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Total Synthesis and Anticancer Activity of Novel Pulsatilla Saponin D Analogues

Authors
 Minkyu Kim  ;  Yongseo Park  ;  Won-Yoon Chung  ;  Kwang-Kyun Park  ;  Mankil Jung 
Citation
 CHEMICAL & PHARMACEUTICAL BULLETIN, Vol.63(9) : 669-677, 2015 
Journal Title
 CHEMICAL & PHARMACEUTICAL BULLETIN 
ISSN
 0009-2363 
Issue Date
2015
MeSH
Antineoplastic Agents, Phytogenic/chemical synthesis ; Antineoplastic Agents, Phytogenic/chemistry ; Antineoplastic Agents, Phytogenic/pharmacology* ; Cell Line, Tumor ; Cell Proliferation/drug effects ; Cell Survival/drug effects ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Humans ; MCF-7 Cells ; Molecular Structure ; Saponins/chemical synthesis ; Saponins/chemistry ; Saponins/pharmacology* ; Structure-Activity Relationship
Keywords
Pulsatilla saponin D ; total synthesis ; stereospecific glycosylation ; hederagenin ; anticancer activity
Abstract
Novel saponins that retain a free carboxyl group at the C-17 position and various sugars linked at the C-3 position of hederagenin aglycone were synthesized via stereospecific glycosylation. Since these natural products represented by Pulsatilla saponin D (PSD) were obtained in very small amounts, the total synthesis developed in this paper will resolve this problem of scarcity. The two types of synthesized arabinose- and rhamnose-cored saponins showed potent anticancer activity against a human lung cancer cell line (A549), and most disaccharide moiety saponins possessed more potent anti-lung cancer activity. Among the novel PSD analogues containing disaccharide saponins, compound 10i showed anti-lung cancer activity (6.6 µM) that was four-fold more potent than the clinical agent Iressa (26.08 µM).
Files in This Item:
T201503995.pdf Download
DOI
10.1248/cpb.c15-00106
Appears in Collections:
2. College of Dentistry (치과대학) > Dept. of Oral Biology (구강생물학교실) > 1. Journal Papers
Yonsei Authors
Park, Kwang Kyun(박광균)
Chung, Won Yoon(정원윤) ORCID logo https://orcid.org/0000-0001-8428-9005
URI
https://ir.ymlib.yonsei.ac.kr/handle/22282913/141550
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