Phloroglucinol (Synonyms: Benzene-s-triol, 1,3,5-Hydroxybenzene, NSC 1572, 1,3,5-Trihydroxybenzene, sym-Trihydroxybenzene)

Phloroglucinol is a naturally occurring phenol that exhibits diverse biological activities.¹ Phloroglucinol protects V79-4 Chinese hamster lung fibroblast cells from oxidative stress and inhibits lipid peroxidation by scavenging reactive oxygen species (ROS).² It induces apoptosis in HT-29 human colon cancer cells and inhibits metastasis of BT549 and MDA-MB-231 human breast cancer cells.^3,4 Phloroglucinol protects primary neurons from β-amyloid-induced dendritic spine loss in vitro and shortens the latency to find the platform in a Morris water maze test in an Alzheimer's disease (AD) mouse model.⁵ Phloroglucinol has been used to stain histological plant sections and in the synthesis of numerous natural products.^6,7,8 Phloroglucinol slows the frequency and decreases the amplitude of contraction in isolated rabbit and rat intestine at a concentration of 100 and 1 μM, respectively.⁹ Formulations containing phloroglucinol have been used as antispasmodics.^10,11

1.Achkar, J., Xian, M., Zhao, H., et al.Biosynthesis of phloroglucinolJ. Am. Chem. Soc.127(15)5332-5333(2005) 2.Kang, K.A., KLee, K.H., Chae, S., et al.Cytoprotective effect of phloroglucinol on oxidative stress induced cell damage via catalase activationJ. Cell. Biochem.97(3)609-620(2006) 3.Kang, M.-H., Kim, I.-H., and Nam, T.-J.Phloroglucinol induces apoptosis through the regulation of insulin-like growth factor 1 receptor signaling pathways in human colon cancer HT-29 cellsInt. J. Oncol.45(3)1036-1042(2014) 4.Kim, R.-K., Suh, Y., Yoo, K.-C., et al.Phloroglucinol suppresses metastatic ability of breast cancer cells by inhibition of epithelial-mesenchymal cell transitionCancer Sci.106(1)94-101(2015) 5.Yang, E.-J., Ahn, S., Ryu, J., et al.Phloroglucinol attenuates the cognitive deficits of the 5XFAD mouse model of Alzheimer's DiseasePLoS One10(8)eD135686(2015) 6.KholovÁ, J., Zindy, P., Malayee, S., et al.Component traits of plant water use are modulated by vapour pressure deficit in pearl millet (Pennisetum glaucum (L.) R.Br.)Func. Plant. Bio.43423-437(2016) 7.de Jesus B. Cavalcante, M., Escoute, J., Madeira, J.P., et al.Reactive oxygen species and cellular interactions between Mycosphaerella fijiensis and bananaTrop. Plant. Biol.4134-143(2011) 8.Singh, I.P., Sidana, J., Bharate, S.B., et al.Phloroglucinol compounds of natural origin: Synthetic aspectsNat. Prod. Rep.27(3)393-416(2010) 9.Inoue, S.Effects of 1,3,5-trihydroxybenzene and 2,4,6-trihydroxy-1-propiophenone on the smooth muscle organsJpn. J. Pharmacol.19(2)224-233(1969) 10.Chassany, O., Bonaz, B., Bruley DES Varannes, S., et al.Acute exacerbation of pain in irritable bowel syndrome: efficacy of phloroglucinol/trimethylphloroglucinol. A randomized, double-blind, placebo-controlled studyAilment Pharmacol. Ther.25(9)1115-1123(2007) 11.Tabassum, S., Afridi, B., and Aman, Z.Phloroglucinol for acceleration of labour: Double blind, randomized controlled trialJ. Pak. Med. Assoc.55(7)270-273(2005)