Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field

Sangkeun Son; Sung Kyun Ko; Jong Won Kim; Jae Kyoung Lee; Mina Jang; In Ja Ryoo; Gwi Ja Hwang; Min Cheol Kwon; Kee Sun Shin; Yushi Futamura; Young Soo Hong; Hyuncheol Oh; Bo Yeon Kim; Masashi Ueki; Shunji Takahashi; Hiroyuki Osada; Jae Hyuk Jang; Jong Seog Ahn

doi:10.1016/j.phytochem.2015.12.008

Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field

Sangkeun Son, Sung Kyun Ko, Jong Won Kim, Jae Kyoung Lee, Mina Jang, In Ja Ryoo, Gwi Ja Hwang, Min Cheol Kwon, Kee Sun Shin, Yushi Futamura, Young Soo Hong, Hyuncheol Oh, Bo Yeon Kim, Masashi Ueki, Shunji Takahashi, Hiroyuki Osada, Jae Hyuk Jang, Jong Seog Ahn^*

^*Corresponding author for this work

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

33 Citations (Scopus)

Abstract

Twelve metabolites, including five highly oxygenated azaphilones, geumsanols A-E, along with seven known analogues were isolated from Penicillium sp. KCB11A109, a fungus derived from a ginseng field. Their structures were assigned by spectroscopic means (NMR and MS), and stereochemistries were determined by extensive spectroscopic analyses (¹H-¹H coupling constants, NOESY, and HETLOC) and chemical derivatizations (modified Mosher's method and acetonide formation). The isolates were evaluated for their anticancer, antimicrobial, antimalarial activities, and phenotypic effects in zebrafish development. Of these compounds possessing no pyranoquinone core, only geumsanol E exhibited cytotoxic activities and toxic effects on zebrafish embryos, suggesting that a double bond at C-11 and C-12 is important for biological activity.

Original language	English
Pages (from-to)	154-164
Number of pages	11
Journal	Phytochemistry
Volume	122
DOIs	https://doi.org/10.1016/j.phytochem.2015.12.008
Publication status	Published - 2016 Feb 1
Externally published	Yes

Keywords

Azaphilone
Geumsanol
Penicillium sp.
Structure elucidation
Trichocomaceae
Zebrafish screening

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Plant Science
Horticulture

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10.1016/j.phytochem.2015.12.008

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Son, S., Ko, S. K., Kim, J. W., Lee, J. K., Jang, M., Ryoo, I. J., Hwang, G. J., Kwon, M. C., Shin, K. S., Futamura, Y., Hong, Y. S., Oh, H., Kim, B. Y., Ueki, M., Takahashi, S., Osada, H., Jang, J. H., & Ahn, J. S. (2016). Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field. Phytochemistry, 122, 154-164. https://doi.org/10.1016/j.phytochem.2015.12.008

Son, S, Ko, SK, Kim, JW, Lee, JK, Jang, M, Ryoo, IJ, Hwang, GJ, Kwon, MC, Shin, KS, Futamura, Y, Hong, YS, Oh, H, Kim, BY, Ueki, M, Takahashi, S, Osada, H, Jang, JH & Ahn, JS 2016, 'Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field', Phytochemistry, vol. 122, pp. 154-164. https://doi.org/10.1016/j.phytochem.2015.12.008

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title = "Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field",

abstract = "Twelve metabolites, including five highly oxygenated azaphilones, geumsanols A-E, along with seven known analogues were isolated from Penicillium sp. KCB11A109, a fungus derived from a ginseng field. Their structures were assigned by spectroscopic means (NMR and MS), and stereochemistries were determined by extensive spectroscopic analyses (1H-1H coupling constants, NOESY, and HETLOC) and chemical derivatizations (modified Mosher's method and acetonide formation). The isolates were evaluated for their anticancer, antimicrobial, antimalarial activities, and phenotypic effects in zebrafish development. Of these compounds possessing no pyranoquinone core, only geumsanol E exhibited cytotoxic activities and toxic effects on zebrafish embryos, suggesting that a double bond at C-11 and C-12 is important for biological activity.",

keywords = "Azaphilone, Geumsanol, Penicillium sp., Structure elucidation, Trichocomaceae, Zebrafish screening",

author = "Sangkeun Son and Ko, {Sung Kyun} and Kim, {Jong Won} and Lee, {Jae Kyoung} and Mina Jang and Ryoo, {In Ja} and Hwang, {Gwi Ja} and Kwon, {Min Cheol} and Shin, {Kee Sun} and Yushi Futamura and Hong, {Young Soo} and Hyuncheol Oh and Kim, {Bo Yeon} and Masashi Ueki and Shunji Takahashi and Hiroyuki Osada and Jang, {Jae Hyuk} and Ahn, {Jong Seog}",

note = "Funding Information: We acknowledge financial support by grants from the Global R&D Center ( GRDC , NRF-2010-00719 ) programs of the National Research Foundation of Korea ( NRF ) funded by the Ministry of Science, ICT and Future Planning of Korea (MSIFP). We also thank financial support by grants from the Chungcheongbuk-do and KRIBB Research Initiative Program. We acknowledge the Korea Basic Science Institute, Ochang, Korea, for providing NMR (700, 800, and 900 MHz), HRESIMS, and CD data. We also thank Dr. F. Ito, and Mss H. Aono, M. Tanaka, N. Morita, and Y. Hirata (RIKEN CSRS) for biological activity tests. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. All rights reserved.",

year = "2016",

month = feb,

day = "1",

doi = "10.1016/j.phytochem.2015.12.008",

language = "English",

volume = "122",

pages = "154--164",

journal = "Phytochemistry",

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T1 - Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field

AU - Son, Sangkeun

AU - Ko, Sung Kyun

AU - Kim, Jong Won

AU - Lee, Jae Kyoung

AU - Jang, Mina

AU - Ryoo, In Ja

AU - Hwang, Gwi Ja

AU - Kwon, Min Cheol

AU - Shin, Kee Sun

AU - Futamura, Yushi

AU - Hong, Young Soo

AU - Oh, Hyuncheol

AU - Kim, Bo Yeon

AU - Ueki, Masashi

AU - Takahashi, Shunji

AU - Osada, Hiroyuki

AU - Jang, Jae Hyuk

AU - Ahn, Jong Seog

N1 - Funding Information: We acknowledge financial support by grants from the Global R&D Center ( GRDC , NRF-2010-00719 ) programs of the National Research Foundation of Korea ( NRF ) funded by the Ministry of Science, ICT and Future Planning of Korea (MSIFP). We also thank financial support by grants from the Chungcheongbuk-do and KRIBB Research Initiative Program. We acknowledge the Korea Basic Science Institute, Ochang, Korea, for providing NMR (700, 800, and 900 MHz), HRESIMS, and CD data. We also thank Dr. F. Ito, and Mss H. Aono, M. Tanaka, N. Morita, and Y. Hirata (RIKEN CSRS) for biological activity tests. Publisher Copyright: © 2015 Elsevier Ltd. All rights reserved.

PY - 2016/2/1

Y1 - 2016/2/1

N2 - Twelve metabolites, including five highly oxygenated azaphilones, geumsanols A-E, along with seven known analogues were isolated from Penicillium sp. KCB11A109, a fungus derived from a ginseng field. Their structures were assigned by spectroscopic means (NMR and MS), and stereochemistries were determined by extensive spectroscopic analyses (1H-1H coupling constants, NOESY, and HETLOC) and chemical derivatizations (modified Mosher's method and acetonide formation). The isolates were evaluated for their anticancer, antimicrobial, antimalarial activities, and phenotypic effects in zebrafish development. Of these compounds possessing no pyranoquinone core, only geumsanol E exhibited cytotoxic activities and toxic effects on zebrafish embryos, suggesting that a double bond at C-11 and C-12 is important for biological activity.

AB - Twelve metabolites, including five highly oxygenated azaphilones, geumsanols A-E, along with seven known analogues were isolated from Penicillium sp. KCB11A109, a fungus derived from a ginseng field. Their structures were assigned by spectroscopic means (NMR and MS), and stereochemistries were determined by extensive spectroscopic analyses (1H-1H coupling constants, NOESY, and HETLOC) and chemical derivatizations (modified Mosher's method and acetonide formation). The isolates were evaluated for their anticancer, antimicrobial, antimalarial activities, and phenotypic effects in zebrafish development. Of these compounds possessing no pyranoquinone core, only geumsanol E exhibited cytotoxic activities and toxic effects on zebrafish embryos, suggesting that a double bond at C-11 and C-12 is important for biological activity.

KW - Azaphilone

KW - Geumsanol

KW - Penicillium sp.

KW - Structure elucidation

KW - Trichocomaceae

KW - Zebrafish screening

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DO - 10.1016/j.phytochem.2015.12.008

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AN - SCOPUS:84955759223

SN - 0031-9422

VL - 122

SP - 154

EP - 164

JO - Phytochemistry

JF - Phytochemistry

ER -

Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field

Abstract

Keywords

ASJC Scopus subject areas

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