Isobutyrylshikonin has a potentially stronger cytotoxic effect in oral cancer cells than its analogue shikonin in vitro

Review of Shikonin and Derivatives: Isolation, Chemistry, Biosynthesis, Pharmacology and Toxicology

“…erythrorhizon roots extract has been used as a traditional medicine in the Asian continent for its effect on skin cancers (Rajasekar et al, 2012). Shikonin and isobutyrylshikonin have potent activity against oral cancer cells, and isobutyrylshikonin is a more effective anti-cancer agent than shikonin in an in vitro study (Park et al, 2020). Moreover, shikonin possesses a differential regulation mechanism against hepatocellular carcinoma, showing variable sensitivity for shikonin (Yang et al, 2021).…”

Pharmacological and analytical aspects of alkannin/shikonin and their derivatives: An update from 2008 to 2022

“…Furthermore, Microwave assisted extraction/isolation followed by reverse phase chromatography was used to obtain shikonin and its derivatives from the dried roots of L. erythorrhizon . Moreover, the Sephadex column has also been used in one of the reports where L. erythrorhizon was taken to elute isobutyrylshikonin ( Park, Woo, Kim, Choi, & Park, 2020 , Yen et al, 2017 ). Lately, the higher yield of acetylshikonin in Echium plantagineum has been reported by overexpression of cloned EpGHQH1 (geranylhydroquinone 3″-hydroxylase candidate gene) ( Fu et al, 2021 ).…”

“… Cheng et al, 2008 Solid-liquid extraction n -hexane/2- propanol (90:10, volume percentage) Chiral HPLC Shikonin (an improved method) Azuma et al, 2016 Maceration 50% hexane in CH 2 Cl 2 , CH 2 Cl 2 , 5% and 33% acetone in CH 2 Cl 2 , and 5% and 33% methanol in CH 2 Cl 2 Silica gel column chromatography and Sephadex column with methanol. Isobutyrylshikonin Park, Woo, Kim, Choi, & Park, 2020 Maceration 0.085% H 3 PO 4 buffer and acetonitrile: 10%–25% for 20 min; 25%–70% for 30 min; 70%–90% for 40 min; 80%–90% for 60 min; and 100% for 65 min. Reverse phase column chromatography Shikonin, bhydroxyisovalerylshikonin, acetylshikonin, β -acetoxyisovalerylshikonin, deoxyshikonin, isobutyrylshikonin, β,β -dimethylacrylshikonin, and methyl- n -butyrylshikonin Yen et al, 2017 Ultrasonic extraction.…”