Bioactivity-guided isolation of cytotoxic sesquiterpenes of Rolandra fruticosa.
Cytotoxicity-guided fractionation of a methanol extract of the leaves and twigs of Rolandra fruticosa using the HT-29 human colon cancer cell line led to the isolation of seven sesquiterpene lactones, including the hitherto unknown isorolandrolide, 13-methoxyisorolandrolide (1), and bourbonenolide, 2alpha,13-diacetoxy-4alpha-hydroxy-8alpha-isobutyroyloxybourbonen-12,6alpha-olide (2), as well as five known compounds, 13-acetoxyrolandrolide (3), 8-desacyl-13-acetoxyrolandrolide-8-O-tiglate (4), 2-epi-glaucolide E (5), 2alpha,13-diacetoxy-4alpha-hydroxy-8alpha-methacryloyloxybourbonen-12,6alpha-olide (6), and 2alpha,13-diacetoxy-4alpha-hydroxy-8alpha-tigloyloxybourbonen-12,6alpha-olide (7). The structures of the two sesquiterpenes were elucidated on the basis of spectroscopic methods. All isolates were evaluated for their cytotoxicity using the HT-29 cell line, and only 13-acetoxyrolandrolide (3) was found to possess a potent inhibitory effect against this cell line. Compounds 3, 5 and 6 were also tested in a NF-kappaB (p65) inhibition assay, and 3 was assessed in an in vivo hollow fiber assay.
Pan
Li
L
Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, OH 43210, USA.
Lantvit
Daniel D
DD
Riswan
Soedarsono
S
Kardono
Leonardus B S
LB
Chai
Hee-Byung
HB
de Blanco
Esperanza J Carcache
EJ
Farnsworth
Norman R
NR
Soejarto
Djaja Doel
DD
Swanson
Steven M
SM
Kinghorn
A Douglas
AD
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D019659:Asteraceae / Q000737:chemistry*; D045744:Cell Line, Tumor; D003110:Colonic Neoplasms / Q000188:drug therapy*; D019073:HT29 Cells; D006801:Humans; D007783:Lactones / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D051379:Mice; D015394:Molecular Structure; D016328:NF-kappa B / Q000037:antagonists & inhibitors; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use*; D018515:Plant Leaves; D012717:Sesquiterpenes / Q000302:isolation & purification / Q000494:pharmacology
C552274:13-acetoxyrolandrolide; C552272:13-methoxyisorolandrolide; D000972:Antineoplastic Agents, Phytogenic; D007783:Lactones; D016328:NF-kappa B; D010936:Plant Extracts; D012717:Sesquiterpenes; C552273:bourbonenolide