Bioactive depsides and anthocyanins from jaboticaba (Myrciaria cauliflora).
A new depside, jaboticabin (1), together with 17 known compounds were isolated from the fruit of jaboticaba (Myrciaria cauliflora). The structure of 1 was elucidated by spectroscopic data interpretation. Known compounds were identified by comparison of their spectroscopic data with literature values or by comparison to authentic standards. Compound 1 and the related depside 2-O-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxyphenylacetic acid (2) significantly inhibited chemokine interleukin (IL)-8 production before and after cigarette smoke treatment of cells. Compound 1 was cytotoxic in the HT29 colon cancer cell line (IC50 = 65 microM), and 2 was active against HCT116 colon cancer cells (IC50 = 30 microM). Compounds 1 and 2 also exhibited antiradical activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay (IC50 = 51.4 and 61.8 microM, respectively). Two anthocyanins, cyanidin 3-glucoside (3) and delphinidin 3-glucoside (4), also showed good activity in these assays.
Reynertson
Kurt A
KA
Department of Biological Sciences, Lehman College and the Graduate Center, City University of New York, 250 Bedford Park Boulevard West, Bronx, New York 10468, USA.
Wallace
Alison M
AM
Adachi
Seiji
S
Gil
Roberto R
RR
Yang
Hui
H
Basile
Margaret J
MJ
D'Armiento
Jeanine
J
Weinstein
I Bernard
IB
Kennelly
Edward J
EJ
D000872:Anthocyanins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001713:Biphenyl Compounds; D053630:Depsides; D004354:Drug Screening Assays, Antitumor; D045325:HCT116 Cells; D006801:Humans; D062385:Hydroxybenzoates / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D016209:Interleukin-8 / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D015394:Molecular Structure; D027822:Myrtaceae / Q000737:chemistry*; D010851:Picrates / Q000494:pharmacology; D012906:Smoke; D014026:Nicotiana
D000872:Anthocyanins; D000972:Antineoplastic Agents, Phytogenic; D001713:Biphenyl Compounds; D053630:Depsides; D062385:Hydroxybenzoates; D016209:Interleukin-8; D010851:Picrates; D012906:Smoke; C513712:jaboticabin; C017154:cyanidin; C004931:1,1-diphenyl-2-picrylhydrazyl