Bassiamide A, a new alkaloid from xero-halophyte Bassia indica Wight.

Abstract

N- [(3-(3-methyl-1-oxo-butyl)amino)propyl]-3- (3,4-dihydroxyphenyl)prop-2-enamide (7), named "Bassiamide A", a new alkaloid, together with six known compounds including one lignan (1) and five lignanamides (2-6), were isolated from the aerial parts of Bassia indica Wight. The study also reported an optimal separation of a rare occurring R-isomer lignanamide derivative (6) from a natural origin, in addition to its known corresponding Sisomer (5). Structures of isolated compounds were elucidated based on NMR spectroscopic data, HR-MS, and comparison with known related ones, and they were identified as syringaresinol (1), N-trans-feruloyl-3-methoxytyramine (2), N-trans-feruloyltyramine (3), S-(-)-N-trans-feruloyl normetanephrine (4), S-(-)-N-trans-feruloyl octopamine (5), R-(+)-N-trans-feruloyl octopamine (6). The isolated compounds were evaluated for their antiacetylcholinesterase activity, and they showed weak inhibitory activity.

Possible neuroprotective effects of amide alkaloids from Bassia indica and Agathophora alopecuroides: in vitro and in silico investigations

“…The methoxy group at C-7 0 was assigned to the peaks at d H 3.17, s and d C 81.5 ppm. 29 S-(À)-N-trans-feruloylnormetanephrine (3), [a] 25 D À 35.00 (c 0.01, MeOH), and the rarely occurring R-(+)-N-trans-feruloyloctopamine ( 5), [a] 25 D + 24.29 (c 0.01, MeOH), were reported in our previous work, 9 and their NMR spectral data are shown in Tables 1 and 2. In addition, the isolated compounds 1, 2, 4, 6 and 7 were subjected to in silico investigation to provide more scientic data regarding their binding mechanisms to some molecular targets implicated in AD.…”

“…The extraction was carried out as described in our previous work. 9 Briey, the shade-dried aerial parts of B. indica (1.3 kg) and A. alopecuroides (0.9 kg) were ground into a ne powder and then extracted by maceration with 80% aqueous methanol. Following evaporation under reduced pressure, 138.5 g and 100 g of crude extracts were obtained from B. indica and A. alopecuroides, respectively.…”

“…Bassia indica and Agathophora alopecuroides (Chenopodiaceae) are halophytic herbs with therapeutic purposes that are widely distributed in the Egyptian ecosystem. [8][9][10][11] In previous reports, chemical investigation of Chenopodiaceae species has revealed the presence of nitrogenous compounds, avonoids, and saponins. [12][13][14][15][16][17] Although phenolics and other secondary metabolites previously reported in B. indica displayed antiacetylcholinesterase activity, their therapeutic potential in the treatment of AD has not yet been elucidated.…”

Comprehensive Chemical Profiling of Bassia indica Wight. Aerial Parts Extract Using UPLC-ESI-MS/MS, and Its Antiparasitic Activity in Trichinella spiralis Infected mice: In Silico Supported In Vivo Study

“…Furthermore, compounds (15)(16)(17) produced the main characteristic fragment ions including loss of one or two caffeoyl moieties at m/z 179 characteristic for chlorogenic acid derivatives. To the best or our knowledge, compounds (1-3, 5, 8-11) were reported from K. indica [38], compounds (4, 6, 7) were reported from K. scoparia [39] and compound (14) was isolated before from B. indica [15]. In addition, compounds (12,13,18) and (15)(16)(17) are reported in our study from B. indica for the rst time [40,41].…”

“…Kochia indica) an Egyptian medicinal plant belongs to the family Chenopodiaceae, it is native to India and widely distributed in the Western Mediterranean to Eastern Asia [13]. Bassia species are rich in phytoconstituents including: sterols, alkaloids, avonoids and saponins [14][15][16], and it have been reported to treat variety of ailments including analgesic, anti-in ammatory, antiallergic, antipyretic, anticancer and antiviral [16][17][18], and as antibacterial, antifungal, antiparasitic [19]. Recently, Aboul-Enein and co-workers examined the in vitro anticancer activity of Kochia indica Wight (a syn.…”