Phloroglucinol Derivatives Present an Antidepressant-like Effect in the Mice Tail Suspension Test (TST)

Abstract

The antidepressant-like effects of phloroglucinol and seven synthetic related derivatives were investigated using the tail suspension test (TST) in mice. Compounds 2-methyl-1-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl] propan-1-one (5), 1-(2,4,6-trihydroxyphenyl)ethan-1-one (6), 1-(3-acetyl-2,4,6-trihydroxyphenyl)ethan-1-one (7), 2-methyl-1-[2,4,6-trihydroxy-3-(2-methylpropanoyl)-5-{[2,4,6-trihydroxy-3,5-bis(2-methylpropanoyl)phenyl]methyl} phenyl] propan-1-one (9) and 1-{3-acetyl-5-[(3,5-diacetyl-2,4,6-trihydroxyphenyl)methyl]-2,4,6-trihydroxyphenyl}ethan-1-one (10), containing acyl groups, decreased the immobile behavior of mice treated orally with equimolar doses of imipramine 20 mg/kg, with no alterations in locomotor activity as assessed by the open-field test. These results suggest that these phloroglucinol derivatives could represent a new molecular model in the search for antidepressant drugs.

Acylphloroglucinol Derivatives from Hypericum andinum: Antidepressant-like Activity of Andinin A

“…Spectra were recorded in CDCl 3 (99.8%, Acros Organics, Fair Lawn, NJ, USA), with tetramethylsilane (TMS) as internal standard, and acetone-d 6 (99.9%, Sigma-Aldrich, St. Louis, MO, USA) referenced against residual nondeuterated solvent (acetone-d 6 : δ H 2.05/δ C 29.8). 1D ( 1 H, 13 C) and 2D NMR (COSY, HMBC, and HSQC) spectra were obtained by using the standard pulse sequences from the Varian and Anasazi user libraries. Spectra of isolated compounds are provided as Supporting Information.…”

“…This evidence, in addition to the presence of carbon signals of a carbonyl unit (C-1, δ C 187.3), four enolic carbons (C-2, δ C 111.3; C-3, δ C 171.1; C-5, δ C 199.0; and C-6, δ C 107.0), and a dimethyl-substituted carbon (C-4, δ C 44.1) in the 13 C NMR spectrum of 1, confirmed the presence of a dimethyl-substituted acylfilicinic acid moiety. The 1 H and 13 C NMR spectrum of 1 showed certain anomalies that are best explained by the expected keto− The acylphloroglucinol moiety was inferred as the second ring by the observation of two signals for chelated hydroxy groups (OH-8′, δ H 11.55; OH-10′, δ H 13.88) and three signals for aromatic oxygen-bearing carbons (C-6′, δ C 160.3; C-8′, δ C 159.7; C-10′, δ C 165.6) in the 1 H and13 C NMR spectra, thus confirming that 1 is a dimeric acylphloroglucinol, consisting of an acylfilicinic acid and an acylphloroglucinol moiety linked by a methylene bridge. This kind of compound is isolated frequently from Hypericum species occurring in the sections Brathys and Trigynobrathys.…”

“…15,17 Previously published 13 C NMR data of uliginosin A in DMSO-d 6 showed many unresolved signals. 17 Likewise, the 13 C NMR spectra acquired in CDCl 3 and acetone-d 6 at 400 MHz were greatly unresolved (Figures S17 and S19, Supporting Information). Nevertheless, when acquired in CDCl 3 at 60 MHz (Table 1), the signals were clearly observed and the chemical shift values were in general agreement with those published for uliginosin B (3) and isouliginosin B (4).…”

A greatly improved procedure for the synthesis of an antibiotic-drug candidate 2,4-diacetylphloroglucinol over silica sulphuric acid catalyst: multivariate optimisation and environmental assessment protocol comparison by metrics

“…This studied. [2][3][4]15,16 The common route to DAPG involves the Friedel-Cras acylation of either phloroglucinol (PhL) 2,[16][17][18][19][20][21] or monoacetylphloroglucinol (MAPG) 16 in the presence of Lewis or Brønsted acids, using an acylating agent (acyl halides, acid anhydrides, and/or carboxylic acids).…”

Sc(OTf)3-Catalyzed Synthesis of Symmetrical Dithioacetals and Bisarylmethanes Using Nitromethane as a Methylene Source

“…In 2016, the same group reported the synthesis of mallotojaponin C ( 6 ), while the synthesis of mallotojaponins B ( 5 ) and C ( 6 ) was reported by Cariou and co-workers . In 2012, Singh and co-workers reported synthesis of structurally related phloroglucinol derivative 8 with potent anticancer and antidepressant activity . Encouraged by the potent biological activity of these molecules, we became interested in the synthesis of tetramethyl mallotojaponin C ( 7 ) and phloroglucinol derivative 8 (Figure ).…”