Novel phenanthrene and isocoumarin from the rhizomes of Dioscorea nipponica Makino subsp. rosthornii (Prain et Burkill) C. T. Ting (Dioscoreaceae)

Bioorg Med Chem Lett. 2017 Aug 1;27(15):3595-3601. doi: 10.1016/j.bmcl.2017.03.095. Epub 2017 Apr 1.

Abstract

The investigation of the constituents in the rhizomes of Dioscorea nipponica Makino subsp. rosthornii (Prain et Burkill) C. T. Ting afforded one new phenanthrene 2,2',7,7'-tetramethoxy-[1,1'-biphenanthrene]-4,4',6,6'-tetrol (7) and one new isocoumarin diorosthornoumarin (8), together with 16 known compounds (1-6 and 9-18). Their structures were established on the basis of extensive spectroscopic evidences (IR, HR-ESI-MS, NMR and optical rotation), as well as comparison with literature values. All the compounds 1-18 were firstly isolated from Dioscorea nipponica Makino subsp. Rosthornii (Prain et Burkill) C. T. Ting, and compound 9 was firstly obtained as a natural product from plants, while the compounds 11 and 14 were obtained from both the genus Dioscorea and the family Dioscoreaceae for the first time. Moreover, the antitumor activities of the compounds were tested against lung carcinoma NCI-H460 cell line. Compound 12, 13, 15 and 16 showed significant cytotoxic activities, whereas 7 displayed moderate cytotoxicity.

Keywords: 2,2′,7,7′-Tetramethoxy-[1,1′-biphenanthrene]-4,4′,6,6′-tetrol; Cytotoxicity; Diorosthornoumarin; Dioscorea nipponica Makino subsp. rosthornii (Prain et Burkill) C. T. Ting; Isocoumarin; Phenanthrene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Line, Tumor
  • Dioscorea / chemistry*
  • Humans
  • Isocoumarins / chemistry*
  • Isocoumarins / pharmacology
  • Lung / drug effects
  • Lung Neoplasms / drug therapy
  • Phenanthrenes / chemistry*
  • Phenanthrenes / isolation & purification
  • Phenanthrenes / pharmacology
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Rhizome / chemistry*

Substances

  • 1,1'-biphenanthrene
  • Antineoplastic Agents, Phytogenic
  • Isocoumarins
  • Phenanthrenes
  • Plant Extracts