Phytochemical analysis, biological evaluation and micromorphological study of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande endemic to central Apennines, Italy

Fitoterapia. 2013 Oct:90:94-103. doi: 10.1016/j.fitote.2013.06.015. Epub 2013 Jul 1.

Abstract

Stachys alopecuros subsp. divulsa (Lamiaceae), a perennial herb endemic to central Italy growing on mountain pastures, was investigated for the first time for the content of secondary metabolites, for the micromorphology and histochemistry of glandular trichomes, and for the biological activity of the volatile oil, namely cytotoxic, antioxidant and antimicrobial. The plant showed the molecular pattern of iridoids, among which a new iridoid diglycoside (4'-O-β-D-galactopyranosyl-teuhircoside) was detected, together with a sterol glucoside and a phenylethanoid glycoside. The essential oil from the flowering aerial parts was characterized by a high proportion of sesquiterpene hydrocarbons (65.1%), with (E)-caryophyllene (33.2%) as the most abundant, while other main components were germacrene D (7.6%), α-humulene (6.4%) and the oxygenated cis-sesquisabinene hydrate (10.2%). Taken together, polar and apolar chemical profiles support the classification of the species within the section Betonica of the genus Stachys. Micromorphological study revealed three types of glandular hairs secreting different classes of compounds, with type A peltate hairs producing the bulk of the essential oil. MTT assay revealed the potential of the volatile oil in inhibiting A375, HCT116 and MDA-MB 231 tumor cells (IC₅₀ values below 20 μg/ml).

Keywords: Biological activity; Essential oil; Iridoids; Lamiaceae; Stachys alopecuros subsp. divulsa; Verbascoside.

MeSH terms

  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Antineoplastic Agents, Phytogenic / therapeutic use*
  • Antioxidants / isolation & purification
  • Antioxidants / pharmacology
  • Antioxidants / therapeutic use*
  • Bacteria / drug effects
  • Cell Line, Tumor
  • Classification
  • Flowering Tops / chemistry
  • Humans
  • Iridoids / isolation & purification
  • Italy
  • Neoplasms / drug therapy*
  • Oils, Volatile / chemistry
  • Oils, Volatile / pharmacology
  • Oils, Volatile / therapeutic use*
  • Phytotherapy
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Plant Extracts / therapeutic use
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Sesquiterpenes / therapeutic use*
  • Stachys / chemistry*
  • Stachys / classification
  • Stachys / ultrastructure
  • Trichomes / ultrastructure*

Substances

  • Antineoplastic Agents, Phytogenic
  • Antioxidants
  • Iridoids
  • Oils, Volatile
  • Plant Extracts
  • Sesquiterpenes