Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE

Zhixiang Yang, Yoshikazu Kitano, Kazuhiro Chiba, Naohiro Shibata, Hiroshi Kurokawa, Yohei Doi, Yoshichika Arakawa, Masahiro Tada

Research output: Contribution to journalArticle

67 Citations (Scopus)

Abstract

Variously oxidized 12 natural abietanes, 6,7-dehydroferruginol methyl ether (3), ferruginol (5), 11-hydroxy-12-oxo-7,9(11),13-abietatriene (7), royleanone (9), demethyl cryptojaponol (12), salvinolone (14), sugiol methyl ether (16), sugiol (17), 5,6-dehydrosugiol methyl ether (19), 5,6-dehydrosugiol (20), 6β-hydroxyferruginol (23), and taxodione (25) were synthesized. Antimicrobial activities of synthesized phenolic diterpenes and their related compounds against MRSA and VRE were evaluated. Phenols (12-hydroxyabieta-8,11,13-trien-6-one 22 and 23), catechols (12 and 14) and taxodione 25 showed potent activity with 4-10 μg/mL of MIC against MRSA and 4-16 μg/mL of MIC against VRE. (-)-Ferruginol showed more potent activity than natural type (+)-ferruginol. Quinone methide 7 showed the most potent activity with 0.5-1 μg/mL of MIC against both MRSA and VRE.

Original languageEnglish
Pages (from-to)347-356
Number of pages10
JournalBioorganic and Medicinal Chemistry
Volume9
Issue number2
DOIs
Publication statusPublished - 10-04-2001
Externally publishedYes

Fingerprint

Abietane Diterpenes
Methyl Ethers
Methicillin-Resistant Staphylococcus aureus
Catechols
Trientine
Diterpenes
Phenols
ferruginol
sugiol
taxodione

All Science Journal Classification (ASJC) codes

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

Cite this

Yang, Zhixiang ; Kitano, Yoshikazu ; Chiba, Kazuhiro ; Shibata, Naohiro ; Kurokawa, Hiroshi ; Doi, Yohei ; Arakawa, Yoshichika ; Tada, Masahiro. / Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE. In: Bioorganic and Medicinal Chemistry. 2001 ; Vol. 9, No. 2. pp. 347-356.
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Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE. / Yang, Zhixiang; Kitano, Yoshikazu; Chiba, Kazuhiro; Shibata, Naohiro; Kurokawa, Hiroshi; Doi, Yohei; Arakawa, Yoshichika; Tada, Masahiro.

In: Bioorganic and Medicinal Chemistry, Vol. 9, No. 2, 10.04.2001, p. 347-356.

Research output: Contribution to journalArticle

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AU - Arakawa, Yoshichika

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