Phytochemical Analysis, Biological Activity, and Secretory Structures of Stachys annua (L.) L. subsp. annua (Lamiaceae) from Central Italy

Abstract

Stachys annua subsp. annua, well-known in central Italy as 'stregona annuale', is an annual, small, slightly-scented herb, commonly found in fields and uncultivated areas in almost all regions of Italy. In folk medicine, its aerial parts were used as anti-catarrhal, febrifuge, tonic, and vulnerary. In the present work, the chemical composition of the flowering aerial parts was studied. The hydrodistilled volatile oil, analysed by GC/MS, showed sesquiterpenoids as the major fraction (42.5%); phytol (9.8%), germacrene D (9.2%), and spathulenol (8.5%) were the most abundant constituents. The volatile oil was assayed for antioxidant and cytotoxic activity by DPPH, ABTS, FRAP, and MTT methods. The cytotoxicity results against HCT116, A375, and MDA-MB 231 human tumor cell lines were significant, with IC50 values of 23.5, 37.2, and 41.5 μg/ml, respectively, whereas the antioxidant power was negligible. The EtOH extract was composed mainly of three glycosidic flavonoids, namely 7-{[2-O-(6-O-acetyl-β-D-allopyranosyl)-β-D-glucopyranosyl]oxy}-5,8-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one (1), 7-{[6-O-acetyl-2-O-(6-O-acetyl-β-D-allopyranosyl)-β-D-glucopyranosyl]oxy}-2-(3,4-dihydroxyphenyl)-5,8-dihydroxy-4H-1-benzopyran-4-one (2), and 7-{[6-O-acetyl-2-O-(β-D-allopyranosyl)-β-D-glucopyranosyl]oxy}-2-(3-hydroxy-4-methoxyphenyl)-5,8-dihydroxy-4H-1-benzopyran-4-one (3). On the contrary, iridoids, considered chemotaxonomic markers of the genus Stachys, were absent in this species. Finally, the morphological and histochemical survey showed that glandular trichomes were composed of two main types, i.e. peltate type A and capitate types B and C giving positive response for both lipids and polyphenols.

Polar Constituents, Essential Oil and Antioxidant Activity of Marsh Woundwort (Stachys palustris L.)

“…Despite its important uses as a food plant, little is known on its chemical composition, especially on the polar constituents. Therefore, as a continuation of our phytochemical studies on Stachys species, in this article, we report on the secondary metabolites, namely polar constituents and essential oils of two accessions of S. palustris from Hungary and France. Notably, the polar constituents and essential oils obtained from the flowering aerial parts were fully characterized by NMR and GC/MS, respectively.…”

Reassessment of the polar fraction of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande (Lamiaceae) from the Monti Sibillini National Park and its potential pharmacologic uses.

“…The genus Stachys is represented by annual or perennial herbs known for their interesting biological activities, i.e., anti-inflammatory [2], antispasmodic, sedative, and diuretic [3-5]. Several phytochemical components, which may be responsible of the biological activities, have been isolated from Stachys species, i.e., iridoids [6,7], phenylethanoid glycosides, flavonoids [8,9], acidic metabolites, polysaccharides, and terpenoids [10]. …”

Türkiye’den Üç Stachys L. Türünün Uçucu Bileşenleri

“…α-Pinene, β-pinene and (E)-β-ocimene were found as the major compounds within this species grown in Turkey. Whereas sesquiterpenoids (42.5% area) were found to be the main components of the same species grown in central Italy [22]. Phytol which is used in the fragrance industry, was found to be the major component of the plant grown in Central Italy [22] although could not be found in the same species grown in Turkey.…”

“…annua var. annua had been reported before [16][17][18][19][20][21][22], but there is no literature data for the comparative evaluation of the volatile chemical composition obtained from S. macrantha, S. sylvatica and S. annua ssp. annua var.…”

“…annua var. annua grown in central Italy [22]. Bulgaria, Kosova, Croatia, Italy and Hungary originated S. sylvatica samples together with S. macrantha samples which were collected from Hungary were previously studied by different groups and sesquiterpene lactones were reported to be the major group of substances at all of researches.…”