title: Bioactive sesquiterpene lactones and other compounds isolated from Vernonia cinerea.
abstract: Four new sesquiterpene lactones, 8α-(2'Z-tigloyloxy)-hirsutinolide (1), 8α-(2'Z-tigloyloxy)-hirsutinolide-13-O-acetate (2), 8α-(4-hydroxytigloyloxy)-hirsutinolide (3), and 8α-hydroxy-13-O-tigloyl-hirsutinolide (4), along with seven known derivatives (5-11), three norisoprenoids (12-14), a flavonoid (15), and a linoleic acid derivative (16), were isolated from the chloroform partition of a methanol extract from the combined leaves and stems of Vernonia cinerea. Their structures were established by 1D and 2D NMR, UV, and MS analyses. Compounds 1-16 were evaluated for their inhibitory effects against the viability of U251MG glioblastoma and MDA-MB-231 breast cancer cells that harbour aberrantly-active STAT3, compared to normal NIH3T3 mouse fibroblasts that show no evidence of activated STAT3. Among the isolates, compounds 2 and 7 inhibited the aberrant STAT3 activity in glioblastoma or breast cancer cells. Further, compounds 7 and 8 inhibited viability of all three cell lines, compounds 2, 4, and 9 predominantly inhibited the viability of the U251MG glioblastoma cell line.
authors.affiliation: Department of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy, University of Hawai'i at Hilo, Hilo, HI, 96720, United States.
authors.forename: Ui Joung
authors.initials: UJ
authors.lastname: Youn
authors.affiliation: Natural Products and Experimental Therapeutics Programs, University of Hawai'i Cancer Center, Honolulu, HI, 96813, United States.
authors.forename: Gabriella
authors.initials: G
authors.lastname: Miklossy
authors.affiliation: Department of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy, University of Hawai'i at Hilo, Hilo, HI, 96720, United States.
authors.forename: Xingyun
authors.initials: X
authors.lastname: Chai
authors.affiliation: Department of Pharmacy Practice, Daniel K. Inouye College of Pharmacy, University of Hawai'i at Hilo, Hilo, HI, 96720, United States.
authors.forename: Supakit
authors.initials: S
authors.lastname: Wongwiwatthananukit
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Silpakorn University, Nakhon Pathom 73000, Thailand.
authors.forename: Onoomar
authors.initials: O
authors.lastname: Toyama
authors.affiliation: Department of Pharmacognosy, Faculty of Pharmacy, Rangsit University, Pathumtani 12000, Thailand.
authors.forename: Thanapat
authors.initials: T
authors.lastname: Songsak
authors.affiliation: Natural Products and Experimental Therapeutics Programs, University of Hawai'i Cancer Center, Honolulu, HI, 96813, United States.
authors.forename: James
authors.initials: J
authors.lastname: Turkson
authors.affiliation: Department of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy, University of Hawai'i at Hilo, Hilo, HI, 96720, United States. Electronic address: lengchee@hawaii.edu.
authors.forename: Leng Chee
authors.initials: LC
authors.lastname: Chang
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D050796:STAT3 Transcription Factor / Q000037:antagonists & inhibitors*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification*; D035741:Vernonia / Q000737:chemistry*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D007783:Lactones; D050796:STAT3 Transcription Factor; C494086:STAT3 protein, human; D012717:Sesquiterpenes
keywords: Asteraceae; STAT3; Sesquiterpene lactone; Vernonia cinerea