Study on the stevioside analogues of steviolbioside, steviol, and isosteviol 19-alkyl amide dimers: Synthesis and cytotoxic and antibacterial activity

Lun Huei Lin, Lin Wen Lee, Shiow Yunn Sheu, Pen Yuan Lin

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

A new group of steviolbioside amide dimers 2a - g, derivatives 2h - i and their related steviol and isosteviol amide dimers 3a and 4a were prepared by reacting aliphatic alkylamine and alkyldiamines with PyBOP and DIEA. The synthesized compounds had cytotoxic effects on cancer and human embryonic lung cells. Compounds 3a, 4a, 2b and 2h were cytotoxic to cancer cells and to a lesser extent to human embryo lung cells. Compounds 2f, 2g and 4 of this series had favorable antibacterial effects, and were superior to penicillin G at inhibiting growth of Bacillus subtilis (BCRC 10029). The cytotoxicity and antibacterial effects may depend on the dimerization and derivative moieties in relation to the respective aglycons.

Original languageEnglish
Pages (from-to)1117-1122
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume52
Issue number9
DOIs
Publication statusPublished - Sep 2004

Fingerprint

Amides
Dimers
Derivatives
Penicillin G
Dimerization
Bacilli
Cytotoxicity
Lung
Cells
Bacillus subtilis
Neoplasms
Embryonic Structures
Growth
steviol
stevioside
steviolbioside
isosteviol
N,N-diisopropylethylamine

Keywords

  • Antibacterial activity
  • Carboxamide dimer
  • Cytotoxicity
  • Steviolbioside analogue
  • Stevioside

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Pharmacology

Cite this

Study on the stevioside analogues of steviolbioside, steviol, and isosteviol 19-alkyl amide dimers : Synthesis and cytotoxic and antibacterial activity. / Lin, Lun Huei; Lee, Lin Wen; Sheu, Shiow Yunn; Lin, Pen Yuan.

In: Chemical and Pharmaceutical Bulletin, Vol. 52, No. 9, 09.2004, p. 1117-1122.

Research output: Contribution to journalArticle

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