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

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

› Author Affiliations

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

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