Synthesis and antibacterial evaluation of novel hydrophilic ocotillol-type triterpenoid derivatives from 20(S)-protopanaxadiol

Yi Bi; Cong Ma; Zhiwen Zhou; Tingting Zhang; Hengyuan Zhang; Xiaochen Zhang; Jing Lu; Qingguo Meng; Peter J. Lewis; Jinyi Xu

Synthesis and antibacterial evaluation of novel hydrophilic ocotillol-type triterpenoid derivatives from 20(S)-protopanaxadiol

Yi Bi, Cong Ma, Zhiwen Zhou, Tingting Zhang, Hengyuan Zhang, Xiaochen Zhang, Jing Lu, Qingguo Meng, Peter J. Lewis, Jinyi Xu

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

27 Citations (Scopus)

Abstract

Triterpenoid saponins are involved in plant defense systems to inhibit bacterial invasion. A new series of hydrophilic ocotillol-type triterpenoid derivatives 5-26 have been synthesized with antibacterial activity against Gram-positive bacteria, including a community associated methicillin-resistant Staphylococcus aureus (CA-MRSA; strain USA300). From this series, compounds 6 and 15 were found to be the most active, both with MIC values of 2 μg/mL against B. subtilis 168 and 8 μg/mL against S. aureus USA300, respectively. Furthermore, subsequent assays showed that compounds 6 and 15 displayed strong synergistic effects at sub-MIC levels against both S. aureus USA300 and B. subtilis 168 when combined with two commercial antibiotics, kanamycin and chloramphenicol. Preliminary structure-activity relationship studies were also performed.

Original language	English
Pages (from-to)	356-368
Number of pages	13
Journal	Records of Natural Products
Volume	9
Issue number	3
Publication status	Published - 4 Jan 2015
Externally published	Yes

Keywords

Antibacterial activity
Ocotillol
Synergistic effect
Triterpenoid

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Plant Science
Organic Chemistry

Cite this

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title = "Synthesis and antibacterial evaluation of novel hydrophilic ocotillol-type triterpenoid derivatives from 20(S)-protopanaxadiol",

abstract = "Triterpenoid saponins are involved in plant defense systems to inhibit bacterial invasion. A new series of hydrophilic ocotillol-type triterpenoid derivatives 5-26 have been synthesized with antibacterial activity against Gram-positive bacteria, including a community associated methicillin-resistant Staphylococcus aureus (CA-MRSA; strain USA300). From this series, compounds 6 and 15 were found to be the most active, both with MIC values of 2 μg/mL against B. subtilis 168 and 8 μg/mL against S. aureus USA300, respectively. Furthermore, subsequent assays showed that compounds 6 and 15 displayed strong synergistic effects at sub-MIC levels against both S. aureus USA300 and B. subtilis 168 when combined with two commercial antibiotics, kanamycin and chloramphenicol. Preliminary structure-activity relationship studies were also performed.",

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

author = "Yi Bi and Cong Ma and Zhiwen Zhou and Tingting Zhang and Hengyuan Zhang and Xiaochen Zhang and Jing Lu and Qingguo Meng and Lewis, {Peter J.} and Jinyi Xu",

year = "2015",

month = jan,

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language = "English",

volume = "9",

pages = "356--368",

journal = "Records of Natural Products",

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TY - JOUR

T1 - Synthesis and antibacterial evaluation of novel hydrophilic ocotillol-type triterpenoid derivatives from 20(S)-protopanaxadiol

AU - Bi, Yi

AU - Ma, Cong

AU - Zhou, Zhiwen

AU - Zhang, Tingting

AU - Zhang, Hengyuan

AU - Zhang, Xiaochen

AU - Lu, Jing

AU - Meng, Qingguo

AU - Lewis, Peter J.

AU - Xu, Jinyi

PY - 2015/1/4

Y1 - 2015/1/4

N2 - Triterpenoid saponins are involved in plant defense systems to inhibit bacterial invasion. A new series of hydrophilic ocotillol-type triterpenoid derivatives 5-26 have been synthesized with antibacterial activity against Gram-positive bacteria, including a community associated methicillin-resistant Staphylococcus aureus (CA-MRSA; strain USA300). From this series, compounds 6 and 15 were found to be the most active, both with MIC values of 2 μg/mL against B. subtilis 168 and 8 μg/mL against S. aureus USA300, respectively. Furthermore, subsequent assays showed that compounds 6 and 15 displayed strong synergistic effects at sub-MIC levels against both S. aureus USA300 and B. subtilis 168 when combined with two commercial antibiotics, kanamycin and chloramphenicol. Preliminary structure-activity relationship studies were also performed.

AB - Triterpenoid saponins are involved in plant defense systems to inhibit bacterial invasion. A new series of hydrophilic ocotillol-type triterpenoid derivatives 5-26 have been synthesized with antibacterial activity against Gram-positive bacteria, including a community associated methicillin-resistant Staphylococcus aureus (CA-MRSA; strain USA300). From this series, compounds 6 and 15 were found to be the most active, both with MIC values of 2 μg/mL against B. subtilis 168 and 8 μg/mL against S. aureus USA300, respectively. Furthermore, subsequent assays showed that compounds 6 and 15 displayed strong synergistic effects at sub-MIC levels against both S. aureus USA300 and B. subtilis 168 when combined with two commercial antibiotics, kanamycin and chloramphenicol. Preliminary structure-activity relationship studies were also performed.

KW - Antibacterial activity

KW - Ocotillol

KW - Synergistic effect

KW - Triterpenoid

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M3 - Journal article

SN - 1307-6167

VL - 9

SP - 356

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JO - Records of Natural Products

JF - Records of Natural Products

IS - 3

ER -

Synthesis and antibacterial evaluation of novel hydrophilic ocotillol-type triterpenoid derivatives from 20(S)-protopanaxadiol

Abstract

Keywords

ASJC Scopus subject areas

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