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