Serotonergic Activity-Guided Phytochemical Investigation of the Roots of Angelica sinensis

• Published in: Journal of natural products (Washington, D.C.) Vol. 69; no. 4; pp. 536 - 541
• Main Authors: Deng, S, Chen, S.N, Yao, P, Nikolic, D, Van Breemen, R.B, Bolton, J.L, Fong, H.H.S, Farnsworth, N.R, Pauli, G.F
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.04.2006; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: 10-angeloylbutylphthalide; Angelica - chemistry; Angelica sinensis; angeliferulate; Animals; ansaspirolide; Apiaceae; Biological and medical sciences; Canada; chemical structure; Chemistry, Medicinal; Cricetinae; cultured cells; esters; General pharmacology; herbaceous plants; Humans; Life Sciences & Biomedicine; Medical sciences; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; phenolic compounds; phthalides; phytochemicals; Plant Roots - chemistry; Plant Sciences; Plants, Medicinal - chemistry; Receptors, Serotonin - metabolism; roots; Science & Technology; serotonin receptor; sinaspirolide; spectral analysis; stereochemistry; China; Asia; Canada; PHTHALIDES; LIGUSTILIDE; CLONING; RECEPTOR; FALCARINDIOL; BINDING; PSORALEN; CONSTITUENTS; Phenolic acid; Ligand; Alcohol; 5-HT7 serotonin receptor; Oxygen heterocycle; Medicinal plant; Folk medicine; Polyynic compound; Dicotyledones; Angiospermae; Below ground plant part; Root; Aliphatic compound; Pharmacognosy; Lactone; In vitro; Biological activity; Enynic compound; Biological fixation; Cinnamic acid derivatives; Plant origin; Phenols; Affinity; Isolation; Spermatophyta; Umbelliferae
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np050301s

Serotonin receptor (5-HT7) binding assay-directed fractionation of a methanol extract of the dried roots of Angelica sinensis led to the isolation and identification of 21 compounds including a new phenolic ester, angeliferulate (1), and three new phthalides, 10-angeloylbutylphthalide (2), sinaspirolide (3), and ansaspirolide (4), along with 17 known compounds, p-hydroxyphenethyl trans-ferulate (5), Z-ligustilide (6), Z-butylidenephthalide ( 7), senkyunolide I (8), Z-6-hydroxy-7-methoxydihydroligustilide ( 9), N-butylbenzenesulfonamide (10), 11(S), 16(R)-dihydroxyoctadeca-9Z, 17-diene-12,14-diyn-1-yl acetate (11), (3R,8S)-falcarindiol (12), heptadeca-1-en-9,10-epoxy-4,6-diyne-3,8-diol(13), oplopandiol (14), 8-hydroxy-1-methoxy-, Z-9-heptadecene-4,6-diyn-3-one (15), imperatorin, ferulic acid, vanillin, stigmasterol, sucrose, and 1,3-dilinolenin. This is the first report of a sulfonamide (10) identified from a higher plant source, although its presence needs further investigation. Biosynthetic pathways for dimeric phthalides 3 and 4 are proposed. Compounds 5, 7, 11, 12, 15, and imperatorin exhibited affinity toward 5-HT7 receptors in a competitive binding assay.