Phytochemical Analysis, Biological Activity, and Secretory Structures of Stachys annua (L.) L. subsp. annua (Lamiaceae) from Central Italy.
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.
Department of Chemistry, La Sapienza University, IT-Rome.|Department of Environmental Biology, La Sapienza University, IT-Rome.
Alessandro
A
Venditti
Department of Chemistry, La Sapienza University, IT-Rome.
Armandodoriano
A
Bianco
School of Pharmacy, University of Camerino, IT-Camerino, (phone: +39 0737404506).
Luana
L
Quassinti
School of Pharmacy, University of Camerino, IT-Camerino, (phone: +39 0737404506).
Massimo
M
Bramucci
School of Pharmacy, University of Camerino, IT-Camerino, (phone: +39 0737404506).
Giulio
G
Lupidi
School of Pharmacy, University of Camerino, IT-Camerino, (phone: +39 0737404506).
Silvia
S
Damiano
School of Pharmacy, University of Camerino, IT-Camerino, (phone: +39 0737404506).
Fabrizio
F
Papa
School of Pharmacy, University of Camerino, IT-Camerino, (phone: +39 0737404506).
Sauro
S
Vittori
Department of Biology, University of Florence, IT-Florence.
Laura
L
Maleci Bini
Department of Biology, University of Florence, IT-Florence.
Claudia
C
Giuliani
School of Biosciences and Veterinary Medicine, University of Camerino, IT-Camerino.
Domenico
D
Lucarini
School of Pharmacy, University of Camerino, IT-Camerino, (phone: +39 0737404506). filippo.maggi@unicam.it.
Filippo
F
Maggi
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D035264:Flowers / Q000737:chemistry; D006801:Humans; D007558:Italy; D009369:Neoplasms / Q000188:drug therapy; D009822:Oils, Volatile / Q000737:chemistry* / Q000494:pharmacology*; D010836:Phytol / Q000737:chemistry / Q000494:pharmacology; D010938:Plant Oils / Q000737:chemistry / Q000494:pharmacology; D012717:Sesquiterpenes / Q000737:chemistry / Q000494:pharmacology; D045788:Sesquiterpenes, Germacrane / Q000737:chemistry / Q000494:pharmacology; D031366:Stachys / Q000737:chemistry*; D064201:Trichomes / Q000737:chemistry / Q000648:ultrastructure
D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D009822:Oils, Volatile; D010938:Plant Oils; D012717:Sesquiterpenes; D045788:Sesquiterpenes, Germacrane; D010836:Phytol; C013258:spathulenol; C027259:germacrene D
Biological activities; Essential oils; Glycosidic flavonoids; Stachys annua; Trichomes