Herqueilenone A, a unique rearranged benzoquinone-chromanone from the Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729

Jae Sik Yu; Chunshun Li; Mincheol Kwon; Taehoon Oh; Tae Hyun Lee; Dong Hyun Kim; Jong Seog Ahn; Sung Kyun Ko; Chung Sub Kim; Shugeng Cao; Ki Hyun Kim

doi:10.1016/j.bioorg.2020.104397

Herqueilenone A, a unique rearranged benzoquinone-chromanone from the Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729

Jae Sik Yu, Chunshun Li, Mincheol Kwon, Taehoon Oh, Tae Hyun Lee, Dong Hyun Kim, Jong Seog Ahn, Sung Kyun Ko, Chung Sub Kim, Shugeng Cao, Ki Hyun Kim

Department of Pharmacy

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

27 Scopus citations

Abstract

The study of a Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729 led to the isolation of one unprecedented benzoquinone-chromanone, herqueilenone A (1) and two phenalenone derivatives (2 and 3). Their structures were determined through extensive analysis of NMR spectroscopic data and gauge-including atomic orbital (GIAO) NMR chemical shifts and ECD calculations. Herqueilenone A (1) contains a chroman-4-one core flanked by a tetrahydrofuran and a benzoquinone with an acetophenone moiety. Plausible pathways for the biosynthesis of 1–3 are proposed. Compounds 2 and 3 inhibited IDO1 activity with IC₅₀ values of 14.38 and 13.69 μM, respectively. Compounds 2 and 3 also demonstrated a protective effect against acetaldehyde-induced damage in PC-12 cells.

Original language	English
Article number	104397
Journal	Bioorganic Chemistry
Volume	105
DOIs	https://doi.org/10.1016/j.bioorg.2020.104397
State	Published - Dec 2020

Keywords

Acetaldehyde-induced damage
Benzoquinone-chromanone
Indoleamine 2,3-dioxygenase 1
Penicillium herquei FT729
Phenalenone derivative
Soil-associated fungus

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@article{02bb1238a08c4e81b96c7604d91648da,

title = "Herqueilenone A, a unique rearranged benzoquinone-chromanone from the Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729",

abstract = "The study of a Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729 led to the isolation of one unprecedented benzoquinone-chromanone, herqueilenone A (1) and two phenalenone derivatives (2 and 3). Their structures were determined through extensive analysis of NMR spectroscopic data and gauge-including atomic orbital (GIAO) NMR chemical shifts and ECD calculations. Herqueilenone A (1) contains a chroman-4-one core flanked by a tetrahydrofuran and a benzoquinone with an acetophenone moiety. Plausible pathways for the biosynthesis of 1–3 are proposed. Compounds 2 and 3 inhibited IDO1 activity with IC50 values of 14.38 and 13.69 μM, respectively. Compounds 2 and 3 also demonstrated a protective effect against acetaldehyde-induced damage in PC-12 cells.",

keywords = "Acetaldehyde-induced damage, Benzoquinone-chromanone, Indoleamine 2,3-dioxygenase 1, Penicillium herquei FT729, Phenalenone derivative, Soil-associated fungus",

author = "Yu, \{Jae Sik\} and Chunshun Li and Mincheol Kwon and Taehoon Oh and Lee, \{Tae Hyun\} and Kim, \{Dong Hyun\} and Ahn, \{Jong Seog\} and Ko, \{Sung Kyun\} and Kim, \{Chung Sub\} and Shugeng Cao and Kim, \{Ki Hyun\}",

note = "Publisher Copyright: {\textcopyright} 2020 Elsevier Inc.",

year = "2020",

month = dec,

doi = "10.1016/j.bioorg.2020.104397",

language = "English",

volume = "105",

journal = "Bioorganic Chemistry",

issn = "0045-2068",

publisher = "Academic Press Inc.",

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T1 - Herqueilenone A, a unique rearranged benzoquinone-chromanone from the Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729

AU - Yu, Jae Sik

AU - Li, Chunshun

AU - Kwon, Mincheol

AU - Oh, Taehoon

AU - Lee, Tae Hyun

AU - Kim, Dong Hyun

AU - Ahn, Jong Seog

AU - Ko, Sung Kyun

AU - Kim, Chung Sub

AU - Cao, Shugeng

AU - Kim, Ki Hyun

PY - 2020/12

Y1 - 2020/12

N2 - The study of a Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729 led to the isolation of one unprecedented benzoquinone-chromanone, herqueilenone A (1) and two phenalenone derivatives (2 and 3). Their structures were determined through extensive analysis of NMR spectroscopic data and gauge-including atomic orbital (GIAO) NMR chemical shifts and ECD calculations. Herqueilenone A (1) contains a chroman-4-one core flanked by a tetrahydrofuran and a benzoquinone with an acetophenone moiety. Plausible pathways for the biosynthesis of 1–3 are proposed. Compounds 2 and 3 inhibited IDO1 activity with IC50 values of 14.38 and 13.69 μM, respectively. Compounds 2 and 3 also demonstrated a protective effect against acetaldehyde-induced damage in PC-12 cells.

AB - The study of a Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729 led to the isolation of one unprecedented benzoquinone-chromanone, herqueilenone A (1) and two phenalenone derivatives (2 and 3). Their structures were determined through extensive analysis of NMR spectroscopic data and gauge-including atomic orbital (GIAO) NMR chemical shifts and ECD calculations. Herqueilenone A (1) contains a chroman-4-one core flanked by a tetrahydrofuran and a benzoquinone with an acetophenone moiety. Plausible pathways for the biosynthesis of 1–3 are proposed. Compounds 2 and 3 inhibited IDO1 activity with IC50 values of 14.38 and 13.69 μM, respectively. Compounds 2 and 3 also demonstrated a protective effect against acetaldehyde-induced damage in PC-12 cells.

KW - Acetaldehyde-induced damage

KW - Benzoquinone-chromanone

KW - Indoleamine 2,3-dioxygenase 1

KW - Penicillium herquei FT729

KW - Phenalenone derivative

KW - Soil-associated fungus

UR - https://www.scopus.com/pages/publications/85094592993

U2 - 10.1016/j.bioorg.2020.104397

DO - 10.1016/j.bioorg.2020.104397

M3 - Article

C2 - 33130348

AN - SCOPUS:85094592993

SN - 0045-2068

VL - 105

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

M1 - 104397

ER -

Herqueilenone A, a unique rearranged benzoquinone-chromanone from the Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729

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Keywords

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