Chemical Constituents of the Culture Broth of Panus rudis

In our ongoing search for new secondary metabolites from fungal strains, one novel compound (1) and nine known compounds (2-10) were isolated from the EtOAc-soluble layer of the culture broth of Panus rudis. The culture broth of P. rudis was extracted in acetone and fractionated by solvent partition; column chromatography using silica gel, Sephadex LH-20, and Sephadex G-10; MPLC; and HPLC. The structures of isolated compounds were elucidated by one- and two-dimensional NMR and LC-ESI-mass measurements. One new compound, panepoxydiol (1), and nine known compounds, (E)-3-(3-hydroxy-3-methylbut-1-en-1-yl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol (2), isopanepoxydone (3), neopanepoxydone (4), panepoxydone (5), panepophenanthrin (6), 4-hydroxy-2,2-dimethyl-6-methoxychromane (7), 6-hydroxy-2,2-dimethyl-3-chromen (8), 2,2-dimethyl-6-methoxychroman-4-one (9), 3,4-dihydroxy-2,2-dimethyl-6-methoxychromane (10), were isolated from the culture broth of P. rudis. This is the first report of isolation of a new compound panepoxydiol (1) and nine other chemical constituents (2-5, 7-10) from the culture broth of P. rudis.     

Two new pyrrole derivatives isolated from Salacia amplifolia Merr

Two new pyrrole derivatives Salaciamole (1), Salaciaglycoside A (2), long with one known compound 1H-pyrrole-3-carboxylic acid (3) were isolated from the roots of Salacia amplifolia Merr (Hippocrateaceae). The structures of the new compounds were deduced from their comprehensive spectroscopic analysis including IR, HR-EI-MS, ¹H NMR, ¹³C NMR, DEPT, COSY, HMBC and HMQC. And the structure of the known compound was identified by comparison of their spectral data with those reported in the literature.     

A new sesquiterpenoid from Sclerorhachis platyrachis (Boiss.) Podlech ex Rech.f

A new eudesmane-type sesquiterpenoid together with two known flavonoids were isolated from the chloroform extract of the aerial part of Sclerorhachis platyrachis. The structure of the new compound was deduced from its comprehensive spectroscopic analysis including IR, EI-MS, ¹H NMR, ¹³C NMR, DEPT, COSY, HMBC and HMQC and was shown to be 4R^*-hydroxy-6S^*-tigloyloxyeudesma-7S^*-11 (13)-en-12-oic acid (1). Finally, the structure of the new compound was unambiguously confirmed by single-crystal X-ray analysis. The structure of known compounds 2 and 3 were identified by comparison of their spectral data with those reported in the literature.     

3,4,8,9,10-Pentahydroxy-dibenzo[b,d]pyran-6-one from Tamarix nilotica

A new natural product, 3,4,8,9,10-pentahydroxy-dibenzo-[b,d]pyran-6-one was isolated from the flowers of Tamarix nilotica which also contains the known compound ellagic acid, 2,3,7,8-tetrahydroxy [1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione. The structure of the new compound was determined by chemical and spectroscopic methods. The ¹³C MNR spectrum of ellagic acid was recorded and assigned.     

A new phenylpropanoid glycoside from the bark of Streblus ilicifolius (Vidal) Corner

A new compound, pheglycoside A (1), along with four known aromatic glycosides (2-5) and three known lignan glycosides (6–8) were isolated from Streblus ilicifolius (Vidal) Corner. The structure of compound 1 was determined by spectral analyses, including HRESIMS, 1D, and 2D NMR (COSY, HSQC, and HMBC) experiments. The absolute configuration of compound 1 was determined using the CD spectrum and experiment data. From the present investigation, all these compounds were isolated for the first time from S. ilicifolius. It is interesting that phenylpropanoid glycoside and aromatic glycosides are reported for the first time in the genus Streblus. The chemotaxonomic significance of these compounds was summarized.     

Further pyrrolizidine alkaloids and furoeremophilanes from Senecio species

The investigation of 17 Senecio species afforded in addition to 14 known pyrrolizidine alkaloids 20 new ones, including some compounds of a novel type with an additional lactone moiety. Furthermore seven known and 11 new furoeremophilanes, two known and a new eremophilone, a further shikimic acid derivative and an acetylenic compound, most likely formed by intramolecular Diels-Alder reaction were isolated. The structures were elucidated by spectroscopic methods, especially high field ¹H and ¹³C NMR and NOE difference spectroscopy. The configuration of the seneremophilondiol esters has been corrected.     

A new guaianolide glucoside from aerial parts of Lactuca aculeata

From aerial parts of Lactuca aculeata one new and ten known sesquiterpene lactone aglycones and glycosides were isolated, including four lactucin-type guaianolides, six costus lactone-type guaianolides and one melampolide-type germacranolide. The structure of the new compound was determined as 11β-hydroxycrepidiaside B by high resolution mass spectrometry and 1D- and 2D-NMR spectroscopy.     

New siphulin derivatives from the lichen Siphula ceratites

From the lichen, Siphula ceratites, two new metabolities, protosiphulin and oxysiphulin, were isolated besides the known compound, siphulin. The structures of the two new chromenones were proved by ¹H NMR and ¹³C NMR spectral analysis in comparison with those of siphulin.     

Sesquiterpene lactones from Laserpitium garganicum

Besides known compounds, the roots of Laserpitium garganicum subsp. garganicum afforded a new slovanolide triester. The locations of the ester moieties were assessed by correlation with a compound of known structure.     

Chemical constituents from the whole plant of Liparis japonica

A new lignanoid (1), together with six known lignanoids (2–7) and four known flavonoids (8–11), were isolated from the EtOAc extract of Liparis japonica. Their structures were determined by analyzing the HRESIMS, NMR, CD spectroscopic data, and comparing with the reported literatures. Among them, 1 was a new compound, 2–11 were first isolated from L. japonica and the genus of Liparis. The chemotaxonomic significance of these isolates was comprehensively discussed.     

A new phenolic acid from Zanthoxylum nitidum var. tomentosum (Rutaceae) and its chemotaxonomic significance

A new compound, nitomentosin (1), along with sixteen known compounds (2–17), were isolated from Zanthoxylum nitidum var. tomentosum (Rutaceae). The structure of compound 1 including absolute configurations was determined by detailed spectroscopic information (HRESIMS and NMR) and from the electronic circular dichroism (ECD) spectra. From the present investigation, compound 3 is a new natural compound although it has been reported previously as a synthetic substance, and compound 15 is found for the first time in a plant. All these compounds except 2, 5–10 and 12 were isolated from Z. nitidum for the first time. Furthermore, the chemotaxonomic significance of the isolated compounds is discussed.     

Helicascolide C,a new lactone from an Indonesian marine algicolous strain of Daldinia eschscholzii (Xylariaceae,Ascomycota)

From an endophytic Daldinia eschscholzii strain isolated from the agar-producing red alga Gracilaria sp. SGR-1, collected from the coast of South Sulawesi, Indonesia, a new lactone helicascolide C (1) was obtained as colourless crystals from the ethyl acetate extract together with the related structurally known compound helicascolide A (2). The structure of the new compound 1 reveals a carbonyl group replacing an alcohol group of compound 2. The structure of 1 was elucidated by X-ray diffraction and spectral analyses. Compound 1 showed fungistatic activity against the phytopathogenic fungus Cladosporium cucumerinum.     

Biotransformation of methyl cholate by Aspergillus niger

Biotransformation of methyl cholate using Aspergillus niger was investigated. This led to the isolation of two derivatives: methyl 3α,7α,12α,15β-tetrahydroxy-5β-cholan-24-oate identified as a new compound, and a known compound methyl 3α,12α-dihydroxy-7-oxo-5β-cholan-24-oate. The structure elucidation of the new compound was achieved using 1D and 2D NMR, MS and X-ray diffraction.     

Dehydroabietane diterpenoids from Calceolaria ascendens

Two new dehydroabietane diterpenes, dehydroabietinol and 19-malonyloxy-dehydroabietinol, and the known compound 4-epi-dehydroabietic acid were isolated from the aerial parts of Calceolaria ascendens. The structures of the new compounds were elucidated by spectroscopic methods.     

Cytotoxic components of Zingiber zerumbet,Curcuma zedoaria and C. domestica

One new and five known compounds, which all showed cytotoxic activity, were isolated from the rhizomes of Zingiber zerumbet. The new compound was 3″,4″-O-diacetylafzelin. The known compounds were zerumbone, zerumbone epoxide, diferuloylmethane, feruloyl-p-coumaroylmethane and di-p-coumaroylmethane. Several substituted cinnamoylmethanes were synthesized and tested for cytotoxic properties. Among these were tricinnamoylmethane and triferuloylmethane. The structures were elucidated mainly by spectroscopic methods and ¹³C NMR data are given.     

A furostanol glucuronide from Solanum lyratum

A new furostanol glucuronide and three known glycosides, SL-O, aspidistrin and methyl proto-aspidistrin, were isolated from the fresh immature berries of Solanum lyratum. The structure of the new compound was characterized as 26-O-β-D-glucopyranosyl-(22ξ,25R-3β,22,26-trihydroxyfurost-5-ene 3-O-α-L-rhamnopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 3)]-β-D-glucuronopyranoside.     

Chemical constituents from Alnus mandshurica (Callier) Hand.-Mazz. and their chemotaxonomic significance

A new phenol compound, (9S)-9-hydroxy-9-[(2-hydroxyphenyl)methoxy]-nonanoic acid methyl ester (1) was isolated from the stem bark of Alnus mandshurica (Callier) Hand.-Mazz., along with eight known compounds (2–9). The structure of compound 1 was determined by spectral analyses, including HR-ESI-MS, 1D and 2D NMR (COSY, HMQC and HMBC) experiments. All the isolated compounds were reported for first time from A. mandshurica. Furthermore, compounds 3–9 were found in the family Betulaceae for the first time.     

Tropane alkaloids from Darlingia darlingiana

A new γ-pyranotropane, darlingine N-oxide, was isolated from the bark and leaves of Darlingia darlingiana, along with the known compound, darlingine. 1D-NOESY NMR experiments indicated that the N-methyl groups of both alkaloids were orientated towards the pyran ring.     

Spicachlorantins A and B,new dimeric sesquiterpenes from the roots of Chloranthus spicatus

Two new lindenane sesquiterpene dimers, spicachlorantins A and B (1 and 2), were isolated from the roots of Chloranthus spicatus along with a known related compound, chloramultilide A (3). Their structures and the absolute stereostructures were established by 1D and 2D NMR as well as by CD spectroscopic analyses.     

Cytotoxic abietane-type diterpenoids from twigs and leaves of Croton laevigatus

Seven new abietane-type diterpenoids, crotolaevigatones A–G (1–7), one new aromatic compound, hexyl Z-ferulate (8), along with three known diterpenoids (9–11) and one known aromatic ester, hexyl E-ferulate (12), were obtained from the twigs and leaves of Croton laevigatus. The structures of all isolated compounds were established on the basis of extensive NMR and MS spectroscopic analyses. Compounds 2 and 7 exhibited weak anti-proliferative activity against the A549 and MDA-MB-231 cancer cells, while compound 10 selectively showed significant inhibitory activity against the A549 cancer cells.