Synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents

Zhiwen Zhou; Cong Ma; Hengyuan Zhang; Yi Bi; Xia Chen; Hua Tian; Xiaoni Xie; Qingguo Meng; Peter John Lewis; Jinyi Xu

doi:10.1016/j.ejmech.2013.07.041

Synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents

Zhiwen Zhou, Cong Ma, Hengyuan Zhang, Yi Bi, Xia Chen, Hua Tian, Xiaoni Xie, Qingguo Meng, Peter John Lewis, Jinyi Xu

Research output: Journal article publication › Journal article › Academic research › peer-review

46 Citations (Scopus)

Abstract

A novel class of ocotillol-type triterpenoid derivatives have been synthesized and evaluated for their in vitro antibacterial activity against several representative pathogenic bacterial strains. Compounds 20(S)-protopanaxadiol (PPD), 3, 5, 16 and 24 exhibited potent antibacterial activity against Gram-positive bacteria. Compounds 3 and 5 also displayed promising antibacterial activity against a community-associated methicillin-resistant Staphylococcus aureus (CA-MRSA; strain USA300). Furthermore, compounds PPD, 3 and 16 combined with two commercially available antibiotics kanamycin and chloramphenicol showed strong synergistic inhibitory effects at their sub-MIC concentrations against S. aureus USA300 and Bacillus subtilis 168. Additionally, cytotoxic activity assay showed that the compounds tested did not affect cell viability of the human epithelial kidney (HEK-293) and human cervical (HeLa) cells at their MICs.

Original language	English
Pages (from-to)	444-453
Number of pages	10
Journal	European Journal of Medicinal Chemistry
Volume	68
DOIs	https://doi.org/10.1016/j.ejmech.2013.07.041
Publication status	Published - 1 Jan 2013
Externally published	Yes

Keywords

Antibacterial activity
Cytotoxicity
Ocotillol
Synergistic effect
Triterpenoid

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

More information

10.1016/j.ejmech.2013.07.041

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title = "Synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents",

abstract = "A novel class of ocotillol-type triterpenoid derivatives have been synthesized and evaluated for their in vitro antibacterial activity against several representative pathogenic bacterial strains. Compounds 20(S)-protopanaxadiol (PPD), 3, 5, 16 and 24 exhibited potent antibacterial activity against Gram-positive bacteria. Compounds 3 and 5 also displayed promising antibacterial activity against a community-associated methicillin-resistant Staphylococcus aureus (CA-MRSA; strain USA300). Furthermore, compounds PPD, 3 and 16 combined with two commercially available antibiotics kanamycin and chloramphenicol showed strong synergistic inhibitory effects at their sub-MIC concentrations against S. aureus USA300 and Bacillus subtilis 168. Additionally, cytotoxic activity assay showed that the compounds tested did not affect cell viability of the human epithelial kidney (HEK-293) and human cervical (HeLa) cells at their MICs.",

keywords = "Antibacterial activity, Cytotoxicity, Ocotillol, Synergistic effect, Triterpenoid",

author = "Zhiwen Zhou and Cong Ma and Hengyuan Zhang and Yi Bi and Xia Chen and Hua Tian and Xiaoni Xie and Qingguo Meng and Lewis, {Peter John} and Jinyi Xu",

year = "2013",

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doi = "10.1016/j.ejmech.2013.07.041",

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AU - Zhou, Zhiwen

AU - Ma, Cong

AU - Zhang, Hengyuan

AU - Bi, Yi

AU - Chen, Xia

AU - Tian, Hua

AU - Xie, Xiaoni

AU - Meng, Qingguo

AU - Lewis, Peter John

AU - Xu, Jinyi

PY - 2013/1/1

Y1 - 2013/1/1

N2 - A novel class of ocotillol-type triterpenoid derivatives have been synthesized and evaluated for their in vitro antibacterial activity against several representative pathogenic bacterial strains. Compounds 20(S)-protopanaxadiol (PPD), 3, 5, 16 and 24 exhibited potent antibacterial activity against Gram-positive bacteria. Compounds 3 and 5 also displayed promising antibacterial activity against a community-associated methicillin-resistant Staphylococcus aureus (CA-MRSA; strain USA300). Furthermore, compounds PPD, 3 and 16 combined with two commercially available antibiotics kanamycin and chloramphenicol showed strong synergistic inhibitory effects at their sub-MIC concentrations against S. aureus USA300 and Bacillus subtilis 168. Additionally, cytotoxic activity assay showed that the compounds tested did not affect cell viability of the human epithelial kidney (HEK-293) and human cervical (HeLa) cells at their MICs.

AB - A novel class of ocotillol-type triterpenoid derivatives have been synthesized and evaluated for their in vitro antibacterial activity against several representative pathogenic bacterial strains. Compounds 20(S)-protopanaxadiol (PPD), 3, 5, 16 and 24 exhibited potent antibacterial activity against Gram-positive bacteria. Compounds 3 and 5 also displayed promising antibacterial activity against a community-associated methicillin-resistant Staphylococcus aureus (CA-MRSA; strain USA300). Furthermore, compounds PPD, 3 and 16 combined with two commercially available antibiotics kanamycin and chloramphenicol showed strong synergistic inhibitory effects at their sub-MIC concentrations against S. aureus USA300 and Bacillus subtilis 168. Additionally, cytotoxic activity assay showed that the compounds tested did not affect cell viability of the human epithelial kidney (HEK-293) and human cervical (HeLa) cells at their MICs.

KW - Antibacterial activity

KW - Cytotoxicity

KW - Ocotillol

KW - Synergistic effect

KW - Triterpenoid

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U2 - 10.1016/j.ejmech.2013.07.041

DO - 10.1016/j.ejmech.2013.07.041

M3 - Journal article

C2 - 23994872

SN - 0223-5234

VL - 68

SP - 444

EP - 453

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

ER -

Synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents

Abstract

Keywords

ASJC Scopus subject areas

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