title: Cytotoxic, cytoprotective and antioxidant effects of isolated phenolic compounds from fresh ginger.
abstract: Twenty-nine phenolic compounds were isolated from the root bark of fresh (Yunnan) ginger and their structures fully characterized. Selected compounds were divided into structural categories and twelve compounds subjected to in-vitro assays including DPPH radical scavenging, xanthine-oxidase inhibition, monoamine oxidase inhibition, rat-brain homogenate lipid peroxidation, and rat pheochromocytoma PC12 cell and primary liver cell viability to determine their antioxidant and cytoprotective properties. Isolated compounds were also tested against nine human tumor cell lines to characterize anticancer potency. Several diarylheptanoids and epoxidic diarylheptanoids were effective DPPH radical scavengers and moderately effective at inhibiting xanthine oxidase. An enone-dione analog of 6-shogaol (compound 2) was isolated and identified to be most effective at protecting PC12 cells from H₂O₂-induced damage. Almost all tested compounds inhibited lipid peroxidation. Three compounds, 6-shogaol, 10-gingerol and an enone-diarylheptanoid analog of curcumin (compound 6) were identified to be cytotoxic in cell lines tested, with KB and HL60 cells most susceptible to 6-shogaol and the curcumin analog with IC₅₀<10 μM. QSAR analysis revealed cytotoxicity was related to compound lipophilicity and chemical reactivity. In conclusion, we observed distinct compounds in fresh ginger to have biological activities relevant in diseases associated with reactive oxygen species.
authors.affiliation: Key Laboratory of Yunnan Insect Drug R&D, College of Pharmaceutical Sciences of Dali University, Wanhua Road, Dali 671000, China.
authors.forename: Fang
authors.initials: F
authors.lastname: Peng
authors.forename: Qiaofeng
authors.initials: Q
authors.lastname: Tao
authors.forename: Xiumei
authors.initials: X
authors.lastname: Wu
authors.forename: Hui
authors.initials: H
authors.lastname: Dou
authors.forename: Shawn
authors.initials: S
authors.lastname: Spencer
authors.forename: Chaoyong
authors.initials: C
authors.lastname: Mang
authors.forename: Lu
authors.initials: L
authors.lastname: Xu
authors.forename: Lianli
authors.initials: L
authors.lastname: Sun
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhao
authors.forename: Haibo
authors.initials: H
authors.lastname: Li
authors.forename: Su
authors.initials: S
authors.lastname: Zeng
authors.forename: Guangming
authors.initials: G
authors.lastname: Liu
authors.forename: Xiaojiang
authors.initials: X
authors.lastname: Hao
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D000975:Antioxidants / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D001713:Biphenyl Compounds / Q000378:metabolism; D002396:Catechols / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D003474:Curcumin / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use; D019610:Cytoprotection; D005233:Fatty Alcohols / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use; D020939:Zingiber officinale / Q000737:chemistry*; D018922:HL-60 Cells; D006801:Humans; D006861:Hydrogen Peroxide; D057927:Hydrophobic and Hydrophilic Interactions; D007624:KB Cells; D015227:Lipid Peroxidation / Q000187:drug effects; D009369:Neoplasms / Q000188:drug therapy*; D016716:PC12 Cells; D010636:Phenols / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D008517:Phytotherapy; D010851:Picrates / Q000378:metabolism; D024301:Plant Bark; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D018517:Plant Roots; D051381:Rats; D014969:Xanthine Oxidase / Q000378:metabolism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D001713:Biphenyl Compounds; D002396:Catechols; D005233:Fatty Alcohols; D010636:Phenols; D010851:Picrates; D010936:Plant Extracts; C040115:shogaol; C007845:gingerol; D006861:Hydrogen Peroxide; C004931:1,1-diphenyl-2-picrylhydrazyl; D014969:Xanthine Oxidase; D003474:Curcumin