Phenolic constituents of Phellodendron chinense bark
Canadian Journal of Chemistry
Abstract and Figures
The bark of Phellodendron chinense is a very important herbal medicine in traditional Chinese medicine. In a detailed phytochemical investigation, a new phenolic lactone, 2,3-dihydroxy-3-vanilloylmethyl--lactone (named as phellolactone) (1), and nine known phenolic compounds (210) were isolated from the bark of P. chinense Schneid. Their structures were characterized by spectroscopic methods, including IR, UV, HR-ESI-MS, NMR, and chemical transformation analysis.
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Phellodendron chinense C.K.Schneid., Rutaceae, is a traditional Chinese medicine that is considered to have heat-clearing and detoxifying actions and is widely used for bacteriostatic and anti-inflammatory effects in clinical treatment and healthcare products. The aim of this study was to discover the pharmacological activity of P. chinense against inflammation. A rat model with carrageenan-induced inflammation model was used to systematically evaluate the anti-inflammatory effect of P. chinense extract on the degree of foot swelling and expression of NF-kB and myeloperoxidase. HPLC-QTOF/MS/MS was used to identify the components in the P. chinense extract. A bivariate correlation analysis was performed on the relative contents of components of serum from P. chinense–treated rats and the rates of inhibition of paw edema and COX-2 levels at different time points, and their correlation coefficients were calculated. The results showed that P. chinense significantly reduced the carrageenan-induced paw edema at 0.5 to 8 h and the levels of NF-κB and myeloperoxidase at 0.5 h, and the anti-inflammatory effects were similar to those of indomethacin. A total of 19 peaks were identified in total ion current chromatograms of the P. chinense extract, including 6 alkaloids, 11 phenolic acids, and 2 flavonoids. A total of 13 peaks were identified in the total ion current chromatograms of the serum of the rats with carrageenan-induced inflammation, including 3 alkaloids and 10 phenolic acids. Correlation coefficients above 0.5 with COX-2 or inhibitory actions on paw edema were found for phellodendrine, palmatine, berberine, quinic acid, caffeic acid, dihydrocaffeic acid sulphate, 3-O-feruloylquinic acid, 4-O-feruloylquinic acid, and 5-O-feruloylquinic acid. This result suggests that the main active components from P. chinense for anti-inflammation are alkaloids and phenolic acids such as quinic acid, caffeic acid, and their metabolites.
In this work, eight compounds from Phellodendron chinense were separated and purified by pH‐zone refining counter‐current chromatography and traditional counter‐current chromatography coupled with online‐storage inner‐recycling counter‐current chromatography (IRCCC). The pH‐zone‐refining mode was adopted for separating 2.0 g of crude extract with the solvent system of chloroform–methanol–water (4:3:3, v / v ), in which 10 mM hydrochloric acid and 10 mM triethylamine were added in the stationary and mobile phases, respectively. Meanwhile, traditional counter‐current chromatography coupled with online‐storage IRCCC separation was performed by the solvent system of n ‐hexane‐ethyl acetate‐methanol‐water (5:5:2:8, v/v ). Finally, eight compounds, including six alkaloids as 6‐methylpiperidin‐2‐one( 1 ), isoplatydesmine( 4 ), berlambine( 5 ), epiberberine( 6 ), palmatine( 7 ), berberine( 8 ) and two phenolic acids as ferulic acid( 2 ), isoferulic acid( 3 ), were successfully obtained using these three different CCC modes with the purities over 95.0%.
Background:
Phellodendri Cortex (PC) or Huang Bai. According to the scientific database of China Plant Species and Chinese pharmacopeia 2015 edition, PC has two main species which are Phellodendron amurense Rupr (PAR) or "Guan Huang bai" in Chinese and Phellodendron chinense Schneid (PCS) or "Chuan Huang bai" in Chinese. The crude drugs of PAR and PCS are also called Phellodendri amurensis cortex (PAC) and Phellodendri chinense cortex (PCC), respectively. The medicinal part of the plant is the dried trunk bark. PC has comprehensive therapeutic effects which include anti-inflammatory, antimicrobial, anticancer, hypotensive, antiarrhythmic, antioxidant, and antipyretic agents. The exact ingredients in PC and its species are not fully summarised.
Aim of the study:
This study was designed to review and evaluate the pharmacological actions of compounds and to explore the pharmacokinetic knowledge of PC and its species and to also identify the chemical compound(s) with a potential therapeutic effect on atopic dermatitis.
Methods:
"Huang Bai" and its English, botanical, and pharmaceutical names were used as keywords to perform database search in Encyclopaedia of traditional Chinese Medicines, PubMed, EMBASE, MEDLINE, Science Direct, Scopus, Web of Science, and China Network Knowledge Infrastructure. The data selection criteria included all the studies that were related to the phytochemical, pharmacological, and pharmacokinetic perspectives of PC and its species or their active constituents. More importantly, the voucher number has been provided to ensure the genuine bark of PC used as the medicinal part in the studies.
Results:
140 compounds were summarized from PC and its species: specifically, 18 compounds from PCC, 44 compounds from PCS, 34 compounds from PAC, and 84 compounds from PAR. Obacunone and obaculactone are probably responsible for antiatopic dermatitis effect. PC and its species possess a broad spectrum of pharmacological actions including anti-inflammatory effect, antibacterial effect, antiviral effect, antitumor effect, antigout effect, antiulcer effect, neuroprotective effect, and antiatopic dermatitis effect. PC could widely distribute in plasma, liver, spleen, kidney, and brain. Berberine may be responsible for the toxic effect on the susceptible users with hemolytic disease or in the peripartum and neonatal period.
Conclusions:
The compounds of the crude bark of PC and its subspecies have showcased a wide range of pharmacological effects. Pharmacological efficacies of PC are supported by its diverse class of alkaloid, limonoid, phenolic acid, quinic acid, lignan, and flavonoid. Obacunone and obaculactone could be the bioactive compounds for atopic dermatitis management. PC and its subspecies are generally safe to use but extra care is required for certain conditions and group of people.
The present study carried out a phytochemical investigation on the root barks of Dictamnus dasycarpus Turcz, leading to the isolation and characterization of two new aromatic ring butyrolactone derivatives, dasycarpusphenol acid A (1) and dasycarpusphenol acid B (2). Their structures were elucidated by using spectroscopic techniques and HR-FAB-MS. Compounds 1 and 2 exhibited antioxidant activity, with their IC50 values being 28.95 and 41.76 mg·mL⁻¹, respectively.
Naturally occurring oplopanane sesquiterpenoids are rarely reported. A phytochemical investigation on the rhizomes of Homalomena occulta (Lours) has resulted in the discovery of six oplopanane sesquiterpenoids (1–6), including four new (1–4) and one 3,5-seco-oplopanane (6), together with three previously reported sesquiterpenoids (7−9). In addition three new oplopananes (2a–4a) were also obtained by chemical transformation. All structures of these sesquiterpenoids were established based on the comprehensive spectroscopic analyses, including NMR, MS, and IR, and comparing with the literatures.
Electronic supplementary material
The online version of this article (doi:10.1007/s13659-016-0104-8) contains supplementary material, which is available to authorized users.
Phellodendri Cortex, phellodendron bark, has been used as a stomachic for intestinal function control and as an antimicro and anti-inflammatory agent. In this phytochemical study, eight compounds, berberine (1), palmatine (2), syringin (3), (+)-syringaresinol di-O-β-D-glucopyranoside (4), salvadoraside (5), citrusin B (6), osmanthuside H (7), and kelampayoside A (8), were isolated from the bark of Phellodendron amurense. Their structures were elucidated by comparing spectroscopic data with reported values. Compounds 1-8 were evaluated for cytotoxic activity against HL-60 human promyelocyte leukemia cells in vitro. Among them, compounds 1 and 2 reduced the viability of HL-60 cells significantly, with IC50 values of 26.0 and 18.5 μM, respectively.
The protective effect of SAPP, an extract from a novel herbal complex, on acute liver injury was investigated using mouse animal model in this study. The content of total phenol in SAPP was increased at dose dependent manner. Consistent with the content of total phenol, SAPP showed the significant anti-oxidative effects on 1, 1-diphenyl-2-picrylhydrazyl (DPPH) method. Acute liver injury was induced by D-galactosamine (D-GalN) in mouse. Treatment with SAPP significantly reduced the level of alanine transaminase (ALT) and aspartate transaminase (AST) in serum. Histological observation revealed that whereas D-GalN treated mouse showed vacuolization of hepatocytes, sinusoidal dilation and congestion, loss of cell boundaries and ballooning degeneration, loss of architecture and cell necrosis, treatment with SAPP improved D-GalN-induced liver injury. These results suggest that SAPP shows protective effects against D-GalN-induced hepatotoxicity in vivo acute mouse model.
The active site of Sporotrichum thermophile type C feruloyl esterase (StFaeC) was probed using a series of C1–C4 alkyl ferulates. The affinities for straight and branched alkyl ferulates were demonstrated by the Km values of 1.64–0.51 and 0.19–0.1, respectively. Comparison of kcat and kcat/Km values shows that the enzyme hydrolyzed n-propyl ferulate faster and iso-propyl ferulate more efficiently. Alkyl ferulates were applied also for substrate selectivity mapping of feruloyl esterase to catalyze feruloyl group transfer to l-arabinose, using as a reaction system a ternary water–organic mixture consisting of n-hexane, t-butanol and water. Lengthening the aliphatic side chain was the most significant factor causing lower synthetic activity of the enzyme. The reaction parameters affecting the feruloylation rate and the conversion of the enzymatic process, such as the temperature and substrate concentration have been investigated. Under identical reaction conditions, the enzyme feruloylated other monosaccharides such as d-arabinose, d-glucose, d-xylose, d-mannose, d-fructose, d-galactose, d-ribose and model substrates such as 4-nitrophenyl α-l-arabinofuranoside and 4-nitrophenyl α-l-arabinopyranoside.
From Antidesma membrananeum, besides three feruloyl amides and (−)-syringaresinol, new phenolic compounds have been isolated. Their structures were established as two series of 2-alkylated 5,7-dihydroxychromones and 2,5,7-trihydroxychromanones, and the dimeric compound, 8,8-bis-(dihydroconiferyl)-diferuloylate, respectively, from their spectroscopic data.
Die Untersuchung von drei Vertretern der neuen Gattung Chromolaena liefert neben bereits bekannten Substanzen zwei neue Sesquiterpene (2 und 3), deren Konstitution geklärt wird. Die biogenetische Verwandtschaft zum bereits bekannten Eupaten (1), das ebenfalls aus dieser Gattung isoliert wurde, ist sehr wahrscheinlich.
Naturally Occurring Terpene Derivatives, 80. Some Constituents of the Genus Chromolaena
The investigation of three representatives of the newly established genus Chromolaena yields besides already known compounds two new sesquiterpenes (2 and 3), the structures of which have been elucidated. The biogenetic relationship to the already known eupatene (1), also isolated from this genus, is very probable.
Linear furanocoumarins (psoralens) were present both inside and on the surface of dry fruits of seven species of Umbelliferae and one species of the Leguminosae and on seeds of three of Rutaceae examined. Surface concentrations varied between traces and 40 μg/g of the mature fruits or seeds, amounting to 0.38–43% of the total. In the whole fruits concentrations were very high in Angelica archangelica, Heracleum lanatum, Pastinaca saliva, and Psoralea bituminosa, reaching levels of milligrams per gram fresh weight of fruits. This high concentration inside the fruit may be the cause of poor germination of embryos in A. archangelica and H. lanatum. Seeds of the Rutaceae had much smaller concentrations of furanocoumarins both on the surface and within the seed. Key words: fruits, seeds, surface, furanocoumarins, Umbelliferae, Rutaceae, dermatitis, plant defense.
Aqueous extracts from stem bark of Petersianthus macrocarpus contain substances exhibiting both estrogenic and antiestrogenic potency. Triterpenic saponins were identified and extracted as a bulk. Their action on the in vitro LH released by cultured rat pituitary cells was investigated. P. macrocarpus saponins stimulated the LH release in a dose-dependent manner (from 10 micrograms/ml to 300 micrograms/ml). When added simultaneously, saponins and LHRH exerted initial additive effects on LH release, demonstrating independent mechanisms of stimulation. If cells were pre-treated with saponins for 15 min, the amount of LH released under a subsequent LHRH stimulation was lowered, presumably due to a partial depletion of the cells in hormone (data not presented). However, the action of saponins on LH release did not appear specific since a general permeabilizing effect of the cell membrane was evidenced both by trypan blue exclusion and by analysis of the total protein output. When using low concentrations of saponins (10 micrograms/ml), scanning electron microscopy did not reveal any significant alteration of the cell structure, which explains why the cells remain responsive to LHRH after withdrawal of saponins. With higher concentrations (greater than 30 micrograms/ml), the same analytical studies evidenced numerous perforations of the cell membrane, with subsequent cell death. Two highly purified saponin species were tested on LH release by cultured cells; one of them (petersaponin I) appeared responsible for the observed biological effects in vitro. But as cells were shown to be efficiently protected from saponin effects by the presence of serum, it may be concluded that saponins of P. macrocarpus extracts are probably not candidate molecules promoting the in vivo estrogenic and antiestrogenic effects.
Two new ferulate compounds, amurenlactone A (1) and amurenamide A (2), along with 11 known compounds have been isolated from the cortex of Phellodendron amurense. The structures of the new compounds were established based on 1D, 2D NMR and mass spectral analyzes. The known compounds were identified by comparison with authentic samples.
Invasive Plants of Asian Origin Established in the US and Their Natural Enemies
- Usds
- Fhtet
USDS FS FHTET. Invasive Plants of Asian Origin Established in the US and Their Natural Enemies [Online]; 2005;
p. 131-132. www.invasive.org/weeds/asian/phellodendron.
pdf (accessed April 1, 2005).
Photocatalogue of Traditional Chinese Medicine
- P G Shiao
Shiao, P. G. Photocatalogue of Traditional Chinese Medicine;