Cytotoxic and other metabolites of Aspergillus inhabiting the rhizosphere of sonoran desert plants

Jian He, E. M Kithsiri Wijeratne, Bharat P. Bashyal, Jixun Zhan, Christopher J. Seliga, Manping X. Liu, Elizabeth E. Pierson, Leland S. Pierson, Hans D. VanEtten, Leslie Gunatilaka

Research output: Contribution to journalArticle

85 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)1985-1991
Number of pages7
JournalJournal of Natural Products
Volume67
Issue number12
DOIs
StatePublished - Dec 2004

Fingerprint

Sonoran Desert
xerophytes
Rhizosphere
Aspergillus
Metabolites
Penicillic Acid
rhizosphere
Cytotoxicity
penicillic acid
Cells
metabolites
cytotoxicity
Fibroblasts
fibroblasts
cell lines
rhizosphere fungi
Larrea tridentata
Brickellia
Larrea
Ambrosia

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Cytotoxic and other metabolites of Aspergillus inhabiting the rhizosphere of sonoran desert plants. / He, Jian; Wijeratne, E. M Kithsiri; Bashyal, Bharat P.; Zhan, Jixun; Seliga, Christopher J.; Liu, Manping X.; Pierson, Elizabeth E.; Pierson, Leland S.; VanEtten, Hans D.; Gunatilaka, Leslie.

In: Journal of Natural Products, Vol. 67, No. 12, 12.2004, p. 1985-1991.

Research output: Contribution to journalArticle

He, J, Wijeratne, EMK, Bashyal, BP, Zhan, J, Seliga, CJ, Liu, MX, Pierson, EE, Pierson, LS, VanEtten, HD & Gunatilaka, L 2004, 'Cytotoxic and other metabolites of Aspergillus inhabiting the rhizosphere of sonoran desert plants', Journal of Natural Products, vol. 67, no. 12, pp. 1985-1991. https://doi.org/10.1021/np040139d
He, Jian ; Wijeratne, E. M Kithsiri ; Bashyal, Bharat P. ; Zhan, Jixun ; Seliga, Christopher J. ; Liu, Manping X. ; Pierson, Elizabeth E. ; Pierson, Leland S. ; VanEtten, Hans D. ; Gunatilaka, Leslie. / Cytotoxic and other metabolites of Aspergillus inhabiting the rhizosphere of sonoran desert plants. In: Journal of Natural Products. 2004 ; Vol. 67, No. 12. pp. 1985-1991.
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abstract = "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.",
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AU - Zhan, Jixun

AU - Seliga, Christopher J.

AU - Liu, Manping X.

AU - Pierson, Elizabeth E.

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AU - VanEtten, Hans D.

AU - Gunatilaka, Leslie

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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.

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