Semisynthesis of justicidone and a 1,2-quinone lignan. Cytotoxic activity of some natural and synthetic lignans.
The dioxo-lignans of the arylnaphthalene-type named justicidone (2) and elenodione (3) were obtained from elenoside (1) through a short and efficient semisynthetic process. Justicidone (2), one of its synthetic precursors, 4-(benzo[d][1,3]dioxol-5-yl)-5,6,8-trimethoxy-3a,4-dihydronaphtho[2,3-c]furan-1(3H)-one (9), and the aglycone of elenoside (5) showed cytotoxic activity towards the HL-60 cell line (IC50 = 7.25 miroM, 5.41 microM and 2.06 miroM, respectively).
Boluda
Carlos J
CJ
Instituto Universitario de Bioorgáinica Antonio González, Universidad de La Laguna, Avda. Astrofisico F. Sánchez, 2, 38206 La Laguna, Tenerife, Canary Islands, Spain.
Trujillo
Juan M
JM
Pérez
José A
JA
López
Hermelo
H
Aragón
Zulma
Z
Díaz
Raquel G
RG
D027901:Acanthaceae / Q000737:chemistry; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006801:Humans; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011809:Quinones / Q000138:chemical synthesis*
D000972:Antineoplastic Agents, Phytogenic; D017705:Lignans; D011809:Quinones; C428195:elenoside; C488481:justicidone