Two Unusual Polycyclic Polyprenylated Acylphloroglucinols, Including a Pair of Enantiomers from Garcinia multiflora

• DOI: 10.1021/acs.orglett.5b00588
• Publication Date: 2015-04-13T12:56:45Z
• Authors: Yi-Min Fan; Ping Yi; Yang Li; Chen Yan; Tao Huang; Wei Gu; Yuan Ma; Lie-Jun Huang; Jian-Xin Zhang; Chong-Lin Yang; Yan Li; Chun-Mao Yuan; Xiao-Jiang Hao
• Keywords: Molecular Structure; HL-60 Cells; Stereoisomerism; Phloroglucinol; Antineoplastic Agents, Phytogenic; 01 natural sciences; 3. Good health; 0104 chemical sciences; Humans; Drug Screening Assays, Antitumor; Garcinia; Lysosomes; HeLa Cells

Two polycyclic polyprenylated acylphloroglucinols, garcimulins A and B ((±)-1 and 2), including a pair of enantiomers with the unique caged tetracyclo[5.4.1.1(1,5).0(9,13)]tridecane skeleton were isolated from Garcinia multiflora. Their structures and absolute configurations were determined by extensive analysis of spectroscopic data and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 exhibited cytotoxic activities against five human cancer cell lines in vitro (IC50 3.42-13.23 μM). The acidification of lysosomes in HeLa cell was obviously affected by compound 2.