Isolation And Bioactivity Of Natural Products From Three Medicinal Plants

Three medicinal plants, Clerodendranthus spicatus (Labiatae), Artocarpus heterophyllus (Moraceae), and Podocarpus imbricatus (Podocarpaceae) were chemically investigated. A total of80compounds including16new ones were obtained by column chromatography on silica gel and Sephadex LH-20together with preparative HPLC. The structures were determined on the basis of NMR, MS, UV, and IR. Some of isolated compounds were tested for their cytotoxic and antioxidant activities. The isopimarane diterpenoids from C. spicatus showed weak cytotoxic activity, while flavonoids from A. heterophyllus exhibited moderate antioxidative and antiproliferative activity.Nine new diterpenes, clerospicasins A-I (1-9), together with27known compounds, orthosiphols A, B, D, E, M, N, O, and Q (10-17), orthosiphonone A (18),7-O-deacetylorthosiphol B (19),2-O-deacetylorthosiphol J (20), neoorthosiphols A and B (21-22), secoorthosiphol B (23), norstamonol B (24), ethyl rosmarinate (25), butyl rosmarinate (26), ethyl3-O-methylrosmarinate (27), lithospermic acid (28), ethyl caffeate (29). vinyl caffeate (30),1-(3-ethanoxy-4-hydroxyphenyl)-2-hydroxyethanone (31), protocatechuic aldehyde (32), salvigenin (33), ladanein (34),5,4’-dihydroxy-3’,7-dimethoxyflavone (35), and (2S)-5,6,7,3’,4’-pentamethoxyflavanone (36) were obtained from the aerial parts of C. spicatus. The structures of the compounds were established on the basis of extensive1D and2D NMR spectroscopic data analysis. Compounds13, 17, and23showed weak cytotoxic activity against the SKOV3, DU145, and PC-3cancer cell lines.Three new flavonoids, artocarpusins A-D (37-39), two new2-arylbenzofuran derivative, artocarstilbenes A and B (40-41), one new aromatic compound, artocarpusin D (42), as well as30known compounds, artocarmitin A (43),3’-[y-hydroxymethyl-(Z)-y-methylallyl]-2’,4’,4-trihydroxychalcone (44), isobavachalcone (45),2’,4’,2,4-tetrahydr-oxy-3-(3-methyl-2-butenyl)-chalcone (46), gemichalcones A and B (47-48), isogemichalcone B (49), artocarmitin B (50),6-(3-methylbut-2-enyl)-apigenin (51), arthocarpesin (52), norartocarpin (53), artocarpin (54), cudraflavone C (55),5,7,4’-trihydroxyflavone (56), norartocarpesin (57), albanin A (58), cudraflavone (59), brosimone I (60), norartocarpanone (61), euchrenone a7(62), moracin M (63), moracin C (64), albafuran B (65), artoindonesianin B-1(66), demethylmoracin I (67), moracin D (68), artocarbene (69),2,6,2’,6’-tetramethoxy-4,4’-bis(2,3-epoxy-l-hydroxy-propyl) biphenyl (70), griffithine A (71), and5a,6a-epoxy-24(R)-methylcholesta-7,22-dien-3β-ol (72) were obtained from the twigs of A. heterophyllus. Their structures were established on the basis of extensive spectroscopic analysis. Among the flavonoids, compounds47,48, and55exhibited moderate inhibitory activity on the proliferation of MCF-7and H460cancer cells, and47showed moderate antioxidant activity.One new diterpene imbricasins A (73), as well as seven known compounds, abieta-8,11,13-triene-3β,6β,12-triol (74), margoclin (75), agathic acid (76), sanjoinenine (77), amentoflavone (78), epipinoresinol (79), and3,3’,4,4’-tetrahydro-6,6’-dimethoxy-3,3’-bi-2H-benzopyran]-4,4’-diol (80) were obtained from the stems and leaves of P. imbricatus. Their structures were elucidated by spectroscopic analysis.