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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
Caffeic acid, ≥98.0% (HPLC)
Sigma-Aldrich
Chlorogenic acid, ≥95% (titration)
Sigma-Aldrich
p-Coumaric acid, ≥98.0% (HPLC)
Sigma-Aldrich
Zimtaldehyd, natural, ≥95%, FG
Sigma-Aldrich
Ferulic acid, 99%
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Sorbic acid, 99.0-101.0% anhydrous basis
Sigma-Aldrich
trans-Cinnamic acid, ≥99%
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trans-Cinnamaldehyde, 97%
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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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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
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
Caffeic acid, matrix substance for MALDI-MS, ≥99.0% (HPLC)
Supelco
Ferulic acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland