X-ray crystal structure, NMR, DFT investigations, pharmaco-kinetic, and toxicity of sarcotrocheliol: A pyrane-based cemranoids of marine origin

Abstract

One of a recently discovered marine origin cembranoids has been studied experimentally and theoretically to obtain its thorough structural, electronic, spectroscopic, and biochemical activity. The exact molecular structure of sarcotrocheliol (C 20 H 34 O 2 ) 1 has been determined for the first time using a single crystal X-ray diffraction analysis. Crystallography shows that the molecule is crystalline as an orthorhombic, space group of P2 1 2 1 2 1 , with a = 9.20(4) Å, b = 10.80(4) Å, c = 19.99(9) Å. 1 H, 13 C and DEPT-135 NMR measurements of sarcotrocheliol 1 have been measured in four different deuterated solvents: CDCl 3 , CD 3 CN, MeOH- d 4 and DMSO- d 6 . Theoretical calculations have been performed to find the main structural and electronic properties of the compound and matched with the experimental properties. The density functional theory (DFT) method at B3LYP/6-311++G(d,p) level of theory has been used for all computed properties. Vibrational frequencies have been determined using DFT calculations and compared with the experimental values. Computed chemical shifts in the NMR have been determined by the GIAO method. The correlation coefficients between the calculated and experimental NMR chemical shifts have been found to be 0.92 and 0.998 for 1 H and 13 C NMR, respectively. Physicochemical parameters of the compound versus reference drugs have been done. The isolated compound meets the main criteria of the employed rules indicating a drug-like character. The molecular docking studies have been performed for the compound toward the breast and prostate cancers.