Indian Journal of Chemistry Vol. 42B, November 2003, pp. 2858-2862 Isolation of some novel phytoconstituents from Anaphalis araneosa roots S K Sharma, M Ali* & S R Mir Faculty of Pharmacy, l a mi a Hamda rd, Hamdard University, P.O. Hamdard Nagar, New Delhi-l 10062, INDIA *E-ma il : ma li _chem@yahoo.com Received 22 November 2002; accepted (revised) 3 May 2003 Three new phytoco nstitu en ts, named anaphalisolea nenoic acid, anapha li soic acid and araneoso ic ac id have been iso- lated from Anaplialis aralleosa roots and their structures have been charact.erized as ac id, 5, 9. 13-trimelhyl-eicos-5-e n- 17 , 18-diol-24-o ic acid and bi sa bol-I (7),2, 4 (13), II ( 12)-lelraen- 15 -o 1- 1 4-oic acid by spectral data ana ly sis and chem ica l reac ti ons. Anaphalis is a genus of perennial, rarely annual, erect, cottony or wooly, pube scent or glabrate herbs distrib- uted in Asia, Europe and America. About 32 species are reported from Ind ia. Anaphalis araneosa, DC. sy n. A. busua (D. Don) DC. (Asteraceae) is distrib- uted from altitude 1200 to 2400 mI . The herb is used locally as an antiseptic for cuts and wounds . Th e f1 a- vones, araneol and araneosol 2 , f1avonoids 3 .4, helipy- rone 4 , sterols and phthalides 5 from the aerial parts of the plant and 5-methyl-n-hexatriacontane, anaphali- sone, acyclic triterpenes, dulcioic acid and areneosol 6 from the flowers of the plant have been reported. This paper describes the isolation and characterization of the phytoconstituents from the roots of the herb. Results and Discussion Compound 1, named anaphalisoleanenoic acid, was obtained as colourless crystals from chloroform- methanol (98:2) eluants. It responded positively to the Liebermann-Burchard, TAC and TNM tests, sugges t- ing that it was a pentacyclic triterpenoid possessing olefinic linkage. The co mpound gave effervescence with sodium bicarbonate so lution. Its mass spe ctrum showed a molec ul ar ion peak at mJ z 456 consisting with a molecular formula C 30H4S0 3 that wa s sup- ported by its \3 C-NMR spectrum. Its IR spectrum ex- hibited absorptions at 3400 (OH), 3140, 1665, (COOH) , 1415, 1340 (gem-dimethyl) and 1630, 795 cm- I (tri-substituted double bond). Th e IH NMR spec- trum of 1 acc ounted for one olefinic proton at 8 5.00 (brs) assigned to H-12 , one carbinol proton at 8 3.73 as a double doublet (J = 5.50 , 9.50 Hz ) ascribed to H- 3a and seven methyl gro ups as broad singlets at 8 1.20 (Me-24), 1.03 (Me-2 5), 0.90 (Me-26, Me-27 ), 0.86 (Me-28), 0.75 (Me-23) and 0.70 (Me-29) . The 30 HOOC 29 2 ", 1 HOQH 16 14 19 17 15 H £OOH 2 14 COOH OH 3 ma ss spectrum of 1 indicated that the double bond triggered the typical retro-Diels-Alder (RDA) frag- mentation of ring C resulting in a fragment at ml z 207. T he ba se peak at ml z 248 was also derived by RDA fragmentation. These fragments are characteristic of to l2 amyr in derivatives c ontaining a hydroxyl group in