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Podophyllotoxin

Podophyllotoxin is a non-alkaloid lignan found in species of Podophyllum that exhibits anticancer and antiviral activities. Podophyllotoxin displays antimitotic action, binding tubulin and inhibiting mitotic spindle formation. Derivatives of this compound inhibit topoisomerase II. In gastric cancer cells, podophyllotoxin induces G2/M phase cell cycle arrest and apoptosis, decreases the mitochondrial membrane potential, increases cytochrome c release, and inhibits cellular proliferation. Podophyllotoxin is occasionally clinically used to treat human papilloma virus (HPV) infection, as it inhibits viral reproduction through inhibition of E2 protein activity.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18955308

Cas No.

518-28-5

Purity

≥90%

Formula

C22H22O8

Formula Wt.

414.41

Chemical Name

(5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo(3,4:6,7)naphtho(2,3-d)- 1,3-dioxol-6(5aH)-one

IUPAC Name

(5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

Synonym

Podofilox; Podophyllinic acid lactone

Melting Point

114-118°C : After drying 183-184°C

Solubility

Slightly soluble in water.

Appearance

White crystal powder

Ji CF, Ji YB. Apoptosis of human gastric cancer SGC-7901 cells induced by podophyllotoxin. Exp Ther Med. 2014 May;7(5):1317-1322. PMID: 24940431.

Ramírez-Fort MK, Au SC, Javed SA, et al. Management of cutaneous human papillomavirus infection: pharmacotherapies. Curr Probl Dermatol. 2014;45:175-85. PMID: 24643186.

Li J, Dai CX, Sun H, et al. Protective effects and mechanisms of curcumin on podophyllotoxin toxicity in vitro and in vivo. Toxicol Appl Pharmacol. 2012 Dec 1;265(2):190-9. PMID: 23088858.

LDK 379