Abstract

Helicrysum melaleucum is a medicinal plant traditionally used in the islands of the Macaronesia region for the treatment of respiratory diseases. In this work, the phenolic compounds of Helicrysum melaleucum plants collected in different geographical locations of Madeira Island and their morphological parts (total aerial parts, leaves, flowers and stems) were extracted and analyzed separately by high-performance liquid chromatography/electrospray ionization tandem mass spectrometry (HPLC-DAD/ESI-MS(n)). A total of 68 compounds were characterized based mainly on their UV and mass spectra. These included derivatives of O-glycosylated flavonoids (flavonol and flavones type), quinic acid, caffeic acid, lignans and polyphenols. The flowers were found to be the morphological part with higher variety of phenolic compounds. The large differences in the phenolic composition of plants collected from different geographical locations allowed the identification of a few components, such as pinoresinol and methoxylated flavone derivatives, likely to be useful as geographical markers. Also, these results promote further comparison of the bioactivities of the different samples analyzed. This paper marks the first report on the chemical analysis of Helichrysum melaleucum species.

Highlights

  • Helicrysum melaleucum is a medicinal plant traditionally used in the islands of the Macaronesia region for the treatment of respiratory diseases

  • To simplify the identification of extracts, samples from Sao Vicente were denominated as SV and the one from Fajada Nogueira as FN

  • It must be mentioned that in Fajada Nogueira, located at 1000 m altitude, H. melaleucum is a rare specimen and it was not possible to collect enough plant material to separate into different morphological parts, as it was done for the plants collected in Sao Vicente

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Summary

Chemical and standards

HPLC grade acetonitrile (CH3CN) (Lab-Scan, 99%), ultrapure water (Milli-Q, Waters) and formic acid (analytical grade) were used for mobile phase preparation in the LC/MS analysis. The methanol used for extraction of Helichrysum devium was AR grade, purchased from Fisher. Eluents prepared for LC/MS analysis were filtered through 0.45 mm (Millipore) membranes. Apigenin (>99%), quercetin (>99%), ferulic acid (>99%) and coumaric acid (>99%) were purchased from ExtraSynthese and 5-O-caffeoylquinic acid (99%), kaempferol (>99%) and ellagic acid (>99%) from Acros Organics. Stock solutions of these compounds (100 mg/mL) were prepared in ethanol and further analyzed by LC-DAD/ESI-MSn

Plant material and sample preparation
Liquid chromatography
Mass spectrometry
RESULTS AND DISCUSSION
Identification of flavonoids
Morphological part
Total aerial parts Leaves Stems Flowers
Leaves Flowers Stems Total aerial parts
Leaves Flowers Stems Leaves Flowers
Leaves Leaves
Leaves Flowers
Coumaric acid derivative
Total aerial parts Leaves Leaves
Hydroxycinnamic derivatives
Coumaroylcaffeoylquinic acid
Malonylcaffeoylquinic acid
Caffeoylferuloylquinic acid
Caffeic acid derivatives
Other compounds
Unknown compounds
CONCLUSIONS
Full Text
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