Picrasma Quassioides Research Articles

Study on chemical constituents of Picrasma quassioides

To study the chemical constituents of Picrasma quassioides. The chemical constituents were isolated and purified by chromatographic methods over Sephadex LH-20 and silica gel column, and structurally elucidated by spectral analysis, including UV, IR, MS, 1H-NMR, 13C-NMR. Fourteen compounds were obtained and identified as trifolirhizin(1), maackiain(2), 3', 7-dihydroxy-4'-methoxylisoflavone(3), umbelliferone(4), emodin(5), nigakilactone F(6), picrasin B(7),picraqualide B (8),4-methoxy-5-hydroxycanthin-6-one(9), 4,5-dimethoxycanthin-6-one (10),5-methoxycanthin-6-one(11), 11-hydroxycanthin-6-one(12) , 1-methoxycarbonyl-beta-carboline(13), 1-hydroxymethyl-beta-carboline(14). Compounds 1-5 are reported from the first time for the genus Pricrasma.

Anti-inflammatory Alkaloids from the Stems of Picrasma quassioides BENNET

During further chemical and biological investigations of Picrasma quassioides BENNET, four new bis-β-carboline alkaloids, quassidines E-H (1-4), and three new β-carboline alkaloids, canthin-16-one-14-butyric acid (5), 3-(1,1-dimethoxylmethyl)-β-carboline (6), and 6,12-dimethoxy-3-formyl-β-carboline (7), were isolated from its anti-inflammatory CHCl(3)-soluble fraction. Structures of new compounds were elucidated and characterized by MS and NMR analysis. A plausible biogenetic pathway for quassidine E (1), the first bis-β-carboline alkaloid in which a canthin-6-one moiety and a β-carboline moiety were connected together by a single carbon-carbon bond from the nature, was proposed. Quassidines E-G (1-3) showed potent inhibitory activity on the production of nitric oxide (NO), tumor necrosis factor α (TNF-α), or interleukin 6 (IL-6) in mouse monocyte-macrophage RAW264.7 cells stimulated by lipopolysaccharide (LPS). Analysis of anti-inflammatory activity of all β-carboline and bis-β-carboline alkaloids from P. quassioides showed that the carbonyl groups or double carbon-carbon bonds at C-14 for β-carbolines and C-14' for bis-β-carbolines were bioactive groups for their in vitro anti-inflammatory activity. Structure-activity relationship of these compounds on inhibitory activity of the three inflammatory cytokines was discussed.

β‐Carboline alkaloids from the stems of Picrasma quassioides

Five new beta-carboline alkaloids, 6,12-dimethoxy-3-(2-hydroxylethyl)-beta-carboline (1), 3,10-dihydroxy-beta-carboline (2), 6,12-dimethoxy-3-(1-hydroxylethyl)-beta-carboline (3), 6,12-dimethoxy-3-(1,2-dihydroxylethyl)-beta-carboline (4), and 6-methoxy-3-(2-hydroxyl-1-ethoxylethyl)-beta-carboline (5), and two new natural products, 6-methoxy-12-hydroxy-3-methoxycarbonyl-beta-carboline (6) and 3-hydroxy-beta-carboline (7) were isolated from the stems of Picrasma quassioides along with 16 known beta-carboline alkaloids (8-23). The structures of new compounds were determined by extensive spectroscopic analyses, and the 1D and 2D NMR data of compounds 6, 7 and 10 were reported for the first time. The bioassays showed that only compounds 14 and 16 could enhance the differentiation of 3T3-L1 preadiocytes accompanied by secretion of adiponectin proteins among these 23 compounds.

Quassidines A−D, Bis-β-carboline Alkaloids from the Stems of Picrasma quassioides

Four new bis-beta-carboline alkaloids, quassidines A-D (1-4), together with a known alkaloid, picrasidine C (5), were isolated from the stems of Picrasma quassioides. Quassidine A (1) is the first reported bis-beta-carboline alkaloid possessing a novel cyclobutane moiety. The structures of the new compounds were determined on the basis of their 1D and 2D NMR and X-ray diffraction data. A possible biogenetic pathway for these alkaloids was proposed, and all compounds were evaluated for anti-inflammatory activity. Only quassidine A (1) showed weak activity.

Cytotoxic Alkaloids from the Wood of Picrasma quassioides

Six alkaloid compounds were isolated from the chloroform soluble fraction of the methanolic extract of the wood of Picrasma quassioides Benn (Simarobaceae) as the cytotoxic components against the tumor cell lines, U937 and HepG2. The compounds were identified as 4,9-dimethoxy-1-vinyl-γ-carboline (1), 1-carbomethoxy-β-carboline (2), 4,5-dimethoxycanthin-6-one (3), 5-hydroxy-4-methoxycanthin-6-one (4), 3-methoxycanthin-5,6-dione (5) and 4,8-dimethoxy-1-vinyl-β-carboline (6) by spectroscopic analysis. Among them, compound 5 showed the most potent cytotoxicity in a dose-dependent manner against the two tumor cell lines. This is the first report of the cytotoxic effect of those isolated compounds 1-5 on U937 and HepG2 cell lines.

Tobacco Mosaic Virus (TMV) Inhibitors from Picrasma quassioides Benn

To investigate natural inhibitors against tobacco mosaic virus (TMV) from plants, 10 known beta-carboline alkaloids and one quassinoid have been isolated from MeOH extract of the wood of Picrasma quassioides Benn. These compounds were screened for their inhibitory activities against tobacco mosaic virus (TMV). The activity of each compound against TMV infection and replication was tested using a half-leaf assay method, a leaf-disk method, and Western blotting analyses. All of the beta-carboline alkaloids showed moderate anti-TMV activities and exhibited synergistic effects when combined with the quassinoid nigakilactone B (11). To our knowledge, this is the first report on anti-TMV activity of beta-carbolines and their synergistic effects against TMV when combined with a quassinoid.

Biological Activities of Fractions from Methanolic Extract of Picrasma quassioides

Antioxidant, antidiabetes, and anticancer activities of fractions (water, hexane, EtOAc, and BuOH) from methanolic (MeOH) extract of Picrasma quassioides were evaluated in vitro. Among the four fractions, BuOH fraction showed cytotoxic activity on the human stomach carcinoma cells (NCI-N87) without cytotoxic effect on the human normal kidney cells (293) by MTT assay. Considering these results, we adapted BuOH fraction of MeOH extract to the assessment of apoptosis by flow cytometry and mRNA expression levels of established apoptotic-related genes on NCI-N87 cells. The experiments showed that BuOH fraction could induce apoptosis on NCI-N87 cells significantly. Take together these results, P. quassioides showed that it could be used for potential pharmaceutical products.

Protective Effect of 4-Methoxy-5-hydroxycanthin-6-one, A Natural Alkaloid, on Dextran Sulfate Sodium-Induced Rat Colitis

In the present study, we evaluated the effect of 4-methoxy-5-hydroxycanthin-6-one (CAN), a natural alkaloid isolated from Picrasma quassioides (D.Don) Benn., on ulcerative colitis induced by dextran sulfate sodium (DSS) in rats in comparison with the positive control drug, sulfasalazine (SASP). Given orally for several days, CAN significantly reduced the severity of colitis and mitigated changes in colon length, colon mucosa myeloperoxidase (MPO) activity, and the level of tumor necrosis factor-alpha (TNF-alpha) in serum. The effect of CAN was similar to that of SASP. These results suggest that CAN treatment might be an effective therapeutic intervention against ulcerative colitis induced by DSS.

Canthin-6-one alkaloids from Picrasma quassioides and their cytotoxic activity

A new alkaloid, 4,5-dimethoxy-10-hydroxycanthin-6-one (1), was isolated from the stem of Picrasma quassioides Bennet (Simaroubaceae) together with four known canthin-6-one alkaloids, 8-hydroxycanthin-6-one (2), 4,5-dimethoxycanthin-6-one (3), 5-hydroxy-4-methoxycanthin-6-one (4), and 3-methylcanthin-5,6-dione (5). Their structures were elucidated on the basis of spectroscopic data. The cytotoxic activity of the canthin-6-one alkaloids was evaluated using human nasopharyngeal carcinoma (CNE2) and human liver cancer (Bel-7402) cell lines. Among these isolates, compounds 1–4 exhibited significant cytotoxic activity against CNE2 cell line.

Effect of <i>Picrasma quassioides</i> plant extract, yeast culture and monensin on <i>in vitro</i> mixed ruminal microorganism fermentation of wheat starch

Effect of <i>Picrasma quassioides</i> plant extract, yeast culture and monensin on <i>in vitro</i> mixed ruminal microorganism fermentation of wheat starch

Five New Quassinoids from the Bark of Picrasma quassioides

AbstractFive new quassinoids, named picraqualides A–E (1–5), together with eleven known ones, nigakilactone E (6), nigakilactone F (7), kusulactone (8), javanicin U (9), 12‐norquassin (10), quassin (11), 2,3‐didehydropicrasin B (12), nigakilactone B (13), nigakilactone C (14), picrasin B (15), and simalikalacton C (16), were isolated from the EtOH extract of the bark of Picrasma quassioides (D. Don) Benn. Their structures were determined mainly by spectroscopic methods, especially by 2D‐NMR techniques and circular dichroism (CD). Some empirical rules were summarized on the basis of 13C‐NMR spectral analysis to distinguish between OH (or Ac) groups attached at C(11) vs. C(13).

Analysis of constituents in Jamaica quassia extract, a natural bittering agent

Jamaica quassia extract, a natural bittering agent, is described as "a substance extracted from bark of Jamaica quassia (Quassia excelsa Sw.)" in the List of Existing Food Additives in Japan. The constituents in Jamaica quassia extract product were investigated as a part of an ongoing study to evaluate its quality and safety as a food additive. The main constituents of the extract were identified as quassin and two isomers of neoquassin by using LC/MS. The main constituent, quassin, was isolated and the structure was determined by spectral means. The quantification of their main constituents was performed by HPLC using quassin as a standard, and the concentrations of quassin and total of neoquassin isomers were 21.4% and 55.5%. In addition, it was confirmed that Jamaica quassia extract was different from quassia extract, which is extracted from bark of Picrasma quassioides Benn. belonging to the same family as Q. excelsa, by comparing their HPLC profiles.

Phenylpropanoids and other secondary metabolites from fresh fruits of Picrasma quassioides

Four new constituents; two benzofuran glucosides (picraquassiosides A and B), a neolignan (picraquassioside C) and a phenol (picraquassioside D) were isolated from fresh fruits of Picrasma quassioides, together with seven known compounds. The structures of the new compounds were elucidated as 6-hydroxy-4-methoxy-5-benzofuran-propionic acid 6- O- β-d- glucopyranoside, 6-hydroxy-4,7-dimethoxy-5-benzofuranpropionic acid 6- O- β-d- glucopyranoside, 1-(4′- O-glucopyranosyl-4′-hydroxy-3′,5′-dimethoxyphenyl)-2{2″,6″-dimethoxy-4″-[1-(E) propen-3-ol]-phenoxy}- propan-1,3-diol(threo), and methylphloroglucinol β- d-glucopyranoside by spectroscopic means.

Full assignments of proton and carbon signals of picrasidine‐G by 1D and 2D NMR methods

AbstractThe alkaloid picrasidine‐G was isolated from Picrasma quassioides. This alkaloid has previously been reported as a new natural product, but its 13C NMR signals still remain unassigned and some ambiguities remains in the proton assignments. Analysis of the 1H and 13C NMR spectra and 1 D NOE and 2D NMR spectra led to the unambiguous assignment of the 1H and 13C signals of picrasidine‐G.

ChemInform Abstract: Isolation of 4‐Hydroxy‐5‐methoxycanthin‐6‐one from Picrasma quassioides and Revision of a Previously Reported Structure.

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New Alkaloids, Picrasidines W, X and Y, from Picrasma quassioides and X-Ray Crystallographic Analysis of Picrasidine Q.

Three new alkaloids, picrasidines W (1), X (2) and Y (3), were isolated from the wood of Picrasma quassioides BENNET (Simaroubaceae). Their structures were determined by spectral and chemical evidence. Previously isolated picrasidine Q (4) was unambiguously determined by X-ray crystallographic analysis.

Isolation of 4‐Hydroxy‐5‐methoxycanthin‐6‐one from Picrasma quassioides and Revision of a Previously Reported Structure

AbstractA new alkaloid, 4‐hydroxy‐5‐methoxycanthin‐6‐one (1), has been isolated from Picrasma quassioides (Simaroubaceae), and its structure has been determined by high‐field 1H‐ and 13C‐NMR, 13C,1H‐HETCOR, 1H,1H‐2D‐COSY, and NOE‐difference spectra. Previous data, interpreted by other workers as being from this compound, is instead tentatively reassigned to another new alkaloid structure, 4‐hydroxy‐3‐methylcanthine‐5,6‐dione (2).

Growth and Isoprenoid Metabolism of Cultured Picrasma quassioides Cells.

Growth and Isoprenoid Metabolism of Cultured Picrasma quassioides Cells.

β-Carboline alkaloids from Picrasma quassioides

A new β-carboline alkaloid, picrasidine V, was isolated from the root wood of Picrasma quassioides. The structure was determined as 8-methoxy-1,2,3,4-tetrahydro-1,3,4-trioxo-β-carboline by spectral evidence.

Cell Suspension Culture of Picrasma quassioides: the Development of a rapidly growing, Shear Resistant Cell Line capable of Quassin Formation

Summary Picrasma quassioides Bennett (Simaroubaceae) produces the tetracyclic triterpenoid quassin. The development of a suspension culture of P. quassioides capable of growing in bioreactors and which produces low levels of quassin is described. The suspension culture was initially highly aggregated and slow growing (doubling time 12 days) but after 2 years cultivation and a number of changes in subculture methods a less aggregated and faster growing (doubling time, 2.9 days) suspension has been achieved. In addition to an increased growth rate the cultures have begun to produce low levels of quassin (30 – 150 μg . g dry weight-1). The growth of P. quassioides suspension cultures in volumes above 100 ml was initially difficult to establish, but after a year growth in 1 litre volumes was achieved followed a year later by growth in a stirred-tank bioreactor. This cell line has been shown to have developed shear resistance in this time.