Anti-inflammatory and anti-melanogenic steroidal saponin glycosides from Fenugreek (Trigonella foenum-graecum L.) seeds

Planta Med. 2011 May;77(7):705-10. doi: 10.1055/s-0030-1250477. Epub 2010 Oct 26.

Abstract

Fenugreek seed ( Trigonella foenum-graecum L.) is used as an herbal medicine for treating metabolic and nutritive dysfunctions. To determine if this plant has other beneficial effects, we tested the inhibitory activities of a methanol (MeOH) extract of fenugreek seed on the production of inflammatory cytokines and melanin synthesis in cultured cell lines in vitro. The MeOH extract inhibited the production of phorbol-12-myristate-13-acetate-induced inflammatory cytokines such as tumor necrosis factor (TNF)-α in cultured THP-1 cells, and also restrained the intracellular synthesis of melanin in murine melanoma B16F1 cells. We isolated three active constituents from fenugreek seed extracts. These were identified as the steroidal saponins 26- O-β-D-glucopyranosyl-(25 R)-furost-5(6)-en-3 β,22 β,26-triol-3- O-α-L-rhamno-pyranosyl-(1'' → 2')-O-[β-D-glucopyranosyl-(1''' → 6')- O]-β-D-glucopyranoside 1, minutoside B 2, and pseudoprotodioscin 3. Compounds 1 and 2 strongly suppressed the production of inflammatory cytokines, whereas 3 showed a weaker suppressing effect. Melanogenesis in B16F1 cells was significantly suppressed by 1 and 3, and weakly suppressed by 2. All three compounds showed moderate cytotoxicities. These results indicate that fenugreek extract and its active constituents could protect against skin damage.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Carbohydrate Sequence
  • Cell Line, Tumor
  • Cytokines / antagonists & inhibitors
  • Cytokines / biosynthesis
  • Humans
  • Melanins / antagonists & inhibitors*
  • Melanins / biosynthesis
  • Melanoma, Experimental / metabolism
  • Mice
  • Molecular Sequence Data
  • Molecular Structure
  • Monocytes / drug effects
  • Monocytes / immunology
  • Multiple Myeloma / metabolism
  • Plant Extracts / pharmacology
  • Plants, Medicinal / chemistry*
  • Saponins / isolation & purification
  • Saponins / pharmacology*
  • Seeds / chemistry
  • Trigonella / chemistry*
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors
  • Tumor Necrosis Factor-alpha / biosynthesis

Substances

  • Anti-Inflammatory Agents
  • Antineoplastic Agents
  • Cytokines
  • Melanins
  • Plant Extracts
  • Saponins
  • Tumor Necrosis Factor-alpha