Tsaokoic Acid: A New Bicyclic Nonene from the Fruits of Amomum tsao-ko with Acetylcholinesterase Inhibitory Activity

Hyunyoung Kim; Hwaryeong Lee; Hee Jin Jung; Sang Gyun Noh; Isoo Youn; Hyunkyung Kwak; Yeju Lee; Sang Jip Nam; Soosung Kang; Hae Young Chung; Eun Kyoung Seo

doi:10.3390/molecules28062602

Tsaokoic Acid: A New Bicyclic Nonene from the Fruits of Amomum tsao-ko with Acetylcholinesterase Inhibitory Activity

Hyunyoung Kim, Hwaryeong Lee, Hee Jin Jung, Sang Gyun Noh, Isoo Youn, Hyunkyung Kwak, Yeju Lee, Sang Jip Nam, Soosung Kang, Hae Young Chung, Eun Kyoung Seo

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

1 Scopus citations

Abstract

A new bicyclic nonene, tsaokoic acid (1), was isolated from the fruits of Amomum tsao-ko, together with three known compounds (2–4). The structure of 1 was elucidated by analyzing spectroscopic data including 1D and 2D NMR spectra and compounds 2–4 were identified as tsaokoin, vanillin, and tsaokoarylone, respectively, by comparing their NMR spectra with previously reported data. Compounds 1–4 showed possible inhibitory activity against acetylcholinesterase (AChE) in silico molecular docking simulations. They were submitted to in vitro assay system and exhibited moderate inhibitory activity with IC₅₀ values of 32.78, 41.70, 39.25, and 31.13 μM, respectively.

Original language	English
Article number	2602
Journal	Molecules
Volume	28
Issue number	6
DOIs	https://doi.org/10.3390/molecules28062602
State	Published - Mar 2023

Bibliographical note

Publisher Copyright:
© 2023 by the authors.

Keywords

Amomum tsao-ko
Zingiberaceae
acetylcholinesterase
bicyclic nonene

Access to Document

10.3390/molecules28062602

Cite this

@article{3db684fae01d4c6e937c7261855b4b29,

title = "Tsaokoic Acid: A New Bicyclic Nonene from the Fruits of Amomum tsao-ko with Acetylcholinesterase Inhibitory Activity",

abstract = "A new bicyclic nonene, tsaokoic acid (1), was isolated from the fruits of Amomum tsao-ko, together with three known compounds (2–4). The structure of 1 was elucidated by analyzing spectroscopic data including 1D and 2D NMR spectra and compounds 2–4 were identified as tsaokoin, vanillin, and tsaokoarylone, respectively, by comparing their NMR spectra with previously reported data. Compounds 1–4 showed possible inhibitory activity against acetylcholinesterase (AChE) in silico molecular docking simulations. They were submitted to in vitro assay system and exhibited moderate inhibitory activity with IC50 values of 32.78, 41.70, 39.25, and 31.13 μM, respectively.",

keywords = "Amomum tsao-ko, Zingiberaceae, acetylcholinesterase, bicyclic nonene",

author = "Hyunyoung Kim and Hwaryeong Lee and Jung, {Hee Jin} and Noh, {Sang Gyun} and Isoo Youn and Hyunkyung Kwak and Yeju Lee and Nam, {Sang Jip} and Soosung Kang and Chung, {Hae Young} and Seo, {Eun Kyoung}",

note = "Publisher Copyright: {\textcopyright} 2023 by the authors.",

year = "2023",

month = mar,

doi = "10.3390/molecules28062602",

language = "English",

volume = "28",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "6",

}

TY - JOUR

T1 - Tsaokoic Acid

T2 - A New Bicyclic Nonene from the Fruits of Amomum tsao-ko with Acetylcholinesterase Inhibitory Activity

AU - Kim, Hyunyoung

AU - Lee, Hwaryeong

AU - Jung, Hee Jin

AU - Noh, Sang Gyun

AU - Youn, Isoo

AU - Kwak, Hyunkyung

AU - Lee, Yeju

AU - Nam, Sang Jip

AU - Kang, Soosung

AU - Chung, Hae Young

AU - Seo, Eun Kyoung

PY - 2023/3

Y1 - 2023/3

N2 - A new bicyclic nonene, tsaokoic acid (1), was isolated from the fruits of Amomum tsao-ko, together with three known compounds (2–4). The structure of 1 was elucidated by analyzing spectroscopic data including 1D and 2D NMR spectra and compounds 2–4 were identified as tsaokoin, vanillin, and tsaokoarylone, respectively, by comparing their NMR spectra with previously reported data. Compounds 1–4 showed possible inhibitory activity against acetylcholinesterase (AChE) in silico molecular docking simulations. They were submitted to in vitro assay system and exhibited moderate inhibitory activity with IC50 values of 32.78, 41.70, 39.25, and 31.13 μM, respectively.

AB - A new bicyclic nonene, tsaokoic acid (1), was isolated from the fruits of Amomum tsao-ko, together with three known compounds (2–4). The structure of 1 was elucidated by analyzing spectroscopic data including 1D and 2D NMR spectra and compounds 2–4 were identified as tsaokoin, vanillin, and tsaokoarylone, respectively, by comparing their NMR spectra with previously reported data. Compounds 1–4 showed possible inhibitory activity against acetylcholinesterase (AChE) in silico molecular docking simulations. They were submitted to in vitro assay system and exhibited moderate inhibitory activity with IC50 values of 32.78, 41.70, 39.25, and 31.13 μM, respectively.

KW - Amomum tsao-ko

KW - Zingiberaceae

KW - acetylcholinesterase

KW - bicyclic nonene

UR - http://www.scopus.com/inward/record.url?scp=85151112311&partnerID=8YFLogxK

U2 - 10.3390/molecules28062602

DO - 10.3390/molecules28062602

M3 - Article

C2 - 36985573

AN - SCOPUS:85151112311

SN - 1420-3049

VL - 28

JO - Molecules

JF - Molecules

IS - 6

M1 - 2602

ER -

Tsaokoic Acid: A New Bicyclic Nonene from the Fruits of Amomum tsao-ko with Acetylcholinesterase Inhibitory Activity

Abstract

Bibliographical note

Keywords

Access to Document

Fingerprint

Cite this