New Sesterterpenoids from Salvia mirzayanii Rech.f. and Esfand. Stereochemical Characterization by Computational Electronic Circular Dichroism

Foroogh Mirzania; Mahdi Moridi Farimani; Yaghoub Sarrafi; Samad Nejad Ebrahimi; Jakob Troppmair; Marcel Kwiatkowski; Hermann Stuppner; Mostafa Alilou

doi:10.3389/fchem.2021.783292

New Sesterterpenoids from Salvia mirzayanii Rech.f. and Esfand. Stereochemical Characterization by Computational Electronic Circular Dichroism

Front Chem. 2022 Jan 20:9:783292. doi: 10.3389/fchem.2021.783292. eCollection 2021.

Authors

Foroogh Mirzania¹, Mahdi Moridi Farimani¹, Yaghoub Sarrafi², Samad Nejad Ebrahimi¹, Jakob Troppmair³, Marcel Kwiatkowski⁴, Hermann Stuppner⁵, Mostafa Alilou⁵

Affiliations

¹ Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Tehran, Iran.
² Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, Iran.
³ Daniel-Swarovski Research Laboratory, Department of Visceral, Transplant and Thoracic Surgery, Innsbruck Medical University, Innsbruck, Austria.
⁴ Functional Proteo-Metabolomics, Department of Biochemistry, University of Innsbruck, Innsbruck, Austria.
⁵ Department of Pharmacognosy, Institute of Pharmacy, Center for Molecular Biosciences (CMBI), University of Innsbruck, Innsbruck, Austria.

Abstract

Phytochemical investigation on the acetone extract of Salvia mirzayanii Rech. f. and Esfand. aﬀorded seven new isoprenoids including six new sesterterpenoids salvimirzacolide A-F (1-6), and one new nor-diterpenoid (7). Their structures were established by comprehensive spectroscopic and spectrometric data analysis (1D and 2D NMR, HRMS) and DP4+ NMR chemical shift probability calculation technique. Moreover, the absolute conﬁguration of compounds was determined by using electronic circular dichroism spectroscopy. Evaluation of antiproliferative properties of compounds isolated against four human melanoma cancer cells displayed no cytotoxic activity at the concentration range used.

Keywords: absolute configuration; cytotoxic activity; diterpenoid; salvia mirzayanii; sesterterpenoid.