Bioactive humulene derivatives from Asteriscus vogelii.
The bioactive fractions obtained from the extract of Asteriscus vogelii afforded a new humulene derivative, the 8-oxo-6,7,9,10-tetrahydrohumulen-1,12-olide (1), in addition to the known asteriscunolides A (2), C (3) and D (4), and the acids 8-oxo-alpha-humula-6Z,9Z-dien-12-oic acid (5), 8-oxo-alpha-humula-6E,9Z-dien- 12-oic acid (6) and 8-oxo-alpha-humula-6E,9E-dien-12-oic acid (7), characterized as their methyl esters. Evaluation of their phytotoxic and cytotoxic activities was accomplished. Compounds 3 and 4 gave the highest inhibition of plant cell cultures and of the plant Lemna paucicostata. Compound 4 was also the most active against P-338 lymphoma in mice, A-549 carcinoma of human lung, HT-29 carcinoma of human colon and MEL-28 human melanoma.
Rauter
A P
AP
Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, Portugal. aprauter@mail.telepac.pt
Branco
I
I
Bermejo
J
J
González
A G
AG
García-Grávalos
M D
MD
Feliciano
A S
AS
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D019684:Magnoliopsida / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D000081222:Monocyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013057:Spectrum Analysis; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D000081222:Monocyclic Sesquiterpenes; D012717:Sesquiterpenes; C042686:humulene