Phytochemical, cytotoxic and chemotaxonomic study on Ajuga forrestii Diels (Labiatae)

Abstract

A phytochemical investigation of Ajuga forrestii Diels led to the isolation of 14 compounds, including eight neo-clerodane diterpenes (1-8), two phytoecdysteroids (9, 11), one stigmastane sterol (10) and three iridoid glycosides (12-14). The structures of these compounds were identified by spectroscopic methods and a comparison of their data with those reported in the literature. This is the first report of compounds 1-14 from A. forrestii. The cytotoxic activities of the aqueous extract of A. forrestii and several compounds have been studied and the chemotaxonomic significance of isolated compounds has also been summarised.

Chemical Composition, in Vitro Antibacterial, and Antioxidant Activity of Essential Oil From Leaves of Ajuga Parviflora Benth

“…Further investigation of methanol and chloroform contained volatile components, namely Pregna-4,9(11)-dien-20-ol-3-on-19-oic acid lactone (19.58%), 20-methyl-pregna-5,17-dien-3β-ol (12.93%), 3,7-dioxocholan-24-oic acid (10.53%), and betulin (10.18%) were detected for the first time [10]. Phytochemical investigation of Ajuga forrestii Diels involves neo-clerodane diterpenes, phytoecdysteroids and stigmastane sterol and iridoid glycosides [11]. Column chromatography, nuclear magnetic resonance spectroscopy, and mass spectroscopy led to isolation and identification of five compounds, namely verbascoside, echinacoside, ajugoside, harpagide, and 8-O-acetylharpagide from Ajuga tenorei C. Presl.…”

Ajuforrestin A, an Abietane Diterpenoid from Ajuga ovalifolia var. calanthe, Induces A549 Cell Apoptosis by Targeting SHP2

“…Ajuforrestin A (compound 2 , Figure 1 ): Orange powder, HRESIMS m/z 347.1247 [M+Na] + (calcd for C 20 H 20 O 4 Na + , 347.1254). 1 H NMR (400 MHz, Acetone-d 6 ) δ: 14.32 (1H, s, 14-OH), 8.36 (1H, brs, 11-OH), 7.52 (1H, s, H-16), 6.22 (1H, s, H-6), 3.50 (1H, dd, J = 13.3, 4.5 Hz, H-1b), 2.58 (1H, br t, H-2b), 2.38 (3H, d, J = 1.4 Hz, H-17), 2.28 (1H, dd, J = 18.7, 5.5 Hz, H-2a), 1.96 (3H, s, H-18), 1.92 (3H, s, H-19), 1.62 (1H, m, H-1a), 1.58 (3H, s, H-20); 13 C NMR (100 MHz, Acetone-d 6 ) δ: 192.1 (C-7), 167.1 (C-9), 154.5 (C-12), 151.4 (C-11), 142.0 (C-3), 141.9 (C-16), 133.5 (C-14), 131.8 (C-8), 125.9 (C-4), 118.9 (C-6), 118.1 (C-15), 117.3 (C-13), 110.0 (C-5), 40.5 (C-10), 30.9 (C-2), 30.5 (C-1), 22.7 (C-20), 20.7 (C-19), 15.2 (C-18), 9.6 (C-17) (The NMR spectra shown in Figures S4 and S5 ) [ 14 ].…”

The phytochemical, biological, and medicinal attributes of phytoecdysteroids: An updated review

“…However, they might interact when used in combination with other extracted PEs. An aqueous extract of A. forrestii containing iridoid compounds exhibited potential cytotoxicity with IC 50 values ranging between 10 and 19 μmol/L, while selected iridoid glycosides exhibited more significant cytotoxicities with IC 50 values ranging between 7 and 14 μmol/L 170 . A lipophilic Leuzea root extract containing the major PE 20-HE demonstrated potent cytotoxic effects on MCF-7 cells.…”

“… In vitro MCF-7, HepG2, A549, B16 cell lines 10–48 μmol/L Cytotoxic and antioxidant activity Growth inhibition, inhibition of SOD generation and elastase release 119 Ajugacetalsterone A ( 160 ) Evaluated cytotoxicity against human lung cancer cell A-549, human hepatoma cell HepG2, human breast cancer cell MCF-7 and proliferating epidermal carcinoma cell HeLa using MTT method and significant activity have been observed. In vitro A-549, HepG2, MCF-7 cell lines IC 50 26.5 ± 1.3, 33.3 ± 1.4, 25.4 ± 1.8 and 28.1 ± 2.9 μmol/L Cytotoxic activity; antiproliferative Cell growth inhibition 170 21-Hydroxyshidasterone ( 172 ), 11 β -hydroxy-20-deoxyshidasterone ( 173 ), 2,3-acetonide-24-hydroxyecdysone ( 174 ) Evaluated anti-inflammatory activity on rat and significant activity have been observed. In vivo Carrageenan-induced inflammation in Sprague‒Dawley Rats 100 mg/kg Anti-inflammatory and analgesic activities Inhibition of paw oedema inflammation, inhibition of histamine and serotonin 123 24- epi -Pinnatasterone ( 175 ), scabrasterone ( 176 ) Evaluated Musca assay for moulting hormone activity and exhibited very low activity.…”