Glycopentanolones A-D, four new geranylated quinolone alkaloids from Glycosmis pentaphylla

Yun Hyeok Choi; Changon Seo; Wonsik Jeong; Ji Eun Lee; Jae Yeon Lee; Eun Kyung Ahn; Jae Shin Kang; Jae Ho Lee; Chun Whan Choi; Joa Sub Oh; Dongho Lee; Seong Su Hong

doi:10.1016/j.bioorg.2019.03.069

Glycopentanolones A-D, four new geranylated quinolone alkaloids from Glycosmis pentaphylla

Yun Hyeok Choi, Changon Seo, Wonsik Jeong, Ji Eun Lee, Jae Yeon Lee, Eun Kyung Ahn, Jae Shin Kang, Jae Ho Lee, Chun Whan Choi, Joa Sub Oh, Dongho Lee, Seong Su Hong

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

19 Citations (Scopus)

Abstract

The ethanolic extract obtained from the stems of Glycosmis pentaphylla was found to suppress antigen-mediated degranulation of rat basophilic leukemia (RBL-2H3) cells. Four new geranylated 2-quinolone alkaloids, named glycopentanolones A–D (1–4), and 12 known metabolites (5–16) were isolated from the ethanolic extract from the stems of G. pentaphylla using bioassay-guided fractionation. Their structures were elucidated by a combination of 1D and 2D NMR, and HRESI-MS. The inhibitory effects of the isolated constituents on β-hexosaminidase release from RBL-2H3 cells were examined, and compounds 1, 5, 8 and 11 exhibited potent inhibitory activity with IC ₅₀ values between 0.05 and 4.28 μM.

Original language	English
Pages (from-to)	714-719
Number of pages	6
Journal	Bioorganic Chemistry
Volume	87
DOIs	https://doi.org/10.1016/j.bioorg.2019.03.069
Publication status	Published - 2019 Jun

Bibliographical note

Funding Information:
This study was supported by a grant from the National Institute of Biological Resources (NIBR) under the Ministry of Environment (MOE) of the Republic of Korea (NIBR No. 2017-04-202 ).

Publisher Copyright:
© 2019 Elsevier Inc.

Keywords

2-Quinolone alkaloid
Glycopentanolone
Glycosmis pentaphylla
β-hexosaminidase

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Drug Discovery
Organic Chemistry

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10.1016/j.bioorg.2019.03.069

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title = "Glycopentanolones A-D, four new geranylated quinolone alkaloids from Glycosmis pentaphylla",

abstract = " The ethanolic extract obtained from the stems of Glycosmis pentaphylla was found to suppress antigen-mediated degranulation of rat basophilic leukemia (RBL-2H3) cells. Four new geranylated 2-quinolone alkaloids, named glycopentanolones A–D (1–4), and 12 known metabolites (5–16) were isolated from the ethanolic extract from the stems of G. pentaphylla using bioassay-guided fractionation. Their structures were elucidated by a combination of 1D and 2D NMR, and HRESI-MS. The inhibitory effects of the isolated constituents on β-hexosaminidase release from RBL-2H3 cells were examined, and compounds 1, 5, 8 and 11 exhibited potent inhibitory activity with IC 50 values between 0.05 and 4.28 μM. ",

keywords = "2-Quinolone alkaloid, Glycopentanolone, Glycosmis pentaphylla, β-hexosaminidase",

author = "Choi, {Yun Hyeok} and Changon Seo and Wonsik Jeong and Lee, {Ji Eun} and Lee, {Jae Yeon} and Ahn, {Eun Kyung} and Kang, {Jae Shin} and Lee, {Jae Ho} and Choi, {Chun Whan} and Oh, {Joa Sub} and Dongho Lee and Hong, {Seong Su}",

note = "Funding Information: This study was supported by a grant from the National Institute of Biological Resources (NIBR) under the Ministry of Environment (MOE) of the Republic of Korea (NIBR No. 2017-04-202 ). Publisher Copyright: {\textcopyright} 2019 Elsevier Inc.",

year = "2019",

month = jun,

doi = "10.1016/j.bioorg.2019.03.069",

language = "English",

volume = "87",

pages = "714--719",

journal = "Bioorganic Chemistry",

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publisher = "Academic Press Inc.",

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T1 - Glycopentanolones A-D, four new geranylated quinolone alkaloids from Glycosmis pentaphylla

AU - Choi, Yun Hyeok

AU - Seo, Changon

AU - Jeong, Wonsik

AU - Lee, Ji Eun

AU - Lee, Jae Yeon

AU - Ahn, Eun Kyung

AU - Kang, Jae Shin

AU - Lee, Jae Ho

AU - Choi, Chun Whan

AU - Oh, Joa Sub

AU - Lee, Dongho

AU - Hong, Seong Su

N1 - Funding Information: This study was supported by a grant from the National Institute of Biological Resources (NIBR) under the Ministry of Environment (MOE) of the Republic of Korea (NIBR No. 2017-04-202 ). Publisher Copyright: © 2019 Elsevier Inc.

PY - 2019/6

Y1 - 2019/6

N2 - The ethanolic extract obtained from the stems of Glycosmis pentaphylla was found to suppress antigen-mediated degranulation of rat basophilic leukemia (RBL-2H3) cells. Four new geranylated 2-quinolone alkaloids, named glycopentanolones A–D (1–4), and 12 known metabolites (5–16) were isolated from the ethanolic extract from the stems of G. pentaphylla using bioassay-guided fractionation. Their structures were elucidated by a combination of 1D and 2D NMR, and HRESI-MS. The inhibitory effects of the isolated constituents on β-hexosaminidase release from RBL-2H3 cells were examined, and compounds 1, 5, 8 and 11 exhibited potent inhibitory activity with IC 50 values between 0.05 and 4.28 μM.

AB - The ethanolic extract obtained from the stems of Glycosmis pentaphylla was found to suppress antigen-mediated degranulation of rat basophilic leukemia (RBL-2H3) cells. Four new geranylated 2-quinolone alkaloids, named glycopentanolones A–D (1–4), and 12 known metabolites (5–16) were isolated from the ethanolic extract from the stems of G. pentaphylla using bioassay-guided fractionation. Their structures were elucidated by a combination of 1D and 2D NMR, and HRESI-MS. The inhibitory effects of the isolated constituents on β-hexosaminidase release from RBL-2H3 cells were examined, and compounds 1, 5, 8 and 11 exhibited potent inhibitory activity with IC 50 values between 0.05 and 4.28 μM.

KW - 2-Quinolone alkaloid

KW - Glycopentanolone

KW - Glycosmis pentaphylla

KW - β-hexosaminidase

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AN - SCOPUS:85063680390

SN - 0045-2068

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SP - 714

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JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

ER -

Glycopentanolones A-D, four new geranylated quinolone alkaloids from Glycosmis pentaphylla

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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