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

^*此作品的通信作者

中醫學系(含學士班、天然藥物、傳統中醫藥碩士班)

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

研究成果: 期刊稿件 › 文章 › 同行評審

9 引文斯高帕斯（Scopus）

摘要

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).

原文	英語
文章編號	22963
頁（從 - 到）	3822-3824
頁數	3
期刊	Bioorganic and Medicinal Chemistry Letters
卷	25
發行號	18
DOIs	https://doi.org/10.1016/j.bmcl.2015.07.074
出版狀態	已出版 - 17 08 2015

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© 2015 Elsevier Ltd.

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10.1016/j.bmcl.2015.07.074

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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",

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day = "17",

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

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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

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