Antiangiogenic Iridoids from Stachys ocymastrum and Premna resinosa

Abstract

In this paper, the isolation of one new iridoid glucoside, 6β-acetoxyipolamiide (1), and thirteen (2 – 14) known congeners from two Lamiaceae species, Stachys ocymastrum and Premna resinosa, leaf extracts is reported. The structural determination of the isolated compounds was performed by mono- and bidimensional NMR spectroscopic analysis as well as MS experiments. The isolates were assayed for their antiangiogenic activity by two in vivo models, zebrafish embryos and chick chorioallantoic membrane assays. The compounds with a significant antiangiogenic activity in both assays were β-hydroxyipolamiide (2), ipolamiide (3), and buddlejoside A5 (8). 6-O-α-l-(3″-O-p-Methoxycinnamoyl-4″-O-acetyl)rhamnopyranosyl catalpol (13) and 6-O-α-l-(2″-trans-caffeoyl)rhamnopyranosyl catalpol (6) showed the best antiangiogenic response on blood vessel growth in zebrafish embryos, whereas saccatoside (10) and 6-O-α-l-(2″-O - p-methoxycinnamoyl-3″-O-acetyl)rhamnopyranosyl catalpol (14) resulted in a strong reduction of capillary formation in the chorioallantoic membrane assay.

Genus Stachys: A Review of Traditional Uses, Phytochemistry and Bioactivity

“…Of note, Iannuzzi et al (2019) isolated from the leaves of S. ocymastrum (syn. S. hirta L.) five iridoids which haven′t been documented in other species, namely 6β-acetoxyipolamiide ( 172 ) 6β-hydroxyipolamiide ( 173 ), ipolamiide ( 174 ), ipolamiidoside ( 175 ) and lamiide ( 176 ) [ 123 ]. A study conducted by Háznagy-Radnai (2006) examined the phytochemical profiles of Stachys spp.…”

“…A study carried out by Iannuzzi et al (2019) studied the antiangiogenic activity in two in vivo models (zebrafish embryos and chick chorioallantoic membrane assays) of the isolated compounds of the leaf extract of S. ocymastrum . The isolated compounds with the best antiangiogenic activity in both assays were β-hydroxyipolamiide ( 173 ) and ipolamiide ( 174 ) [ 123 ]. Recently, Lee et al (2020) studied the anti-obesity and anti-dyslipidemic property of the roots powder of S. sieboldii in rats, following a high-fat and high-cholesterol diet (HFC) [ 161 ].…”

Proapoptotic Activity of Achillea membranacea Essential Oil and Its Major Constituent 1,8-Cineole against A2780 Ovarian Cancer Cells

“…Medicinal plants and their constituents have countless biological properties, based mainly on their ability to interact with key enzymes linked to several ailments, including: cancer, diabetes, inflammation, hypertension and Alzheimer's disease [1][2][3][4][5]. Recently, EOs have caught the attention of scientists due to their ability to prevent and treat cancer, as well as their state-of-the-art application in the most advanced and sophisticated technologies in nanoscience [6][7][8].…”

New Rare Ent-Clerodane Diterpene Peroxides from Egyptian Mountain Tea (Qourtom) and Its Chemosystem as Herbal Remedies and Phytonutrients Agents

“…In folk medicine, the infusions, decoctions, and ointments made from flowers and leaves of these herbs have been used in the treatment of some disorders such as skin infections, inflammation, wounds, digestive problems, cough, ulcers, and stomach ache, and applied as antispasmodic, sedative, and diuretic agents, and cardiac tonic [3,5,[7][8][9][10], and recently administrated for genital tumours, sclerosis of the spleen, and inflammatory cancerous ulcers [11][12][13]. Phenolic extracts and essential oils of Stachys species showed a number of important biological activities such as antioxidant [14][15][16][17][18], anti-inflammatory [16,19], antiangiogenic [20], anti-nociceptive [21,22], antimicrobial [3,4,23,24], cytotoxic, and anticancer [25][26][27][28][29][30]. Additionally, the genus Stachys is rich with flavonoids and phenolic [17,[31][32][33][34][35][36], diterpenoids [10,21,27,[37][38][39][40][41]<...>…”

“…Phenolic extracts and essential oils of Stachys species showed a number of important biological activities such as antioxidant [14][15][16][17][18], anti-inflammatory [16,19], antiangiogenic [20], anti-nociceptive [21,22], antimicrobial [3,4,23,24], cytotoxic, and anticancer [25][26][27][28][29][30]. Additionally, the genus Stachys is rich with flavonoids and phenolic [17,[31][32][33][34][35][36], diterpenoids [10,21,27,[37][38][39][40][41][42], iridoids [20,[43][44][45], and phenylethanoid glycosides [46,47] metabolites.…”