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

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.

MATERIALS
Product Number
Brand
Product Description

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