C-Glucosidic ellagitannin oligomers from Melaleuca squarrosa Donn ex Sm., Myrtaceae

Takashi Yoshida, Hideyuki Ito, Morio Yoshimura, Kyoko Miyashita, Tsutomu Hatano

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

C-Glucosidic ellagitannin dimers were classified as types A-C according to a putative biogenetic oligomerization mode. They were characterized by different positions of the C-C bond between the phenolic acyl unit in one monomer and the benzylic C-1 of the open-chain glucose core in the other monomer. In recent years, four C-glucosidic tannins, melasquanins A-D (18-21), have been found in the leaves of Melaleuca squarrosa Donn ex Sm. (Myrtaceae). These are characterized as a dimer (melasquanin A) of a dimerization mode (type D), and trimers (melasquanins B-D) based on spectroscopic analysis including various two-dimensional nuclear magnetic resonance (2D NMR) experiments. Melasquanins B (19) and D (21) are C-glucosidic tannin trimers with a structure containing, non-repeating condensation modes, which was hitherto unknown.

Original languageEnglish
Pages (from-to)3070-3079
Number of pages10
JournalPhytochemistry
Volume69
Issue number18
DOIs
Publication statusPublished - Dec 2008

Fingerprint

Melaleuca
Myrtaceae
Tannins
Oligomers
Dimers
tannins
Monomers
Nuclear magnetic resonance
Dilatation and Curettage
Oligomerization
Spectroscopic analysis
dimerization
Dimerization
nuclear magnetic resonance spectroscopy
Condensation
Magnetic Resonance Spectroscopy
Glucose
glucose
leaves
Experiments

Keywords

  • C-Glucosidic ellagitannin
  • C-Glucosidic tannin trimer
  • Complex tannin
  • Melaleuca squarrosa
  • Melasquanin B
  • Melasquanin C
  • Melasquanin D
  • Myrtaceae

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Horticulture

Cite this

C-Glucosidic ellagitannin oligomers from Melaleuca squarrosa Donn ex Sm., Myrtaceae. / Yoshida, Takashi; Ito, Hideyuki; Yoshimura, Morio; Miyashita, Kyoko; Hatano, Tsutomu.

In: Phytochemistry, Vol. 69, No. 18, 12.2008, p. 3070-3079.

Research output: Contribution to journalArticle

Yoshida, Takashi ; Ito, Hideyuki ; Yoshimura, Morio ; Miyashita, Kyoko ; Hatano, Tsutomu. / C-Glucosidic ellagitannin oligomers from Melaleuca squarrosa Donn ex Sm., Myrtaceae. In: Phytochemistry. 2008 ; Vol. 69, No. 18. pp. 3070-3079.
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