive (Ulubelen et al. 1994), and anticholinesterase (Topcu et al. 2013) activities were reported for ferruginol and the mechanism of its antioxidant properties was also investigated (Saijo et al. 2015).
Taxodione (3) is a diterpenoid with quinone methide skeleton which was reported from different genus like Taxudium, Clerodendrum, and Salvia (Machumi et al. 2010; Kolak et al. 2009; Kusumoto et al. 2009). Different biological properties have been reported for this compound, including antibacterial (Yang et al. 2001), antioxidant (Kolak et al. 2009), antitermitic (Kusumoto et al. 2009), antifeedant (Acosta et al. 2008), antifungal (Topçu and Gören 2007), and anticholinesterase activities (Topcu et al. 2013). Moreover, cytotoxic and tumor inhibitory properties of taxodione have been investigated in in situ and in vivo experiments (Kupchan et al. 1969; Ulubelen et al. 1999; Abou Dahab et al. 2007). The mechanism of action of taxodione for its cytotoxic properties was investigated in several articles with focus on its DNA binding and DNA damaging character (Zaghloul et al. 2008), and its enzyme inhibitory action (Hanson et al. 1970).
Arucadiol (miltiodiol) (4) was previously extracted from S. argentea (Michavila et al. 1986), S. miltiorrhiza (Ginda et al. 1988), S. prionitis (Yong 1995), and S. apiana (González et al. 1992). Cytotoxic properties have been reported for arucadiol (Fronza et al. 2011).
Deoxyneocryptotanshinone (5) is a para-quinone abitanne diterpenod with cytotoxic activity which was isolated from S. miltiorrhiza for the first time (Ikeshiro et al. 1991).
7α-Ethoxyroyleanone (6) has been reported from S. lavandulaefolia, S. lanigra, and Peltodon longipes and its cytotoxic and antioxidant effects were investigated (Fronza et al. 2011; Shaheen et al. 2011; Michavila et al. 1985; Burmistrova et al. 2013).
Microstegiol (7) is a rearranged abietane with a seven-member ring skeleton. This compound has solely been reported from Salvia genus so far (Topcu et al. 2013; Ulubelen et al. 1992). It has been shown to have mild antibacterial effects (Topçu and Gören 2007).
12-hydroxysapriparaquinone (8), a rearranged 4,5-seco-abietane diterpenoid, previously isolated from S. limbata (Topcu et al. 1996).
General experimental procedures
NMR spectra were recorded at a target temperature of 18 °C on a Bruker Avance III 500 MHz spectrometer operating at 500.13 MHz for 1H and 125.77 MHz for 13C. 2D NMR experiments (1H-1H COSY, HSQC, HMBC, NOESY) were performed using Bruker microprograms. CDCl3 was purchased from Armar Chemicals. TLC was performed on silica gel (Merck, Kieselgel 60, F254, 0.25 mm) phase. Column chromatography (CC) was carried out using silica gel (70–230 mesh, Merck). Flash column chromatography (FCC) was performed on silica gel (230–400 mesh, Merck).
The roots of Salvia rhytidea were collected from Taftan Mountain, 28°36′ N and 61°4′ E, in the Baluchistan of Iran at an altitude of 2497 m, in autumn 2012. The plant was authenticated by Dr. Valizadeh and a voucher specimen (no. 4938) was deposited in the Herbarium of the School of Biology (Dr. Akhani Herbarium), University of Tehran.
Extraction and purification
1H-NMR (500 MHz, in CDCl3): δ 1.14 (3H, d, J = 6.9 Hz, Me-16), 1.19 (3H, d, J = 6.9 Hz, Me-17), 1.22 (6H, s, Me-18 and Me-19), 1.58 (2H, m, H-3), 1.72 (2H, m, H-2), 2.78 (2H, t, J = 6.3 Hz, H-1), 2.90 (1H, sept., J = 6.9 Hz, H-15), 6.78 (1H, s, H-14), 7.02 (1H, d, J = 7.0 Hz, H-7), 7.43 (1H, d, J = 7.0 Hz); 13C-NMR (125 MHz, in CDCl3): 18.5 (C-2), 20.6 (C-16 and C-17), 27.6 (C-1), 31.8 (C-18 and C-19), 32.4 (C-15), 34.0 (C-4), 38.0 (C-3), 126.5 (C-7), 128.4 (C-9), 129.8 (C-6), 131.6 (C-14), 134.6 (C-10), 139.7 (C-13), 140.4 (C-8), 148.8 (C-5), 152.9 (C-11), 161.2 (C-12).
1H-NMR (500 MHz, in CDCl3); δ 0.92 and 0.95 (each 3H, s, Me-18 and Me-19), 1.17 (3H, s, Me-20), 1.22 (1H, m, H-3), 1.25 and 1.26 (each 3H, d, J = 7.0 Hz, Me-16 and Me-17), 1.33 (1H, d, J = 12.0 and 2.2 Hz, H-5), 1.37 (1H, m, H-1),1.48 (1H, m, H-3) 1.58 (1H, dt, J = 13.9 and 3.4 Hz, H-2), 1.68 (1H, brd, J = 12.9 Hz, H-6), 1.72 (1H, m, H-2), 1.88 (1H, tdd, J = 13.2, 7.4, and 1.8 Hz, H-6), 2.14 (1H, brd, J = 12.5 Hz, H-1), 2.80 (1H, dd, J = 11.4 and 7.4 Hz, H-7), 2.88 (1H, ddd, J = 11.4 and 7.4 Hz, H-7), 3.20 (1H, sept., J = 6.9 Hz, H-15), 5.34 (s, OH), 6.69 (1H, s, H-11), 6.86 (1H, s, H-14), 13C-NMR (125 MHz, in CDCl3): δ 20. 1(C-2), 20.4 (C-6), 22.7 (C-19), 23.7 (C-16), 23.8 (C-17), 26.2 (C-20), 27.7 (C-15), 31.0 (C-7), 33.4 (C-18), 34.5 (C-4), 38.8 (C-10), 40.0 (C-1), 42.8 (C-3), 51.5 (C-5), 111.8 (C-11), 127.5 (C-14), 127.8 (C-8), 132.5 (C-13), 149.5 (C-9), 151.8 (C- 12).
1H-NMR (500 MHz, in CDCl3): δ 1.18 and 1.21 (each 3H, d, J = 6.9 Hz, Me-16 and Me-17), 1.15, 1.30 and 1.30 (each 3H, s, Me-18, Me-19 and Me-20), 1.20 and 1.44 (1H, m, H-3), 1.67 and 1.86 (each 1H, m, H-2), 2.64 (1H, brs, H-5), 2.97 (1H, ddd, J = 10.7, 3.6 and 1.3 Hz, H-1), 3.10 (1H, dsept., J = 6.9 and 0.8 Hz, H-15), 6.26 (1H, s, H-7), 6.91 (1H, brs, H-14), 7.66 (s, 11-OH); 13C-NMR (125 MHz, in CDCl3): δ 19.3 (C-2), 22.7 (C-20), 22.7 (C-16), 22.8 (C-17), 22.8 (C-19), 28.1 (C- 15), 33.0 (C-4), 33.6 (C-18), 38.3 (C-1), 42.7 (C-3), 43.5 (C-10), 63.1 (C-5), 126.7 (C-9), 135.1 (C-7), 137.5 (C-14), 140.0 (C-8), 145.1 (C-11), 146.2 (C- 13), 182.7 (C-12), 201.7 (C-6).
1H-NMR (500 MHz, in CDCl3); δ 1.37 (6H, d, J = 6.9 Hz Me-16 and Me-17), 1.47 (6H, s, Me-18 and Me-19), 2.09 (2H, t, J = 6.8 Hz, H-3), 2.94 (2H, t, J = 6.8 Hz, H-2), 3.47 (1H, sept., J = 6.9 Hz, H-15), 6.89 (brs, 11-OH), 7.28 (1H, s, H-14), 7.33 (1H, d, J = 8.6 Hz, H-6), 7.95 (1H, d, J = 8.6 Hz, H-7), 10.73 (s, 11-OH), 13C-NMR (125 MHz, in CDCl3): δ 22.0 (C-16 and C-17), 27.4 (C-15), 29.6 (C-18 and C-19), 35.5 (C-3), 36.2 (C-2), 118.5 (C-14), 120.0 (C-11), 120.1 (C-6), 126.7 (C-10), 127.7 (C-9), 128.4 (C-8), 136.6 (C-13), 137.8 (C-7), 148.2 (C-12), 158.3 (C-5), 204.3 (C-1).
1H-NMR (500 MHz, in CDCl3): δ 1.29 (6H, d, J = 7.0 Hz, Me-16 and Me-17), 1.30 (6H, s, Me-18 and Me-19), 1.79 (4H, m, H-2 and H-3), 3.20 (2H, t, J = 6.4 Hz), 3.37 (1H, sept., J = 6.5 Hz, H-15), 7.71 (1H, d, J = 8.2 Hz, H-6), 7.97 (1H, d, J = 8.2 Hz, H-7), 7.82 (1H, s, 12-OH); 13C-NMR (125 MHz, in CDCl3): 19.2 (C-2), 19.9 (C-16 and C-17), 24.5 (C-15), 30.0 (C-1), 31.8 (C-18 and C-19), 37.8 (C-3), 123.8 (C-13), 125.1 (C-7), 126.5 (C-9), 132.8 (C-8), 133.4 (C-6), 140.7 (C-4), 152.5 (C-10), 153.3 (C-12), 183.4 (C-11), 184.6 (C-14).
1H-NMR (500 MHz, in CDCl3): δ 0.84 and 0.87 (each 3H, s, Me-18 and Me-19), 1.11 (3H, t, J = 5.9 Hz, Me-2′), 1.12 and 1.15 (each 3H, d, J = 7.1 Hz, Me-16 and Me-17), 1.13 (3H, s, Me-20), 1.13 (1H, overlap, H-1), 1.17 (1H, overlap, H-3), 1.29 (1H, m, H-6), 1.39 (1H, brd, J = 13.1 Hz, H-3), 1.47 (1H, dt, J = 14.0, 3.5 Hz, H-2), 1.57 (1H, d, J = 12.8 Hz, H-8), 1.64 (1H, m, H-2), 1.93 (1H, d, J = 14.1 Hz, H-14), 2.60 (1H, brd, J = 13.1 Hz, H-1), 3.10 (1H, sept., J = 7.1 Hz, H-15), 3.61 (2H, m, H-1′), 4.35 (1H, dd, J = 3.2 and 1.6 Hz, H-7); 13C-NMR (125 MHz, in CDCl3): 15.5 (C-2′), 18.5 (C-2), 18.7 (C-16 and C-17), 18.8 (C-20), 21.5 (C-19), 22.8 (C-6), 23.4 (C-15), 32.5 (C-18), 33.0 (C-4), 35.2 (C-1), 38.9 (C-10), 40.5 (C-5), 45.2 (C-5), 65.0 (C-1′), 68.6 (C-7), 124.8 (C-13), 141.2 (C-8), 146.9 (C-9), 150.2 (C-12), 184.0 (C-11), 186.1 (C-14).
1H-NMR (500 MHz, in CDCl3): δ 0.80 and 0.81 (each 3H, s, Me-18 and Me-19), 1.17 and 1.22 (each 3H, d. J = 6.9 Hz, Me-16 and Me-17), 1.27 and 2.4 (each 1H, m, H-3), 1.42 and 1.69 (each 1H, m, H-2), 2.33 (3H, s, H-20), 2.80 (1H, ddd, J = 14.0, 6.2 and 2.3 Hz, H-1), 3.03 (1H, dsept, J = 6.7 and 0.7 Hz, H-15), 3.61 (1H, dt, J = 2.1 and 13.1 Hz, H-1), 4.53 (s, 11-OH), 6.91 and 7.07 (1H, d, J = 7.6 Hz, H-7 and H-6), 6.97 (1H, d, J = 0.5 Hz, H-14); 13C-NMR (125 MHz, in CDCl3): 21.1 (C-16), 21.4 (C-20), 21.5 (C-18), 22.1 (C-17), 23.5 (C-2), 26.9 (C-1), 27.1 (C-15), 28.0 (C-19), 39.0 (C-4), 42.9 (C-3), 84.3 (C-11), 126.7 (C-7), 129.1 (C-8), 130.1 (C-6), 137.3 (C-5), 139.3 (C-9), 140.4 (C-14), 141.0 (C-13), 143.3 (C-10), 206.18 (C-12).
1H-NMR(500 MHz, in CDCl3): δ 1.29 (6H, d, J = 7.0 Hz, Me-16 and Me-17), 1.60 and 1.70 (each 3H, s, Me-18 and Me-19), 1.65 (2H, m, H-3), 2.15 (2H, q, J = 8.2 Hz, H-2), 2.42 (3H, s, Me-20), 3.16 (2H, brt, J = 8.2 Hz, H-1), 3.37 (1H, sept., J = 6.5 Hz, H-15), 5.27 (1H, t, J = 6.9 Hz, H-3), 7.47 (1H, d, J = 7.9 Hz, H-6), 7.83 (1H, s, 12-OH), 7.93 (1H, J = 7.9 Hz, H-7); 13C-NMR (125 MHz, in CDCl3): 17.6 (C-19), 19.9 (C-18 and C-19), 20.4 (C-20), 24.6 (C-15), 27.1 (C-1), 30.3 (C-2), 38.5 (C-3), 124.7 (C-13), 125.5 (C-7), 126.2 (C-9), 132.8 (C-8), 136.3 (C-6), 143.3 (C-5), 144.4 (C-10), 145.6 (C-4), 153.3 (C-12), 183.4 (C-11), 184.5 (C-14).
Our results showed that the root of S. rhytidea contained different types of abietane and rearranged abietane diterpenoids. Biological properties of some of these compounds have been reported previously. Accordingly, S. rhytidea could be considered as a new and rich source of natural agents for the treatment of cancer, malaria, and microbial strains.
Analysis and interpretation of data: by FE, MM and NH. All authors read and approved the final manuscript.
Financial support by the University of Sistan & Baluchestan Research Council is gratefully acknowledged. All spectra were performed at the Department of Pharmaceutical Sciences, Division of Pharmaceutical Biology, University of Basel. The kind assistance of Prof. M. Hamburger, Dr. S.N. Ebrahimi, and all other staff is gratefully appreciated.
The authors declare that they have no competing interests.
Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
- Abou Dahab MA, El-Bahr MK, Taha HS, Habib AM, Bekheet SA, Gabr AMM, Refaat A (2007) Cytotoxic activity of Taxodium Calli Extracts on rat liver cells. J Appl Sci Res 3(12):1987–1996Google Scholar
- Acosta MB, Villalobos MJP, Rodríguez B (2008) The antifeedant activity of natural plant products towards the larvae of Spodoptera littoralis. Span J agric Res 1:85–91View ArticleGoogle Scholar
- Akaberi M, Mehri S, Iranshahi M (2015) Multiple pro-apoptotic targets of abietane diterpenoids from Salvia species. Fitoterapia 100:118–132View ArticleGoogle Scholar
- Bahadori MB, Valizadeh H, Asghari B, Dinparast L, Moridi Farimani M, Bahadori S (2015) Chemical composition and antimicrobial, cytotoxicity, antioxidant and enzyme inhibitory activities of Salvia spinosa L. J Funct Foods 18:727–736View ArticleGoogle Scholar
- Burmistrova O, Simões MF, Rijo P, Quintana J, Bermejo J, Estévez F (2013) Antiproliferative activity of abietane diterpenoids against human tumor cells. J Nat Prod 76:1413–1423View ArticleGoogle Scholar
- Ebrahimi SN, Zimmermann S, Zaugg J, Smiesko M, Brun R, Hamburger M (2013) Abietane diterpenoids from Salvia sahendica–antiprotozoal activity and determination of their absolute configurations. Planta Med 79:150–156View ArticleGoogle Scholar
- Ebrahimi SN, Moridi Farimani M, Mirzania F, Soltanipoor MA, De Mieri M, Hamburger M (2014) Manoyloxide sesterterpenoids from Salvia mirzayanii. J Nat Prod 77:848–854View ArticleGoogle Scholar
- Fronza M, Murillo R, Ślusarczyk S, Adams M, Hamburger M, Heinzmann B, Laufer S, Merfort I (2011) In vitro cytotoxic activity of abietane diterpenes from Peltodon longipes as well as Salvia miltiorrhiza and Salvia sahendica. Bioorg med chem 19(16):4876–4881View ArticleGoogle Scholar
- Ginda H, Kusumi T, Ishitsuka MO, Kakisawa H, Weijie Z, Jun C, Tian GY (1988) Salviolone, a cytotoxic bisnorditerpene with a benzotropolone chromophore from a chinese drug dan-shen (Salvia miltiorrhiza). Tetrahedron Lett 29:4603–4606View ArticleGoogle Scholar
- González AG, Aguiar ZE, Grillo TA, Luis JG (1992) Diterpenes and diterpene quinones from the roots of Salvia apiana. Phytochemistry 31(5):1691–1695View ArticleGoogle Scholar
- Hanson RL, Lardy HA, Kupchan SM (1970) Inhibition of phosphofructokinase by quinone methide and α-methylene lactone tumor inhibitors. Science 168(3929):378–380View ArticleGoogle Scholar
- Ikeshiro Y, Hashimoto I, Iwamoto Y, Mase I, Tomita Y (1991) Diterpenoids from Salvia miltiorrhiza. Phytochemistry 30(8):2791–2792View ArticleGoogle Scholar
- Jamzad Z, Assadi M, Maassoumi A, Mozaffarian V (2012) Lamiaceae. In: Flora of Iran, vol. 76. Research Institute of Forest and Rangelands, TehranGoogle Scholar
- Jassbi AR, Mehrdad M, Eghtesadi F, Ebrahimi SN, Baldwin IT (2006) Novel rearranged abietane diterpenoids from the roots of Salvia sahendica. Chem Biodivers 3:916–922View ArticleGoogle Scholar
- Kintzios SE (2000) Sage: the genus salvia. Harwood Academic Publishers, Amsterdam, pp 55–68Google Scholar
- Kolak U, Kabouche A, Öztürk M, Kabouche Z, Topçu G, Ulubelen A (2009) Antioxidant diterpenoids from the roots of Salvia barrelieri. Phytochem Anal 20(4):320–327View ArticleGoogle Scholar
- Kupchan SM, Karim A, Marcks C (1969) Tumor inhibitors. XLVIII. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum. J Org Chem 34(12):3912–3918View ArticleGoogle Scholar
- Kusumoto N, Ashitani T, Hayasaka Y, Murayama T, Ogiyama K, Takahashi K (2009) Antitermitic activities of abietane-type diterpenes from Taxodium distichum cones. J Chem Ecol 35(6):635–642View ArticleGoogle Scholar
- Machumi F, Samoylenko V, Yenesew A, Derese S, Midiwo JO, Wiggers FT, Jacob MR, Tekwani BL, Khan SI, Walker LA, Muhammad I (2010) Antimicrobial and antiparasitic abietane diterpenoids from the roots of Clerodendrum eriophyllum. Nat Prod Commun 5(6):853Google Scholar
- Michavila A, Fernández-Gadea F, Rodríguez B (1985) Abietane diterpenoids from the root of Salvia lavandulaefolia. Phytochemistry 25(1):266–268View ArticleGoogle Scholar
- Michavila A, María C, Rodríguez B (1986) 20-Nor-abietane and rearranged abietane diterpenoids from the root of Salvia argentea. Phytochemistry 25(8):1935–1937View ArticleGoogle Scholar
- Moridi Farimani M, Mazarei Z (2014) Sesterterpenoids and other constituents from Salvia lachnocalyx Hedge. Fitoterapia 98:234–240View ArticleGoogle Scholar
- Moridi Farimani M, Miran M (2014) Labdane diterpenoids from Salvia reuterana. Phytochemistry 108:264–269View ArticleGoogle Scholar
- Moridi Farimani M, Taheri S, Matloubi Moghaddam F, Amin G (2008) Chemical constituents from Salvia macrosiphon Boiss. Chem Nat Comp 44:518–519View ArticleGoogle Scholar
- Moridi Farimani M, Matloubi Moghaddam F, Esmaeili MA, Amin GA (2012) Lupane triterpenoid and other constituents of Salvia eremophila. Nat Prod Res 26(21):2045–2049View ArticleGoogle Scholar
- Moridi Farimani M, Ebrahimi SN, Salehi P, Bahadori MB, Sonboli A, Khavasi HR, Zimmermann S, Kaiser M, Hamburger M (2013) Antitrypanosomal triterpenoid with an ε-lactone E-ring from Salvia urmiensis. J Nat Prod 76:1806–1809View ArticleGoogle Scholar
- Moujir L, Gutiérrez-Navarro AM, San Andrés L, Luis JG (1996) Bioactive diterpenoids isolated from Salvia mellifera. Phytother Res 10(2):172–174View ArticleGoogle Scholar
- Rechinger KH (1987) Flora Iranica. Akademische Druck- und Verlagsanstalt, Graz, pp 403–476Google Scholar
- Saijo H, Kofujita H, Takahashi K, Ashitani T (2015) Antioxidant activity and mechanism of the abietane-type diterpene ferruginol. Nat Prod Res 29(18):1739–1743View ArticleGoogle Scholar
- Shaheen UY, Hussain MH, Ammar HA (2011) Cytotoxicity and antioxidant activity of new biologically active constituents from Salvia Lanigra and Salvia Splendens. Pharmacogn J 3(21):36–48View ArticleGoogle Scholar
- Tan N, Kaloga M, Radtke OA, Kiderlen AF, Öksüz S, Ulubelen A, Kolodziej H (2002) Abietane diterpenoids and triterpenoic acids from Salvia cilicica and their antileishmanial activities. Phytochemistry 61(8):881–884View ArticleGoogle Scholar
- Topçu G, Gören AC (2007) Biological activity of diterpenoids isolated from Anatolian Lamiaceae plants. Rec Nat Prod 1(1):1–16View ArticleGoogle Scholar
- Topcu G, Eriş C, Ulubelen A (1996) Rearranged abietane diterpenes from Salvia limbata. Phytochemistry 41(4):1143–1147View ArticleGoogle Scholar
- Topcu G, Kolak U, Ozturk M, Boga M, Hatipoglu SD, Bahadori F, Culhaoglu B, Dirmenci T (2013) Investigation of anticholinesterase activity of a series of Salvia extracts and the constituents of Salvia staminea. Nat Prod J 3(1):3–9Google Scholar
- Ulubelen A (2003) Cardioactive and antibacterial terpenoids from some Salvia species. Phytochemistry 64(2):395–399View ArticleGoogle Scholar
- Ulubelen A, Topcu G, Tan N, Lin LJ, Cordell GA (1992) Microstegiol, a rearranged diterpene from Salvia microstegia. Phytochemistry 31(7):2419–2421View ArticleGoogle Scholar
- Ulubelen A, Topcu G, Eri C, Sönmez U, Kartal M, Kurucu S, Bozok-Johansson C (1994) Terpenoids from Salvia sclarea. Phytochemistry 36(4):971–974View ArticleGoogle Scholar
- Ulubelen A, Öksüz S, Kolak U, Tan N, Bozok-Johansson C, Çelik C, Kohlbau HJ, Voelter W (1999a) Diterpenoids from the roots of Salvia bracteata. Phytochemistry 52(8):1455–1459View ArticleGoogle Scholar
- Ulubelen A, Topçu G, Chai HB, Pezzuto JM (1999b) Cytotoxic activity of diterpenoids isolated from Salvia hypargeia. Pharm Boil 37(2):148–151View ArticleGoogle Scholar
- Ulubelen A, Oksüz S, Kolak U, Birman H, Voelter W (2000) Cardioactive terpenoids and a new rearranged diterpene from Salvia syriaca. Planta Med 66:627–629View ArticleGoogle Scholar
- Wu YB, Ni ZY, Shi QW, Dong M, Kiyota H, Gu YC, Cong B (2012) Constituents from Salvia species and their biological activities. Chem Rev 112:5967–6026View ArticleGoogle Scholar
- Yang Z, Kitano Y, Chiba K, Shibata N, Kurokawa H, Doi Y, Arakawa Y, Tada M (2001) Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE. Bioorg Med Chem 9(2):347–356View ArticleGoogle Scholar
- Yong ZJH (1995) Two new diterpenoids, prtoketolactone and neoprionitone, from Salvia prionitis. Nat Prod Res Develop 4:1Google Scholar
- Zaghloul AM, Gohar AA, Naiem ZAA, Bar FMA (2008) Taxodione, a DNA-binding compound from Taxodium distichum L. (Rich.). Z Naturforsch C 63(5–6):355–360Google Scholar