Glycosmis citrifolia (Willd.) Lindl. (Rutaceae) is a wild shrub used in folk medicine to treat skin itch, scabies, boils, and ulcers. Prior to this study, only the phenylalkylamine candicine had been isolated from its bark. Here, sixteen acridone alkaloids were isolated from the stem and root barks of G. citrifolia collected in Taiwan, including seven novel compounds: linear pyranoacridones glycofoline (1a) and pyranofoline (2a), furoacridone furofoline-II (3b), hexa-oxygenated acridone glyfoline (4a), and prenylated acridones glycocitrine-I (5a), glycocitrine-II (5c), and 3-O-methylglycocitrine-II (5d), along with nine known acridones. Their structures were elucidated using spectral data (UV, IR, ¹H/¹³C NMR, MS) and chemical transformations. Nuclear Overhauser effect (N.O.e.) experiments on methoxymethyl derivatives of phenolic acridones determined hydroxy group positions. The prenyl group location of (5c) was established via cyclization with benzeneselenenyl chloride, while formic acid-catalyzed cyclization of (5c) induced undesirable prenyl rearrangement to form products (9) and (10). Key findings: (1) Glycofoline and pyranofoline are the first linear pyranoacridones isolated from nature (all prior natural pyranoacridones have angular ring systems); (2) Furofoline-I and II represent the first isolation of furoacridone alkaloids (not just dihydro derivatives) from natural sources; (3) Glyfoline is the first hexa-oxygenated N-methyl-9-acridone from nature. These results expand the diversity of natural acridone alkaloids and provide structural insights into their biosynthesis.