Lanceolarin, a new isoflavone glycoside of Dalbergia lanceolaria

✍ Scribed by A. Malhotra; V.V.S. Murti; T.R. Seshadri

• Publisher: Elsevier Science
• Year: 1967
• Tongue: French
• Weight: 374 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)83326-3

✦ Synopsis

The roo&ark of L&II&~@ kanctokr~ contains a new isoflavonc glyanidc, now nfuned lantxolnrin. By the use of physical, chemical and dcgradativc evidence its structure is deduced as tbc 'I-apioglucosidc of biochanin-A. It hru also ban shown tha~ the position of linkage befwan apiose and glucose is 1 -. 2 and that the glycosidic bonds are of B configuration.

Dolbergicl, an important genus of trees (Leguminosae) has fifteen reported species in India,'** many of which are of considerable commercial value and some provide folk medicines. The chemical study of these trees has revealed new isoflavones,"' Cphenyl coumarinsd and dalbergenonesg-rr (dalberginoids, neogavanoids). Ddbergia Ianceoluriu is cultivated in India as a host to the economically important lac insect and its leaves are used in the treatment of arthritic disabilities." The present paper records the presence of %apioglucoside of biochania-A, now named lanceolarin, in the rootbark of this tree. This is another example of the occurrence of the branched chain sugar apiose in giycosidic combination, the only instances known earlier being apiirP and graveobiosides A and B. r4 It may be pointed out that these compounds are flavones while laoceolarin is the first example of an isoflavone apioglucoside.

The root-bark was successively extracted with light petroleum, ether, acetone and alcohol aod from the acetone concentrate lanceolarin was isolated as a colourless crystalline solid having a bitter taste. Its colour reactions and UV spectrum indicated that it &longed to the isofiavone group. A purple-violet ferric reaction suggested the I Preliminary communjadon: