Research on Anti-inflammatory Targets and Mechanisms of alkaloids in Picrasma quassioides Benn Through Network Pharmacology

Abstract This study aimed to investigate the molecular mechanism of Picrasma quassioides Benn against inflammation by means of network pharmacology. The paper will provide a reference for multi-target and multi-channel treatment of inflammation with traditional Chinese medicine. Through screening and analysis, 11 active ingredients and 109 anti-inflammation prediction targets were obtained and constructed a compound-target network. The targets such as VEGFA, TLR4 and STAT3 may play a crucial role. Network enrichment analysis showed that the 109 potential targets constitute a number of pathways or inflammatory reactions closely related to inflammation, including NF-κB signaling pathway and MAPK signaling pathway. The docking results indicated that the binding energy of Picrasidine Y and the inflammatory factors VEGFA is the highest. This study predicted the role of multiple active compounds in the alkaloids of Picrasma in the inflammatory response, and provided a theoretical basis for the anti-inflammatory mechanism of Picrasma

Chemical constituents of Picrasma quassioides / 中草药

Objective: To study the chemical constituents of Picrasma quassioidies. Methods: The isolation and purification were carried out by column chromatography on silica gel, ODS, Sephadex LH-20 and semi-preparative RP-HPLC. The structures were elucidated on the basis of physicochemical properties and spectroscopic analysis. Results: A total of 12 alkaloids and four quassinoids were isolated and identified from 80% ethanol aqueous extract of the stems of P. quassioides. They were named as 1-hydroxymethyl-4-methoxy-β-carboline (1), 1-methoxicabony-β-carboline (2), 1-methoxicabony-4-methoxy-β-carboline (3), 1-methoxicabony-4,8-dimethoxy-β-carboline (4), 1-ethyl-4-methoxy-β-carboline (5), 1-ethyl-4,8-dimethoxy-β-carboline (6), picrasidine I (7), canthin-6-one (8), 5-methoxyl-canthin-6-one (9), 4-methoxyl-5-hydroxyl-canthin-6-one (10), 4,5-dimethoxyl- canthin-6-one (11), quassidine B (12), quassin (13), nigakilactone B (14), nigakilactone E (15) and norquassin (16). Conclusion: Compound 1 is a new β-carboline alkaloid, named as kumujantine D, and compound 4 is isolated from P. quassioidies for the first time.

A pair of new tirucallane triterpenoid epimers from the stems of Picrasma quassioides / 中国天然药物

A pair of new tirucallane triterpenoid epimers, picraquassins M and N (1> and 2), were isolated from the stems of Picrasma quassioides (D. Don) Benn. Their structures were determined based on comprehensive spectroscopic and X-ray crystallographic analyses. In addition, their AChE inhibitory activity, cytotoxicity against five human tumour cell lines (SW480, MCF-7, HepG2, Hela, and PANC-1), and antimicrobial activity against two bacteria (Staphylococcus. aureus 209P and Escherichia coli ATCC0111) and two fungi (Candida albicans FIM709 and Aspergillus niger R330) were evaluated.

Chemical constituents of total alkaloids from Picrasma quassioides and its effects on collagen induced arthritis in rats / 中国药科大学学报

@#This study aimed to investigate the effects of total alkaloids from Picrasma quassioides(TAPQ)on collagen-induced arthritis(CIA)in rats. TAPQ were prepared by acid extraction and alkali precipitation. The qualitative analysis of TAPQ by HPLC-Q-TOF-MS/MS was carried out. Fourteen alkaloids were obtained and three of them were quantitatively analyzed by HPLC. The anti-inflammatory activity of TAPQ was investigated on RAW264. 7 induced by LPS. Dexamethasone was used as a positive control. The model of bovine type II collagen-induced rheumatoid arthritis in SD rats was established. Daily tail intravenous injection of 0. 907 or 1. 814 mg/kg of TAPQ was administered for 18 days continuously, using dexamethasone as a positive control. The changes of mean arthritis scores in the paw of the rats and the volume of the paw were measured every day. Compared with the model group, the TAPQ significantly reduced the degree of paw swelling(P< 0. 001). After the rats were sacrificed, the levels of TNF-α and IL-6 in the serum were measured. The TAPQ could significantly reduce the level of TNF-α(P< 0. 01)and IL-6(P< 0. 001). The pathological changes of the joints were observed by HE staining, the anti-inflammatory activity of TAPQ was good, and the degree of joint damage in rats was obviously reduced.

Study on Improvement Effects of External Application of Water Extract from Picrasma quassioides on Allergic Contact Dermatitis Model Mice / 中国药房

OBJECTIVE： To investigate the improvement effects of external application of water extract from Picrasma quassioides on allergic contact dermatitis （ACD） model mice， and to provide reference for its further development and utilization. METHODS： A total of 48 mice were randomly divided into blank control group （normal saline）， model group （normal saline）， hydrocortisone group （positive control， about 0.15 g/ear） and water extract from P. quassioides low-dose， medium-dose and high-dose groups （0.15， 0.3， 0.6 g/ear， calculated by extract）， with 8 mice in each group. The mice were given medicine on ear at 8 a.m. and 4 p.m. for 7 d continuously. Except for blank control group， other groups were given acetone-olive oil solution containing 0.5％ 2，4-dinitrofluorobenzene （DNFB） on the abdomen of mice to induce ACD model. After 7 d medication， modeling group was given acetone-olive oil of 0.25％ DNFB on left ear to induce dermatitis. 24 h later， the pathological changes of left ear tissue were observed by naked eye and skin lesion was scored. The thickness difference and weight difference of left and right ears in mice were measured. The serum contents of IL-6 and IgE were determined. The pathomorphology changes of ear tissue were observed by microscope after HE staining. RESULTS： Compared with blank control group， the skin lesion score of left ear was increased significantly in model group （P＜0.01）； the thickness difference and weight difference of left and right ears， serum contents of IgE and IL-6 were increased significantly （P＜0.01）. Pathological changes were observed in left tissue of mice by microscope， such as lymphocytic infiltration， intercellular edema， erythrocyte exudation. Compared with model group， skin lesion score of left ear in mice was decreased significantly in hydrocortisone group and water extract from P. quassioides high-dose group （P＜0.05 or P＜0.01）； the thickness difference and weight difference of left and right ears in mice were decreased significantly in all administration groups （P＜0.01）. The serum contents of IgE and IL-6 in mice were decreased significantly in hydrocortisone group， water extract from P. quassioides medium-dose and high-dose groups （P＜0.01）； the inflammatory lesions of left ear in mice were alleviated to varying degrees in different administration groups. CONCLUSIONS： External application of water extract from P. quassioides has a good improvement effect on ACD model mice.

Chemical constituents from the stems of Picrasma quassioides Bennet / 中国药科大学学报

The phytochemical studies on the stems of Picrasma quassioides Bennet led to the isolation of seven β-carboline alkaloids (1-6),five cantin-6-one alkaloids (7-11),two canthin-5,6-dione (12,13),three sesquiterpe nes (14-16),and one steroids (17).Their structures were elucidated by the combination of spectroscopic analyses (ESI-MS,1H NMR and 13C NMR) and the comparisons with the reference.Compound 16 is a new natural product,and this is the first report for compounds 5,6,14-17 from the species P.quassioides.

Three bis-β-carboline alkaloids from Picrasma quassioides and their bioactivities / 中草药

To study the chemical constituents from the stems of Picrasma quassioides. The constituents were isolated and purified by silica gel, Sephadex LH-20, ODS column chromatographies, and preparative HPLC. Their structures were determined on the basis of their physicochemical properties and spectral data. The cytotoxic and antibacterial activities were assessed by MTT and MIC, respectively. Three β-carboline alkaloids were obtained from the 95% ethanol extract of the stems of P. quassioides and identified as picrasidine F (1), picrasidine G (2), and picrasidine S (3). Compound 1 showed selective cytotoxicity to HeLa cell, while compounds 2 and 3 showed the potent cytotoxicity against human HeLa cervical, gastric MKN-28, and mouse melanoma B-16 cancer cells. Compounds 1-3 showed the potent antibacterial activity against two strains of pathogenic bacteria methicillin-resistant Staphylococcus aureus (MRSA) and two strains of pathogenic bacteria methicillin-sensitive Staphylococcus aureus (MSSA). The assignments of NMR data of compound 1 are reported in this paper for the first time. Compounds 1-3 show the potent cytotoxic and antibacterial activities.

GC-MS Analysis on Volatile Oil from Branches of Picrasma quassioides / 中草药·英文版

Objective: To analyze the volatile oil from the branches of Picrasma quassioides. Methods: Volatile oil was extracted from the branches of P. quassioides by steam distillation. GC-MS method was used to analyze the components. Results: A total of 49 compounds were isolated, and 46 compounds were successfully identified, which represented over 98% of the total oil composition. The major components of the volatile oil in the branches of P. quassioides included caryophyllene (12.83%), 12-oxabicyclo[9.1.0]dodeca-3,7-diene,1,5,5,8-tetramethyl-[1R-(1. R*,3. E,7. E,11-R*)] (12.29%), 1-hexanol (9.96%), naphthalene, 1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methyletheyl)-[1. S-(1a,7a,8aa)] (7.32%), aromadendrene oxide-(2) (6.69%), and α-caryophyllene (3.88%). Conclusion: The major components in volatile oil are terpenoids, hydroxy compounds, and other acyclic alkane compounds. © 2013 Tianjin Press of Chinese Herbal Medicines.

Alkaloids from twigs and leaves of Picrasma quassioides / 中草药

Objective To study alkaloids from the twigs and leaves of Picrasma quassioides. MethodsCompounds were isolated and purified by column chromatography over Sephadex LH-20 and silica gel column. Their chemical structures were elucidated on the basis of physicochemical properties and spectral data. Results Sixteen alkaloids were isolated, purified, and identified as: 5-methoxycanthin-6-one (Ⅰ), 11-hydroxycanthin-6-one (Ⅱ), canthin-6-one (Ⅲ), 4, 5-dimethoxycanthin-6-one (Ⅳ), 4-methoxy-5-hydroxycanthin-6-one (Ⅴ), 3-methylcanthin-2, 6-dione (Ⅵ), 1-formyl-4-methoxy-?-carboline (Ⅶ), 1-methoxy-?-carboline (Ⅷ), 1-ethyl-4, 8-dimethoxy-?-carboline (Ⅸ), 1-methoxycarbonyl-4-hydroxyl-?-carboline (Ⅹ), 1-methyl-4-methoxy-?-carboline (Ⅺ), 1-ethoxycarbonyl-?-carboline (ⅩⅡ), 1-formyl-?-carboline (ⅩⅢ), 1-methoxycarbonyl-?-carboline (ⅩⅣ), 1-ethyl-4-methoxy-?-carboline (ⅩⅤ), and 1, 2, 3, 4-tetrahydro-1, 3, 4-trioxo-?-carboline (ⅩⅥ). Conclusion Compound Ⅺ is separated from the natural plant for the first time and compounds Ⅱ, Ⅷ, and ⅩⅤ are separated from plants of Picrasma Bl. for the first time.