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.
NestlerEJ, KrishnanV. (2008) The molecular neurobiology of depression. Nature, 455, 894–902.
3.
Dall'agnolR, FerrazA, BernardiA, AlbringD, NorC, SchapovalE, von PoserGL. (2005) Bioassay-guided isolation of antimicrobial benzopyrans and phloroglucinol derivatives from Hypericum species. Phytoterapy Research, 19, 291–293.
4.
VianaA, Do RegoJC, von PoserG, FerrazA, HecklerA, CostentinJ, RatesSMK. (2005) The antidepressant like effect of Hypericum caprifoliatum Cham & Schltdl. (Guttiferae) on forced swimming test results from an inhibition of neuronal monoamine uptake. Neuropharmacology, 49, 1042–1052.
5.
HussainS, AnsariZ, ArifM. (2009) Hyperforin: A lead for antidepressants. International Journal of Health Research, 2, 83–90.
6.
KrausG A, LiuF. (2012) Synthesis of uliginosins A and B. Natural Product Communications, 7, 191–192.
7.
SteinAC, VianaAF, MüllerLG, NunesJM, StolzED, Do RegoJC, Costentin J, von PoserGL, RatesSMK. (2012) Uliginosin B, a phloroglucinol derivative from Hypericum polyanthemum: A promising new molecular pattern for the development of antidepressant drugs. Behavioral Brain. Research, 228, 66–73.
8.
SocolskyC, RatesS, SteinAC, AsakawaY, BardónA. (2012) Acylphloroglucinols from Elaphoglossum crassipes: Antidepressant-like activity of crassipin A. Journal of Natural Products, 75, 1007–1017.
9.
SteruL, ChermatR, ThierryB, SimonP. (1985) The tail suspension test: a new method for screening antidepressants in mice. Psychopharmacology, 85, 367–370.
10.
MeikleTA, StevensR. (1978) ϟ-Tricarbonyl compounds. Part 1. Synthesis of the antibiotics uliginosin A, dihydrouliginosin B, and analogues thereof. Journal of the Chemical Society Perkin Transactions1, 1303–1312.
11.
MeikleTA, StevensR. (1979) 6-Tricarbonyl compounds. Part 2. Synthesis of 5,7-dihydroxy-8-isobutyryl-2,2-dimethyl-2H-chromen and the antibiotics uliginosin B-iBiB and uliginosin B-iBiV. Journal of the Chemical Society Perkin Transactions1, 2563–2573.
HuangC, ZhangZ, LiY. (1998) Total synthesis of (R,S)- sophoraflavanone C. Journal of Natural Products, 61, 1283–1285.
14.
LeeYR, LiX, KimJH. (2008) Concise total synthesis of biologically interesting mallotophilippens C and E. Journal of Organic Chemistry, 73, 4313–4316.
15.
ChautheSK, BharateSB, SabdeS, MitraD, BhutaniKK, SinghIP. (2010) Biomimetic synthesis and anti-HIV activity of dimeric phloroglucinols. Bioorganic and Medicinal Chemistry, 8, 2029–2036.
16.
Council for International Organizations of Medical Sciences. (1985) International Guiding Principles for Biomedical Research Involving Animals, Geneva
17.
Brazil, Law N° 11794/2008. (2008) Brazilian federal law on the scientific use of animals
18.
ESF-EMRC [European Science Foundation and European Medical Research Councils]. (2009) Position on the proposed revision of the directive on the protection of animals used for experimental and other scientific purposes (86/609/EEC), September. ESF Standing Committee for Medical Sciences.
19.
MüllerLG, SallesLA, SteinAC, BettiAH, SakamotoS, CasselE, VargasRF, von PoserGL, RatesSMK. (2012) Antidepressant-like effect of Valeriana glechomifolia Meyer (Valerianaceae) in mice. Progress in Neuro-Psychopharmacology & Biological Psychiatry, 10, 101–109.
20.
KwonS, LeeB, KimM, LeeH, ParkHJ, HahmDH. (2010) Antidepressant-like effect of the methanolic extract from Bupleurum falcatum in the tail suspension test. Progress in Neuro-Psychopharmacology & Biological Psychiatry, 34, 265–270.
