Celerin, a New Coumarin from Apium graveolens

Abstract

The isolation of cclcrin, LI ncw coumari~l from chc petrol extrncr of A p b m graveolens sccds is rcporred.As a part of our programme for the systematic chemical investigation of some Indian medicinal plants, we reported [I-31 the isolation of several coumarins from Apiurn graveolens LINN (Apiaceae) seeds commonly known as celery seeds. The present communication deals with the isolation and structural elucidation of another new coumarin, celerin (I), from the petrol extract of the seeds. Spectral studies of I (M+ 260; C, jH,,,Od and its methyl ether I1 concluded the pre sence of a coumarin skeleton unsubstitutel at 3, 4 and 5 positio~ls and having a hy droxyl, a methoxyl and a l,l-dimethyl ally1 group in it. Negative GIBBS test [ 4~ of I a n d , & demethylated derivative 111, suggested 6 and 7 positions for hydroxyl and rnechoxyl groups and limited the placement of 1,l-dimethylaJJyl group at 8 position in T. The absence of a bathochromic shift in the UV maxima of I on addi-' tion of sodium acetate precluded the pos~i-bilicy of a free hydroxyl at 7 Downloaded by: University of British Columbia. Copyrighted material.

Coumarins

“…villosum and H . tenue.2s2 The known 7-prenyloxy-8methoxycoumarin (289) has been given the trivial name lacinartin, and the optically active epoxide, lactinartinepoxide (290), and diol, lacinartindiol (291), both of unknown absolute configuration have also been isolated from Artemisia laciniata leaves. 283…”

Botanical origin of Indian celery seed (fruit)

“…In this study, we proved that the Indian celery seeds containing coumarin derivatives (1-9) are not derived from A. graveolens by using genetic and phytochemical approaches, even though Indian workers reported that A. graveolens seeds contain these compounds [2][3][4][5][6][7][8][9][10]. Furthermore, our results strongly suggested that the seeds were derived from S. diffusum based on their ITS sequences, characteristic components and distribution area.…”

“…The contradicting constituents of celery seeds reported by the Indian [2][3][4][5][6][7][8][9][10] and the Japanese researchers [11] are possibly due to the indiscriminative handling of celery and celery-related seeds in Indian (and also Pakistani) crude drugs/spices markets. The contradicting constituents of celery seeds reported by the Indian [2][3][4][5][6][7][8][9][10] and the Japanese researchers [11] are possibly due to the indiscriminative handling of celery and celery-related seeds in Indian (and also Pakistani) crude drugs/spices markets.…”

Apium extract alleviates indomethacin-induced gastric ulcers in rats via modulating the VEGF and IK-κB/NF-κB p65 signaling pathway: insights from in silico and in vivo investigations

“…In this vein, two coumarins with the molecular formulas C 15 H 16 O 4 and C 14 H 14 O 3 were characterized as celerin (4) and osthenol (5) based on the mass ion peaks at m/z 261.112 [M + H] + and 231.101 [M + H] + , respectively. These compounds were reported among the formerly isolated phytoconstituents from A. graveolens seeds [ 38 , 65 , 66 ]. Another coumarin with the molecular formula C 11 H 8 O 4 was characterized as 6-acetyl-7-hydroxy-2H-1-benzopyran-2-one (6), in line with the mass ion peak at m/z 203.033 [M-H] − ; this molecule had been formerly described from A. petroselinum [ 67 ].…”