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Crystal and Molecular Structure of Secoisolariciresinol

Marco Milanesio ; Dipartimento di Chimica IFM, Universita, Via P. Giuria 7, 1-10125 Torino, and Dipartimento di Scienze e Tecnologie Avanzate, Universita del Piemonte Orientale »A. Avogadro«, Corso T. Borsalino 54, 1-15100 Alessandria, ltaly
Davide Viterbo ; Dipartimento di Chimica IFM, Universita, Via P. Giuria 7, 1-10125 Torino, and Dipartimento di Scienze e Tecnologie Avanzate, Universita del Piemonte Orientale »A. Avogadro«, Corso T. Borsalino 54, 1-15100 Alessandria, ltaly
Sunil K. Chattopadhyay ; Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Lucknow, 226 015 India
Manish Kulshrestha ; Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Lucknow, 226 015 India
Giovanni Appendino ; Dipartimento di Scienza e Tecnologia del Farmaco, Università, Via P. Giuria 9, I-10125 Torino, Italy

Puni tekst: engleski, pdf (139 KB) str. 351-363 preuzimanja: 100* citiraj
APA 6th Edition
Milanesio, M., Viterbo, D., Chattopadhyay, S.K., Kulshrestha, M. i Appendino, G. (1999). Crystal and Molecular Structure of Secoisolariciresinol. Croatica Chemica Acta, 72 (2-3), 351-363. Preuzeto s https://hrcak.srce.hr/132177
MLA 8th Edition
Milanesio, Marco, et al. "Crystal and Molecular Structure of Secoisolariciresinol." Croatica Chemica Acta, vol. 72, br. 2-3, 1999, str. 351-363. https://hrcak.srce.hr/132177. Citirano 31.03.2020.
Chicago 17th Edition
Milanesio, Marco, Davide Viterbo, Sunil K. Chattopadhyay, Manish Kulshrestha i Giovanni Appendino. "Crystal and Molecular Structure of Secoisolariciresinol." Croatica Chemica Acta 72, br. 2-3 (1999): 351-363. https://hrcak.srce.hr/132177
Harvard
Milanesio, M., et al. (1999). 'Crystal and Molecular Structure of Secoisolariciresinol', Croatica Chemica Acta, 72(2-3), str. 351-363. Preuzeto s: https://hrcak.srce.hr/132177 (Datum pristupa: 31.03.2020.)
Vancouver
Milanesio M, Viterbo D, Chattopadhyay SK, Kulshrestha M, Appendino G. Crystal and Molecular Structure of Secoisolariciresinol. Croatica Chemica Acta [Internet]. 1999 [pristupljeno 31.03.2020.];72(2-3):351-363. Dostupno na: https://hrcak.srce.hr/132177
IEEE
M. Milanesio, D. Viterbo, S.K. Chattopadhyay, M. Kulshrestha i G. Appendino, "Crystal and Molecular Structure of Secoisolariciresinol", Croatica Chemica Acta, vol.72, br. 2-3, str. 351-363, 1999. [Online]. Dostupno na: https://hrcak.srce.hr/132177. [Citirano: 31.03.2020.]

Sažetak
The R,R-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butandiol lignan secoisolariciresinol (1) is a constituent of Gymnosperms used in the treatment of benign prostatic hyperplasya. The results of crystallographic and ab initio theoretical studies are reported and discussed. In the crystal, the molecule of (1) assumes a clustered conformation, characterized by the facing of the two phenyl rings.
This geometry is stabilized by the formation of a network of hydrogen bonds. Theoretical calculations indicate that: i) the intramolecular hydrogen bond O1−H1⋅⋅⋅O1' is the major factor dictating the facing of the two phenyl groups, while intermolecular hydrogen bonds and crystal packing have smaller effects; ii) the 1−4O⋅⋅⋅O non-bonded interactions in the vanillyl groups are important in determining the most stable conformation; iii) calculations with two explicit water molecules in the model give a good simulation of the local effects of a water solvent and indicate that (1) probably assumes a clustered conformation also in polar solvents.

Ključne riječi
secoisolariciresinol; lignan; structure; bioactivity; ab initio calculations

Hrčak ID: 132177

URI
https://hrcak.srce.hr/132177

Posjeta: 191 *