A new angular naphthopyrone from feather star Comanthus parvicirrus (Müller, 1841)

Zong You Ke; Jun Wen Chen; Bo Yan Wu; Yi Yan Jhan; Zhi Hong Wen; Te An Kung; Ping Jyun Sung; Jih Jung Chen; Kuei Hung Lai; Hsu Ming Chung

doi:10.1016/j.molstruc.2021.132261

A new angular naphthopyrone from feather star Comanthus parvicirrus (Müller, 1841)

Zong You Ke, Jun Wen Chen, Bo Yan Wu, Yi Yan Jhan, Zhi Hong Wen, Te An Kung, Ping Jyun Sung, Jih Jung Chen, Kuei Hung Lai, Hsu Ming Chung

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

1 Citation (Scopus)

Abstract

A chemical investigation was carried out on a feather star Comanthus parvicirrus collected from the waters of Southern Taiwan, which led to the isolation of three angular naphthopyrones (1–3), including one new metabolite, 8‑hydroxy-5,6,9,10-tetramethoxy-2-methyl-4H-benzo[h]chromen-4-one (1). The structures of compounds 1–3 were assigned based on spectroscopic methods, including UV, MS, 1D- and 2D-NMR spectra, and the structure of 1 was established by single-crystal X-ray diffraction analysis directly. The compound 3 were found to exhibit significant anti-inflammatory activity in lipopolysaccharide (LPS)-induced RAW264.7 mouse macrophages through attenuating the expression of the inducible nitric oxide synthase (iNOS) proteins.

Original language	English
Article number	132261
Journal	Journal of Molecular Structure
Volume	1253
DOIs	https://doi.org/10.1016/j.molstruc.2021.132261
Publication status	Published - Apr 5 2022

Keywords

Comanthus parvicirrus
Crinoid
Feather star
iNOS
Naphthopyrone
X-ray

ASJC Scopus subject areas

Analytical Chemistry
Spectroscopy
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1016/j.molstruc.2021.132261

Cite this

@article{f684d072c4354e9ebc5e0ea56537cce5,

title = "A new angular naphthopyrone from feather star Comanthus parvicirrus (M{\"u}ller, 1841)",

abstract = "A chemical investigation was carried out on a feather star Comanthus parvicirrus collected from the waters of Southern Taiwan, which led to the isolation of three angular naphthopyrones (1–3), including one new metabolite, 8‑hydroxy-5,6,9,10-tetramethoxy-2-methyl-4H-benzo[h]chromen-4-one (1). The structures of compounds 1–3 were assigned based on spectroscopic methods, including UV, MS, 1D- and 2D-NMR spectra, and the structure of 1 was established by single-crystal X-ray diffraction analysis directly. The compound 3 were found to exhibit significant anti-inflammatory activity in lipopolysaccharide (LPS)-induced RAW264.7 mouse macrophages through attenuating the expression of the inducible nitric oxide synthase (iNOS) proteins.",

keywords = "Comanthus parvicirrus, Crinoid, Feather star, iNOS, Naphthopyrone, X-ray",

author = "Ke, {Zong You} and Chen, {Jun Wen} and Wu, {Bo Yan} and Jhan, {Yi Yan} and Wen, {Zhi Hong} and Kung, {Te An} and Sung, {Ping Jyun} and Chen, {Jih Jung} and Lai, {Kuei Hung} and Chung, {Hsu Ming}",

note = "Funding Information: This research was supported by the grants from the National Pingtung University and the Ministry of Science and Technology, Taiwan (Grant Nos: MOST 110-2320-B-153-001) awarded to Hsu-Ming Chung; by the grant from the Ministry of Science and Technology (MOST 110-2320-B-038-034), Ministry of Education (DP2-110-21121-01-N-12-03), and Taipei Medical University (TMU109-AE1-B15) awarded to Kuei-Hung Lai. The authors are thankful the High Valued Instrument Center, National Sun Yat-sen University, for the mass (MS000600) and NMR (NMR001100) Spectra (MOST 110-2731-M-110-001); and to the Instrumentation Center, National Taiwan University for providing X-ray facilities (MOST 110–2731-M-002–001, XRD000200). Funding Information: This research was supported by the grants from the National Pingtung University and the Ministry of Science and Technology, Taiwan (Grant Nos: MOST 110-2320-B-153-001) awarded to Hsu-Ming Chung; by the grant from the Ministry of Science and Technology (MOST 110-2320-B-038-034), Ministry of Education (DP2-110-21121-01-N-12-03), and Taipei Medical University (TMU109-AE1-B15) awarded to Kuei-Hung Lai. The authors are thankful the High Valued Instrument Center, National Sun Yat-sen University, for the mass (MS000600) and NMR (NMR001100) Spectra (MOST 110-2731-M-110-001); and to the Instrumentation Center, National Taiwan University for providing X-ray facilities (MOST 110?2731-M-002?001, XRD000200). Publisher Copyright: {\textcopyright} 2021 The Author(s)",

year = "2022",

month = apr,

day = "5",

doi = "10.1016/j.molstruc.2021.132261",

language = "English",

volume = "1253",

journal = "Journal of Molecular Structure",

issn = "0022-2860",

publisher = "Elsevier",

}

TY - JOUR

T1 - A new angular naphthopyrone from feather star Comanthus parvicirrus (Müller, 1841)

AU - Ke, Zong You

AU - Chen, Jun Wen

AU - Wu, Bo Yan

AU - Jhan, Yi Yan

AU - Wen, Zhi Hong

AU - Kung, Te An

AU - Sung, Ping Jyun

AU - Chen, Jih Jung

AU - Lai, Kuei Hung

AU - Chung, Hsu Ming

N1 - Funding Information: This research was supported by the grants from the National Pingtung University and the Ministry of Science and Technology, Taiwan (Grant Nos: MOST 110-2320-B-153-001) awarded to Hsu-Ming Chung; by the grant from the Ministry of Science and Technology (MOST 110-2320-B-038-034), Ministry of Education (DP2-110-21121-01-N-12-03), and Taipei Medical University (TMU109-AE1-B15) awarded to Kuei-Hung Lai. The authors are thankful the High Valued Instrument Center, National Sun Yat-sen University, for the mass (MS000600) and NMR (NMR001100) Spectra (MOST 110-2731-M-110-001); and to the Instrumentation Center, National Taiwan University for providing X-ray facilities (MOST 110–2731-M-002–001, XRD000200). Funding Information: This research was supported by the grants from the National Pingtung University and the Ministry of Science and Technology, Taiwan (Grant Nos: MOST 110-2320-B-153-001) awarded to Hsu-Ming Chung; by the grant from the Ministry of Science and Technology (MOST 110-2320-B-038-034), Ministry of Education (DP2-110-21121-01-N-12-03), and Taipei Medical University (TMU109-AE1-B15) awarded to Kuei-Hung Lai. The authors are thankful the High Valued Instrument Center, National Sun Yat-sen University, for the mass (MS000600) and NMR (NMR001100) Spectra (MOST 110-2731-M-110-001); and to the Instrumentation Center, National Taiwan University for providing X-ray facilities (MOST 110?2731-M-002?001, XRD000200). Publisher Copyright: © 2021 The Author(s)

PY - 2022/4/5

Y1 - 2022/4/5

N2 - A chemical investigation was carried out on a feather star Comanthus parvicirrus collected from the waters of Southern Taiwan, which led to the isolation of three angular naphthopyrones (1–3), including one new metabolite, 8‑hydroxy-5,6,9,10-tetramethoxy-2-methyl-4H-benzo[h]chromen-4-one (1). The structures of compounds 1–3 were assigned based on spectroscopic methods, including UV, MS, 1D- and 2D-NMR spectra, and the structure of 1 was established by single-crystal X-ray diffraction analysis directly. The compound 3 were found to exhibit significant anti-inflammatory activity in lipopolysaccharide (LPS)-induced RAW264.7 mouse macrophages through attenuating the expression of the inducible nitric oxide synthase (iNOS) proteins.

AB - A chemical investigation was carried out on a feather star Comanthus parvicirrus collected from the waters of Southern Taiwan, which led to the isolation of three angular naphthopyrones (1–3), including one new metabolite, 8‑hydroxy-5,6,9,10-tetramethoxy-2-methyl-4H-benzo[h]chromen-4-one (1). The structures of compounds 1–3 were assigned based on spectroscopic methods, including UV, MS, 1D- and 2D-NMR spectra, and the structure of 1 was established by single-crystal X-ray diffraction analysis directly. The compound 3 were found to exhibit significant anti-inflammatory activity in lipopolysaccharide (LPS)-induced RAW264.7 mouse macrophages through attenuating the expression of the inducible nitric oxide synthase (iNOS) proteins.

KW - Comanthus parvicirrus

KW - Crinoid

KW - Feather star

KW - iNOS

KW - Naphthopyrone

KW - X-ray

UR - http://www.scopus.com/inward/record.url?scp=85121935157&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85121935157&partnerID=8YFLogxK

U2 - 10.1016/j.molstruc.2021.132261

DO - 10.1016/j.molstruc.2021.132261

M3 - Article

AN - SCOPUS:85121935157

SN - 0022-2860

VL - 1253

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

M1 - 132261

ER -

A new angular naphthopyrone from feather star Comanthus parvicirrus (Müller, 1841)

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 2117795: Experimental Crystal Structure Determination

Cite this

A new angular naphthopyrone from feather star Comanthus parvicirrus (Müller, 1841)

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 2117795: Experimental Crystal Structure Determination

Cite this