Osage Orange Pigments. XIV. The Structure of Macluraxanthone^1a-c

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.…”

“… Structures of flavanones and xanthones from the root bark of the osage orange tree, Maclura pomifera 1–4, 19…”

“…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.…”

Xanthones, Benzophenones and Triterpenes from the Stem Bark of Garcinia ovalifolia

“…The remaining signals in the PMR spectrum were made up of a singlet at 61.66 for six protons and an ABX system centred at 65.07, 5.17 and 6.73. This is typical of the I, I -dimethylallyl moiety [12]. As the assignments made require protons at C-7 and C-8, a linear pyran ring (which must be C-2 to C-3 linked), a C-i hydroxyl and ortho hydroxyls (which can only be C-5 and C-6) then this second prenyl substituent must be placed at C-4 and leads to the assignment of structure (I) to the xanthone.…”

A Cultural and Entomological Review of the Osage Orange (Maclura pomifera (Raf.) Schneid.) (Moraceae) and the Origin and Early Spread of “Hedge Apple” Folklore

“…Yellow dye, called aurantine, was made from Osage Orange and used during World War I as a substitute for fustic (Matos 1916). Other pigments were also isolated, but all have been replaced by synthetic dyes (Smith and Perino 1981;Wolfrom et al 1963Wolfrom et al , 1964.…”