Gymnasterkoreaynes A-F, cytotoxic polyacetylenes from Gymnaster koraiensis.
Six new polyacetylenes, gymnasterkoreaynes A-F (1-6), were isolated from the roots of Gymnaster koraiensis, together with 2,9,16-heptadecatrien-4,6-diyn-8-ol (7) and 1,9,16-heptadecatriene-4,6-diyn-3,8-diol (8), by bioassay-guided fractionation using the L1210 tumor cell line as a model for cytotoxicity. The structures of compounds 1-6 were established spectroscopically, which included 2D NMR experiments. Gymnasterkoreaynes A-F (1-6) are linear diacetylenes and are structurally related to falcarinol, panaxynol, panaxydiol, and panaxytriol. Of the compounds isolated, gymnasterkoreaynes B (2), C (3), F (6), and 1,9,16-heptadecatrien-4,6-diyn-3,8-diol (8) exhibited significant cytotoxicity against L1210 tumor cells with ED(50) values of 0.12-3.3 microg/mL.
Jung
Hyun-Ju
HJ
College of Pharmacy, Chungnam National University, Taejon 305-764, Korea.
Min
Byung-Sun
BS
Park
Jin-Young
JY
Kim
Young-Ho
YH
Lee
Hyeong-Kyu
HK
Bae
Ki-Hwan
KH
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000480:Alkynes; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019659:Asteraceae / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D053280:Diynes; D004354:Drug Screening Assays, Antitumor; D005233:Fatty Alcohols / Q000737:chemistry; D007723:Korea; D007938:Leukemia; D051379:Mice; D008954:Models, Biological; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D053279:Polyynes; D014315:Triterpenes / Q000737:chemistry; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000480:Alkynes; D000972:Antineoplastic Agents, Phytogenic; D001952:Bridged-Ring Compounds; D053280:Diynes; D005233:Fatty Alcohols; D011108:Polymers; D014315:Triterpenes; C515174:gymnastatin F; C018541:falcarinol; D053279:Polyynes; D000114:Acetylene