ChemInform Abstract: NATURALLY OCCURRING TERPENE DERIVATIVES, 81. FURTHER CONSTITUENTS OF REPRESENTATIVES FROM THE EUPATORIUM GROUP

Isolation of Austroinulin Possessing Cell Cycle Inhibition Activity fromBlumea glomerataand Revision of Its Absolute Configuration

“…The structures of these compounds (2 ± 11) were elucidated by spectroscopic methods ( 1 HNMR, EI-and/or FAB-MS, and [a] D ) and were confirmed by comparison of their spectroscopic data with those in the literature [2], [3], [4], [5], [7], [8], [9]. On the other hand, compound 1 was obtained as an amorphous solid, and the molecular formula was suggested to be [13], Stevia rebaudiana [14], [15], and Stevia aristata [16] (Compositae). Zdero et al described the absolute configuration of austroinulin as 1a (ent-labdane form), since the CD data of a 6-keto derivative prepared from austroinulin through PCC oxidation showed a negative Cotton effect at 295 nm and the ent-labdane form was likely by following the octant rule [16].…”

“…Esterification under these conditions afforded only 12, and formation of 6-O-MTPA ester was not detected, possibly because the C-6 hydroxy group was hindered by the equatorial methyl group (C-18) on C-4. The corresponding (R)-MTPA ester(13) was prepared by the same procedures using (S)-MTPA-Cl. 1 H-NMR data of 12…”

Chemical constituents of hybrids of Ligularia cyathiceps and L. lamarum/L. subspicata collected in China: Structures of subspicatins M, N, O1, and O2, and related compounds

“…The known compounds were furanoeremophilane (7) (Ishii et al, 1966), furanoeremophilan-6β-ol (8 = ligularol) (Ishii et al, 1965), 6β-isobutyroyloxyfuranoeremophilane 9 et al, 1974), 6β-isobutyroyloxyfuranoeremophilan-10β-ol (16) (Jennings et al, 1976), 6β-angeloyloxyfuranoeremophilan-9-one (17) (Bohlmann et al, 1986) (Naya et al, 1968), 7αH-eremophil-11-en-8-one (24) (Bohlmann et al 1986), bakkenolide A (25) (Abe et al, 1968), (2R,3S)-5-acetyl-6-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-3-yl (Z)-2-methylbut-2-enoate (26) (Bohlmann et al, 1977) (Bohlmann et al, 1977), 5,6dimethoxy-2-(prop-1-en-2-yl)benzofuran (28) (Murae et al, 1968), and 5-acetyl-6-hydroxy-2-(prop-1-en-2-yl)benzofuran (29 = euparin) (Kamthong and Robertson, 1939) (Fig. 7).…”

Constituents of the leaves and roots of Ligularia stenocephala MATSUM. et KOIDZ.

“…The Et 2 O extract (14.6 g) was subjected to silica gel column chromatography (nhexane-EtOAc, EtOAc and MeOH) and subsequent preparative HPLC (TSKgel ODS-120 T, MeOH) to afford (1) (0. . The structures of 1-9 were identified as (2E,6E,10E,14E,18E)-2,6,10, 15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaen-1-ol [3], (3E,6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyl-3,6,10,14,18,22-tetracosahexaen-2-ol [4], neophytadiene [5], 5-acetyl-6-hydroxy-2a-isopropenyl-3b-methoxy-2, 3H-benzofuran [6], 3b-acetoxy-6-acetyl-5-hydroxy2a-isopropenyl-2,3H-benzofuran [7], p-hydroxybenzaldehyde, vanillin, 4-hydroxyacetophenone and 4-hydroxy-3-methoxyacetophenone [8], respectively, by comparison of their spectral data with those in the literature (1)(2)(3)(4)(5)9) or by direct comparison with respective authentic samples (6)(7)(8). Compounds 1 and 2 have already been synthesized [3,4] but have not been isolated from a natural source before.…”