102036-29-3Relevant articles and documents
Protosappanins E-1 and E-2, stereoisomeric dibenzoxocins combined with Brazilin from sappan lignum
Nagai,Nagumo
, p. 1490 - 1494 (1990)
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Protosappanin C from Sappan Lignum and Absolute Configuration of Protosappanins
Nagai, Masahiro,Nagumo, Seiji
, p. 3002 - 3005 (2007/10/02)
A new dibenzoxocin derivative, named protosappanin C (3), C16H14O6, amorphous powder, 23D -39.8 deg (MeOH), was isolated from Sappan Lignum (the dried heart-wood of Caesalpina sappan L. (Leguminosae)).It yielded sappanin (4) on alkaline fusion, an oxime (5), a dimethyl acetal (6) on treatment with p-toluenesulfonic acid in methanol, and protosappanin B (2) on reduction with sodium borohydride.The circular dichroism spectra of 3 and 6 indicated that their biphenyl system preferentially takes S configuration, from which R configuration was assigned to C-7 of 3.On the basis of the above chemical and spectroscopic evidence, the chemical structure of 3 was established as (7R)-7,8-dihydro-3,7,10,11-tetrahydroxy-7(6H)-dibenzoxocincarbaldehyde.A possible route of biosynthesis of protosappanins from sappanchalcone is discussed.Keywords - Leguminosae; Caesalpina sappan; Sappan Lignum; dibenzoxocin; biphenyl; protosappanin C; sappanin; stereochemistry