Flavonol glucuronides and C-glucosidic ellagitannins from Melaleuca squarrosa

Morio Yoshimura; Hideyuki Ito; Kyoko Miyashita; Tsutomu Hatano; Shoko Taniguchi; Yoshiaki Amakura; Takashi Yoshida

doi:10.1016/j.phytochem.2008.04.004

Flavonol glucuronides and C-glucosidic ellagitannins from Melaleuca squarrosa

Morio Yoshimura, Hideyuki Ito, Kyoko Miyashita, Tsutomu Hatano, Shoko Taniguchi, Yoshiaki Amakura, Takashi Yoshida

Research output: Contribution to journal › Article › peer-review

29 Citations (Scopus)

Abstract

Two flavonoids and three ellagitannins, squarrosanins A, B, and C, were isolated from the leaves of Melaleuca squarrosa. The flavonoids were characterized structurally as kaempferol-3-O-(2″-O-galloyl)-glucuronide and herbacetin-3-O-glucuronide, while the ellagitannins were characterized as monomeric and dimeric C-glucosidic ellagitannins by application of spectroscopic and chemical methods. The antioxidant effect of the polyphenolic constituents of the M. squarrosa leaves was also examined in vitro, and C-glucosidic tannins including oligomers were shown to be more effective radical scavengers against 1,1-diphenyl-2-picrylhydrazyl (DPPH) than flavonoids and ordinary ellagitannins.

Original language	English
Pages (from-to)	3062-3069
Number of pages	8
Journal	Phytochemistry
Volume	69
Issue number	18
DOIs	https://doi.org/10.1016/j.phytochem.2008.04.004
Publication status	Published - Dec 2008

Keywords

Antioxidant
C-Glucosidic ellagitannin
Flavonol glucuronide
Melaleuca squarrosa
Myrtaceae
Squarrosanin A
Squarrosanin B
Squarrosanin C

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Plant Science
Horticulture

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10.1016/j.phytochem.2008.04.004

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title = "Flavonol glucuronides and C-glucosidic ellagitannins from Melaleuca squarrosa",

abstract = "Two flavonoids and three ellagitannins, squarrosanins A, B, and C, were isolated from the leaves of Melaleuca squarrosa. The flavonoids were characterized structurally as kaempferol-3-O-(2″-O-galloyl)-glucuronide and herbacetin-3-O-glucuronide, while the ellagitannins were characterized as monomeric and dimeric C-glucosidic ellagitannins by application of spectroscopic and chemical methods. The antioxidant effect of the polyphenolic constituents of the M. squarrosa leaves was also examined in vitro, and C-glucosidic tannins including oligomers were shown to be more effective radical scavengers against 1,1-diphenyl-2-picrylhydrazyl (DPPH) than flavonoids and ordinary ellagitannins.",

keywords = "Antioxidant, C-Glucosidic ellagitannin, Flavonol glucuronide, Melaleuca squarrosa, Myrtaceae, Squarrosanin A, Squarrosanin B, Squarrosanin C",

author = "Morio Yoshimura and Hideyuki Ito and Kyoko Miyashita and Tsutomu Hatano and Shoko Taniguchi and Yoshiaki Amakura and Takashi Yoshida",

year = "2008",

month = dec,

doi = "10.1016/j.phytochem.2008.04.004",

language = "English",

volume = "69",

pages = "3062--3069",

journal = "Phytochemistry",

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T1 - Flavonol glucuronides and C-glucosidic ellagitannins from Melaleuca squarrosa

AU - Yoshimura, Morio

AU - Ito, Hideyuki

AU - Miyashita, Kyoko

AU - Hatano, Tsutomu

AU - Taniguchi, Shoko

AU - Amakura, Yoshiaki

AU - Yoshida, Takashi

PY - 2008/12

Y1 - 2008/12

N2 - Two flavonoids and three ellagitannins, squarrosanins A, B, and C, were isolated from the leaves of Melaleuca squarrosa. The flavonoids were characterized structurally as kaempferol-3-O-(2″-O-galloyl)-glucuronide and herbacetin-3-O-glucuronide, while the ellagitannins were characterized as monomeric and dimeric C-glucosidic ellagitannins by application of spectroscopic and chemical methods. The antioxidant effect of the polyphenolic constituents of the M. squarrosa leaves was also examined in vitro, and C-glucosidic tannins including oligomers were shown to be more effective radical scavengers against 1,1-diphenyl-2-picrylhydrazyl (DPPH) than flavonoids and ordinary ellagitannins.

AB - Two flavonoids and three ellagitannins, squarrosanins A, B, and C, were isolated from the leaves of Melaleuca squarrosa. The flavonoids were characterized structurally as kaempferol-3-O-(2″-O-galloyl)-glucuronide and herbacetin-3-O-glucuronide, while the ellagitannins were characterized as monomeric and dimeric C-glucosidic ellagitannins by application of spectroscopic and chemical methods. The antioxidant effect of the polyphenolic constituents of the M. squarrosa leaves was also examined in vitro, and C-glucosidic tannins including oligomers were shown to be more effective radical scavengers against 1,1-diphenyl-2-picrylhydrazyl (DPPH) than flavonoids and ordinary ellagitannins.

KW - Antioxidant

KW - C-Glucosidic ellagitannin

KW - Flavonol glucuronide

KW - Melaleuca squarrosa

KW - Myrtaceae

KW - Squarrosanin A

KW - Squarrosanin B

KW - Squarrosanin C

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DO - 10.1016/j.phytochem.2008.04.004

M3 - Article

C2 - 18501392

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SN - 0031-9422

VL - 69

SP - 3062

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JO - Phytochemistry

JF - Phytochemistry

IS - 18

ER -

Flavonol glucuronides and C-glucosidic ellagitannins from Melaleuca squarrosa

Abstract

Keywords

ASJC Scopus subject areas

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