Osage Orange Pigments. XVI. The Structure of Alvaxanthone^1a

Characterization of prenylated xanthones and flavanones by liquid chromatography/atmospheric pressure chemical ionization mass spectrometry

“…1), and four xanthones, osajaxanthone, alvaxanthone, macluraxanthone and 8‐prenylxanthone (Fig. 1), that had already been reported in similar plant extracts 1–4. In addition, a new xanthone was isolated 18.…”

“…The osage orange tree ( Maclura pomifera Raf, Moracea) is a hardwood tree native to southwestern USA. Several prenylated flavanones and xanthones have been isolated from the bark of the roots of the osage orange tree 1–4. Prenylated plant phenolics, and in particular prenylated xanthones, have been found in only a few plant families 5.…”

Pomiferin

“…(Moraceae), the Osage orange, a hardwood tree native to the southwestern United States (Wolfrom et al, 1946). Several¯avonoids have also been isolated from the root bark (Delle Monache et al, 1984) and heartwood (Deshpande et al, 1973;Gerber, 1986) of the plant, while xanthones (Wolfrom et al, 1965;Cotterile & Scheimann, 1975) and stilbenes (Gerber, 1986) have been obtained from the root bark and the heartwood, respectively. The fruit extract, which contains pomiferin, has displayed interesting antimicrobial activity (Mahmoud, 1981).…”

Components of Root Bark ofCudrania tricuspidatal.1,2Structures of Four New Isoprenylated Xanthones, Cudraxanthones A, B, C and D

“…From these spectral data along with the result of Gibbs test, two possible structures (2 and 2') were suggested. The structure 2 was suggested to be more likely than 2' from the biogenetic analogy to other xanthone derivatives isolated from the Moraceae (13,14,15), as well as from the biogenetic pathway of macluraxanthone (1, 3, 5, 6-tetraoxygenated xanthone derivative) (13). Moreover, the chemical shift value of the singlet at ô 6.85 was similar to those of the C-S protons of the 6,7dioxygenated xanthone derivatives (16).…”