Serotonergic activity-guided phytochemical investigation of the roots of Angelica sinensis.
Serotonin receptor (5-HT(7)) 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-HT(7) receptors in a competitive binding assay.
Deng
Shixin
S
UIC/NIH Center for Botanical Dietary Supplements Research, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA.
Chen
Shao-Nong
SN
Yao
Ping
P
Nikolic
Dejan
D
van Breemen
Richard B
RB
Bolton
Judy L
JL
Fong
Harry H S
HH
Farnsworth
Norman R
NR
Pauli
Guido F
GF
D029969:Angelica / Q000737:chemistry*; D000818:Animals; D002170:Canada; D006224:Cricetinae; D006801:Humans; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011985:Receptors, Serotonin / Q000378:metabolism*
D011985:Receptors, Serotonin