In vitro effects of hydroxybenzaldehydes from Gastrodia elata and their analogues on GABAergic neurotransmission, and a structure-activity correlation

J. H. Ha; S. M. Shin; S. K. Lee; J. S. Kim; U. S. Shin; K. Huh; J. A. Kim; C. S. Yong; N. J. Lee; D. U. Lee

doi:10.1055/s-2001-18844

In vitro effects of hydroxybenzaldehydes from Gastrodia elata and their analogues on GABAergic neurotransmission, and a structure-activity correlation

J. H. Ha, S. M. Shin, S. K. Lee, J. S. Kim, U. S. Shin, K. Huh, J. A. Kim, C. S. Yong, N. J. Lee, D. U. Lee

Department of Medicine

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56 Scopus citations

Abstract

The present study was designed to characterize the modulatory effects of the constituents of Gastrodia elata and their analogues on the GABAergic neurotransmission. 4-Hydroxybenzaldehyde (1) and 4-hydroxy-3-methoxybenzaldehyde (4) inhibited potently the activity of GABA transaminase (IC₅₀ = 4.1 and 5.4 μg/ml, respectively), while the activity of another constituent, 4-hydroxybenzyl alcohol (2), was very weak. Further investigation with 10 analogues revealed a structure-activity correlation, suggesting that the aldehyde group and the hydroxy group at C-4 are necessary for the inhibitory effect on the enzyme activity. Some potent enzyme inhibitors were examined for the effect on the radioligands to the GABAA receptor complexes of rat cerebral cortices. Among them, the component 4 dose-dependently increased (20-30%) the binding of [³H]flunitrazepam in the presence of GABA.

Original language	English
Pages (from-to)	877-880
Number of pages	4
Journal	Planta Medica
Volume	67
Issue number	9
DOIs	https://doi.org/10.1055/s-2001-18844
State	Published - 2001

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title = "In vitro effects of hydroxybenzaldehydes from Gastrodia elata and their analogues on GABAergic neurotransmission, and a structure-activity correlation",

abstract = "The present study was designed to characterize the modulatory effects of the constituents of Gastrodia elata and their analogues on the GABAergic neurotransmission. 4-Hydroxybenzaldehyde (1) and 4-hydroxy-3-methoxybenzaldehyde (4) inhibited potently the activity of GABA transaminase (IC50 = 4.1 and 5.4 μg/ml, respectively), while the activity of another constituent, 4-hydroxybenzyl alcohol (2), was very weak. Further investigation with 10 analogues revealed a structure-activity correlation, suggesting that the aldehyde group and the hydroxy group at C-4 are necessary for the inhibitory effect on the enzyme activity. Some potent enzyme inhibitors were examined for the effect on the radioligands to the GABAA receptor complexes of rat cerebral cortices. Among them, the component 4 dose-dependently increased (20-30%) the binding of [3H]flunitrazepam in the presence of GABA.",

author = "Ha, {J. H.} and Shin, {S. M.} and Lee, {S. K.} and Kim, {J. S.} and Shin, {U. S.} and K. Huh and Kim, {J. A.} and Yong, {C. S.} and Lee, {N. J.} and Lee, {D. U.}",

year = "2001",

doi = "10.1055/s-2001-18844",

language = "English",

volume = "67",

pages = "877--880",

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TY - JOUR

T1 - In vitro effects of hydroxybenzaldehydes from Gastrodia elata and their analogues on GABAergic neurotransmission, and a structure-activity correlation

AU - Ha, J. H.

AU - Shin, S. M.

AU - Lee, S. K.

AU - Kim, J. S.

AU - Shin, U. S.

AU - Huh, K.

AU - Kim, J. A.

AU - Yong, C. S.

AU - Lee, N. J.

AU - Lee, D. U.

PY - 2001

Y1 - 2001

N2 - The present study was designed to characterize the modulatory effects of the constituents of Gastrodia elata and their analogues on the GABAergic neurotransmission. 4-Hydroxybenzaldehyde (1) and 4-hydroxy-3-methoxybenzaldehyde (4) inhibited potently the activity of GABA transaminase (IC50 = 4.1 and 5.4 μg/ml, respectively), while the activity of another constituent, 4-hydroxybenzyl alcohol (2), was very weak. Further investigation with 10 analogues revealed a structure-activity correlation, suggesting that the aldehyde group and the hydroxy group at C-4 are necessary for the inhibitory effect on the enzyme activity. Some potent enzyme inhibitors were examined for the effect on the radioligands to the GABAA receptor complexes of rat cerebral cortices. Among them, the component 4 dose-dependently increased (20-30%) the binding of [3H]flunitrazepam in the presence of GABA.

AB - The present study was designed to characterize the modulatory effects of the constituents of Gastrodia elata and their analogues on the GABAergic neurotransmission. 4-Hydroxybenzaldehyde (1) and 4-hydroxy-3-methoxybenzaldehyde (4) inhibited potently the activity of GABA transaminase (IC50 = 4.1 and 5.4 μg/ml, respectively), while the activity of another constituent, 4-hydroxybenzyl alcohol (2), was very weak. Further investigation with 10 analogues revealed a structure-activity correlation, suggesting that the aldehyde group and the hydroxy group at C-4 are necessary for the inhibitory effect on the enzyme activity. Some potent enzyme inhibitors were examined for the effect on the radioligands to the GABAA receptor complexes of rat cerebral cortices. Among them, the component 4 dose-dependently increased (20-30%) the binding of [3H]flunitrazepam in the presence of GABA.

UR - http://www.scopus.com/inward/record.url?scp=0035676789&partnerID=8YFLogxK

U2 - 10.1055/s-2001-18844

DO - 10.1055/s-2001-18844

M3 - Article

C2 - 11745032

AN - SCOPUS:0035676789

SN - 0032-0943

VL - 67

SP - 877

EP - 880

JO - Planta Medica

JF - Planta Medica

IS - 9

ER -

In vitro effects of hydroxybenzaldehydes from Gastrodia elata and their analogues on GABAergic neurotransmission, and a structure-activity correlation

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