Labdane Diterpenoids from Salvia leriifolia: Absolute Configuration, Antimicrobial and Cytotoxic Activities

Mahdi Moridi Farimani; Akram Taleghani; Abbas Aliabadi; Atousa Aliahmadi; Mohammad Ali Esmaeili; Nazanin Namazi Sarvestani; Hamid Reza Khavasi; Martin Smieško; Matthias Hamburger; Samad Nejad Ebrahimi

doi:10.1055/s-0042-107798

Planta Medica, Table of Contents

Planta Med 2016; 82(14): 1279-1285
DOI: 10.1055/s-0042-107798

Natural Product Chemistry and Analytical Studies

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Labdane Diterpenoids from Salvia leriifolia: Absolute Configuration, Antimicrobial and Cytotoxic Activities

Authors

Mahdi Moridi Farimani

¹Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran, Iran
Akram Taleghani

¹Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran, Iran
Abbas Aliabadi

²Khorasan Razavi Agricultural and Natural Resources Research Center, Sabzevar Branch, Sabzevar, Khorasan Razavi, Iran
Atousa Aliahmadi

³Department of Biology, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran, Iran
Mohammad Ali Esmaeili

³Department of Biology, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran, Iran
Nazanin Namazi Sarvestani

⁴Department of Animal Biology, School of Biology, College of Science, University of Tehran, Tehran, Iran
Hamid Reza Khavasi

⁵Department of Chemistry, Faculty of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran, Iran
Martin Smieško

⁶Division of Molecular Modeling, University of Basel, Basel, Switzerland
Matthias Hamburger

⁷Division of Pharmaceutical Biology, University of Basel, Basel, Switzerland
Samad Nejad Ebrahimi

¹Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran, Iran

Abstract

Fractionation of an n-hexane extract of the aerial parts of Salvia leriifolia led to the isolation of two new (1, 2) and two known (3, 4) labdane diterpenoids, together with three other known compounds. The structures were established by a combination of 1D and 2D NMR, and HRESIMS. The structures of 1 and 3 were confirmed by single-crystal X-ray analysis. The absolute configuration of 1–4 was established by electronic circular dichroism spectroscopy. Compounds 1–4 were evaluated for their cytotoxic activities against MCF-7 human breast cancer cells. Labdanes 3 and 4 were additionally tested against MDA-MB231 human breast cancer and DU-145 human prostate cancer cell lines. Compound 4 showed IC₅₀ values of 25, 50, and 50 µM against MCF-7, MDA-MB231, and DU-145 cells, respectively. Compounds 1–4 were tested for activity against gram-positive (Staphylococcus aureus) and gram-negative (Escherichia coli) bacteria. Compound 3 showed an MIC of 213 µM against methicillin-resistant S. aureus.

Key words

Salvia leriifolia - Lamiaceae - diterpene - absolute configuration - antibacterial activity - cytotoxicity

Full Text

References

References
1 Pederson JA. Distribution and taxonomic implications of some phenolics in the family Lamiaceae determined by ESR spectroscopy. Biochem Syst Ecol 2000; 28: 229-253
2 Foster S, Tyler VE. Tylerʼs honest herbal: a sensible guide to the use of herbs and related remedies. 4th edition Binghamton, NY: The Haworth Press; 2000: 327-329
3 Dobrynin VN, Kolosov MN, Chernov BK, Derbentseva NA. Antimicrobial substances of Salvia officinalis . Chem Nat Compd 1976; 12: 623-624
4 Janosik I. Liquid preparation for treating psoriasis and seborrhoic eczemas. Czech Patent # 185 262, 1980
5 Chang HM, But PP. Pharmacology and applications of Chinese Materia Medica, Vol. 1. Singapore: World Scientific Publishing Co.; 1986: 255
6 Savelev SU, Okello EJ, Perry EK. Butyryl- and acetyl-cholinesterase inhibitory activities in essential oils of Salvia species and their constituents. Phytother Res 2004; 18: 315-324
7 Howes MJR, Perry NSL, Houghton PJ. Plants with traditional uses and activities relevant to the management of Alzheimerʼs disease and other cognitive disorders. Phytother Res 2003; 17: 1-18
8 Perry NSL, Houghton PJ, Jenner P, Keith A, Perry EK. Salvia lavandulaefolia essential oil inhibits cholinesterase in vivo . Phytomedicine 2002; 9: 48-51
9 Rechinger KH. Flora Iranica, Vol. 150. Graz-Austria: Akademische Druck- und Verlagsanstalt; 1982: 403-476
10 Hosseinzadeh H, Lary P. Effect of Salvia leriifolia extract on morphine dependence in mice. Phytother Res 2000; 14: 384-387
11 Hosseinzadeh H, Haddadkhodaparast MH, Shokoohizadeh H. Antihyperglycemic effect of Salvia leriifolia Benth. leaf and seed extract in mice. Iran J Med Sci 1998; 28: 74-80
12 Hosseinzadeh H, Yavari M. Anti-inflammatory effects of Salvia leriifolia Benth. leaf extract in mice and rats. Pharm Pharmacol Lett 1999; 9: 60-62
13 Hosseinzadeh H, Haddadkhodaparast MH, Arash A. Antinociceptive, antiinflammatory and acute toxicity effects of Salvia leriifolia Benth. seed extract in mice and rats. Phytother Res 2003; 17: 422-425
14 Hosseinzadeh H, Arabsanavi J. Anticonvulsant effect of Salvia leriifolia Benth. seed and leaf extracts in mice. Iran J Med Sci 2001; 3: 166-170
15 Tundis R, Monica R, Federica L, Bonesia MM, Colica C, Menichini F. In vitro cytotoxic activity of extracts and isolated constituents of Salvia leriifolia Benth. against a panel of human cancer cell lines. Chem Biodivers 2011; 8: 1152-1162
16 Loizzo M, Menichini F, Tundis R, Bonesi M, Nadjafi F, Saab AM, Frega NG. Comparative chemical composition and antiproliferative activity of aerial parts of Salvia leriifolia Benth. and Salvia acetabulosa L. essential oils against human tumor cell in vitro models. J Med Food 2010; 13: 62-69
17 Loizzo RM, Tundis R, Conforti F, Menichini F, Bonesia M, Nadjafi F, Frega NG, Menichini F. Salvia leriifolia Benth (Lamiaceae) extract demonstrates in vitro antioxidant properties and cholinesterase inhibitory activity. Nutr Res 2010; 30: 823-830
18 Hosseinzadeh H, Haddadkhodaparast MH, Hosseini E. Anti-ulcer effect of Salvia leriifolia Benth. leaf extracts in mice. Pharm Pharmacol Lett 2000; 2: 63-64
19 Hosseinzadeh H, Hosseini A, Nassiri-Asl M, Sadeghnia HR. Effect of Salvia leriifolia Benth. root extracts on ischemia reperfusion in rat skeletal muscle. BMC Complement Altern Med 2007; 7: 23-31
20 Habibi Z, Eftekhar F, Samiee K, Rustaiyan A. Structure and antibacterial activity of a new labdane diterpenoid from Salvia leriaefolia . J Nat Prod 2000; 63: 270-271
21 Choudhary MI, Hussain A, Ali Z, Adhikari A, Sattar SA, Ayatollahi SA, Al-Majid AM. Diterpenoids including a novel dimeric conjugate from Salvia leriaefolia . Planta Med 2012; 78: 269-275
22 Choudhary MI, Hussain A, Adhikari A, Marasini BP, Sattar SA, Wahab AT, Hussain N, Ayatollahi SAM. Atta-ur-Rahman. Anticancer and α-chymotrypsin inhibiting diterpenes and triterpenes from Salvia leriifolia . Phytochem Lett 2013; 6: 139-143
23 Ayatollahi SAM, Shojaii A, Kobarfard F, Mohammadzadeh M, Choudhary MI. Two flavones from Salvia leriaefolia . Iran J Pharm Res 2009; 8: 179-184
24 Moridi Farimani M, Miran M. Labdane diterpenoids from Salvia reuterana . Phytochemistry 2014; 108: 264-269
25 Moridi Farimani N, Mazarei Z. Sesterterpenoids and other constituents from Salvia lachnocalyx Hedge. Fitoterapia 2014; 98: 234-240
26 Ebrahimi SN, Moridi Farimani M, Mirzania F, Soltanipoor MA, De Mieri M, Hamburger M. Manoyloxide sesterterpenoids from Salvia mirzayanii . J Nat Prod 2014; 77: 848-854
27 Rafatian G, Khodagholi F, Moridi Farimani M, Abraki SB, Gardaneh M. Increase of autophagy and attenuation of apoptosis by Salvigenin promote survival of SH-SY5Y cells following treatment with H₂O₂ . Mol Cell Biochem 2012; 371: 9-22
28 Sarvestani NN, Khodagholi F, Ansari N, Moridi Farimani M. Involvement of p-CREB and phase II detoxifying enzyme system in neuroprotection mediated by the flavonoid calycopterin isolated from Dracocephalum kotschyi . Phytomedicine 2013; 20: 939-946
29 Moridi Farimani M, Sarvestani NN, Ansari N, Khodagholi F. Calycopterin promotes survival and outgrowth of neuron-like PC12 cells by attenuation of oxidative- and ER-stress-induced apoptosis along with inflammatory response. Chem Res Toxicol 2011; 24: 2280-2292
30 Moghaddam FM, Saeidian H, Mirjafary Z, Javan MJ, Moridi Farimani M, Seirafi M. Convenient synthesis of chlorohydrins from epoxides using zinc oxide: Application to 5,6-epoxysitosterol. Heteroatom Chem 2009; 20: 157-163
31 Moghaddam FM, Moridi Farimani M, Taheri S, Tafazoli M, Amin G. Chemical constituents from Salvia macrosiphon . Chem Nat Compd 2008; 44: 518-519
32 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Aghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision A02. Wallingford: Gaussian, Inc.; 2009
33 Bruhn T, Hemberger Y, Schaumlöffel A, Bringmann G. SpecDis, Version 1.61. Würzburg: University of Würzburg; 2013

Supplementary Material

Supporting Information (PDF)