Cytotoxic indole diterpenoids and rare pyridoxatin atropisomers from the endophytic fungus Tolypocladium sp. SHJJ1.

Phytochemical investigation on the extract of endophytic fungus Tolypocladium sp. SHJJ1 resulted in the identification of a pair of previously undescribed pyridoxatin atropisomers [1 (M/P)] and three new indole diterpenoids (3-5), together with a pair of known pyridoxatin atropisomers [2 (M/P)] and ten known indole diterpenoids (6-15). Their structures, including their absolute configurations were elucidated by extensive spectroscopic analysis, quantum chemical calculations, and X-ray diffraction. Among the undescribed natural products, [1 (M/P)] that two rapidly interconverting atropisomers are the third example to report in the pyridoxatin atropisomers. Except for compounds 1 (M/P) and 2 (M/P), all other compounds were tested for their cytotoxicity using HepG2, A549, and MCF-7 human cell lines. Compound 9 displayed moderate cytotoxicity against the HepG2, A549, and MCF-7 cell lines with IC50 values of 32.39 ± 1.48 µM, 26.06 ± 1.14 µM, and 31.44 ± 1.94 µM, respectively, which was similar to the positive drug cisplatin (with IC50 values of 32.55 ± 1.76 µM, 18.40 ± 1.43 µM, and 27.31 ± 1.22 µM, respectively).

Butyrolactone and sesquiterpene derivatives as inhibitors of iNOS from the roots of Lindera glauca.

Nine previously undescribed butyrolactone and sesquiterpene derivatives, named cyclopentanone A (1), subamolides F and G (2 and 3), secosubamolide F (4), rupestonic acids J - L (5-7), linderaguaianols A and B (8 and 9), together with six known ones 10-15 were isolated from the roots of Lindera glauca. Their structures, including their absolute configurations were elucidated by extensive spectroscopic analysis, quantum chemical calculations, and Mo2(AcO)4-induced circular dichroism. Compound 1 that possessed a unique five-membered cyclopentane skeleton with a side chain was rarely found from natural sources. The biogenetic pathway for 1-4 was postulated. Secosubamolide F (4) inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW264.7 cells with IC50 value of 1.73 ± 0.18 µM and also significantly suppressed the production of iNOS. The binding interactions between 4 and iNOS were investigated using docking analyses.

Pseudoguaianelactones A-C: three unusual sesquiterpenoids from Lindera glauca with anti-inflammatory activities by inhibiting the LPS-induced expression of iNOS and COX-2.

The pseudoguaianelactones A (1) and B (2), two novel sesquiterpene lactones with an unprecedented [5,7,7] ring system featuring an α-methylene-γ-lactone moiety, together with a new pseudoguaianelactone C (3) were isolated from the roots of Lindera glauca. Pseudoguaianelactones A-C (1-3) inhibited nitric oxide (NO) production, with IC50 values ranging from 1.38 to 4.00 µM. Moreover, all compounds significantly suppressed the production of pro-inflammatory mediators (TNF-α, IL-6, IL-1ß and PGE2) and the protein expression of the enzymes iNOS and COX-2.

Caesalminaxins O-T, cassane diterpenoids from the seeds of Caesalpinia minax and their anti-inflammation.

Six previously undescribed cassane diterpenoids, named caesalminaxins O-T (1-6), together with 28 known compounds (7-34), were isolated from the seeds of Caesalpinia minax Hance. Their structures, including their absolute configurations were elucidated by extensive spectroscopic analysis, X-ray diffraction, and quantum chemical calculations. Among the undescribed diterpenoids, compound 6 that possessed an unusual enol group at C-7 with a highly deshielded 1H NMR signal was the first example in cassane diterpenoids. All of the isolates were evaluated for their inhibitory activity against lipopolysaccharide-activated NO production in RAW264.7 cells. Compound 16 showed moderate inhibitory activity with an IC50 value of 17.3 µM, which was more potent than the positive control (indomethacin, IC50 = 29.7 µM).

A facile and selective approach to the qualitative and quantitative analysis of triterpenoids and phenylpropanoids by UPLC/Q-TOF-MS/MS for the quality control of Ilex rotunda.

Ilex rotunda, in which triterpenoids and phenylpropanoids are major bioactive constituents, has been widely used in traditional Chinese medicines. In this study, a validated UPLC/Q-TOF-MS/MS method was developed to simultaneously identify and quantify the triterpenoids and phenylpropanoids in the stem bark, fruit, leaves, roots and stem xylem of this herbal medicine. A total of seventy triterpenoids and twelve phenylpropanoids were identified with the assistance of the modified mass defect filter and key product ion filter data processing strategies, and forty-eight of them were confirmed by reference substances. Meanwhile, the contents of twelve triterpenoids and three phenylpropanoids in the five plant parts were determined with good linearity (R2 ≥ 0.9993), precision (RSD ≤ 2.04%), repeatability (RSD ≤ 1.99%), stability (RSD ≤ 1.88%) and recovery (96.65-103.17% and RSD ≤ 3.54%). Furthermore, PCA and OPLS-DA methods were employed to visualize the relationships and discrimination of the forty-two stem bark samples from two origins based on the contents of fifteen analytes. Our findings may provide early scientific evidence for quality control and for elucidating the therapeutic principle of Ilex rotunda.

[Study on ecological environment and accompanying plants' community characteristics study of wild Panax japonicus in Enshi].

The paper is aimed to study the distribution, population density, soil conditions and community characteristics of accompanying plants' in Enshi sub-regional different areas, with a typical habitats investigation method. The results showed that the wild Panax japonicus mainly distributed in moist places under the forests, by streams, or secondary forests of high grass, within east longitude 29°-30°, north latitude 108°-110°and about 1 000-15 00 meters above sea level. The soils were mainly tide soil and humus with yellow-brown soil, yellow soil and red soil, and the humus thickness was5-30 centimeter, pH 6.0-6.8, the moisture content of 16.8%-24.2%, soil bulk density of 1.39-2.12. Its geographical vegetation types were mainly evergreen coniferous forest, evergreen-deciduous mixture broad leaved forest and evergreen coniferous forest mixed deciduous broad-leaved forest, including three levels community structure of arbors, shrubs and herbaceous; Its accompanying plants reached 86 families, 118 genera, 134 species of seed plants, the arbors included 15 families, 21 genera, 26 species and the dominant species community mainly Pinaceae such as Pinus massoniana, P. tabuliformis, P. henryi and Taxodiaceae such as Cunninghamia lanceolata, Cryptomeria fortunei etc. The shrubs included 39 families, 54 genera, 62 species with the dominant species such as Camellia oleifera, Kalopanax septemlobus, Akebia trifoliata, Trachycarpusfortunei, Rhamnus globosa, Smilax corbularia and so on. The herbaceous included 32 families, 43 genera, 46 species, and Ferns such as the black-footed Dryopteris, Dryopteris crassirhizom, Coniogramme affinis, Polystichum tripteron, Adiantum pedatum, Lunathyrium acrostichoides, Woodsia ilvensis and Woodwardia japonica were dominant species. The cover layer covered a large number of lichens and mosses. The wild P. japonicus can be found among the P. massoniana, P. tabuliformis, P. henryi, lichens and mosses. These may indicate that the wild P. japonicusin Enshi requires higher demands on the ecological environment, its accompanying plants are mainly the tree layer-shrub layer-herb layer, and vertical structure is obvious. The study provides a basis for domestication and conservation of P. japonicus resources.

catena-Poly[[diaquacadmium(II)]bis-(µ-pyridine-3-sulfonato)-κN:O;κO:N].

In the title polymeric complex, [Cd(C(5)H(4)NO(3)S)(2)(H(2)O)(2)](n), the Cd atom is located on a centre of inversion and is coordinated by two O atoms and two N atoms, derived from four different pyridine-3-sulfonate ligands, and two O atoms derived from two water mol-ecules, forming a distorted trans-N(2)O(4) octa-hedral geometry. The topology of the polymer is a one-dimensional chain mediated by bridging pyridine-3-sulfonate anions. These are connected into a three-dimensional architecture via hydrogen bonds.

catena-Poly[[diaqua-manganese(II)]-di-µ-pyridine-3-sulfonato-κN:O;κO:N].

In the title polymeric complex, [Mn(C(5)H(4)NO(3)S)(2)(H(2)O)(2)](n), the Mn atom is located on a centre of inversion and is coordinated by two O atoms and two N atoms derived from four different pyridine-3-sulfonate (pySO(3)) ligands, and two O atoms derived from two water mol-ecules in a distorted trans-N(2)O(4) octa-hedral geometry. The metal atoms are bridged by the pySO(3) ligands to form a one-dimensional chain. The chains are further connected into a three-dimensional architecture via hydrogen bonds.

Poly[[µ(3)-3-(3-pyrid-yl)acrylato-κN:O:O'][µ(2)-3-(3-pyrid-yl)acrylato-κO,O':O][µ(2)-3-(3-pyrid-yl)acrylato-κO:O')]gadolinium(III)].

In the title compound, [Gd(C(8)H(6)NO(2))(3)](n), the Gd(III) ion is in a bicapped trigonal prismatic coordination environment formed by seven O atoms and one N atom, derived from seven different 3-(3-pyrid-yl)acrylate (3-PYA) ligands. Gd(III) ions are bridged by bidentate and tridentate 3-PYA ligands, resulting in a two-dimensional structure.

catena-Poly[[aqua-[3-(3-pyrid-yl)acrylato]gadolinium(III)]-bis-[µ-3-(3-pyrid-yl)acrylato]].

In the title compound, [Gd(C(8)H(6)NO(2))(3)(H(2)O)](n), the gadolinium(III) ion is coordinated by eight carboxyl-ate O atoms and one water mol-ecule. The carboxyl-ate ligands bridge pairs of gadolinium(III) ions, forming a zigzag chain along [100]. Hydrogen bonds link the chains into sheets parallel to (001).