Reaction SMILES: [CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:10]2[O:25][C:15]3[CH:16]=[C:17]([O:23]C)[C:18]([O:21][CH3:22])=[C:19]([OH:20])[C:14]=3[C:12](=[O:13])[C:11]=2OC)=[CH:7][C:8]=1[OH:9].C1C(C2OC3C(=C(O)C=C(O)C=3[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C:36](=[O:37])C=2)=CC(O)=C(O)C=1.C1C(C2OC3C=C(O)C([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=C(O)C=3C(=O)C=2)=CC(O)=C(O)C=1.C1C(C2OC3C=C(O)C=C(O)C=3C(=O)C=2)=CC(O)=C(O)C=1.COC1C=C(O)C2C(=O)C=C(C3C=C(OC)C(OC)=C(OC)C=3)OC=2C=1.OC1C=C(C=CC=1OC)C1CC(=O)C2C(=CC(OC)=C(OC)C=2O)O1>>[CH:5]1[C:6]([C:10]2[O:25][C:15]3[CH:16]=[C:17]([OH:23])[CH:18]=[C:19]([OH:20])[C:14]=3[C:12](=[O:13])[CH:11]=2)=[CH:7][C:8]([OH:9])=[C:3]([OH:2])[CH:4]=1.[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:10]2[O:25][C:15]3[C:16]([O:37][CH3:36])=[C:17]([OH:23])[C:18]([O:21][CH3:22])=[C:19]([OH:20])[C:14]=3[C:12](=[O:13])[CH:11]=2)=[CH:7][C:8]=1[OH:9]
Reactant: COc1ccc(-c2oc3cc(OC)c(OC)c(O)c3c(=O)c2OC)cc1O
Reactant: O=c1cc(-c2ccc(O)c(O)c2)oc2c([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)cc(O)c12
Agent: COc1cc(O)c2c(=O)cc(-c3cc(OC)c(OC)c(OC)c3)oc2c1
Agent: COc1ccc(C2CC(=O)c3c(cc(OC)c(OC)c3O)O2)cc1O
Agent: O=c1cc(-c2ccc(O)c(O)c2)oc2cc(O)c([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)c12
Product: COc1ccc(-c2cc(=O)c3c(O)c(OC)c(O)c(OC)c3o2)cc1O

Procedure:
A large number of flavonoids viz., casticin, orientin, isoorientin, luteolin, luteolin-7-0-glucoside, corymbosin, gardenins A and B, 3-0-desmethylartemetin,5-0-desmethylnobiletin,3\4\5,5\6J,8-heptamethoxyflavanone and 3\,5-dihydroxy-4′,6,7-trimethoxy flavanone and 3′,5-dihydroxy-4′,6,7-trimethoxyflavanone have been reported from this plant [Sirait, L. M., Rimpler, H. and Haensal, R., Experientia 1962, 18, 72; Haensal, R. et al. Phytochemistry 1965, 4 ,19; Banerji A. et al. Phytochemistry 1969, 8,511; Ferdous, A. J. et al. Bangladesh Acad. Sci. 1984, 8,23; Dayrit, F. M. et al. Philipp. J. Sci. 1987, 116, 403; Banerji, J. et al. Indian J. Chem. 1988; 27B, 597; Achari, B. et al. Phytochemistry. 1984, 23, 703]. Stem-bark afforded five new flavone glycosides along with luteolin and acerosin. The new flavone glycosides are 6p-glucopyranosyl-7-hydroxy-3′,4′,5′,8-tetramethoxyflavone-5-O-α-L-rhamnopyranoside, 3′,7-dihydroxy-4′,6,8-trimethoxyflavone-5-O-(6″-O-acetyl-p-D-glucopyranoside),3,3′,4′,6,7,-pentamethoxyflavone 5′-O-(4″-O-β-D-glucopyranosyl-cc-rhamnopyranoside, 4′,5,7-tri-hydroxyflavone-8-(2″-caffeoyl-a-glucopyranoside) and 3′,5,5′,7-tetrahydroxy-4-methoxyflavone -3′-O-(4″-O-α-D-galactopyranosyl) galactopyranoside [Rao, V. K. et al. Indian J. Pharm. 1977,39, 41; Subramamian, P. M. and Misra, G. S. Indian J. Chem. 1978, 16B, 615; Subramaniam, P. M. and Misra, G. S. J. Nat. Prod. 1979,42, 540]. A diterpenoid, 5β-hydro-8,11,13-abieta-trien-6a-ol and three triterpenoids, 2 cc, 3a-dihydroxyoleana-5 12-dien-28-oic acid, 2a, 3a-diacetoxyoleana-5, 12-dien-28-oic acid, 2,3 a-diacetoxy-18-hydroxyoleana-5,12-dien-28-oib acid have been isolated from the seeds, These compounds exhibited antiinflammatory activity [Chawla, A. S., Sharma, A. K., Handa, S. S. and Dhar, K. L. Indian J. Chem. 1991, 30B, 773 and J. Nat. Prod. 1992,55,163. From the roots acetyloleanolic acid was isolated [Vishnol, S. P., Shoeb, A., Kapil, R. S. and Popli, S. P. Phytochemistry 1983, 22, 597].