title: Structures of spiroindicumides A and B, unprecedented carbon skeletal spirolactones, and determination of the absolute configuration by vibrational circular dichroism exciton approach.
abstract: Spiroindicumides A (1) and B (2), novel spirolactone polyketides, were isolated from a filamentous fungus, Chaetomium indicum, cultivated in the presence of a histone deacetylase inhibitor. Their structures including relative configurations were determined by spectroscopic analyses. Their absolute configurations were unambiguously assigned by the vibrational circular dichroism (VCD) exciton chirality method using only ca. 0.3 mg of each sample. This study presents the first application of the VCD exciton approach to novel natural products. A possible biosynthetic pathway of the new compounds was also proposed.
authors: Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba-yama, Sendai 980-8578, Japan. tasai@m.tohoku.ac.jp
authors: Teigo
authors: T
authors: Asai
authors: Tohru
authors: T
authors: Taniguchi
authors: Takashi
authors: T
authors: Yamamoto
authors: Kenji
authors: K
authors: Monde
authors: Yoshiteru
authors: Y
authors: Oshima
mesh_terms: D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification*; D002597:Chaetomium / Q000737:chemistry*; D002942:Circular Dichroism; D056572:Histone Deacetylase Inhibitors / Q000737:chemistry / Q000494:pharmacology; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D056572:Histone Deacetylase Inhibitors; D007783:Lactones; D061065:Polyketides; D013141:Spiro Compounds; C586348:spiroindicumide A; C586349:spiroindicumide B