UV/Visible spectra of a series of natural and synthesised anthraquinones: experimental and quantum chemical approaches.
Root decoctions of anthraquinone-containing plants are often taken as postpartum tonic and aphrodisiac. Anthraquinones are known for their diverse biological activities, especially antioxidant and anticancer. A series of 35 anthraquinones was generated by isolation from Rubiaceae plants and synthesis. Their UV/vis spectrum depends on the nature and relative positions of auxochromic substituents on the basic skeleton. To predict the maximum absorption bands for the current series of anthraquinones, excited sate calculations were performed using TD-DFT, CIS, ZINDO methods. The results showed that the use of PBE0 or its combination with B3LYP and B3P86 hybrid functionals are the most suitable to reproduce accurately the experimental λMAX. The structure-property relationships (SPRs) were established based on structural and electronic properties of the anthraquinones and showed (i) the importance of the number and position of OH groups and (ii) the positive contribution of the electrophilicity and hardness as electronic descriptors on position and amplitude of the maximum absorption bands.
Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, D. E. Malaysia.
El Hassane
el H
Anouar
Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, D. E. Malaysia ; Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, D. E. Malaysia.
Che Puteh
CP
Osman
Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, D. E. Malaysia ; Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor, D. E. Malaysia.
Jean-Frédéric F
JF
Weber
Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, D. E. Malaysia ; Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, D. E. Malaysia.
Nor Hadiani
NH
Ismail
Anthraquinones; Excited states; IEFPCM; TD-DFT; UV/vis