Protosappanin C from Sappan Lignum and Absolute Configuration of Protosappanins(Organic,Chemical)

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概要

• 論文の詳細を見る

• A new dibenz[b,d]oxocin derivative, named protosappanin C (3), C_<16>H_<14>O_6, amorphous powder, [α]^<23>_D 〜39.8° (MeOH), was isolated from Sappan Lignum(the dried heart-wood of Cacsalplnia sappan L. (Leguminosae)). It yielded sappanin (4) on alkaline fusion, an oxime (5), a dimethyl acetal (6) on treatment with jrj-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 5 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)-dibenz[b,d]oxoctncarbal-dehyde. A possible route of biosynthesis of protosappanins from sappanchalcone is discussed.

• 公益社団法人日本薬学会の論文
• 1987-07-25

著者

• 南雲 清二

  Faculty of Pharmaceutical Sciences

• 南雲 清二

  Faculty Of Pharmaceutical Sciences Hoshi University

• 長井 正博

  Institute of Medicinal Chemistry, Hoshi University

• 長井 正博

  Institute Of Medicinal Chemistry Hoshi University

関連論文

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• Protosappanins E-1 and E-2,Stereoisomeric Dibenzoxocins Combined with Brazilin from Sappan Ligunm
• New Glucosides of a 4-Hydroxy-5-methylcoumarin and a Dihydro-α-pyrone from Gerbera jamesonii hybrida
• Cyanogenic Glycosides and 4-Hydroxycoumarin Glycosides from Gerbera jamesonii hybrida
• Protosappanin C from Sappan Lignum and Absolute Configuration of Protosappanins(Organic,Chemical)
• Bitter Principles of Pertya glabrescens : Two Sesquiterpene Glucosides

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