Bioactive cyclopentenone derivatives from marine isolates of fungi

Zhile Feng; Alain S. Leutou; Guohua Yang; Viviane N. Nenkep; Xavier N. Siwe; Hong Dae Choi; Jung Sook Kang; Byeng Wha Son

doi:10.5012/bkcs.2009.30.10.2345

Bioactive cyclopentenone derivatives from marine isolates of fungi

Zhile Feng, Alain S. Leutou, Guohua Yang, Viviane N. Nenkep, Xavier N. Siwe, Hong Dae Choi, Jung Sook Kang, Byeng Wha Son^*

^*Corresponding author for this work

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

16 Citations (Scopus)

Abstract

As part of an effort to discover bioactive natural products from marine sources, we investigated the bioactive secondary metabolites from two marine isolates of the fungi, Trichoderma viride and Rhizopus stolonifer. Three cyclopentenones, myrothenones A (1) and B (2) and trichodenone A (3), were isolated from T. viride and two cyclopentenones, 2-bromomyrothenone B (4) and botrytinone (5), were isolated from R. stolonifer. The molecular structures and absolute stereochemistries of the cyclopentenones were determined from chemical and physicochemical evidence, including quantum chemistry calculations, X-ray analysis, and the circular dichroism (CD) exciton chirality method. Myrothenone A (1) displays tyrosinase inhibitory activity, with an IC₅₀ value of 6.6 μM, and is therefore more active than the positive control, kojic acid.

Original language	English
Pages (from-to)	2345-2350
Number of pages	6
Journal	Bulletin of the Korean Chemical Society
Volume	30
Issue number	10
DOIs	https://doi.org/10.5012/bkcs.2009.30.10.2345
Publication status	Published - Oct 2009
Externally published	Yes

Keywords

Botrytinone
Cyclopentenone
Myrothenone
Rhizopus stolonifer
Trichoderma viride

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10.5012/bkcs.2009.30.10.2345

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title = "Bioactive cyclopentenone derivatives from marine isolates of fungi",

abstract = "As part of an effort to discover bioactive natural products from marine sources, we investigated the bioactive secondary metabolites from two marine isolates of the fungi, Trichoderma viride and Rhizopus stolonifer. Three cyclopentenones, myrothenones A (1) and B (2) and trichodenone A (3), were isolated from T. viride and two cyclopentenones, 2-bromomyrothenone B (4) and botrytinone (5), were isolated from R. stolonifer. The molecular structures and absolute stereochemistries of the cyclopentenones were determined from chemical and physicochemical evidence, including quantum chemistry calculations, X-ray analysis, and the circular dichroism (CD) exciton chirality method. Myrothenone A (1) displays tyrosinase inhibitory activity, with an IC50 value of 6.6 μM, and is therefore more active than the positive control, kojic acid.",

keywords = "Botrytinone, Cyclopentenone, Myrothenone, Rhizopus stolonifer, Trichoderma viride",

author = "Zhile Feng and Leutou, {Alain S.} and Guohua Yang and Nenkep, {Viviane N.} and Siwe, {Xavier N.} and Choi, {Hong Dae} and Kang, {Jung Sook} and Son, {Byeng Wha}",

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doi = "10.5012/bkcs.2009.30.10.2345",

language = "English",

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AU - Feng, Zhile

AU - Leutou, Alain S.

AU - Yang, Guohua

AU - Nenkep, Viviane N.

AU - Siwe, Xavier N.

AU - Choi, Hong Dae

AU - Kang, Jung Sook

AU - Son, Byeng Wha

PY - 2009/10

Y1 - 2009/10

N2 - As part of an effort to discover bioactive natural products from marine sources, we investigated the bioactive secondary metabolites from two marine isolates of the fungi, Trichoderma viride and Rhizopus stolonifer. Three cyclopentenones, myrothenones A (1) and B (2) and trichodenone A (3), were isolated from T. viride and two cyclopentenones, 2-bromomyrothenone B (4) and botrytinone (5), were isolated from R. stolonifer. The molecular structures and absolute stereochemistries of the cyclopentenones were determined from chemical and physicochemical evidence, including quantum chemistry calculations, X-ray analysis, and the circular dichroism (CD) exciton chirality method. Myrothenone A (1) displays tyrosinase inhibitory activity, with an IC50 value of 6.6 μM, and is therefore more active than the positive control, kojic acid.

AB - As part of an effort to discover bioactive natural products from marine sources, we investigated the bioactive secondary metabolites from two marine isolates of the fungi, Trichoderma viride and Rhizopus stolonifer. Three cyclopentenones, myrothenones A (1) and B (2) and trichodenone A (3), were isolated from T. viride and two cyclopentenones, 2-bromomyrothenone B (4) and botrytinone (5), were isolated from R. stolonifer. The molecular structures and absolute stereochemistries of the cyclopentenones were determined from chemical and physicochemical evidence, including quantum chemistry calculations, X-ray analysis, and the circular dichroism (CD) exciton chirality method. Myrothenone A (1) displays tyrosinase inhibitory activity, with an IC50 value of 6.6 μM, and is therefore more active than the positive control, kojic acid.

KW - Botrytinone

KW - Cyclopentenone

KW - Myrothenone

KW - Rhizopus stolonifer

KW - Trichoderma viride

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DO - 10.5012/bkcs.2009.30.10.2345

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SN - 0253-2964

VL - 30

SP - 2345

EP - 2350

JO - Bulletin of the Korean Chemical Society

JF - Bulletin of the Korean Chemical Society

IS - 10

ER -

Bioactive cyclopentenone derivatives from marine isolates of fungi

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Keywords

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