TY - JOUR
T1 - A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity
AU - Wijeratne, E. M.Kithsiri
AU - Turbyville, Thomas J.
AU - Fritz, Anne
AU - Whitesell, Luke
AU - Gunatilaka, A. A.Leslie
N1 - Funding Information:
Financial support from the NCI/NIH (Grant R01 CA 90265), Arizona Biomedical Research Commission (Grant 9014), and the College of Agriculture and Life Sciences of the University of Arizona is gratefully acknowledged. We thank Drs. Alice Dawson and Michael Carducci of the Molecular Structure Laboratory of the University of Arizona for their assistance in obtaining the X-ray crystallographic data and acknowledge the NSF Grant CHE9610374 which provided the diffractometer. We are thankful to Dr. Robert Dorr and Ms. Mary A. Raymond for the preliminary in vivo evaluation of globosuxanthone A. We also thank Drs. Hans D. VanEtten and Anita Harlan for providing the fungal strain and identification of the plant from which the fungus was obtained, and Ms. Manping Liu for her help with some cytotoxicity assays.
PY - 2006/12/1
Y1 - 2006/12/1
N2 - Bioassay-guided fractionation of a cytotoxic EtOAc extract of the fungal strain, Chaetomium globosum, inhabiting the rhizosphere of the Christmas cactus, Opuntia leptocaulis, of the Sonoran desert afforded a new dihydroxanthenone, globosuxanthone A (1), a new tetrahydroxanthenone, globosuxanthone B (2), two new xanthones, globosuxanthone C (3) and D (4), 2-hydroxyvertixanthone (5), and two known anthraquinones (6 and 7). The structures of the new compounds 1-4 were elucidated by NMR and MS techniques, and the relative stereochemistry of 1 was determined by X-ray crystallographic analysis. Of the compounds encountered, 1 was found to exhibit strong cytotoxicity against a panel of seven human solid tumor cell lines, disrupt the cell cycle leading to the accumulation of cells in either G2/M or S phase, and induce classic signs of apoptosis.
AB - Bioassay-guided fractionation of a cytotoxic EtOAc extract of the fungal strain, Chaetomium globosum, inhabiting the rhizosphere of the Christmas cactus, Opuntia leptocaulis, of the Sonoran desert afforded a new dihydroxanthenone, globosuxanthone A (1), a new tetrahydroxanthenone, globosuxanthone B (2), two new xanthones, globosuxanthone C (3) and D (4), 2-hydroxyvertixanthone (5), and two known anthraquinones (6 and 7). The structures of the new compounds 1-4 were elucidated by NMR and MS techniques, and the relative stereochemistry of 1 was determined by X-ray crystallographic analysis. Of the compounds encountered, 1 was found to exhibit strong cytotoxicity against a panel of seven human solid tumor cell lines, disrupt the cell cycle leading to the accumulation of cells in either G2/M or S phase, and induce classic signs of apoptosis.
KW - Cell-cycle disruptor
KW - Chaetomium globosum
KW - Cytotoxicity
KW - Globosuxanthones A-D
KW - Opuntia leptocaulis
KW - Plant-associated fungus
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U2 - 10.1016/j.bmc.2006.07.048
DO - 10.1016/j.bmc.2006.07.048
M3 - Article
C2 - 16904330
AN - SCOPUS:33750090717
VL - 14
SP - 7917
EP - 7923
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
SN - 0968-0896
IS - 23
ER -