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

doi:10.1016/S0968-0896(00)00253-4

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 journal › Article › peer-review

86 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 language	English
Pages (from-to)	347-356
Number of pages	10
Journal	Bioorganic and Medicinal Chemistry
Volume	9
Issue number	2
DOIs	https://doi.org/10.1016/S0968-0896(00)00253-4
Publication status	Published - 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

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

Access to Document

10.1016/S0968-0896(00)00253-4

Cite this

@article{81f766144b394af49c34a5ded0072f48,

title = "Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE",

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.",

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

year = "2001",

doi = "10.1016/S0968-0896(00)00253-4",

language = "English",

volume = "9",

pages = "347--356",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Ltd",

number = "2",

}

TY - JOUR

T1 - Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE

AU - Yang, Zhixiang

AU - Kitano, Yoshikazu

AU - Chiba, Kazuhiro

AU - Shibata, Naohiro

AU - Kurokawa, Hiroshi

AU - Doi, Yohei

AU - Arakawa, Yoshichika

AU - Tada, Masahiro

PY - 2001

Y1 - 2001

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0035086456

UR - https://www.scopus.com/pages/publications/0035086456#tab=citedBy

U2 - 10.1016/S0968-0896(00)00253-4

DO - 10.1016/S0968-0896(00)00253-4

M3 - Article

C2 - 11249127

AN - SCOPUS:0035086456

SN - 0968-0896

VL - 9

SP - 347

EP - 356

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 2

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this