Planta Med 2012; 78(3): 269-275
DOI: 10.1055/s-0031-1280454
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Diterpenoids Including a Novel Dimeric Conjugate from Salvia leriaefolia

Muhammad Iqbal Choudhary1 , 2 , Amjad Hussain1 , Zulfiqar Ali2 , 3 , Achyut Adhikari1 , Samina A. Sattar1 , Syed A. Majid Ayatollahi4 , Abdullah M. A. Al-Majid2 ,  Atta-ur-Rahman1
  • 1H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, Pakistan
  • 2Department of Chemistry, College of Science, King Saud University, Riyadh, Saudi Arabia
  • 3National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
  • 4Phytochemistry Research Center and Department of Pharmacognosy, School of Pharmacy, Shaheed Beheshti University of Medical Sciences, Tehran, Iran
Further Information

Publication History

received Sept. 8, 2011 revised Nov. 1, 2011

accepted Nov. 28, 2011

Publication Date:
15 December 2011 (online)

Abstract

Salvialeriafone (1), a novel diterpene-norditerpene conjugate, was isolated from Salvia leriaefolia. Additionally, two new abietane-type diterpenoids, salvialerial (2) and salvialerione (3), as well as four known compounds, sugiol (4), salvicanaric acid (5), dehydroroyleanone (6), and cariocal (7), were isolated and identified. Their structures were determined by spectroscopic data analyses. Known compounds were isolated from this plant for the first time. Compounds 1, 5, 6, and 7 exhibited in vitro antiproliferative activity against the human cervical cancer cell line (Hela), while 6 showed cytotoxicity against the human prostate cancer cell line (PC3).

References

  • 1 Clebsch B. The new book of salvias: Sages for every garden. Portland, Cambridge: Timber Press; 2003: 344
  • 2 Kamatou G P P, Makunga N P, Ramogola W P N, Viljoen A M. South African Salvia species: a review of biological activities and phytochemistry.  J Ethnopharmacol. 2008;  119 664-672
  • 3 Topçu G, Gören A C. Biological activity of diterpenoids isolated from Anatolian Lamiaceae plants.  Rec Nat Prod. 2007;  1 1-16
  • 4 Kabouche A, Kabouche Z. Bioactive diterpenoids of Salvia species. In: Atta-ur-Rahman, editor Studies in natural products chemistry. Volume 35 Amsterdam: Elsevier; 2008: 753-833
  • 5 Lu Y, Foo L Y. Polyphenolics of Salvia – a review.  Phytochemistry. 2002;  59 117-140
  • 6 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
  • 7 Ayatollahi S A, Shojaii A, Kobarfard F, Mohammadzadeh M, Choudhary M I. Two flavones from Salvia leriaefolia.  Iranian J Pharm Res. 2009;  8 179-184
  • 8 Uchida M, Miyase T, Yoshizaki F, Bieri J H, Rüedi P, Eugster C H. 14-Hydroxytaxodion als Hauptditerpen in Plectranthus grandidentatus Gürke; Isolierung von sieben neuen dimeren Diterpenen aus P. grandidentatus, P. myrianthus Briq. und Coleus carnosus Hassk.: Strukturen der Grandidone A, 7-epi A, B, 7-epi B, C, D und 7-epi D.  Helv Chim Acta. 1981;  64 2227-2250
  • 9 Li M, Zhang J S, Chen M Q. A novel dimeric diterpene from Salvia prionitis.  J Nat Prod. 2001;  64 971-972
  • 10 Marques C G, Pedro M, Simões M F A, Nascimento M S J, Pinto M M M, Rodríguez B. Effect of abietane diterpenes from Plectranthus grandidentatus on the growth of human cancer cell lines.  Planta Med. 2002;  68 839-840
  • 11 Gonzalez A G, Rodriguez C M, Luis J G. Diterpenes from the flowers of Salvia canariensis.  Phytochemistry. 1987;  26 1471-1474
  • 12 Miyase T, Rüedi P, Eugster C H. Diterpenoide Drüsenfarbstoffe aus Labiaten: 3β-Acetoxyfuerstion, Nilgherron A und Nilgheron B, neue Chinomethane aus Plectranthus nilgherricus Benth., absolute Konfiguration von Fuerstion.  Helv Chim Acta. 1977;  60 2789-2803
  • 13 Xu J, Chang J, Zhao M, Zhang J S. Abietane diterpenoid dimers from the roots of Salvia prionitis.  Phytochemistry. 2006;  67 795-799
  • 14 Galli B, Gasparrini F, Lanzotti V, Misiti D, Riccio R, Villani C, Guan-fu H, Zhong-wu M, Wan-fen Y. Grandione, a new heptacyclic dimeric diterpene from Torreya grandis. Fort.  Tetrahedron. 1999;  55 11385-11394
  • 15 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  65 55-63
  • 16 Chen Y L, Lan Y H, Hsieh P W, Wu C C, Chen S L, Yen C T, Chang F R, Hung W C, Wu Y C. Bioactive cembrane diterpenoids of Anisomeles indica.  J Nat Prod. 2008;  71 1207-1212
  • 17 Gao M, Zhang R, Jia W, Zhang J, Takaishi Y, Duan H. Immunosuppressive diterpenes from Veronicastrum sibiricum.  Chem Pharm Bull. 2004;  52 136-137
  • 18 Sun C-M, Chin T-M, Lin Y-L, Chen C-J, Chen W-C, Wu T-S, Don M-J. Isolation, structure elucidation, and syntheses of isoneocryptotanshinone II and tanshinlactone A from Salvia miltiorrhiza.  Heterocycles. 2006;  68 247-255
  • 19 Gao J, Han G. Cytotoxic abietane diterpenoids from Caryopteris incana.  Phytochemistry. 1997;  44 759-761
  • 20 Gonzalez A G, Herrera J R, Luis J G, Ravelo A G, Perales A. Salvicanaric acid, a new diterpene from Salvia canariensis.  J Nat Prod. 1987;  50 341-348
  • 21 Edwards O E, Feniak G, Los M. Diterpenoid quinones of Inula royleana DG.  Can J Chem. 1962;  40 1540-1546
  • 22 Kelecom A, Santos T C D. Cariocal, a new seco-abietane diterpene from the labiate Coleus barbatus.  Tetrahedron Lett. 1985;  26 3659-3662

Prof. M. Iqbal Choudhary

H. E. J. Research Institute of Chemistry
International Center for Chemical and Biological Sciences
University of Karachi

Karachi 75270

Pakistan

Phone: +92 21 34 81 90 10 ext. 106

Fax: +92 21 34 81 90 18

Email: hej@cyber.net.pk