3-Benzylchroman derivatives related to brazilin from Sappan Lignum.

Xanthine Oxidase Inhibitors from the Heartwood of Vietnamese Caesalpinia sappan

“…6) The known compounds were identified by analysis of their spectroscopic data and comparison with literature data to be protosappanin E-2 (2), 7) protosappanin B (5), 8) protosappanin C dimethyl acetal (6), 9) protosappanin A (7), 10) brazilin (8), 11) 3Ј-O-methylbrazilin (9), 12) 3Ј-deoxysappanol (10), 13,14) 3Ј-deoxy-4-O-methylsappanol (11), 15) 4-O-methylsappanol (12), 12,16) sappanol (13), 15) 4-Omethylepisappanol (14), 12,16) sappanone B (15), 12,15) 3-deoxysappanone B (16), 12,16) and sappanchalcone (17). 17) Neoprotosappanin (1) This suggested that the two singlets in unit II should be para to each other.…”

“…12,16) Fraction 3 (IC 50 , 8.5 mg/ml) was further separated by silica gel comlumn chromatography, followed by reversed-phase preparative TLC with CH 3 CN : MeOH : H 2 Oϭ1 : 1 : 3, to give neosappanone A (4, 3.3 mg), protosappanin A dimethyl acetal (3, 15.2 mg), 7 (21.6 mg), 8 (4.6 mg), 12 (23.7 mg), sappanol (13, 1.4 mg), 15) 4-O-methylepisappanol (14, 6.9 mg), 12,16) 12,16) and sappanchalcone (17, 13.0 mg).…”

“…In this paper, we have identified a novel benzindenopyran, neoprotosappanin (1) and a novel dibenzoxocin, protosappanin A dimethyl acetal (3), and protosappanin E-2 (2) together with 14 known phenolic compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17). To the best of our knowledge, 1 represents a novel carbon framework, a benzindenopyran system, produced from two monomeric units, brazilin (8), while 3 might be an artifact formed from 7 during isolation procedure as demonstrated by the reverse reaction.…”

A new homoisoflavan from Caesalpinia sappan

“…A portion of the EtOAcsoluble fraction was separated by chromatographic procedures to give a new homoisoflavan, 7,3 0 ,4 0 -trihydroxy-3-benzyl-2H-chromene (1) (Fig. 1), along with seven known phenolic compounds, 4-O-methylsappanol (2) [5], 4-Omethylepisappanol [5], 3 0 -deoxy-4-O-methylsappanol [6], intricatinol [7], caesalpin J [8], protosappanin A [9], and brazilin [10]. The structures of the known compounds were determined by comparison of their spectroscopic data with those reported in the literature.…”

Synthesis and NMR elucidation of homoisoflavanone analogues

“…The basic homoisoflavanone structure consists of a 16-carbon skeleton, which includes a chromane system with a benzyl or benzylidine group at position 3 [2]. Natural homoisoflavanone (3-benzylidine-4-chromanones) such as bonducellin, isobonducellin, 2 0 -methoxybonducellin and Sappanone A have been isolated from different plants [3][4][5][6][7][8]. Few reports on the biological activity of homoisoflavanones have been found.…”