Neoclerodane diterpenoids from Scutellaria caerulea.
Five new neoclerodane diterpenoids have been isolated from Scutellaria caerulea: (11S*)-6 alpha-acetoxy-7 beta,11-diisobutiryloxy-1 beta,8 beta-dihydroxy-4(18),13-neoclerodadien-15,16-olide (scuterulein A) (1); (13R*)-1 beta-6 alpha-7 beta-triacetoxy-11 beta-benzoyloxy-8 beta,13-epoxy-4(18)-neocleroden-15,16-olide (scuterulein B) (2); (11S*)-1 beta,6 alpha,11-triacetoxy-7 beta-isobutiryloxy-8 beta-hydroxy-4(18),13-neoclerodadien-15,16-olide (scuterulein C) (3); (11S*)-6 alpha,11-diacetoxy-7 beta-isobutiryloxy-1 beta,8 beta-dihydroxy-4(18),13-neoclerodadien-15,16-olide (deacetyl scuterulein C) (4), and (11E)-6 alpha-acetoxy-7 beta-isobutiryloxy-1 beta,8 beta-dihydroxy-4(18),11,13-neoclerodatrien-15,16-olide (scuterulein D) (5). Structures were established by spectroscopic and chemical methods. An X-ray analysis was carried out on scuterulein B (2).
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Instituto de Química de la Universidad Nacional Autónoma de México, Circuito Exterior Cd. Universitaria, Coyoacán, 04510, México, D.F. baldo@sevidor.unam.mx
Domínguez
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RM
Toscano
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RA
D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D008800:Mexico; D008958:Models, Molecular; D008968:Molecular Conformation; D010946:Plants, Medicinal / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared
D004224:Diterpenes