Studies on Nepalese crude drugs. XXV. Phenolic constituents of the leaves of Didymocarpus leucocalyx C. B. Clarke (Gesneriaceae)

Akiko Segawa, Yukinori Miyaichi, Tsuyoshi Tomimori, Fumiyuki Kiuchi, Tomihisa Ohta

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Seven new phenolic compounds (814) including three ones having unique structure named didymocalyxins A (12), B (13) and C (14) have been isolated from the leaves of Didymocarpus leucocalyx, along with five known flavonoids (5-hydroxy-6,7-dimethoxyflavanone, 5,8-dihydroxy-6,7-dimethoxyflavanone, 2',6'-dihydroxy-3',4'-dimethoxychalcone, 3'-hydroxy-2',4',5',6'- tetramethoxychalcone and 2',5'-dihydroxy-4'-methoxy-3',6'-dioxochalcone) and two known anthraquinoids (physcion and catenarin). The structures of 814 were determined to be 3',4-dihydroxy-2',4',5',6'-tetramethoxychalcone (8), 5,8- dihydroxy-6,7-dimethoxyisoflavone (9), 1,6,8-trihydroxy-4-benzoyloxy-3- methylanthraquinone (10), (2S)-2,3-dihydroxypropyl 1,6, 8-trihydroxy-3- methyl-9,10-dioxoanthracene-2-carboxylate (11), (±)-1,4-dihydroxy-2,3,6,7- tetramethoxy-10-phenyl-9,10-dihydrocyclohepta[2,1-b]4H-chromene-8,11-dione (12), 3-((1E,2E)-1-hydroxy-3-phenylprop-2-enylidene)-7-((2E)-3-phenyl-prop-2- enoyl)-6-hydroxy-4,5-dimethoxybenzo[b]furan-2-one (13) and 2((1E)-2- phenylvinyl)-5,6-dihydroxy-7,8-dimethoxy-4H-pyrano[3,2-d]benzo[b]furan-4-one (14) on the basis of chemical and spectroscopic evidence and X-ray analysis.

Original languageEnglish
Pages (from-to)1404-1411
Number of pages8
JournalChemical and Pharmaceutical Bulletin
Volume47
Issue number10
Publication statusPublished - 1999 Oct
Externally publishedYes

Fingerprint

Benzopyrans
X ray analysis
Flavonoids
X-Rays
Pharmaceutical Preparations
physcione
3-hydroxy-3',4'-dimethoxychalcone
furan
benzofuran
4'-hydroxy-2,4-dimethoxychalcone

Keywords

  • Anthraquinone
  • Didymocalyxin
  • Didymocarpus leucocalyx
  • Flavonoid
  • Gesneriaceae
  • Phenolic compound

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

Studies on Nepalese crude drugs. XXV. Phenolic constituents of the leaves of Didymocarpus leucocalyx C. B. Clarke (Gesneriaceae). / Segawa, Akiko; Miyaichi, Yukinori; Tomimori, Tsuyoshi; Kiuchi, Fumiyuki; Ohta, Tomihisa.

In: Chemical and Pharmaceutical Bulletin, Vol. 47, No. 10, 10.1999, p. 1404-1411.

Research output: Contribution to journalArticle

Segawa, Akiko ; Miyaichi, Yukinori ; Tomimori, Tsuyoshi ; Kiuchi, Fumiyuki ; Ohta, Tomihisa. / Studies on Nepalese crude drugs. XXV. Phenolic constituents of the leaves of Didymocarpus leucocalyx C. B. Clarke (Gesneriaceae). In: Chemical and Pharmaceutical Bulletin. 1999 ; Vol. 47, No. 10. pp. 1404-1411.
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abstract = "Seven new phenolic compounds (814) including three ones having unique structure named didymocalyxins A (12), B (13) and C (14) have been isolated from the leaves of Didymocarpus leucocalyx, along with five known flavonoids (5-hydroxy-6,7-dimethoxyflavanone, 5,8-dihydroxy-6,7-dimethoxyflavanone, 2',6'-dihydroxy-3',4'-dimethoxychalcone, 3'-hydroxy-2',4',5',6'- tetramethoxychalcone and 2',5'-dihydroxy-4'-methoxy-3',6'-dioxochalcone) and two known anthraquinoids (physcion and catenarin). The structures of 814 were determined to be 3',4-dihydroxy-2',4',5',6'-tetramethoxychalcone (8), 5,8- dihydroxy-6,7-dimethoxyisoflavone (9), 1,6,8-trihydroxy-4-benzoyloxy-3- methylanthraquinone (10), (2S)-2,3-dihydroxypropyl 1,6, 8-trihydroxy-3- methyl-9,10-dioxoanthracene-2-carboxylate (11), (±)-1,4-dihydroxy-2,3,6,7- tetramethoxy-10-phenyl-9,10-dihydrocyclohepta[2,1-b]4H-chromene-8,11-dione (12), 3-((1E,2E)-1-hydroxy-3-phenylprop-2-enylidene)-7-((2E)-3-phenyl-prop-2- enoyl)-6-hydroxy-4,5-dimethoxybenzo[b]furan-2-one (13) and 2((1E)-2- phenylvinyl)-5,6-dihydroxy-7,8-dimethoxy-4H-pyrano[3,2-d]benzo[b]furan-4-one (14) on the basis of chemical and spectroscopic evidence and X-ray analysis.",
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