A new eremophilane-type sesquiterpene from Ligularia virgaurea

A new eremophilane-type sesquiterpene,1α,8β,10β-trihydroxy-6β-(2-methylacryloyl)oxyeremophil-7(11)-en-8α,12-olide, was isolated from the roots of Ligularia virgaurea.Its structure was established on the basis of various spectroscopic analyses, including the 1D,2D NMR techniques and HR-ESI-MS.     

Siamenols A-D, four new coumarins from Mammea siamensis

Further investigation of the dichloromethane extract of the twigs of Mammea siamensis led to the isolation of four novel coumarins, named siamenols A-D (1-4) together with three known xanthones. The structures of the new coumarins were elucidated by spectroscopic analysis, including 2D NMR spectroscopic data. In addition, the absolute stereochemistry of hydroxyl group of siamenol C (3) was determined to be S configuration by using modified Mosher's method.     

Dysidavarones A-D, new sesquiterpene quinones from the marine sponge Dysidea avara

Dysidavarones A-D (1-4), four new sesquiterpene quinones possessing the unprecedented "dysidavarane" carbon skeleton, were isolated from the South China Sea sponge Dysidea avara. The structures were established by spectroscopic methods, and the absolute configurations were determined using quantum mechanical calculation of the electronic circular dichroic (ECD) spectrum and exciton chirality CD method. Their cytotoxic activity against four human cancer cell lines and PTP1B inhibitory activity were also evaluated.     

Isolation of new eremophilane-type sesquiterpenoids, subspicatins A-D and subspicatolide from Ligularia subspicata, and chemical and genetic diversity of the species

New C-1 oxidized eremophilane-type sesquiterpenoids, subspicatins A, B, C, and D, and subspicatolide, were isolated from the root of Ligularia subspicata and their structures were established by spectroscopic and X-ray analyses. Subspicatins A and B were the major components. The species were found to be diverse both in the composition of the root chemicals and in the nucleotide sequences of the internal transcribed spacers (ITS) of the ribosomal RNA gene and the atpB-rbcL intergenic region, but the difference among the samples was not distinct but continuous.     

Saiyutones A-D: four new unusual biflavones from Desmos chinensis

Four new unusual biflavones, saiyutones A-D, were isolated from the leaves of Desmos chinensis together with 16 known compounds. Their structures were determined on the basis of UV, IR, NMR, and MS analysis, and by comparison of their spectroscopic data with those reported. Saiyutones A and B had a unique biflavone skeleton with a 3-6″ linkage through a methylene group. It was proposed that the formation of a cyclic hemiketal was the key step in the biosynthetic pathway of saiyutones C and D.     

Suberitine A-D, four new cytotoxic dimeric aaptamine alkaloids from the marine sponge Aaptos suberitoides

Suberitine A-D (1-4), four new bis-aaptamine alkaloids with two aaptamine skeleton units, 8,9,9-trimethoxy-9H-benzo[de][1,6]-naphthyridine and demethyl(oxy)-aaptamine, linked through a rare C-3-C-3' or C-3-C-6' σ-bond between the 1,6-naphthyridine rings, together with two known monomers 5 and 6, were isolated from the marine sponge Aaptos suberitoides. Their structures were elucidated using NMR spectroscopy. Compounds 2 and 4 showed potent cytotoxicity against P388 cell lines, with IC(50) values of 1.8 and 3.5 μM, respectively.     

Monasnicotinates A-D, four new pyridine alkaloids from the fungal strain Monascus pilosus BCRC 38093

Four new pyridine derivatives, monasnicotinates A-D (1-4) were isolated from the red yeast rice of Monascus pilosus BCRC 38093. Their structures were elucidated on the basis of physicochemical evidence, in-depth NMR spectroscopic analysis, and high-resolution mass spectrometry. Their inhibitory effects on NO production was also evaluated.     

Britanlins A-D, four novel sesquiterpenoids from Inula britannica

A phytochemical investigation on the flowers of Inula britannica has led to the isolation of four novel sesquiterpenoids, britanlins A-D. Britanlins A-C feature the rare presilphiperfolane-type frameworks, which play an important role in biogenesis of triquinane sesquiterpenoids. Britanlin D possessed a rearranged pseudoguaiane skeleton, which was first isolated from nature. The structures of britanlins A to D were elucidated on the basis of extensive spectroscopic methods. The structures of britanlins A and D were further confirmed by single crystal X-ray diffraction.     

Four new eremophilane-type alcohols from Cremanthodium helianthus collected in China

Four new eremophilane-type sesquiterpenoid alcohols were isolated from Cremanthodium helianthus collected in China and their structures established on the basis of spectroscopic analyses. All of them had 9-en-8-one partial structures with one more double bond either delta11, delta11(13), or delta7(11). Two of them had a hydroxy group at C-1 position.     

Chuktabularins A-D, four new limonoids with unprecedented carbon skeletons from the stem bark of Chukrasia tabularis

Chuktabularins A-D (1-4), four novel 16-norphragmalin-type limonoids that feature unprecedented skeletons with a biosynthetically extended C2 or C3 unit at C-15 forming a unique 2,7-dioxabicyclo[2.2.1]heptane moiety, were isolated from the stem bark of Chukrasia tabularis. Their structures were elucidated by spectroscopic analysis and computer modeling. The biosynthetic pathway of 1-4 was postulated.     

Monoterpene and tetrahydronaphthene derivatives from Senecio argunensis

Two new compounds,senarguines A and B,were isolated from Senecio argunensis.They were respectively identified as (Z)-3-ethylidene-9-hydroxyl-9-methyl-6,7-dioxaspiro [4.4]nonane-5,8--dione (1) and 3,6,6-trimethyl 6,7,8-tetrahydronaphtha-[1,2b]furan (2) on the basis of spectral data.     

Four new colchicinoids, gloriosamines A-D, from Gloriosa rothschildiana

Four new colchicinoids, gloriosamines A-D, were isolated from the aerial parts of Gloriosa rothschildiana. The structure of gloriosamine A, including the absolute configuration, was determined by chemical conversion from colchicine.     

Communiols A-D: new mono- and bis-tetrahydrofuran derivatives from the coprophilous fungus Podospora communis

Communiols A-D (1-4), new tetrahydrofuran and bis-tetrahydrofuran derivatives, have been isolated from cultures of the coprophilous fungus Podospora communis, and identified by spectroscopic methods.     

Igalan, a new sesquiterpene lactone from Inula grandis

Conclusions A new sesquiterpene lactone C₁₅H₂₀O₂ with mp 79–79.5°C, [] _D ²⁰ +105° (chloroform) has been isolated from the roots ofInula grandis Schrenk., and we have called it igalan. On the basis of chemical and spectral characteristics, it has been established that its most probable structure is eleman-8,11-olide.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 508–512, September–October, 1970.     

Igalan,a new sesquiterpene lactone from Inula grandis

Chemistry of Natural Compounds - A new sesquiterpene lactone C15H20O2 with mp 79–79.5°C, [α] D 20 +105° (chloroform) has been isolated from the roots ofInula grandis Schrenk.,...     

Fusaspirols A-D,novel oxaspirol derivatives isolated from Fusarium solani B-18

Four novel compounds with γ-methylidene-spirobutanolide core, fusaspirols A-D, were isolated from the brown rice culture of Fusarium solani B-18. Their structures were established by extensive spectroscopic analyses of 1D/2D-NMR, HRESITOFMS, and chemical derivatization. The absolute configurations of secondary alcohols in fusaspirols A and D were determined using modified Mosher's ester method. Fusaspirol A and 4,9-di-O-acetylfusaspirol A activated a signaling pathway in osteoclastic differentiation of murine macrophage derived RAW264.7?cells.     

Two new pyrrolizidine alkaloids from Senecio nemorensis

Two new compounds, including petasinoside A and chloridate-[N-chloromethyl-hectorine], were isolated from Senecio nemorensis. The structures of these compounds were elucidated by spectroscopic methods including 1D and 2D NMR experiments.     

A new sesquiterpene from Kalimeris integrifolia

A new sesquiterpene kalinturoside A (1), and 17 known compounds friedelan-3-ol (2), 24-ethyl-5a-cholesta-7, 22(E)-dien-3-one (3), friedelin (4), syringaresinol (5), α-spinasterol (6), ciwujiatone (7), syringic acid (8), scopoletin (9), apocynin (10), 1-(3-hydroxy-4, 5-dimethoxyphenyl)ethan-1-one (11), apigenin (12), 5-hydroxymethylfurfural (13), stigmasterol-3-O-β-d-glucopy-ranoside (14), bidenoside C (15), citrusin (16), irioresinol A (17) and syringaresinol-4-O-β-d-glucopyranoside (18) were isolated from the herbs of Kalimeris integrifolia. The structures of these compounds were elucidated using spectroscopic techniques such as NMR and MS. All of the compounds were isolated from this genus for the first time.     

A new eremophilanolide from Senecio sinuatus Gilib

From the hexane extracts of Senecio sinuatus roots, the new 3beta-angeloyloxy-6beta-hydroxyeremophil-1(10)-en-8beta,12-olide (3), along with the known compounds 3beta-angeloyloxy-6beta-hydroxyeremophil-1(10)-ene (1), 3beta-senecioyloxy-6beta-hydroxyeremophil-1(10)-ene (2), and 3beta-angeloyloxy-6beta,8alpha-dihydroxyeremophil-1(10)-en-8beta,12-olide (4), were isolated. Complete 1H and 13C NMR chemical shift assignments of 1-4 were achieved using one- and two-dimensional NMR techniques, including gHMQC and gHMBC experiments. A Monte Carlo search, followed by B3LYP/6-31G*DFT calculation, provided the theoretical conformations of the eremophilane rings, which were in agreement with results derived from 1H-1H NMR coupling constant analysis, and confirmed by NOESY experiments.