A new benzofuran from Penicillium oxalicum, an endophytic fungus isolated from Pseudostellariaheterophylla / 中草药

Objective: To study the secondary metabolites of Penicillium oxalicum, an endophytic fungus isolated from the medicinal plant Pseudostellariaheterophylla. Methods: The secondary metabolites were isolated by silica gel, Sephadex LH-20 column chromatographies, and prep-TLC methods. Their structures were elucidated by using various spectroscopic techniques including HRESIMS and NMR spectra. Results: A benzofuran compound 5,7-dihydroxy-2-methylbenzofuran-3-carboxylic acid (1), five isocoumarins including (3R,4R)-(-)-4-hydroxymellein (2), O-methylmellein (3), acremonone G (4), decarboxycitrinone (5) and decarboxyhydroxycitrinone (6), four bisabolane-type sesquiterpenoids including (7S,11S)-(+)-12-acetoxysydonic acid (7), (S)-(+)-11-dehydrosydonic acid (8), sydonic acid (9) and 1-hydroxy-boivinianin A (10), as well as two meroterpenoid-type alkaloids decaturin D (11) and decaturinC (12) were isolated. Conclusion: Compound 1 is a new benzofuran compound and named as oxafuranone A, while compounds 2-6 and 10 are characterized from P. oxalicum for the first time.

In vivo chemotherapeutic insight of a novel isocoumarin (3-hexyl-5,7-dimethoxy-isochromen-1-one): Genotoxicity, cell death induction, leukometry and phagocytic evaluation

Abstract Chemotherapy is one of the major approaches for the treatment of cancer. Therefore, the development of new chemotherapy drugs is an important aspect of medicinal chemistry. Chemotherapeutic agents include isocoumarins, which are privileged structures with potential antitumoral activity. Herein, a new 3-substituted isocoumarin was synthesized from 2-iodo-3,5-dimethoxy-benzoic acid and oct-1-yne in a cross-coupling Sonogashira reaction followed by a copper iodide-catalyzed intramolecular cyclization as key step using MeOH/Et3N as the solvent system. The present study also evaluated the leukometry, phagocytic activity, genotoxic potential and cell death induction of three different doses (5 mg/kg, 10 mg/kg and 20 mg/kg) of this newly synthesized isocoumarin, alone and in combination with the commercial chemotherapeutic agents cyclophosphamide (100 mg/kg) and cisplatin (6 mg/kg) in male Swiss mice. The results suggest that the isocoumarin has genotoxicity and causes cell death. Noteworthy, this new compound can increase splenic phagocytosis and lymphocyte frequency, which are related to immunomodulatory activity. When combined with either cyclophosphamide or cisplatin, chemopreventive activity led to a reduction in the effects of both chemotherapeutic drugs. Thus, the new isocoumarin is not a candidate for chemotherapeutic adjuvant in treatments using cyclophosphamide or cisplatin. Nevertheless, the compound itself is an important prototype for the development of new antitumor drugs.

Chemical constituents of stems and leaves of Clausena hainanensis / 中草药

Objective To study the chemical constituents of the stems and leaves of Clausena hainanensis. Methods The chemical constituents of C. hainanensis were separated and purified by silica gel, ODS, Sephadex LH-20 gel column chromatographies, and preparative HPLC. Their structures were identified by physicochemical properties, spectroscopic analysis, as well as comparisons with the data reported in literature. Results Eighteen compounds were isolated from the 90% ethanol extract of the stems and leaves of C. hainanensis, which were identified as mukonine (1), methyl carbazole-3-carboxylate (2), lansine (3), murrayanine (4), 3-formylcarbazole (5), 3-formyl-6-methoxycarbazole (6), lansamide 4 (7), 4-methoxy-N-methyl-2-quinolone (8), (E)-N- (4-methoxyphenethyl)-2-methylbut-2-enamide (9), (E)-N-methyl cinnamon amide (10), N-(2-hydroxy-2-phenylethyl) cinnamamide (11), N-benzoyltyramine (12), aurantiamide (13), N-methyl-2-pyrolidinone (14), coumaric acid (15), 6,8-dimethoxy-4,5-dimethyl-3- methyleneisochromanl-one (16), 8-methoxypsoralen (17), and isololiolide (18). Conclusion This is the first time reporting the chemical constituents from C. hainanensis, all compounds are isolated from C. hainanensis for the first time, and compounds 12-16 are isolated from the genus Clausena for the first time.

Chamerilactone A: one new isocoumarin isolated from Chamerion angustifolium / 药学学报

A new isocoumarin, chamerilactone A (1) was isolated from the ethanol extract of Chamerion angustifolium with normal phase silica column chromatography, Sephadex LH-20, MCI CHP-20 and semipreparative HPLC methods. Its structure and stereochemistry were elucidated by spectroscopic methods, including 2D-NMR and optical rotation techniques.