TY - JOUR
T1 - Cytotoxic and other metabolites of Aspergillus inhabiting the rhizosphere of sonoran desert plants
AU - He, Jian
AU - Wijeratne, E. M.Kithsiri
AU - Bashyal, Bharat P.
AU - Zhan, Jixun
AU - Seliga, Christopher J.
AU - Liu, Manping X.
AU - Pierson, Elizabeth E.
AU - Pierson, Leland S.
AU - VanEtten, Hans D.
AU - Gunatilaka, A. A.Leslie
PY - 2004/12
Y1 - 2004/12
N2 - In a study to discover potential anticancer agents from rhizosphere fungi of Sonoran desert plants cytotoxic EtOAc extracts of four Aspergillus strains have been investigated. Two new metabolites, terrequinone A (1) and terrefuranone (2), along with Nα-acetyl aszonalemin (LL-S490β) (3) were isolated from As. terreus occurring in the rhizosphere of Ambrosia ambrosoides, whereas As. terreus inhabiting the rhizosphere of an unidentified Brickellia sp. afforded dehydrocurvularin (4), 11-methoxycurvularin (5), and 11-hydroxycurvularin (6). As. cervinus isolated from the rhizosphere of Anicasanthus thurberi contained two new compounds, 4R*,5S*- dihydroxy-3-methoxy-5-methylcyclohex-2-enone (7) and 6-methoxy-5(6)- dihydropenicillic acid (8), in addition to penicillic acid (9). Penicillic acid was also isolated from As. wentii occurring in the rhizosphere of Larrea tridentata. The structures of 1-9 were elucidated by spectroscopic methods and chemical derivatizations. Acetylation of 2 afforded 14-acetylterrefuranone (13) and 14-deoxy-13(14)-dehydroterrefuranone (14). Metabolites 1-9, the dienone 14, and 5(6)-dihydropenicillic acid (16) were evaluated for cytotoxicity in a panel of four human cancer cell lines and in normal human primary fibroblast cells. Compounds 4 and 5 displayed considerable cytotoxicity, whereas 1, 6, 9, and 14 were found to be moderately active, with 6 and 9 exhibiting selective cytotoxicity against cancer cell lines compared with the normal fibroblast cells.
AB - In a study to discover potential anticancer agents from rhizosphere fungi of Sonoran desert plants cytotoxic EtOAc extracts of four Aspergillus strains have been investigated. Two new metabolites, terrequinone A (1) and terrefuranone (2), along with Nα-acetyl aszonalemin (LL-S490β) (3) were isolated from As. terreus occurring in the rhizosphere of Ambrosia ambrosoides, whereas As. terreus inhabiting the rhizosphere of an unidentified Brickellia sp. afforded dehydrocurvularin (4), 11-methoxycurvularin (5), and 11-hydroxycurvularin (6). As. cervinus isolated from the rhizosphere of Anicasanthus thurberi contained two new compounds, 4R*,5S*- dihydroxy-3-methoxy-5-methylcyclohex-2-enone (7) and 6-methoxy-5(6)- dihydropenicillic acid (8), in addition to penicillic acid (9). Penicillic acid was also isolated from As. wentii occurring in the rhizosphere of Larrea tridentata. The structures of 1-9 were elucidated by spectroscopic methods and chemical derivatizations. Acetylation of 2 afforded 14-acetylterrefuranone (13) and 14-deoxy-13(14)-dehydroterrefuranone (14). Metabolites 1-9, the dienone 14, and 5(6)-dihydropenicillic acid (16) were evaluated for cytotoxicity in a panel of four human cancer cell lines and in normal human primary fibroblast cells. Compounds 4 and 5 displayed considerable cytotoxicity, whereas 1, 6, 9, and 14 were found to be moderately active, with 6 and 9 exhibiting selective cytotoxicity against cancer cell lines compared with the normal fibroblast cells.
UR - https://www.scopus.com/pages/publications/19944427730
UR - https://www.scopus.com/pages/publications/19944427730#tab=citedBy
U2 - 10.1021/np040139d
DO - 10.1021/np040139d
M3 - Article
C2 - 15620238
AN - SCOPUS:19944427730
SN - 0163-3864
VL - 67
SP - 1985
EP - 1991
JO - Journal Of Natural Products
JF - Journal Of Natural Products
IS - 12
ER -