SERCA-inhibiting activity of C-19 terpenolides from Thapsia garganica and their possible biogenesis.
An investigation of Thapsia garganica afforded a series of tetracyclic C-19 dilactones, whose production was dependent on the time and location of the collection. These unusual tetrahomosesquiterpenoids are presumably biosynthesized via a carbon dioxide-triggered electrophilic polyolefin cyclization. Despite the structural differences with thapsigargin, these compounds showed SERCA-inhibiting properties.
Appendino
Giovanni
G
Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università del Piemonte Orientale, Viale Ferrucci 33, 28100 Novara, Italy. appendino@pharm.unipmn.it
Prosperini
Simona
S
Valdivia
Carola
C
Ballero
Mauro
M
Colombano
Giampiero
G
Billington
Richard A
RA
Genazzani
Armando A
AA
Sterner
Olov
O
D000818:Animals; D019661:Apiaceae / Q000737:chemistry*; D000252:Calcium-Transporting ATPases / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D053498:Sarcoplasmic Reticulum Calcium-Transporting ATPases; D012617:Sea Urchins / Q000201:enzymology* / Q000378:metabolism; D013237:Stereoisomerism; D019284:Thapsigargin / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology
D004791:Enzyme Inhibitors; D019284:Thapsigargin; D053498:Sarcoplasmic Reticulum Calcium-Transporting ATPases; D000252:Calcium-Transporting ATPases