Two New Bioactive Furoquinoline Alkaloids from Zanthoxylum armatum

Synthesis of 2‐Substituted Furo[2,3‐b]‐ and Furo[3,2‐c]quinolines via Heterogeneous Palladium‐catalyzed Heteroannulation

“…Furoquinoline scaffolds are one of the important heterocycles and their analogues are found not only in nature but also in pharmacological and biological materials, whose properties include anti‐inflammatory, TLR8 (Toll‐like receptor‐8) agonistic, anti‐cancerous, a protein inhibitory, and antimicrobial activity . Owing to their diverse biological activities, there have been great efforts to extract or synthesize furoquinolines, i.e ., [3 + 2] cyclization reaction for furo[2,3‐ b ]quinolines, [4 + 2] cycloaddition of imines with enol ethers, and a three component reaction of 4‐hydroxyquinolin‐2( 1H )‐one, aromatic aldehyde and isonitrile, and so on . Recently we have paid much attentions to develop green and practical synthetic methods for synthesizing various furoheterocycles 1–6 as shown in Scheme…”

Furoquinoline Alkaloids: Insights into Chemistry, Occurrence, and Biological Properties

“…Alkaloids such as dictamnine (1), γ-fagarine (3), maculine (36), flindersiamine (35), and kokusaginine (8) from the bark of Helietta apiculata demonstrated inhibitory activity against Candida krusei, with MICs ranging from 25 to 50 µg/mL [34]. Furoquinoline alkaloids found in Zanthoxylum armatum displayed activity against Aspergillus flavus and Aspergillus niger, although individual compounds were not studied [40]. Dictamnin (1), isolated from Dictamnus dasycarpus, exhibited antifungal activity against the plant pathogen Cladosporium cucumerinum (MIC 125.628 µM) [1].…”

“…It suppressed the proliferation and migration of human esophageal squamous cell carcinoma by blocking the activation of ERK1/2 [46]. Isodictamnine (39), iso-γ-fagarine (40), and γ-fagarine (3), occurring in Glycosmis arborea, showed inhibitory effects toward the tumor promoter 12-O-tetradecanoylphorbol 13-acetate-induced Epstein-Barr virus early antigen [20]. Compounds isolated from Zanthoxylum buesgenii, including maculine (36) and kokusaginine (8), demonstrated greater activity than doxorubicin on several tested cancer cell lines (leukemia CCRF-CEM and CEM/ADR5000, breast cancer MDA-MB231 and its resistant sub-line MDAMB231/BCRP, colon cancer HCT116p53 and its resistant sub-line, glioblastoma U87MG, hepatocarcinoma ∆EGFR, and HepG2) [1].…”

“…Evolitrine (18) effectively inhibited (57% inhibition at the dose of 20 mg/kg) the formation of edema caused by subplantar carrageenan injection in rats but did not cause side effects [20]. Seven furoquinoline alkaloids isolated from Dictamnus dasycarpus, namely skimmianine (2), dictamnine (1), γ-fagarine (3), iso-γ-fagarine (40), haplopine (6), dictangustine-A (42), and isomaculosidine (43), showed anti-inflammatory activity. Skimmianine (2) showed the most potent inhibition (IC50 values of 7.0 µM) of LPS-induced NO production in BV2 cells.…”