Facile purification of honokiol and its antiviral and cytotoxic properties.
A separation of honokiol 1 from the closely structurally related magnolol 2 was developed. Honokiol demonstrated weak activity against HIV-1 in human lymphocytes.
Animals↗
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Glucosinolate breakdown products as insect fumigants and their effect on carbon dioxide emission of insects.
BACKGROUND: Glucosinolate breakdown products are volatile, therefore good candidates for insect fumigants. However, although they are insecticidal, the mode of action of such natural products is not clear. We studied the insecticidal effect of these compounds as fumigants, and monitored the production of carbon dioxide by the insects as a probe to the understanding of their mode of action. RESULTS: The fumigation 24-h LC50 against the house fly (Musca domestica L.) of allyl thiocyanate, allyl isothiocyanate, allyl cyanide, and l-cyano-2-hydroxy-3-butene was 0.1, 0.13, 3.66, and 6.2 microg cm-3, respectively; they were 0.55, 1.57, 2.8, and > 19.60 microg cm-3, respectively, against the lesser grain borer (Rhyzopertha dominica Fabricius). The fumigation toxicity of some of the glucosinolate products was very close to or better than that of the commercial insect fumigants such as chloropicrin (LC50: 0.08 and 1.3 microg cm-3 against M. domestica and R. dominica, respectively) and dichlorovos (LC50: < 0.02 and 0.29 microg cm-3 against M. domestica and R. dominica, respectively) in our laboratory tests. Significantly increased CO2 expiration was found in insects exposed to the vapor of allyl isothiocyanate, allyl thiocyanate and allyl isocyanate. Allyl isothiocyanate was also found to increase the CO2 expiration of the American cockroach (Periplaneta americana L.). CONCLUSIONS: Glucosinolate breakdown products have potential as biodegradable and safe insect fumigants. They may act on the insect respiratory system in their mode of action.
Allyl Compounds↗
Effects of magnolol and honokiol derived from traditional Chinese herbal remedies on gastrointestinal movement.
AIM: To study the effects of magnolol and honokiol on isolated smooth muscle of gastrointestinal tract and their relationship with Ca2+, and on the gastric emptying and the intestinal propulsive activity in mice. METHODS: Routine experimental methods using isolated gastric fundus strips of rats and isolated ileum segments of guinea pigs were adopted to measure the smooth muscle tension. The effects of magnolol 10(-3), 10(-4), 10(-5) mol/L, and honokiol 10(-4), 10(-5), 10(-6) mol/L on the contractility of gastric fundus strips of rats and ileum of guinea pigs induced by acetylcholine (Ach) and 5-hydroxytryptamine (5-HT) was assessed respectively. The method using nuclein and pigment methylene blue was adopted to measure the gastric retention rate of nuclein and the intestinal propulsive ratio of a nutritional semi-solid meal for assessing the effect of magnolol and honokiol (0.5, 2, 20 mg/kg) on gastric emptying and intestinal propulsion. RESULTS: Magnolol and honokiol significantly inhibited the contractility of isolated gastric fundus strips of rats treated with Ach or 5-HT and isolated ileum guinea pigs treated with Ach or CaCl2, and both of them behaved as non-competitive muscarinic antagonists. Magnolol and honokiol inhibited the contraction induced by Ach in Ca2+-free medium and extracellular Ca2+-dependent contraction induced by Ach. Each group of magnolol and honokiol experiments significantly decreased the residual rate of nuclein in the stomach and increased the intestinal propulsive ratio in mice. CONCLUSION: The inhibitory effect of magnolol and honokiol on contractility of the smooth muscles of isolated gastric fundus strips of rats and isolated ileum of guinea pigs is associated with a calcium-antagonistic effect. Magnolol and honokiol can improve the gastric emptying of a semi-solid meal and intestinal propulsive activity in mice.
Animals↗
Inhibition of cytochrome P4502E1 expression by organosulfur compounds allylsulfide, allylmercaptan and allylmethylsulfide in rats.
Cytochrome P4502E1 (CYP2E1) is active in both detoxication and activation of small organic molecules. The effects of organosulfur compounds including allylsulfide (AS), allylmercaptan (AM) and allylmethylsulfide (AMS) on the expression of CYP2E1 were examined in rats. 4-Nitrophenol, aniline hydroxylase and N-nitrosodimethylamine demethylase activities, the rates of which represent the level of CYP2E1, decreased in hepatic microsomes isolated from rats treated with AS in a time-dependent manner by 45% to 90%, as compared to control. Pyrazine-induced hepatic microsomes exhibited approximately 5-fold increases in CYP2E1-catalysed metabolic activities, whereas the hepatic microsomes obtained after treatment of animals with both AS and pyrazine showed rates comparable to or less than those in control microsomes. AM or AMS suppressed constitutive and pyrazine-inducible levels of CYP2E1 similarly to AS. Immunoblot analyses of hepatic microsomes, using an anti-CYP2E1 antibody, showed that AS, AM and AMS significantly suppressed constitutive levels of CYP2E1 apoprotein after 24, 48 and 72 hr. Time-dependent induction of CYP2E1 by pyrazine was also completely blocked by treatment of animals with AS throughout the experimental period, as evidenced by immunoblot analysis. The levels of CYP2E1 apoprotein in the hepatic microsomes isolated from animals treated with both AM and pyrazine, or with both AMS and pyrazine were comparable to those in control hepatic microsomes at days 1-3 post-treatment. Treatment of rats with each of these organosulfur compounds caused no significant changes in the levels of CYP2E1 mRNA, as assessed by slot and northern blot analyses, suggesting that post-transcriptional regulation may be associated with the suppression of CYP2E1 apoprotein levels. The results of metabolic activities, immunoblot analyses and RNA blot analyses demonstrated that these organosulfur compounds are effective in suppressing constitutive and inducible expression of CYP2E1.
Allyl Compounds↗
Magnolol and honokiol isolated from Magnolia officinalis protect rat heart mitochondria against lipid peroxidation.
In isolated rat heart mitochondria lipid peroxidation was induced with ADP and ferrous sulfate (FeSO4). Oxygen consumption and malondialdehyde (MDA) production were measured to quantitate lipid peroxidation. The antioxidant effects of magnolol and honokiol purified from Magnolia officinalis were 1000 times higher than that of alpha-tocopherol. The IC50 values of magnolol and honokiol for inhibition of oxygen consumption were 8.0 x 10(-8) M and 1.0 x 10(-7) M, respectively, while that of alpha-tocopherol was 1.0 x 10(-4) M. Magnolol at 0.5 microM inhibited 71.4 +/- 9.4% of oxygen consumption and 59.3 +/- 4.6% MDA production. At the same concentration, honokiol inhibited 78.1 +/- 4.7% of oxygen consumption and 86.9 +/- 4.0% of MDA production. Of conjugated diene formation 48.4 +/- 4.6% and 53.1 +/- 3.4% were inhibited by 0.5 microM magnolol and honokiol, respectively. Also both magnolol and honokiol exhibited free radical scavenging activities as shown by the diphenyl-p-picrylhydrazyl assay, but they were less potent than alpha-tocopherol.
Animals↗
Honokiol and magnolol induce Ca2+ mobilization in rat cortical neurons and human neuroblastoma SH-SY5Y cells.
We examined the intracellular Ca(2+) response in primary cultured rat cortical neurons and human neuroblastoma SH-SY5Y cells by Fluo 3 fluorescence imaging analysis. In these two kinds of neuronal cells, honokiol and magnolol increased cytoplasmic free Ca(2+) with a characteristic lag phase. The cytoplasmic free Ca(2+) increase was independent of extracellular Ca(2+), but dependent on activation of phospholipase C and inositol 1,4,5-triphosphate (IP(3)) receptors. These results suggest that honokiol and magnolol increase cytoplasmic free Ca(2+) through a phospholipase C-mediated pathway, and that the release of Ca(2+) from intracellular stores mainly contributes to the increase in cytoplasmic free Ca(2+). Thus, honokiol and magnolol may be involved in a new activation mechanism closely associated with intracellular Ca(2+) mobilization.
Animals↗
Disposition of magnolol after intravenous bolus and infusion in rabbits.
A simple and sensitive high-performance liquid chromatographic method was developed for the determination and identification of magnolol to study its pharmacokinetics in rabbits after a 5 mg/kg i.v. bolus and 76 micrograms/kg/min i.v. infusion. Plasma concentration time profiles were suited to a two-compartment open model. The elimination half-lives of magnolol were 14.56 and 15.71 min, and the total body clearances were 75.86 and 72.72 ml/min/kg for i.v. bolus and i.v. infusion, respectively. There were no significant differences in elimination half-life and total body clearance between i.v. bolus and i.v. infusion, which suggests that magnolol pharmacokinetics are linear.
Animals↗
Chemoprevention of chemically induced skin tumor development by diallyl sulfide and diallyl disulfide.
Garlic and onion oil have been shown to inhibit chemically induced skin tumor development in mice. In the present study, the effects of diallyl sulfide and diallyl disulfide, oil-soluble constituents of garlic and onion, on 7,12-dimethylbenz(a)anthracene-induced and 12,O-tetradecanoylphorbol-13-acetate-promoted skin tumor formation were examined in SENCAR mice. Topical application of diallyl sulfide or diallyl disulfide significantly inhibited skin papilloma formation from the ninth week of promotion and significantly increased the rate of survival in the murine model. Our findings support earlier evidence that these naturally occurring compounds may be useful for the chemoprevention of certain types of tumors.
9,10-Dimethyl-1,2-benzanthracene↗
Beneficial effects of a polar fraction of garlic (Allium sativum Linn) oil in rats fed with two different high fat diets.
Feeding a diet containing 20% of sesame oil (SO) or coconut oil (CNO) along with 2% cholesterol to rats for two months showed differences in their serum and tissue lipid profile and certain enzyme activities. Hyperlipidemia and related oxidative effects were more pronounced in coconut oil fed rats than those fed sesame oil. Feeding a combination of the oils (10% CNO +10% SO) lowered significantly the hyperlipidemia and certain other deleterious effects of CNO. Feeding a polar fraction of garlic oil (PFGO) prepared in the same way as for ajoene and administered at a dosage of 100 mg/kg along with each of the above oil containing diets counteracted significantly the hyperlipidemic, oxidant and also most of the other deleterious effects of the oils like raised lipid levels in serum and tissues, raised serum levels of AST and tissue levels of HMGCoA reductase and the lowered serum and tissue levels of glutathione reductase. The results support the claims that ajoene, the major polar compound of garlic oil, has very good biological action, which warrants further study.
Allyl Compounds↗
Carbon nanotube/poly(methyl methacrylate) composite electrode for capillary electrophoretic measurement of honokiol and magnolol in Cortex Magnoliae Officinalis.
This paper describes the development and the application of a novel carbon nanotube/poly(methyl methacrylate) (CNT/PMMA) composite electrode as a sensitive amperometric detector of CE. The composite electrode was fabricated on the basis of the in situ polymerization of a mixture of CNT and prepolymerized methylmethacrylate in the microchannel of a piece of fused-silica capillary under heat. The performance of this unique system has been demonstrated by separating and detecting honokiol and magnolol in traditional Chinese medicine, Cortex Magnoliae Officinalis. Factors influencing their separation and detection processes were examined and optimized. Honokiol and magnolol were well separated within 7 min in a 40 cm long capillary at a separation voltage of 15 kV using a 50 mM borate buffer (pH 9.2). The new CNT-based CE detector offered significantly lower operating potentials, yielded substantially enhanced S/N characteristics, and exhibited resistance to surface fouling and hence enhanced stability. It demonstrated long-term stability and reproducibility with RSDs of less than 5% for the peak current (n = 9) and should also find a wide range of applications in microchip CE, flowing injection analysis, and other microfluidic analysis systems.
Biphenyl Compounds↗
Deodorization with ku-ding-cha containing a large amount of caffeoyl quinic acid derivatives.
Caffeoyl quinic acid (CQA) derivatives in ku-ding-cha, mate, coffee, and related plants were determined by HPLC. One ku-ding-cha contained a large amount of 3,5-dicaffeoylquinic acid (3,5-diCQA, 10.6% in dry weight) as well as 3-CQA (1.7%), 4-CQA (1.1%), 5-CQA (6.3%), 3,4-diCQA (1.8%), and 4,5-diCQA (4.3%). In this ku-ding-cha, the total caffeic acid moiety was 90.3 mmol/100 g of dry weight. The leaves of Ilex latifolia, which is one original species of ku-ding-cha, and another plant of the same genus, I. rotunda, also contained 3,5-diCQA (9.5 and 14.6%), 3-CQA (4.3 and 1.9%), and 5-CQA (4.8 and 3.8%), respectively, whereas raw coffee bean contained 5.5% 5-CQA and other low CQA derivatives. 3,5-DiCQA and 5-CQA with an apple acetone powder (AP) containing polyphenol oxidase showed high capturing activities toward thiols, and two addition compounds between 3,5-diCQA and methane thiol were also identified. Ku-ding-cha indicated extremely strong capturing activities toward methanethiol, propanethiol, and 2-propenethiol in the presence of apple AP. Furthermore, drinking ku-ding-cha reduced the amount of allyl methyl sulfide gas, well-known to persist as malodorous breath long after the ingestion of garlic.
Allyl Compounds↗
Liver subcellular fractions from rats treated by organosulfur compounds from Allium modulate mutagen activation.
The effects of in vivo administration of naturally occurring organosulfur compounds (OSCs) from Allium species were studied on the activation of several mutagens. Male SPF Wistar rats were given p.o. one of either diallyl sulfide (DAS), diallyl disulfide (DADS), dipropyl sulfide (DPS) or dipropyl disulfide (DPDS) during 4 consecutive days and the ability of hepatic S9 and microsomes from treated rats to activate benzo[a]pyrene (BaP), cyclophosphamide (CP), dimethylnitrosamine (DMN), N-nitrosopiperidine (N-PiP) and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) was determined in the Ames test. Administration of DAS, DPS and DPDS resulted in a significant increase of the activation of BaP, CP, N-PiP and PhIP mediated by S9 and microsomes while DADS treatment only increased the mutagenicity of PhIP. In contrast, S9 from DADS-treated rats significantly inhibited the mutagenicity of N-PiP and BaP. DAS, DADS and DPS strongly inhibited DMN mutagenicity while DPDS enhanced it. To understand the mechanisms underlying these effects, the modifications of the activities of specific isozymes of CYP involved in the activation of these mutagens were studied. DAS, DPS and DPDS strongly enhanced pentoxyresorufin O-dealkylase (PROD) activity related to CYP2B and slightly increased ethoxyresorufin O-deethylase (EROD) and methoxyresorufin O-demethylase (MROD) activities related to CYP1A family. DADS exerted the same effects than other OSCs but to a lesser extent. p-Nitrophenol hydroxylase (PNPH) activity related to CYP2E1 was inhibited by DAS and DADS, whereas DPDS significantly increased this activity. Hence, the effects of OSCs on the mutagenicity of several genotoxic compounds are mediated by modification (enhancement or inhibition) of specific CYP involved in their activation.
Allium↗
Honokiol protects against carbon tetrachloride induced liver damage in the rat.
This study aims to investigate the possible hepato-protective effects of honokiol against liver damage and cirrhosis induced by carbon tetrachloride (CCl(4)) in the rat. Rats were treated acutely, or chronically with CCl(4) at 5 day intervals (0.06 mL/100 g body weight, administered as 50% vol/vol solution in liquid paraffin) by gavage, in combination with phenobarbitone in drinking water (0.5 g/L for 7 days prior to, and during CCl(4) treatment) to induce liver damage. Some were also co-treated with 0.1 mg/kg or 0.03 mg/kg honokiol (i.p.) or with appropriate vehicle. In vivo measurement of the liver sinusoidal area was performed using confocal microscopy following i.v. fluorescein isothiocyanate (FITC) dextran. Liver histology and function tests were performed, and liver and body weights were measured. Confocal microscopy showed that acute and chronic CCl(4) treatment significantly reduced the sinusoidal area. Honokiol (0.1 mg/kg, but not 0.03 mg/kg) partially reversed the decrease in the sinusoidal area after acute or chronic treatments with CCl(4). Acute and chronic CCl(4) treatment produced significant histological liver damage. Honokiol (0.1 mg/kg) significantly reduced the histological damage caused by chronic treatment. Chronic treatment with CCl(4) caused a significant increase in the bilirubin level that was not observed following the high dose of honokiol (0.1 mg/kg). In conclusion, this study showed that honokiol exhibits potent hepato-protective effects in rats treated with CCl(4).
Animals↗
Acidity trends in alpha,beta-unsaturated alkanes, silanes, germanes, and stannanes.
The gas-phase acidity of ethyl-, vinyl-, ethynyl-, and phenyl-substituted silanes, germanes, and stannanes has been measured by means of FT-ICR techniques. The effect of unsaturation on the intrinsic acidity of these compounds and the corresponding hydrocarbons was analyzed through the use of G2 ab initio and DFT calculations. In this way, it was possible to get a general picture of the acidity trends within group 14. As expected, the acid strength increases down the group, although the acidity differences between germanium and tin derivatives are already rather small. As has been found before for amines, phosphines, and arsines, the carbon, silicon, germanium, and tin alpha,beta-unsaturated compounds are stronger acids( )than their saturated analogues. The acidifying effect of unsaturation is much larger for carbon than for Si-, Ge-, and Sn-containing compounds. The allyl anion is better stabilized by resonance than its Si, Ge, and Sn analogues, [CH(2)(-)(delta)--CH(+)(delta)(') --CH(2)(-)(delta)](-) vs [CH(2)(-)(delta)()II = CH(-)(delta)()III - XH(2)(-)(delta)()IV](-) (X = Si, Ge, Sn). The enhanced acid strength of unsaturated compounds is essentially due to a greater stabilization of the anion with respect to the neutral, because the electronegativity of the alpha,beta-unsaturated carbon group increases with its degree of unsaturation. The phenyl derivatives are systematically weaker acids than the corresponding ethynyl derivatives by 15-20 kJ mol(-)(1). Experimentally, toluene acidity is very close to that of propyne, because the deprotonation of propyne takes place preferentially at the =CH group rather than at the -CH(3) group.
Journal Article↗
Antiarrhythmic effect of magnolol and honokiol during acute phase of coronary occlusion in anesthetized rats: influence of L-NAME and aspirin.
This study was designed to evaluate the in vivo effect of magnolol and honokiol on the acute phase of coronary ligation in the presence of nitric oxide inhibitor (L-NAME) or cyclooxygenase inhibitor (aspirin). After Sprague-Dawley rats were anesthetized with urethane, the changes of ventricular arrhythmia induced by coronary ligation for 30 min were determined with or without pretreatment with study medications. The incidence and duration of ventricular arrhythmia were significantly reduced after intravenous pretreatment (15 min before coronary ligation) with 10(-7) g/kg magnolol or 10(-7) g/kg honokiol. However, the antiarrhythmic effect of magnolol or honokiol could be abolished with the pretreatment of 1 mg/kg L-NAME, but not with pretreatment of 100 mg/kg aspirin. The abolishment of the myocardial beneficial effect of magnolol and honokiol by L-NAME, instead of aspirin, suggests an involvement of an increased nitric oxide synthesis in the protection offered by magnolol and honokiol against arrhythmia during myocardial ischemia.
Anesthesia↗
Inhibition of smooth muscle contraction by magnolol and honokiol in porcine trachea.
Magnolol and honokiol are the two major phenolic constituents of the plant medicine "Houpo" ( Magnolia obovata), which is used in the treatment of chest tightness and asthma. The aim of this study was to investigate the influence of magnolol and honokiol on smooth muscle tone in porcine trachea. Magnolol and honokiol (0.1 - 100 microM) inhibited carbachol- and high K +-induced muscle contractions in a concentration-dependent fashion, but did not affect basal muscle tension. After washout of these pretreatments, carbachol- and high K +-evoked muscle contractions were still abolished, suggesting that the inhibition was irreversible. Magnolol and honokiol also concentration-dependently decreased the Ca 2+-dependent muscle contraction induced by high K + depolarization. Ca 2+ channel antagonists attenuated carbachol-induced muscular response by approximately 30 %, but did not further potentiate the inhibitory actions of magnolol and honokiol on muscle contraction. However, the inhibitory effects of magnolol and honokiol on carbachol-evoked muscular contractile response were partially reversed after removal of Ca 2+ channel antagonist pretreatment. Alternatively, caffeine-elicited muscle contractions were not altered by magnolol, honokiol, and verapamil. In conclusion, the relaxant effects of magnolol and honokiol on porcine tracheal smooth muscle suggest an association with the blockade of Ca 2+ influx through voltage-operated Ca 2+ channels instead of Ca 2+ release from intracellular Ca 2+ stores. The magnolol- and honokiol-induced inhibitions on tracheal smooth muscle contraction may be relevant to the claimed therapeutic effects of the extract from magnolia bark and contribute to their pharmacological effects by acting as anti-asthmatic agents.
Animals↗
Effects of water garlic extracts on cell cycle and viability of HepG2 hepatoma cells.
Garlic extracts, either aqueous or oily, are commonly employed to prepare garlic derivative supplements used as nutraceuticals for the treatment of different pathologies. In this study, we investigated the effects of water garlic extracts from two different areas of Italy well known for garlic production, Latina (GEL) and Sulmona (GES), on cell cycle and death of HepG2 hepatoma cells. The effects of the treatments with GEL and GES were also compared with the oil-soluble sulfur compound of garlic, diallyl disulfide (DADS). GEL and GES induced a p53/p21-dependent cell cycle arrest in G2/M phase and apoptosis, although to a different extent, whereas DADS, under the experimental conditions used, was not detrimental to HepG2 cells. GEL and GES committed HepG2 cells to apoptosis by the activation of c-Jun-NH(2) terminal kinase (JNK)/c-Jun phosphorylative cascade without a detectable increase in the flux of reactive oxygen species. Moreover, differentiation of HepG2 cells induced by retinoic acid determined resistance to GEL and GES treatments without the activation of JNK signaling pathway. Overall, the results obtained indicate that water-soluble garlic extracts are more inhibitory of the growth of transformed hepatoma cells than the oil-soluble isolated compound DADS, and that their antiproliferative properties are different depending on the area of origin of the starting material.
Allyl Compounds↗
Pungent products from garlic activate the sensory ion channel TRPA1.
Garlic belongs to the Allium family of plants that produce organosulfur compounds, such as allicin and diallyl disulfide (DADS), which account for their pungency and spicy aroma. Many health benefits have been ascribed to Allium extracts, including hypotensive and vasorelaxant activities. However, the molecular mechanisms underlying these effects remain unknown. Intriguingly, allicin and DADS share structural similarities with allyl isothiocyanate, the pungent ingredient in wasabi and other mustard plants that induces pain and inflammation by activating TRPA1, an excitatory ion channel on primary sensory neurons of the pain pathway. Here we show that allicin and DADS excite an allyl isothiocyanate-sensitive subpopulation of sensory neurons and induce vasodilation by activating capsaicin-sensitive perivascular sensory nerve endings. Moreover, allicin and DADS activate the cloned TRPA1 channel when expressed in heterologous systems. These and other results suggest that garlic excites sensory neurons primarily through activation of TRPA1. Thus different plant genera, including Allium and Brassica, have developed evolutionary convergent strategies that target TRPA1 channels on sensory nerve endings to achieve chemical deterrence.
Allyl Compounds↗