Alvaradoins E-N, antitumor and cytotoxic anthracenone C-glycosides from the leaves of Alvaradoa haitiensis.
Bioactivity-directed fractionation of an extract of the leaves of Alvaradoa haitiensis, using the KB (human oral epidermoid carcinoma) cell line, led to the isolation and identification of 10 new anthracenone C-glycosides, alvaradoins E-N (1-10), along with the known compound chrysophanol (11). The cytotoxicity of all compounds was evaluated, and preliminary structure-activity relationships are suggested. The most potent compounds in the in vitro assays (1 and 2) were evaluated in vivo versus the P388 (murine lymphocytic leukemia) model, and alvaradoin E (1) showed antileukemic activity (125% T/C) at a dose of 0.2 mg kg-1 per injection when administered intraperitoneally.
Phifer
Sharnelle S
SS
Natural Products Laboratory, Research Triangle Institute, P.O. Box 12194, Research Triangle Park, North Carolina 27709, USA.
Lee
Dongho
D
Seo
Eun-Kyoung
EK
Kim
Nam-Cheol
NC
Graf
Tyler N
TN
Kroll
David J
DJ
Navarro
Hernan A
HA
Izydore
Robert A
RA
Jiménez
Francisco
F
Garcia
Ricardo
R
Rose
William C
WC
Fairchild
Craig R
CR
Wild
Robert
R
Soejarto
Djaja D
DD
Farnsworth
Norman R
NR
Kinghorn
A Douglas
AD
Oberlies
Nicholas H
NH
Wall
Monroe E
ME
Wani
Mansukh C
MC
D000818:Animals; D000873:Anthracenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004293:Dominican Republic; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007624:KB Cells; D007941:Leukemia P388; D008954:Models, Biological; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D029641:Simaroubaceae / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000873:Anthracenes; D000972:Antineoplastic Agents, Phytogenic; D009005:Monosaccharides; C500945:alvaradoin E