Vasicinone

Antitumor quinazoline alkaloids from the seeds of Peganum harmala.[Pubmed:26166311]

J Asian Nat Prod Res. 2015 May;17(5):595-600.

A phytochemical study on the methanol extracts from the seeds of Peganum harmala L. led to a new quizonaline alkaloid (S)-Vasicinone-1-O-beta-d-glucopyranoside (1) and four known ones, (R)-Vasicinone-1-O-beta-d-glucopyranoside (2), (S)-Vasicinone (3), vasicine (4), and deoxyVasicinone (5). Their structures were elucidated by spectroscopic analysis including IR, HR-ESI-MS, 1D and 2D NMR, and specific rotation as well as by comparison of the data with those in the literature. All of the alkaloids were screened for antiproliferative activity against human gastric cancer cells MCG-803 with MTT method. Compounds 1 and 3 exhibited moderate inhibitory activity.

Antitussive, expectorant, and bronchodilating effects of quinazoline alkaloids (+/-)-vasicine, deoxyvasicine, and (+/-)-vasicinone from aerial parts of Peganum harmala L.[Pubmed:26547531]

Phytomedicine. 2015 Nov 15;22(12):1088-95.

BACKGROUND: The aerial parts of Peganum harmala L. (APP) is a well-known and effective herbal medicine in China, and has been commonly used for treating various ailments, including cough and asthma. OBJECTIVES: To evaluate the antitussive, expectorant, and bronchodilating effects of the quinazoline alkaloids (+/-)-vasicine (VAS), deoxyvasicine (DVAS) (both isolated from the alkaloid fraction of APP) and (+/-)-Vasicinone (VAO) (synthesized from VAS). METHODS: The three quinazoline alkaloids were tested as antitussive on cough models in mice and guinea pigs. VAO was synthesized from VAS via the oxidation of hydrogen peroxide. VAS, VAO, and DVAS were orally administered at dosages of 5, 15, and 45 mg/kg. Cough in these models was induced by ammonia, capsaicin, and citric acid. Phenol red secretion experiments in mice were performed to evaluate the expectorant activity of the alkaloids. Bronchodilating effects were evaluated by using a bronchoconstrictive induced by acetylcholine chloride and histamine in guinea pigs. RESULTS: In antitussive tests, VAS, VAO, and DVAS significantly inhibited coughing frequency and prolonged the cough latency period in animals. At the highest doses tested (45 mg/kg), they showed antitussive activities similar to codeine phosphate (30 mg/kg) in mice and guinea pigs. Expectorant evaluation showed that VAS, VAO, and DVAS could significantly increase phenol red secretion in mice by 0.54-, 0.79- and 0.97-fold, by 0.60-, 0.99-, and 1.06-fold, and by 0.46-, 0.73-, and 0.96-fold, respectively, at dosages of 5, 15, and 45 mg/kg compared with the control (0.5% CMC-Na, 20 ml/kg). Ammonium chloride at 1500 mg/kg increased phenol red secretion in mice by 0.97-fold compared with the control. Bronchodilation tests showed that VAS, VAO, and DVAS prolonged the pre-convulsive time for 28.59%, 57.21%, and 29.66%, respectively, at a dose of 45 mg/kg in guinea pigs, whereas aminophylline prolonged the pre-convulsive time by 46.98% compared with pretreatment. CONCLUSIONS: Quinazoline alkaloids VAS, VAO, and DVAS have significant antitussive, expectorant, and bronchodilating activities. VAS, VAO, and DVAS are the active ingredients in APP, which can be used to treat respiratory disease.

Evaluation of hepatoprotective activity of vasicinone in mice.[Pubmed:25059038]

Indian J Exp Biol. 2014 Jul;52(7):705-11.

Justicia adhatoda (vasaka) leaves have long been used in Indian Ayurvedic system of medicine as antitussive. Its crude extract has been previously reported to have hepatoprotective activity. Vasicinone was isolated from leaves of J. adhatoda, column purified and characterized using, TLC UV, FT-IR and 1H NMR. The isolated Vasicinone was evaluated for hepatoprotective activity using (CCl4)-induced acute hepatotoxicity model in mice. CCl4 treatments lead to significant increase in SGOT, SGPT, ALP levels. Pre-treatment with Vasicinone and silymarin (25 mg/kg/day for 7 days) significantly decreased these enzyme levels. Histopathology of the livers from Vasicinone and silymarin pre-treated animals showed normal hepatic cords and absence of necrotic changes suggesting pronounced recovery from CCl4 induced liver damage. Both Vasicinone and silymarin significantly decrease the CCl4 mediated increase in pentobarbital indiced sleeping time in experimental animals, thus indicating recovery of liver function. Based on the above results it can be concluded that Vasicinone may act as hepatoprotective in mice and warrants further investigation on human volunteers.