Anticholinesterase and Antioxidant Constituents from Gloiopeltis furcata

Activity-directed isolation of the ethyl acetate, methylene chloride and n-hexane fractions of Gloiopeltis furcata resulted in the isolation of 18 compounds. Their structures were elucidated as 2-(3-hydroxy-5-oxotetrahydrofuran-3-yl)acetic acid (1), glutaric acid (2), succinic acid (3), nicotinic ac...

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Published inChemical & Pharmaceutical Bulletin Vol. 58; no. 9; pp. 1236 - 1239
Main Authors Fang, Zhe, Jeong, Su Yang, Jung, Hyun Ah, Choi, Jae Sue, Min, Byung Sun, Woo, Mi Hee
Format Journal Article
LanguageEnglish
Japanese
Published TOKYO The Pharmaceutical Society of Japan 01.09.2010
Pharmaceutical Society of Japan
Pharmaceutical Soc Japan
Japan Science and Technology Agency
Subjects
(5E,7E)-9-oxodeca-5,7-dienoic acid
2-(3-hydroxy-5-oxotetrahydrofuran-3-yl)acetic acid
Acetylcholinesterase - metabolism
antioxidant activity
Antioxidants - chemistry
Antioxidants - isolation & purification
Antioxidants - pharmacology
Biphenyl Compounds - metabolism
Butyrylcholinesterase - metabolism
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
cholinesterase inhibition
Cholinesterase Inhibitors - chemistry
Cholinesterase Inhibitors - isolation & purification
Cholinesterase Inhibitors - pharmacology
Free Radicals - metabolism
Gloiopeltis furcata
Life Sciences & Biomedicine
Molecular Structure
Pharmacology & Pharmacy
Physical Sciences
Picrates - metabolism
Rhodophyta - chemistry
Science & Technology
Structure-Activity Relationship
cholinesterase inhibition
Gloiopeltis furcata
(5E,7E)-9-oxodeca-5,7-dienoic acid
ACETYLCHOLINESTERASE
ACIDS
ALZHEIMERS-DISEASE
ALGAE
2-(3-hydroxy-5-oxotetrahydrofuran-3-yl)acetic acid
antioxidant activity
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Abstract Activity-directed isolation of the ethyl acetate, methylene chloride and n-hexane fractions of Gloiopeltis furcata resulted in the isolation of 18 compounds. Their structures were elucidated as 2-(3-hydroxy-5-oxotetrahydrofuran-3-yl)acetic acid (1), glutaric acid (2), succinic acid (3), nicotinic acid (4), (E)-4-hydroxyhex-2-enoic acid (5), cholesterol (6), 7-hydroxycholesterol (7), uridine (8), glycerol (9), 5-(hydroxymethyl)-2-methoxybenzene-1,3-diol (10), (5E,7E)-9-oxodeca-5,7-dienoic acid (11), (Z)-3-ethylidene-4-methylpyrrolidine-2,5-dione (12), dehydrovomifoliol (13), loliolide (14), cholesteryl stearate (15), palmitic acid (16), cis-5,8,11,14,17-eicosapentaenoic acid (17) and α-linolenic acid (18) on the basis of spectroscopic and chemical evidences. Their anticholinesterase and antioxidant activities were evaluated via inhibitory activities on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) as well as scavenging activities on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and peroxynitrite (ONOO−). All isolated compounds (1—18) exhibited moderate AChE inhibitory activities with IC50 values ranging from 1.14—12.50 μg/ml, whereas 1, 7, 9, 17, and 18 showed mild BChE inhibitory activities with IC50 values ranging from 5.57—15.89 μg/ml. Although most of the compounds isolated were lacking the scavenging activity on DPPH radical and ONOO−, 5 and 10 showed good DPPH radical scavenging activity, and 5, 10, and 16 showed potent ONOO− scavenging activity.
AbstractList Activity-directed isolation of the ethyl acetate, methylene chloride and n-hexane fractions of Gloiopeltis furcata resulted in the isolation of 18 compounds. Their structures were elucidated as 2-(3-hydroxy-5-oxotetrahydrofuran-3-yl)acetic acid (1), glutaric acid (2), succinic acid (3), nicotinic acid (4), (E)-4-hydroxyhex-2-enoic acid (5), cholesterol (6), 7-hydroxycholesterol (7), uridine (8), glycerol (9), 5-(hydroxymethyl)-2-methoxybenzene-1,3-diol (10), (5E,7E)-9-oxodeca-5,7-dienoic acid (11), (Z)-3-ethylidene-4-methylpyrrolidine-2,5-dione (12), dehydrovomifoliol (13), loliolide (14), cholesteryl stearate (15), palmitic acid (16), cis-5,8,11,14,17-eicosapentaenoic acid (17) and alpha-linolenic acid (18) on the basis of spectroscopic and chemical evidences. Their anticholinesterase and antioxidant activities were evaluated via inhibitory activities on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) as well as scavenging activities on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and peroxynitrite (ONOO(-)). All isolated compounds (1-18) exhibited moderate AChE inhibitory activities with IC(50) values ranging from 1.14-12.50 microg/ml, whereas 1, 7, 9, 17, and 18 showed mild BChE inhibitory activities with IC(50) values ranging from 5.57-15.89 microg/ml. Although most of the compounds isolated were lacking the scavenging activity on DPPH radical and ONOO(-), 5 and 10 showed good DPPH radical scavenging activity, and 5, 10, and 16 showed potent ONOO(-) scavenging activity.
Activity-directed isolation of the ethyl acetate, methylene chloride and n-hexane fractions of Gloiopeltis furcata resulted in the isolation of 18 compounds. Their structures were elucidated as 2-(3-hydroxy-5-oxotetrahydrofuran-3-yl)acetic acid (1), glutaric acid (2), succinic acid (3), nicotinic acid (4), (E)-4-hydroxyhex-2-enoic acid (5), cholesterol (6), 7-hydroxycholesterol (7), uridine (8), glycerol (9), 5-(hydroxymethyl)-2-methoxybenzene-1,3-diol (10), (5E,7E)-9-oxodeca-5,7-dienoic acid (11), (Z)-3-ethylidene-4-methylpyrrolidine-2,5-dione (12), dehydrovomifoliol (13), loliolide (14), cholesteryl stearate (15), palmitic acid (16), cis-5,8,11,14,17-eicosapentaenoic acid (17) and α-linolenic acid (18) on the basis of spectroscopic and chemical evidences. Their anticholinesterase and antioxidant activities were evaluated via inhibitory activities on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) as well as scavenging activities on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and peroxynitrite (ONOO-). All isolated compounds (1-18) exhibited moderate AChE inhibitory activities with IC50 values ranging from 1.14-12.50μg/ml, whereas 1, 7, 9, 17, and 18 showed mild BChE inhibitory activities with IC50 values ranging from 5.57-15.89μg/ml. Although most of the compounds isolated were lacking the scavenging activity on DPPH radical and ONOO-, 5 and 10 showed good DPPH radical scavenging activity, and 5, 10, and 16 showed potent ONOO- scavenging activity.
Activity-directed isolation of the ethyl acetate, methylene chloride and n-hexane fractions of Gloiopeltis furcata resulted in the isolation of 18 compounds. Their structures were elucidated as 2-(3-hydroxy-5-oxotetrahydrofuran-3-yl)acetic acid (1), glutaric acid (2), succinic acid (3), nicotinic acid (4), (E)-4-hydroxyhex-2-enoic acid (5), cholesterol (6), 7-hydroxycholesterol (7), uridine (8), glycerol (9), 5-(hydroxymethyl)-2-methoxybenzene-1,3-diol (10), (5E,7E)-9-oxodeca-5,7-dienoic acid (11), (Z)-3-ethylidene-4-methylpyrrolidine-2,5-dione (12), dehydrovomifoliol (13), loliolide (14), cholesteryl stearate (15), palmitic acid (16), cis-5,8,11,14,17-eicosapentaenoic acid (17) and α-linolenic acid (18) on the basis of spectroscopic and chemical evidences. Their anticholinesterase and antioxidant activities were evaluated via inhibitory activities on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) as well as scavenging activities on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and peroxynitrite (ONOO-). All isolated compounds (1--18) exhibited moderate AChE inhibitory activities with IC50 values ranging from 1.14--12.50 μg/ml, whereas 1, 7, 9, 17, and 18 showed mild BChE inhibitory activities with IC50 values ranging from 5.57--15.89 μg/ml. Although most of the compounds isolated were lacking the scavenging activity on DPPH radical and ONOO-, 5 and 10 showed good DPPH radical scavenging activity, and 5, 10, and 16 showed potent ONOO- scavenging activity.
Activity-directed isolation of the ethyl acetate, methylene chloride and n-hexane fractions of Gloiopeltis furcata resulted in the isolation of 18 compounds. Their structures were elucidated as 2-(3-hydroxy-5-oxotetrahydrofuran-3-yl)acetic acid (1), glutaric acid (2), succinic acid (3), nicotinic acid (4), (E)-4-hydroxyhex-2-enoic acid (5), cholesterol (6), 7-hydroxycholesterol (7), uridine (8), glycerol (9), 5-(hydroxymethyl)-2-methoxybenzene-1,3-diol (10), (5E,7E)-9-oxodeca-5,7-dienoic acid (11), (Z)-3-ethylidene-4-methylpyrrolidine-2,5-dione (12), dehydrovomifoliol (13), loliolide (14), cholesteryl stearate (15), palmitic acid (16), cis-5,8,11,14,17-eicosapentaenoic acid (17) and α-linolenic acid (18) on the basis of spectroscopic and chemical evidences. Their anticholinesterase and antioxidant activities were evaluated via inhibitory activities on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) as well as scavenging activities on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and peroxynitrite (ONOO−). All isolated compounds (1—18) exhibited moderate AChE inhibitory activities with IC50 values ranging from 1.14—12.50 μg/ml, whereas 1, 7, 9, 17, and 18 showed mild BChE inhibitory activities with IC50 values ranging from 5.57—15.89 μg/ml. Although most of the compounds isolated were lacking the scavenging activity on DPPH radical and ONOO−, 5 and 10 showed good DPPH radical scavenging activity, and 5, 10, and 16 showed potent ONOO− scavenging activity.
Activity-directed isolation of the ethyl acetate, methylene chloride and n-hexane fractions of Gloiopeltis furcata resulted in the isolation of 18 compounds. Their structures were elucidated as 2-(3-hydroxy-5-oxotetrahydrofuran-3-yl)acetic acid (1), glutaric acid (2), succinic acid (3), nicotinic acid (4), (E)-4-hydroxyhex-2-enoic acid (5), cholesterol (6), 7-hydroxycholesterol (7), uridine (8), glycerol (9), 5-(hydroxymethyl)-2-methoxybenzene-1,3-diol (10), (5E,7E)-9-oxodeca-5,7-dienoic acid (11), (Z)-3-ethylidene-4-methylpyrrolidine-2,5-dione (12), dehydrovomifoliol (13), loliolide (14), cholesteryl stearate (15), palmitic acid (16), cis-5,8,11,14,17-eicosapentaenoic acid (17) and alpha-linolenic acid (18) on the basis of spectroscopic and chemical evidences. Their anticholinesterase and antioxidant activities were evaluated via inhibitory activities on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) as well as scavenging activities on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and peroxynitrite (ONOO-). All isolated compounds (1-18) exhibited moderate AChE inhibitory activities with IC50 values ranging from 1.14-12.50 mu g/ml, whereas 1, 7, 9, 17, and 18 showed mild BChE inhibitory activities with IC50 values ranging from 5.57-15.89 mu g/ml. Although most of the compounds isolated were lacking the scavenging activity on DPPH radical and ONOO-, 5 and 10 showed good DPPH radical scavenging activity, and 5, 10, and 16 showed potent ONOO- scavenging activity.
Author Jeong, Su Yang
Fang, Zhe
Woo, Mi Hee
Min, Byung Sun
Jung, Hyun Ah
Choi, Jae Sue
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  organization: Division of Food Science and Biotechnology, Pukyong National University
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  organization: College of Pharmacy, Catholic University of Daegu
– sequence: 6
  fullname: Woo, Mi Hee
  organization: College of Pharmacy, Catholic University of Daegu
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Issue 9
Keywords cholinesterase inhibition
Gloiopeltis furcata
(5E,7E)-9-oxodeca-5,7-dienoic acid
ACETYLCHOLINESTERASE
ACIDS
ALZHEIMERS-DISEASE
ALGAE
2-(3-hydroxy-5-oxotetrahydrofuran-3-yl)acetic acid
antioxidant activity
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SSID ssj0025073
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Score 2.1585774
Snippet Activity-directed isolation of the ethyl acetate, methylene chloride and n-hexane fractions of Gloiopeltis furcata resulted in the isolation of 18 compounds....
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SubjectTerms (5E,7E)-9-oxodeca-5,7-dienoic acid
2-(3-hydroxy-5-oxotetrahydrofuran-3-yl)acetic acid
Acetylcholinesterase - metabolism
antioxidant activity
Antioxidants - chemistry
Antioxidants - isolation & purification
Antioxidants - pharmacology
Biphenyl Compounds - metabolism
Butyrylcholinesterase - metabolism
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
cholinesterase inhibition
Cholinesterase Inhibitors - chemistry
Cholinesterase Inhibitors - isolation & purification
Cholinesterase Inhibitors - pharmacology
Free Radicals - metabolism
Gloiopeltis furcata
Life Sciences & Biomedicine
Molecular Structure
Pharmacology & Pharmacy
Physical Sciences
Picrates - metabolism
Rhodophyta - chemistry
Science & Technology
Structure-Activity Relationship
Title Anticholinesterase and Antioxidant Constituents from Gloiopeltis furcata
URI https://www.jstage.jst.go.jp/article/cpb/58/9/58_9_1236/_article/-char/en
http://mol.medicalonline.jp/library/journal/download?GoodsID=cs7chemi/2010/005809/020&name=1236-1239e
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Volume 58
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