Structures of Four New Isoprenylated Xanthones, Cudraxanthones L, M, N, and O fromCudrania tricuspidata^1,2

Abstract

Four new isoprenylated xanthones, cudraxanthones L, M, N, and O were isolated from the ethanol extract of the root bark of CUDRANIA TRICUSPIDATA (Carr.) Bur. (Moraceae), collected in China. The structures of cudraxanthones L, M, N, and O were shown to be 1-4, respectively, on the basis of chemical and spectral evidences.

Cytotoxic Prenylated Xanthones from the Young Fruit of Garcinia mangostana

“…19) In the HMBC spectrum ( (Fig. 1) further supported the placement of the 2,3-dihydroxy-3-methylbutyl group at C-8 in 3.…”

“…19) 13 C-NMR assignments (Table 2) were established by comparison with those of garcinone D 10) and cudraxanthone N. 19) On the basis of all spectroscopic evidence, the structure of mangostenone E (3) was established to be 1,3,6-trihydroxy-8-(2,3-dihydroxy-3-methylbutyl)-2-(3-methylbut-2-enyl)-7-methoxyxanthone.…”

“…Compounds 4-19 were identified as thwaitesixanthone (4), 12) demethylcalabaxanthone (5), 11) garcinone B (6), 10) compound 7, 11) b-mangostin (8), 10) 8-desoxygartanin (9), 13) gartanin (10), 14) garcinone E (11), 15) the major metabolite amangostin (12), 10) mangostinone (13), 10) the second major metabolite g-mangostin (14), 11) mangostanol (15), 10) mangostanin (16), 11) garcinone D (17), 11) garcinone C (18), 16) and the third major metabolite 11-hydroxy-1-isomangostin (19) Table 2. Based on these observations, the following conclusions can be drawn regarding these isolates: 1) For high activity, the xanthones should contain tetraoxygen functions with two C 5 units in rings A and C (as in 8, 11, 12, 14).…”

“…In our previous study, the isolation of 17 xanthones including three new xanthones, mangostenol and mangostenones A and B, from the green fruit (14-week maturity stage) of this plant and their antituberculosis activity were already described. 10,11) In a continuation of this work, the EtOAc-soluble extract obtained from the young fruit (7-week maturity stage) of G. mangostana was subjected to a chemical investigation leading to the isolation and structural elucidation of three new prenylated xanthones, mangostenones C (1), D (2), and E (3), in addition to 16 previously reported xanthones, thwaitesixanthone (4), 12) demethylcalabaxanthone (5), 11) garcinone B (6), 10) compound 7, 11) b-mangostin (8), 10) 8-desoxygartanin (9), 13) gartanin (10), 14) garcinone E (11), 15) the major metabolite a-mangostin (12), 10) mangostinone (13), 10) the second major metabolite g-mangostin (14), 11) mangostanol (15), 10) mangostanin (16), 11) garcinone D (17), 11) garcinone C (18), 16) and the third major metabolite 11-hydroxy-1-isomangostin (19). 17) We here report on the structural elucidation of the three new compounds and the in vitro cytotoxic activities of xanthones 1-19 against three human cancer cell lines, epidermoid carcinoma of the mouth (KB), breast cancer (BC-1), and small cell lung cancer (NCI-H187).…”

Prenylated Xanthones from the Roots of Cudrania tricuspidata as Inhibitors of Lipopolysaccharide‐Stimulated Nitric Oxide Production

“…Twenty‐eight known compounds were identified as 2,6‐dihydroxyxanthone ( 1 ) , isogentisin ( 2 ) , alloathyriol ( 3 ) , laxanthone‐Ι ( 4 ) , isocudraniaxanthone A ( 5 ) , isocudraniaxanthone B ( 6 ) , 1,3,5‐trihydroxy‐4‐prenylxanthone ( 7 ) , cudraxanthone H ( 8 ) , cudratricusxanthone K ( 9 ) , dulxanthone B ( 10 ) , macluraxanthone B ( 11 ) , cudracuspixanthone A ( 12 ) , cudratricusxanthone A ( 13 ) , gerontoxanthone I ( 14 ) , macluraxanthone C ( 15 ) , alvaxanthone ( 17 ) , isoalvaxanthone ( 18 ) , cudraxanthone L ( 19 ) , toxyloxanthone C ( 20 ) , 2‐deprenylrheediaxanthone B ( 21 ) , 8‐prenylxanthone ( 22 ) , cudraxanthone M ( 23 ) , cudratrixanthone H ( 24 ) , cudracuspixanthone B ( 25 ) , cudracuspixanthone C ( 26 ) , cudraxanthone B ( 27 ) , cudracuspixanthone D ( 28 ) , and cudraxanthone A ( 30 ) by the direct comparison of their physicochemical and spectroscopic data with reported values (Fig. ).…”