The present study investigated the chemical constituents from Uncaria sessilifructus and their neuroprotective activities. The compounds were separated and purified from the 90% ethanol extract of U. sessilifructus by various chromatographic methods, including silica gel, Sephadex LH-20, and semi-preparative HPLC. Seven compounds were obtained, and their structures were identified as uncanidine J(1), uncanidine K(2), 17-O-ethylhirsutine(3), tetrahydroalstonine(4), akuammigine(5), hirsutine(6), and hirsuteine(7) by physicochemical properties and various spectral techniques, including UV, IR, MS, and NMR. Compounds 1 and 2 are two new compounds. Compound 3 is a new natural product, and compound 4 was isolated from U. sessilifructus for the first time. In addition, the isolated compounds were evaluated for their neuroprotective effects on oxygen and glucose deprivation/reoxygenation(OGD/R) injury in primary cortical neurons in rats. The results showed that compounds 1-7 had different degrees of protective effects on OGD/R injury. The EC_(50) values of compounds 2-4 were(0.17±0.03),(1.70±0.38), and(1.79±0.23) μmol·L~(-1), respectively.
Animals ; Biological Products ; Drugs, Chinese Herbal/pharmacology* ; Ethanol ; Glucose ; Indole Alkaloids ; Neuroprotective Agents/pharmacology* ; Oxygen ; Rats ; Secologanin Tryptamine Alkaloids ; Silica Gel ; Uncaria/chemistry*

Chemical investigation of the leaves of Gelsemium elegans growing in Vietnam resulted in the isolation of the indol alkaloids: gelsevirine, gelsenicine and koumine. The isolated compounds from this plant were tested for the antimicrobial and cytotoxicity activity
Indole Alkaloids ; Biological Markers ; Alkaloids

Catharanthus roseus (L.) G. Don is a plant of the Catharanthus genus of Apocynaceae which has been reported to have therapeutic effects of detoxication and anticancer. In order to further study the alkaloid constituents of C. roseus, the aerial parts of the plant were extracted with 95% EtOH, and then treated with 2% H2SO4 and NH3H2O to obtain total alkaloids. The total alkaloids were separated and purified by column chromatography over silica gel and prepared by high performance liquid chromatography (HPLC). Their structures were elucidated on the basis of physicochemical properties and spectral data. A new alkaloid together with five known compounds were isolated and identified as vindolinine B (1), lochnericine (2), horhammericine (3), vindorosine (4), vindoline (5), and coronaridine (6). Compound 1 is a new compound and named as vindolinine B.
Antineoplastic Agents, Phytogenic ; chemistry ; isolation & purification ; Catharanthus ; chemistry ; Ibogaine ; analogs & derivatives ; chemistry ; isolation & purification ; Indole Alkaloids ; chemistry ; isolation & purification ; Molecular Structure ; Plant Components, Aerial ; chemistry ; Plants, Medicinal ; chemistry ; Vinblastine ; analogs & derivatives ; chemistry ; isolation & purification

OBJECTIVES: To establish a LC-MS/MS method which is accurate and sensitive for determination of koumine, gelsemine, and gelsenicine in biological samples and to verify the method. METHODS: Strychnine was used as internal standard. Analytes in blood, urine and liver with 1% sodium hydroxide solution were extracted by ethyl acetate. Chromatographic separation was achieved on a ZORBAX SB-C₁₈ column （150 mm×2.1 mm, 5 μm）, and gradient elution was performed with the buffer solution of methanol-20 mmol/L ammonium acetate （including 0.1% formic acid and 5% acetonitrile） as mobile phase. Qualitative and quantitative analysis was performed in the multiple reaction monitoring mode coupled with an electrospray ionization source under positive ion mode（ESI⁺）. RESULTS: The linearity of koumine, gelsemine and gelsenicine in blood, urine and liver was good within corresponding linear limitation and the correlation coefficients （r）>0.995 0. The limits of detection were 0.1 ng/mL （0.1 ng/g）, 0.1 ng/mL （0.1 ng/g） and 0.01 ng/mL （0.01 ng/g）, respectively. The extraction recovery and accuracy of the alkaloids ranged from 61.9% to 114.6% and 92.4% to 114.3%, respectively. The relative standard deviations of the intra-day and inter-day precisions were not more than 11.0%. CONCLUSIONS The method is selective, sensitive and suitable for simultaneous determination of koumine, gelsemine and gelsenicine in body fluids and tissues, which offering technical support for clinical diagnosis and treatment and forensic toxicological analysis of Gelsemium elegans poisoning.
Alkaloids/urine* ; Chromatography, High Pressure Liquid ; Chromatography, Liquid ; Forensic Toxicology ; Formates ; Humans ; Indole Alkaloids/urine* ; Liver ; Reproducibility of Results ; Strychnine ; Tandem Mass Spectrometry

OBJECTIVETo predict the absorption of corynanthine (COR), yohimbine (YOH), ajmalicine (AMC) and ajmaline (AML) as chemical constituents of some traditional Chinese medicines in human intestinal epithelial.

METHODBy using Caco-2 (the human colonic adenocarcinoma cell lines) cell monolayers as a human intestinal epithelial cell model, the permeability of COR, YOH, AMC and AML were studied from apical side (AP side) to basolateral side (BL side) or from BL side to AP side. The four alkaloids were measured by high performance liquid chromatography (HPLC) coupled with UV detector. Transport parameters and apty) and atenolol (a control substance of poor permeability). The relationship between P(app) and log D values of four alkaloids was investigated by using drugs ADMET predict software.

RESULTThe P(app) values of COR, YOH, AMC and AML were (1.863 +/- 0.055) x 10(-5), (1.540 +/- 0.082) x 10(-5), (2.522 +/- 0.246) x 10(-5) and (1.155 +/- 0.099) x 10(-5) cm x s(-1) from AP side to BL side, and (2.390 +/- 0.017) x 10(-5), (1.987 +/- 0.154) x 10(-5), (1.374 +/- 0.260) x 10(-5) and (2.418 +/- 0.124) x 10(-5) cm x s(-1) from BL side to AP side, respectively, which P(app) values were identical with that of propranolol [(2.23 +/- 0.10) x 10(-5) cm x s(-1) from AP to BL side]. The ratio of P(app B --> A)/P(app A -->B) of COR, YOH, AMC and AML were 1.28, 1.29, 0.54 and 2.09, respectively, which suggested that the efflux transport of AML was 2.09 times higher more than its influx transport.

CONCLUSIONCOR, YOH, AMC and AML can be transported and absorbed across the human Caco-2 cells monolayers, and they belong to completely absorbed compounds. AML may have been involved in efflux mechanism in Caco-2 cells monolayers model from the BL to AP side direction. The oil-water partition coefficient play key roles in the transport and absorption of the four alkaloids.

Ajmaline ; metabolism ; Caco-2 Cells ; Chromatography, High Pressure Liquid ; Epithelial Cells ; metabolism ; Humans ; Intestinal Mucosa ; cytology ; Molecular Structure ; Secologanin Tryptamine Alkaloids ; metabolism ; Yohimbine ; metabolism

Chemical investigation on a colonial marine tunicate, Didemnum sp. led to the isolation of a series of indole alkaloids including a new (1) and two known metabolites (2-3). Based on the spectroscopic analysis including 1D and 2D NMR along with MS spectra, the structure of 1 (16-epi-18-acetyl herdmanine D) was elucidated as a new amino acid derivative. The absolute configuration of 1 was determined by comparison of specific rotation with the known compound. The structures of compounds 2 and 3 were also identified as bromoindole containing compounds N-(6-bromo-1H-indole-3-carbonyl)-L-arginine and (6-bromo-1H-indol-3-yl) oxoacetamide, respectively, based on 1H and 13C NMR data, MS data and specific rotation value. Their pharmacological potentials as antibacterial agents and FXR antagonists were investigated, but no significant activity was found. However, the structural similarity of compound 1 to compound 4 suggested the antiinflammatory potential of compound 1.
Anti-Bacterial Agents ; Indole Alkaloids ; Urochordata*

The aim of this study was to investigate the relationship between the acetylcholine concentration in the blood and gelsenicine-induced death in mice. Kunming mice were given intraperitoneal injections of normal saline, gelsenicine or different doses of acetylcholine chloride. Atropine was given to the mice which received gelsenicine or medium dose acetylcholine chloride injection. The blood was sampled immediately when the mice died or survived for 20 min after injection. The acetylcholine concentration and acetylcholinesterase activity in the blood were measured by the testing kits, and the mortality was calculated and analyzed. The results showed that half lethal dose of gelsenicine (0.15 mg/kg) reduced the acetylcholinesterase activity and increased the blood acetylcholine concentration. The blood acetylcholine concentration of the dead mice in the gelsenicine group was increased to 43.0 μg/mL (from 31.1 μg/mL in the control), which was lower than that (53.9 μg/mL) of the dead mice in the medium dose acetylcholine chloride group, but almost equal to that (42.7 μg/mL) of the survival mice in the medium dose acetylcholine chloride group. Atropine could successfully rescue the mice from acetylcholine poisoning, but its efficiency of rescuing the mice from gelsenicine intoxication was weak. These results suggest that gelsenicine can inhibit acetylcholinesterase activity and increase blood acetylcholine concentration, but the accumulation of acetylcholine may not be the only or main cause of the death induced by gelsenicine in mice.
Acetylcholine ; Animals ; Death ; Indole Alkaloids ; Mice

To study chemical constituents of the leaves of Nauclea officinalis, eight alkaloids were isolated from 95% ethanol extract by various chromatographic methods. The structures were elucidated on the basis of spectroscopic data (IR, UV, ESI-MS, 1D and 2D NMR) and identified as naucleactonin C (1), strictosamide (2), vincosamide (3), pumiloside (4), angustoline (5), angustine (6), 18, 19-dihydroangustine (7) and naucleofficine D (8). Compound 1 is a new indole alkaloid. Compounds 6 and 7 were isolated from this plant for the first time.
Alkaloids ; chemistry ; isolation & purification ; Camptothecin ; analogs & derivatives ; chemistry ; isolation & purification ; Indole Alkaloids ; chemistry ; isolation & purification ; Indoles ; chemistry ; isolation & purification ; Molecular Structure ; Plant Leaves ; chemistry ; Plants, Medicinal ; chemistry ; Rubiaceae ; chemistry ; Vinca Alkaloids ; chemistry ; isolation & purification

In order to study the chemical constituents in the water extract of the stem of Nauclea officinalis, column chromatography over D101 macroporous resin and silica gel and an automatic purification system were used to isolate and purify the chemical constituents from the extract. Nine compounds were obtained. By analysis of the physicochemical properties and spectral data, their structures were identified as naucleamide G (1), 3, 4-dimethoxyphenol-beta-D-apiofuranosyl (1-->6)-beta-D-glucopyranoside (2), kelampayoside A (3), 3alpha, 5alpha-tetrahydrodeoxycordifoline lactam (4), naucleamide A-10-O-beta-D-glucopyranoside (5), pumiloside (6), 3-epi-pumiloside (7), strictosamide (8) and vincosamide (9), separately. Among them, compound 1 is a new compound, compound 2 was found in plants of the genus Nauclea for the first time, and compounds 3 and 4 were isolated from this plant for the first time.
Camptothecin ; analogs & derivatives ; chemistry ; isolation & purification ; Carbolines ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; Indole Alkaloids ; chemistry ; isolation & purification ; Molecular Structure ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry ; Rubiaceae ; chemistry ; Vinca Alkaloids ; chemistry ; isolation & purification

Uncaria genus( Rubiaceae) contains 34 species all over the world,of which 11 species and one variant are present in China. Five species,namely U. rhynchophylla,U. macrophylla,U. hirsuta,U. sinensis and U. sessilifructus,are documented in Chinese Pharmacopoeia as the raw materials of Uncariae Ramulus Cum Uncis. Indole alkaloids are the characteristic constituents of Uncaria plants,in addition to triterpenes,lignans and flavones. This paper reviews the progress of indole alkaloids and their distribution within the five Uncaria species documented in Chinese Pharmacopoeia for better understanding the active constituents of Uncariae Ramulus Cum Uncis.
Alkaloids ; China ; Drugs, Chinese Herbal ; Indole Alkaloids ; Medicine, Chinese Traditional ; Uncaria