Indian Journal of Chemistry Vol. 47B, April 2008, pp. 619-622 Note Two new phytoconstituents from Rumex maritimus S Tarique Abdullah 1 , Hinna Hamid 1 , M Sarwar Alam* 1 , S H Ansari 2 & Mohammad Ali 2 1 Department of Chemistry, Faculty of Science 2 Department of Pharmacognosy and Phytochemistry, Faculty of Pharmacy Hamdard University, Hamdard Nagar, New Delhi 110 062, India E-mail: msalam747@yahoo.co.in Received 18 December 2006; accepted (revised) 10 January 2008 A new polyhydroxy ketone derivative and a terpene glycoside have been isolated from the seeds of Rumex maritimus. Their structures have been established as 3,7,11,15-tetramethyl-n- octadac-13-en-3,4,6,7,8,11-hexol-12-one 1 and 8β-hydroxy-14β- methyl-7-oxopodocarp-5-en-13-(19α-hydroxy-19,22,22-trimethyl- heptyl)-22-O-(β-D-glucopyranosyl)-(4→1) β-D-glucopyranoside 2, respectively, on the basis of chemical and spectral data analysis. Keywords: Rumex maritimus, polyhydroxy ketone, terpene glycoside, 3,7,11,15-tetramethyl-n-octadac-13-en-3,4,6,7,8,11- hexol-12-one, 8β-hydroxy-14β-methyl-7-oxopodocarp-5-en-13- (19α-hydroxy-19,22,22-trimethylheptyl)-22-O-(β-D-glucopyrano- syl)-(4→1) β-D-glucopyranoside, antipyretic, cathartic, aphrodisiac Rumex maritimus Linn. is a stout erect annual, 30-120 cm high occurring in temperate Himalayas, and on wet ground along riverbanks in the plains of north India. It is found growing in marshes in Assam and Bengal, Western ghats, Nilgiri and Palni hills 1-3 . The plant is an important drug used in Indian systems of medicine as antipyretic, cathartic and aphrodisiac 1-4 . The alcoholic extract is reported to have antifungal activity 5,6 . Presence of anthraquinones, sterols, flavonoids, tannins and carbohydrates has been reported from the plant so far 7-18 . In the present study is reported the isolation and structural elucidation of a new polyhydroxy ketone and a terpene glycoside from the alcoholic extract of the seeds of Rumex maritimus. Results and Discussion Compound 1 was obtained as white crystals from chloroform-methanol (9.2:0.8) eluents. Its IR spectrum exhibited absorption bands for carbonyl group (1718 cm -1 ), hydroxyl group (3370 cm -1 ) and unsaturation (1625 cm -1 ). It responded positively to tetranitromethane and decolourized bromine water, indicating unsaturated nature. It formed 2,4- dinitrophenylhydrazone derivative suggesting the presence of carbonyl group. Methylation of the compound produced hexamethoxy derivative, indicating the presence of six-hydroxyl groups. The EIMS of this compound showed a molecular ion peak at m/z 418 corresponding to C 22 H 42 O 7 , which was supported by 1 H, 13 C and 13 C DEPT NMR spectra. The important ion peaks 375, 71, 97, 125, 169, 147, 129, 117, 103, 357, 297, 85 and 55 suggested that the compound 1 was a polyhydroxy ketone, possessing a long hydrocarbon chain with carbonyl group at C-12 and unsaturation at C-13, respectively. These observations were fully supported by 1 H and 13 C NMR data. The 1 H NMR spectrum of 1 exhibited two downfield one-proton signals at δ 6.14 and 5.62 (J=2.1 Hz) corresponding to C-14 and C-13 vinylic protons, respectively. Two one-proton double doublets at δ 4.37 and 4.48 with coupling interaction of 9.32, 4.72 and 8.68, 4.50 Hz were ascribed to α- oriented C-6 and C-8 carbinol protons, respectively and a broad signal at δ 3.76 with half width of 15.5 Hz was associated with α-oriented C-4 carbinol proton. C-19, C-20 and C-21 methyl groups attached to the oxygenated carbons were observed as broad singlets, integrating for three protons each, at δ 1.17, 1.18 and 1.19, respectively. The remaining methyl groups resonated at δ 1.20 (CH 3 -22), 0.92 (CH 3 -1) and 0.75 (CH 3 -18). C-15 methine proton appeared as doublet of doublets at δ 2.20 (J=5.8, 6.20 Hz). The methylene protons resonated between δ 1.80-1.22. Further evidence for the structure was provided by 13 C NMR data. 13 C NMR spectrum of 1 showed 22 carbon signals. The signals at δ 202.25, 120.41 and 165.18 were assigned to C-12 carbonyl carbon, C-13 and C- 14 olefinic carbons, respectively. 13 C DEPT experiments showed the presence of six methyl, six methylene, four methine, and four quaternary carbons (Figure 1). 1 H- 13 C HETCOR spectrum showed correlation of H-4 with C-3 and C-5; H-6 with C-7 and C-5; H-8 with C-7 and C-9; H-13 with C-12 and C-4 and H-15 with C-14 and C-16. On the basis of