Bioactive polar compounds from stem bark of Magnolia officinalis

ArticleinFitoterapia 83(2):356-61 · December 2011with20 Reads
DOI: 10.1016/j.fitote.2011.11.020 · Source: PubMed
Two new phenylethanoid glycosides magnoloside D (1) and E (2), together with nine known compounds, were isolated from the polar part of methanol extract of the stem bark of Magnolia officinalis. The structures of the new compounds were established on the basis of spectral analysis. Anti-spasmodic activity of four major constituents (3, 4, 9 and 11) was tested in isolated colon of rat, compounds 3, 4, and 9 showed inhibition against acetylcholine, with the effect similar to that of magnolol and honokiol. At the same time, antioxidant activity of the isolated compounds was investigated using a DPPH and an ORAC assay. All of the compounds, except compound 8 showed potent antioxidant capacity in the ORAC assay, while compounds 1-5 and 11 exhibited potent antioxidant activity in the DPPH assay.
    • "In the MS/MS spectrum, [M + H + ] ion of Nandigerine observed two fragment ions at 280 and 295 m/z, protonated Nandigerine previously was reported with the same condition [14]. Also, the fragmentation behaviors of protonated Reticuline (2), (R)-3,4- Dehydromagnocurarine (3) and Gitingensine (4) were found and published with the same condition [15][16][17]. The last 6 alkaloids were reported or tentatively characterized in other species [18][19][20][21][22][23]. "
    [Show abstract] [Hide abstract] ABSTRACT: Purslane (Portulacaoleracea L.) leaves are well-known traditional Kurdish favorite foods. In the present study, from Purslane leaves ten alkaloids were extracted, isolated and Identified for the first time, By using HPLC/ESI-MS. The identified alkaloids were; Nandigerine(1), Reticuline(2), (R)-3,4-Dehydromagnocurarine(3), itingensine(4), (S)-Tembetarine(5), Homolycorine(6), Angustureine (7), Cyclobullatine-A (8), 10-(5-p-coumaroyl-6-methylpiperidin-2-yl) dodecan-2- one(9) and 10-(5-p-coumaroyl-6-methylpiperidin-2-yl)tetradecan-2-one(10).
    Full-text · Article · Jun 2016 · BMC Complementary and Alternative Medicine
    • "In cases where apiose is not the terminal sugar in a glycosidic chain, sugar moieties are attached to apiose exclusively in regiopositions β-(1 → 2) or β-(1 → 3′), as seen in 4. Moreover, at least one apiosyl-β-D-alloside—magnolioside E 15 (Yu et al. 2012 ), and two apio- syl-β-D-ribo-hexopyranos-3-ulosides rhododendroketoside (Morikawa, Tao, Ueda, et al. 2003) and aceroketoside 16 (Morikawa, Tao, Toguchida, et al. 2003) were identified in the stem bark of Magnolia officinalis (15) and Acer nikoense (16). In some apiosylated glycosides, aglycons possessing a carboxyl functional group may react with terminal Api to form a cyclic ester, as shown in the example of linderofruticoside A 17 (5-O-[β-D-apiofur- anosyl-(1″→2′)-O-β-D-xylopyranosyl] gentisic acid-7,5″-ester), isolated from the roots of Lindera fruticosa (Song et al. 2008). "
    [Show abstract] [Hide abstract] ABSTRACT: Apiose is a unique branched-chain pentose found principally in plants. It is a key component of structurally complex cell wall polysaccharides, as well as being present in a large number of naturally-occurring secondary metabolites. This review provides a comprehensive overview of the current state of knowledge on the metabolism and natural occurrence of apiose, using cyanogenic glycosides and their related compounds as a case study. The biological function of apiose and of apiosylated compounds is discussed.
    Full-text · Article · Feb 2016
    • "Modern pharmacological reports also demonstrated its antimicrobial, anti-inflammatory and analgesic , antianxiety and antidepressant, antitumor and anticoagulant effects as well as myocardial/cerebral ischemia protections [15]. ML and HL are two main phenolic constituents primarily isolated from Hou-po and also found in other Magnolia sp., together with other nonphenolic constituents such as alkaloids and essential oils161718. The antimicrobial effects of Hou-po extracts on Bacillus anthracis, S. aureus and other pathogens were found as early as six decades ago192021. "
    [Show abstract] [Hide abstract] ABSTRACT: Background: Methicillin-resistant Staphylococcus aureus (MRSA) is a problematic pathogen posing a serious therapeutic challenge in the clinic. It is often multidrug-resistant (MDR) to conventional classes of antibacterial agents and there is an urgent need to develop new agents or strategies for treatment. Magnolol (ML) and honokiol (HL) are two naturally occurring diallylbiphenols which have been reported to show inhibition of MRSA. In this study their synergistic effects with antibacterial agents were further evaluated via checkerboard and time-kill assays. Methods: The susceptibility spectrum of clinical MRSA strains was tested by the disk diffusion method. The minimal inhibitory concentrations (MICs) and minimal bactericidal concentrations (MBCs) of ML and HL were assayed by broth microdilution. The synergy was evaluated through checkerboard microdilution and time-killing experiments. Results: ML and HL showed similar activity against both MSSA and MRSA with MIC/MBC at 16 ~ 64 mg/L, with potency similar to amikacin (AMK) and gentamicin (GEN). When they were used in combination with conventional antibacterial agents, they showed bacteriostatic synergy with FICIs between 0.25 ~ 0.5, leading to the combined MICs decreasing to as low as 1 ~ 2 and 1 ~ 16 mg/L for ML (HL) and the agents, respectively. MIC50 of the combinations decreased from 16 mg/L to 1 ~ 4 mg/L for ML (HL) and 8 ~ 128 mg/L to 2 ~ 64 mg/L for the antibacterial agents, which exhibited a broad spectrum of synergistic action with aminoglycosides (AMK, etilmicin (ETM) and GEN), floroquinolones (levofloxacin (LEV), ciprofloxacin and norfloxacin), fosfomycin (FOS) and piperacillin. The times of dilution (TOD, the extent of decreasing in MIC value) were determined up to 16 for the combined MIC. A more significant synergy after combining was determined as ML (HL) with AMK, ETM, GEN and FOS. ML (HL) combined with antibacterial agents did not show antagonistic effects on any of the ten MRSA strains. Reversal effects of MRSA resistance to AMK and GEN by ML and HL were also observed, respectively. All the combinations also showed better dynamic bactericidal activity against MRSA than any of single ML (HL) or the agents at 24 h incubation. The more significant synergy of combinations were determined as HL (ML) + ETM, HL + LEV and HL + AMK (GEN or FOS), with △LC24 of 2.02 ~ 2.25. Conclusion: ML and HL showed synergistic potentiation of antibacterial agents against clinical isolates of MRSA and warrant further pharmacological investigation.
    Full-text · Article · Dec 2015
Show more