A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity

E. M.Kithsiri Wijeratne; Thomas J. Turbyville; Anne Fritz; Luke Whitesell; A. A.Leslie Gunatilaka

doi:10.1016/j.bmc.2006.07.048

A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity

E. M.Kithsiri Wijeratne, Thomas J. Turbyville, Anne Fritz, Luke Whitesell, A. A.Leslie Gunatilaka

Research output: Contribution to journal › Article › peer-review

71 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	7917-7923
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	14
Issue number	23
DOIs	https://doi.org/10.1016/j.bmc.2006.07.048
State	Published - Dec 1 2006

Keywords

Cell-cycle disruptor
Chaetomium globosum
Cytotoxicity
Globosuxanthones A-D
Opuntia leptocaulis
Plant-associated fungus

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2006.07.048

Cite this

@article{205ef52ad11a492a80cdeceec7e15b1a,

title = "A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity",

abstract = "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.",

keywords = "Cell-cycle disruptor, Chaetomium globosum, Cytotoxicity, Globosuxanthones A-D, Opuntia leptocaulis, Plant-associated fungus",

author = "Wijeratne, {E. M.Kithsiri} and Turbyville, {Thomas J.} and Anne Fritz and Luke Whitesell and Gunatilaka, {A. A.Leslie}",

note = "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.",

year = "2006",

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doi = "10.1016/j.bmc.2006.07.048",

language = "English (US)",

volume = "14",

pages = "7917--7923",

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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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SN - 0968-0896

VL - 14

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EP - 7923

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 23

ER -

A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 610092: Experimental Crystal Structure Determination

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A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity

Abstract

Keywords

ASJC Scopus subject areas

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Datasets

CCDC 610092: Experimental Crystal Structure Determination

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