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Contribution of cinnamic acid analogues in rosmarinic acid to inhibition of snake venom induced hemorrhage.

Bioorganic & medicinal chemistry (2011-03-11)
Hnin Thanda Aung, Tadashi Furukawa, Toshiaki Nikai, Masatake Niwa, Yoshiaki Takaya
ABSTRACT

In our previous paper, we reported that rosmarinic acid (1) of Argusia argentea could neutralize snake venom induced hemorrhagic action. Rosmarinic acid (1) consists of two phenylpropanoids: caffeic acid (2) and 3-(3,4-dihydroxyphenyl)lactic acid (3). In this study, we investigated the structural requirements necessary for inhibition of snake venom activity through the use of compounds, which are structurally related to rosmarinic acid (1). By examining anti-hemorrhagic activity of cinnamic acid analogs against Protobothrops flavoviridis (Habu) venom, it was revealed that the presence of the E-enoic acid moiety (-CH=CH-COOH) was critical. Furthermore, among the compound tested, it was concluded that rosmarinic acid (1) (IC(50) 0.15 μM) was the most potent inhibitor against the venom.

MATERIALI
N° Catalogo
Marchio
Descrizione del prodotto

Sigma-Aldrich
Acido caffeico, ≥98.0% (HPLC)
Sigma-Aldrich
Chlorogenic acid, ≥95% (titration)
Sigma-Aldrich
p-Coumaric acid, ≥98.0% (HPLC)
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Zimtaldehyd, natural, ≥95%, FG
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trans-Ferulic acid, 99%
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Sorbic acid, 99.0-101.0% anhydrous basis
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trans-Cinnamic acid, ≥99%
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trans-Cinnamaldehyde, 97%
Sigma-Aldrich
Rosmarinic acid, 96%
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Cinnamyl alcohol, 98%
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Crotonic acid, 98%
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trans-Cinnamic acid, 97%
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trans-Cinnamaldehyde, ≥99%
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trans-Cinnamaldehyde, FCC, FG
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trans-Ferulic acid, ≥99%
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3,4-Dihydroxyhydrocinnamic acid, 98%
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trans-Cinnamic acid, ≥99%, FG
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Methyl cinnamate, natural, ≥98%, FCC, FG
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Methyl trans-cinnamate, 99%
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trans-Cinnamic acid, natural, ≥99%, FCC, FG
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Cinnamyl alcohol, ≥98%, FG
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Methyl trans-cinnamate, ≥98%, stabilized, FCC, FG
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trans-3-Hydroxycinnamic acid, 99%
Supelco
trans-Ferulic acid, matrix substance for MALDI-MS, ≥99.0% (HPLC)
Chlorogenic acid, primary reference standard
Sigma-Aldrich
Sorbic acid, tested according to Ph. Eur.
Supelco
Acido caffeico, matrix substance for MALDI-MS, ≥99.0% (HPLC)
Supelco
trans-Ferulic acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland