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

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

4 Citations (Scopus)

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
Publication status	Published - 2015 Aug 17

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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@article{fc991f155c6a42249ec4559c877e4e77,

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).",

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}",

year = "2015",

month = aug,

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

language = "English",

volume = "25",

pages = "3822--3824",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "18",

}

Total synthesis of cordatanine, structural reassignment of drymaritin, and anti-inflammatory activity of synthetic precursor. / Fang, Hsin Wei; Liao, Yu Ren; Hwang, Tsong Long; Shieh, Po Chuen; Lee, Kuo Hsiung; Hung, Hsin Yi; Wu, Tian Shung.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 25, No. 18, 22963, 17.08.2015, p. 3822-3824.

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

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).

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