Configurational Assignment of a Flexible Benzo[g]isochromene Stereodiad fromRubia philippinensisand Inhibition of Soluble Epoxide Hydrolase Activity

Khong Trong Quan; In Wha Park; Chung Sub Kim; Wesley Yoshida; Daneel Ferreira; Phuong Thien Thuong; Young Ho Kim; Min Kyun Na; Joonseok Oh

doi:10.1021/acs.jnatprod.1c00037

Configurational Assignment of a Flexible Benzo[g]isochromene Stereodiad fromRubia philippinensisand Inhibition of Soluble Epoxide Hydrolase Activity

Khong Trong Quan, In Wha Park, Chung Sub Kim, Wesley Yoshida, Daneel Ferreira, Phuong Thien Thuong, Young Ho Kim, Min Kyun Na, Joonseok Oh

Department of Pharmacy

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

3 Scopus citations

Abstract

A new benzo[g]isochromene possessing a conformationally mobile moiety was identified fromRubia philippinensis. The 2D structure was established utilizing spectrometric and spectroscopic techniques with variable temperatures. The configurational investigation of the flexible moiety was investigated utilizing contemporary NMR-combined computational tools such as DP4, directJ-DP4, and DP4 Plus. The probabilities computed from DP4 Plus analysis, featuring inclusion of an additional geometry optimization process, demonstrated more conclusive probability scores among the analyses used. The configurational assignment was also supported by compositional and molecular orbital analyses. Compound1inhibited soluble epoxide hydrolase (IC₅₀= 0.6 ± 0.01 μM), an enzyme associated with cardiovascular disorders.

Original language	English
Pages (from-to)	2594-2599
Number of pages	6
Journal	Journal of Natural Products
Volume	84
Issue number	9
DOIs	https://doi.org/10.1021/acs.jnatprod.1c00037
State	Published - 24 Sep 2021

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title = "Configurational Assignment of a Flexible Benzo[g]isochromene Stereodiad fromRubia philippinensisand Inhibition of Soluble Epoxide Hydrolase Activity",

abstract = "A new benzo[g]isochromene possessing a conformationally mobile moiety was identified fromRubia philippinensis. The 2D structure was established utilizing spectrometric and spectroscopic techniques with variable temperatures. The configurational investigation of the flexible moiety was investigated utilizing contemporary NMR-combined computational tools such as DP4, directJ-DP4, and DP4 Plus. The probabilities computed from DP4 Plus analysis, featuring inclusion of an additional geometry optimization process, demonstrated more conclusive probability scores among the analyses used. The configurational assignment was also supported by compositional and molecular orbital analyses. Compound1inhibited soluble epoxide hydrolase (IC50= 0.6 ± 0.01 μM), an enzyme associated with cardiovascular disorders.",

author = "Quan, \{Khong Trong\} and Park, \{In Wha\} and Kim, \{Chung Sub\} and Wesley Yoshida and Daneel Ferreira and Thuong, \{Phuong Thien\} and Kim, \{Young Ho\} and Na, \{Min Kyun\} and Joonseok Oh",

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year = "2021",

month = sep,

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doi = "10.1021/acs.jnatprod.1c00037",

language = "English",

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T1 - Configurational Assignment of a Flexible Benzo[g]isochromene Stereodiad fromRubia philippinensisand Inhibition of Soluble Epoxide Hydrolase Activity

AU - Quan, Khong Trong

AU - Park, In Wha

AU - Kim, Chung Sub

AU - Yoshida, Wesley

AU - Ferreira, Daneel

AU - Thuong, Phuong Thien

AU - Kim, Young Ho

AU - Na, Min Kyun

AU - Oh, Joonseok

PY - 2021/9/24

Y1 - 2021/9/24

N2 - A new benzo[g]isochromene possessing a conformationally mobile moiety was identified fromRubia philippinensis. The 2D structure was established utilizing spectrometric and spectroscopic techniques with variable temperatures. The configurational investigation of the flexible moiety was investigated utilizing contemporary NMR-combined computational tools such as DP4, directJ-DP4, and DP4 Plus. The probabilities computed from DP4 Plus analysis, featuring inclusion of an additional geometry optimization process, demonstrated more conclusive probability scores among the analyses used. The configurational assignment was also supported by compositional and molecular orbital analyses. Compound1inhibited soluble epoxide hydrolase (IC50= 0.6 ± 0.01 μM), an enzyme associated with cardiovascular disorders.

AB - A new benzo[g]isochromene possessing a conformationally mobile moiety was identified fromRubia philippinensis. The 2D structure was established utilizing spectrometric and spectroscopic techniques with variable temperatures. The configurational investigation of the flexible moiety was investigated utilizing contemporary NMR-combined computational tools such as DP4, directJ-DP4, and DP4 Plus. The probabilities computed from DP4 Plus analysis, featuring inclusion of an additional geometry optimization process, demonstrated more conclusive probability scores among the analyses used. The configurational assignment was also supported by compositional and molecular orbital analyses. Compound1inhibited soluble epoxide hydrolase (IC50= 0.6 ± 0.01 μM), an enzyme associated with cardiovascular disorders.

UR - https://www.scopus.com/pages/publications/85114467970

U2 - 10.1021/acs.jnatprod.1c00037

DO - 10.1021/acs.jnatprod.1c00037

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SN - 0163-3864

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JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 9

ER -

Configurational Assignment of a Flexible Benzo[g]isochromene Stereodiad fromRubia philippinensisand Inhibition of Soluble Epoxide Hydrolase Activity

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