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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
RESUMEN

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.

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