Total synthesis of cordatanine, structural reassignment of drymaritin, and anti-inflammatory activity of synthetic precursor

Hsin Wei Fang; Yu Ren Liao; Tsong Long Hwang; Po Chuen Shieh; Kuo Hsiung Lee; Hsin Yi Hung; Tian Shung Wu

doi:10.1016/j.bmcl.2015.07.074

Total synthesis of cordatanine, structural reassignment of drymaritin, and anti-inflammatory activity of synthetic precursor

Hsin Wei Fang
, Yu Ren Liao
, Tsong Long Hwang
, Po Chuen Shieh
, Kuo Hsiung Lee
, Hsin Yi Hung^*
, Tian Shung Wu

^*Corresponding author for this work

School of Traditional Chinese Medicine

National Cheng Kung University
Tajen University
University of North Carolina at Chapel Hill
China Medical University Taichung

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

9 Scopus citations

Abstract

Abstract In this study, cordatanine, with a canthin-6-one skeleton, was totally synthesized in four steps via a Pictet-Spengler reaction using tryptamine and methyl glyoxylate with a total yield of 8%. The NMR spectra of synthesized cordatanine compared well with those of drymaritin isolated by Hsieh et al., confirming the need to revise the original structural assignment. In addition, kumujian A, a synthetic intermediate, showed significant anti-inflammatory effects, inhibiting both superoxide anion generation (IC₅₀ 4.87 μg/mL) and elastase release (IC₅₀ 6.29 μg/mL).

Original language	English
Article number	22963
Pages (from-to)	3822-3824
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	25
Issue number	18
DOIs	https://doi.org/10.1016/j.bmcl.2015.07.074
State	Published - 17 08 2015

Bibliographical note

Publisher Copyright:
© 2015 Elsevier Ltd.

Keywords

Cordatanine
Drymaritin
Kumujian A

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10.1016/j.bmcl.2015.07.074

Cite this

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title = "Total synthesis of cordatanine, structural reassignment of drymaritin, and anti-inflammatory activity of synthetic precursor",

abstract = "Abstract In this study, cordatanine, with a canthin-6-one skeleton, was totally synthesized in four steps via a Pictet-Spengler reaction using tryptamine and methyl glyoxylate with a total yield of 8\%. The NMR spectra of synthesized cordatanine compared well with those of drymaritin isolated by Hsieh et al., confirming the need to revise the original structural assignment. In addition, kumujian A, a synthetic intermediate, showed significant anti-inflammatory effects, inhibiting both superoxide anion generation (IC50 4.87 μg/mL) and elastase release (IC50 6.29 μg/mL).",

keywords = "Cordatanine, Drymaritin, Kumujian A",

author = "Fang, \{Hsin Wei\} and Liao, \{Yu Ren\} and Hwang, \{Tsong Long\} and Shieh, \{Po Chuen\} and Lee, \{Kuo Hsiung\} and Hung, \{Hsin Yi\} and Wu, \{Tian Shung\}",

note = "Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

year = "2015",

month = aug,

day = "17",

doi = "10.1016/j.bmcl.2015.07.074",

language = "英语",

volume = "25",

pages = "3822--3824",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

number = "18",

}

TY - JOUR

T1 - Total synthesis of cordatanine, structural reassignment of drymaritin, and anti-inflammatory activity of synthetic precursor

AU - Fang, Hsin Wei

AU - Liao, Yu Ren

AU - Hwang, Tsong Long

AU - Shieh, Po Chuen

AU - Lee, Kuo Hsiung

AU - Hung, Hsin Yi

AU - Wu, Tian Shung

PY - 2015/8/17

Y1 - 2015/8/17

N2 - Abstract In this study, cordatanine, with a canthin-6-one skeleton, was totally synthesized in four steps via a Pictet-Spengler reaction using tryptamine and methyl glyoxylate with a total yield of 8%. The NMR spectra of synthesized cordatanine compared well with those of drymaritin isolated by Hsieh et al., confirming the need to revise the original structural assignment. In addition, kumujian A, a synthetic intermediate, showed significant anti-inflammatory effects, inhibiting both superoxide anion generation (IC50 4.87 μg/mL) and elastase release (IC50 6.29 μg/mL).

AB - Abstract In this study, cordatanine, with a canthin-6-one skeleton, was totally synthesized in four steps via a Pictet-Spengler reaction using tryptamine and methyl glyoxylate with a total yield of 8%. The NMR spectra of synthesized cordatanine compared well with those of drymaritin isolated by Hsieh et al., confirming the need to revise the original structural assignment. In addition, kumujian A, a synthetic intermediate, showed significant anti-inflammatory effects, inhibiting both superoxide anion generation (IC50 4.87 μg/mL) and elastase release (IC50 6.29 μg/mL).

KW - Cordatanine

KW - Drymaritin

KW - Kumujian A

UR - https://www.scopus.com/pages/publications/84939156068

U2 - 10.1016/j.bmcl.2015.07.074

DO - 10.1016/j.bmcl.2015.07.074

M3 - 文章

C2 - 26248804

AN - SCOPUS:84939156068

SN - 0960-894X

VL - 25

SP - 3822

EP - 3824

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 18

M1 - 22963

ER -

Total synthesis of cordatanine, structural reassignment of drymaritin, and anti-inflammatory activity of synthetic precursor

Abstract

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Keywords

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