Bioactive spirans and other constituents from the leaves of Cannabis sativa f. sativa

J Asian Nat Prod Res. 2017 Aug;19(8):793-802. doi: 10.1080/10286020.2016.1248947. Epub 2016 Nov 16.

Abstract

In this paper, 17 compounds (1-17) were isolated from the leaves of Hemp (Cannabis sativa f. sativa). Among the isolates, two were determined to be new spirans: cannabispirketal (1), and α-cannabispiranol 4'-O-β-D-glucopyranose (2) by 1D and 2D NMR spectroscopy, LC-MS, and HRESIMS. The known compounds 7, 8, 10, 13, 15, and 16 were isolated from Hemp (C. sativa f. sativa) for the first time. Furthermore, compounds 8 and 13 were isolated from the nature for the first time. All isolated compounds were evaluated for cytotoxicity on different tissue-derived passage cancer cell lines through cell viability and apoptosis assay. Among these compounds, compounds 5, 9 and 16 exhibited a broad-spectrum antitumor effect via inhibiting cell proliferation and promoting apoptosis. These results obtained have provided valuable clues to the understanding of the cytotoxic profile for these isolated compounds from Hemp (C. sativa f. sativa).

Keywords: Cannabaceae; Cannabis sativa f. sativa; cytotoxicity; flavonoids; spirans.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Apigenin
  • Cannabis / chemistry*
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Flavones
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology*
  • Humans
  • MCF-7 Cells
  • Molecular Structure
  • Plant Leaves / chemistry*
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*

Substances

  • Antineoplastic Agents, Phytogenic
  • Drugs, Chinese Herbal
  • Flavones
  • Flavonoids
  • Spiro Compounds
  • Apigenin
  • cannflavin
  • vitexin