Tropolactones A-D, four meroterpenoids from a marine-derived fungus of the genus Aspergillus

Mercedes Cueto; John B. MacMillan; Paul R. Jensen; William Fenical

doi:10.1016/j.phytochem.2006.01.008

Tropolactones A-D, four meroterpenoids from a marine-derived fungus of the genus Aspergillus

Mercedes Cueto, John B. MacMillan, Paul R. Jensen, William Fenical

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

51 Scopus citations

Abstract

Four cytotoxic meroterpenoids, tropolactones A-D, were isolated from the whole broth extract of a marine-derived fungus of the genus Aspergillus. The structures of the meroterpenoids were established through a variety of two-dimensional NMR techniques. The absolute configuration of tropolactone A was determined using the modified Mosher method. Tropolactones A-C contain an interesting substituted 2,4,6-cycloheptatriene (tropone) ring, which presumably arises through an oxidative ring expansion from tropolactone D. Tropolactones A, B and C showed in vitro cytotoxicity against human colon carcinoma (HCT-116) with IC₅₀ values of 13.2, 10.9 and 13.9 μg/mL.

Original language	English (US)
Pages (from-to)	1826-1831
Number of pages	6
Journal	Phytochemistry
Volume	67
Issue number	16
DOIs	https://doi.org/10.1016/j.phytochem.2006.01.008
State	Published - Aug 2006

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Plant Science
Horticulture

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10.1016/j.phytochem.2006.01.008

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title = "Tropolactones A-D, four meroterpenoids from a marine-derived fungus of the genus Aspergillus",

abstract = "Four cytotoxic meroterpenoids, tropolactones A-D, were isolated from the whole broth extract of a marine-derived fungus of the genus Aspergillus. The structures of the meroterpenoids were established through a variety of two-dimensional NMR techniques. The absolute configuration of tropolactone A was determined using the modified Mosher method. Tropolactones A-C contain an interesting substituted 2,4,6-cycloheptatriene (tropone) ring, which presumably arises through an oxidative ring expansion from tropolactone D. Tropolactones A, B and C showed in vitro cytotoxicity against human colon carcinoma (HCT-116) with IC50 values of 13.2, 10.9 and 13.9 μg/mL.",

author = "Mercedes Cueto and MacMillan, {John B.} and Jensen, {Paul R.} and William Fenical",

note = "Funding Information: We appreciate the financial support provided by the NIH, National Cancer Institute under grant CA44848. M. Cueto acknowledges a postdoctoral fellowship from the Ministerio de Educacion of Spain. We gratefully acknowledge Chris Kauffman for his technical support of this project and the Khaled bin Sultan Living Oceans Foundation and the crew and officers of the M/V Golden Shadow for their support of our Hawaiian Islands research program.",

year = "2006",

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language = "English (US)",

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journal = "Phytochemistry",

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T1 - Tropolactones A-D, four meroterpenoids from a marine-derived fungus of the genus Aspergillus

AU - Cueto, Mercedes

AU - MacMillan, John B.

AU - Jensen, Paul R.

AU - Fenical, William

N1 - Funding Information: We appreciate the financial support provided by the NIH, National Cancer Institute under grant CA44848. M. Cueto acknowledges a postdoctoral fellowship from the Ministerio de Educacion of Spain. We gratefully acknowledge Chris Kauffman for his technical support of this project and the Khaled bin Sultan Living Oceans Foundation and the crew and officers of the M/V Golden Shadow for their support of our Hawaiian Islands research program.

PY - 2006/8

Y1 - 2006/8

N2 - Four cytotoxic meroterpenoids, tropolactones A-D, were isolated from the whole broth extract of a marine-derived fungus of the genus Aspergillus. The structures of the meroterpenoids were established through a variety of two-dimensional NMR techniques. The absolute configuration of tropolactone A was determined using the modified Mosher method. Tropolactones A-C contain an interesting substituted 2,4,6-cycloheptatriene (tropone) ring, which presumably arises through an oxidative ring expansion from tropolactone D. Tropolactones A, B and C showed in vitro cytotoxicity against human colon carcinoma (HCT-116) with IC50 values of 13.2, 10.9 and 13.9 μg/mL.

AB - Four cytotoxic meroterpenoids, tropolactones A-D, were isolated from the whole broth extract of a marine-derived fungus of the genus Aspergillus. The structures of the meroterpenoids were established through a variety of two-dimensional NMR techniques. The absolute configuration of tropolactone A was determined using the modified Mosher method. Tropolactones A-C contain an interesting substituted 2,4,6-cycloheptatriene (tropone) ring, which presumably arises through an oxidative ring expansion from tropolactone D. Tropolactones A, B and C showed in vitro cytotoxicity against human colon carcinoma (HCT-116) with IC50 values of 13.2, 10.9 and 13.9 μg/mL.

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Tropolactones A-D, four meroterpenoids from a marine-derived fungus of the genus Aspergillus

Abstract

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