Synthetic analogues of durantoside I from Citharexylum spinosum L. and their cytotoxic activity

Jutamas Apisornopas; Patamawadee Silalai; Teerapich Kasemsuk; Anan Athipornchai; Uthaiwan Sirion; Kanoknetr Suksen; Pawinee Piyachaturawat; Apichart Suksamrarn; Rungnapha Saeeng

doi:10.1016/j.bmcl.2018.03.068

Synthetic analogues of durantoside I from Citharexylum spinosum L. and their cytotoxic activity

Bioorg Med Chem Lett. 2018 May 15;28(9):1558-1561. doi: 10.1016/j.bmcl.2018.03.068. Epub 2018 Mar 27.

Authors

Jutamas Apisornopas¹, Patamawadee Silalai¹, Teerapich Kasemsuk², Anan Athipornchai¹, Uthaiwan Sirion¹, Kanoknetr Suksen³, Pawinee Piyachaturawat³, Apichart Suksamrarn⁴, Rungnapha Saeeng⁵

Affiliations

¹ Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Burapha University, Chonburi 20131, Thailand.
² Department of Chemistry, Faculty of Science and Technology, Rambhai Barni Rajabhat University, Chanthaburi 22000, Thailand.
³ Department of Physiology, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
⁴ Department of Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok 10240, Thailand.
⁵ Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Burapha University, Chonburi 20131, Thailand. Electronic address: rungnaph@buu.ac.th.

PMID: 29606574
DOI: 10.1016/j.bmcl.2018.03.068

Abstract

New iridoid glycoside derivatives from durantoside I, the latter from the dried flowers and leaves of Citharexylum spinosum, were synthesized by variously modifying a sugar moiety by silylation or acetylation and/or removal of cinnamate group at C-7 position and subsequent screening for comparative cytotoxicity against several cancer cell lines. Addition of alkylsilane to durantoside I and removal of cinnamate group were most effective in improving cytotoxicity.

Keywords: Citharexylum spinosum L.; Cytotoxic activity; Durantoside I; Iridoid glycoside.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Glycosides / chemistry
Glycosides / isolation & purification
Glycosides / pharmacology*
Humans
Iridoid Glycosides / chemistry
Iridoid Glycosides / isolation & purification
Iridoid Glycosides / pharmacology*
Iridoids / chemistry
Iridoids / isolation & purification
Iridoids / pharmacology*
Mice
Molecular Structure
Rats
Structure-Activity Relationship
Verbenaceae / chemistry*

Substances

Antineoplastic Agents, Phytogenic
Glycosides
Iridoid Glycosides
Iridoids
durantoside I