α-Pyrone derivatives with cyto-protective activity from two Takla Makan desert soil derived actinomycete Nocardiopsis strains recovered in seawater based medium.

In this paper, we described the discovery of two Nocardiopsis strains HDN154-146 and HDN154-168 from Takla Makan desert soil samples using seawater based medium. Chemical investigation of these two strains led to the discovery of eight new α-pyrone derivatives named nocahypyrones A-H (1-8), together with one known analogue germicidin G (9). The structures of these compounds, including absolute configurations, were elucidated by extensive NMR, MS, and CD analyses. Compounds 1-9 were tested for their cyto-protective activities and for the first time we found α-pyrones 5 and 8 exhibited capabilities to induce expression of phase II detoxifying enzymes.

Fusaricates H-K and fusolanones A-B from a mangrove endophytic fungus Fusarium solani HDN15-410.

Seven compounds including four undescribed fusaric acid derivatives, namely fusaricates H-K, and two undescribed γ-pyrone derivatives, named fusolanones A-B, as well as a known compound fusaric acid, were isolated from a mangrove endophytic fungus Fusarium solani. Fusaricates H-K represent the first cases of fusaric acid butanediol esters and are diastereoisomers. Their structures including absolute configurations were elucidated based on NMR, MS, chemical synthesis, chiral HPLC analysis and ECD calculations. The antibacterial activity of all undescribed compounds were tested and fusolanone B showed the best activity with MIC value 6.25 µg/mL on Vibrio parahaemolyticus.

Peniphenylanes A-G from the Deep-Sea-Derived Fungus Penicillium fellutanum HDN14-323.

Seven new 6-methylsaligenin derivatives, including the trimeric peniphenylanes A-B (1-2) and dimeric peniphenylanes C-G (3-7), together with four known biogenetically related compounds (8-11) were discovered from the extract of the deep-sea-derived fungus Penicillium fellutanum HDN14-323. The structures of the new compounds were established through extensive analysis. Their cytotoxic activity against HeLa, HL-60, and HCT-116 cell lines was evaluated, with compound 4 exhibiting the best activity against the HeLa cell line (IC50 = 9.3 µM).

Cytotoxic and antioxidative phenolic compounds from the traditional Chinese medicinal plant, Myristica fragrans.

Two new phenolic compounds were isolated from the fruits of Myristica fragrans and their structures were elucidated as (-)-1-(2,6-dihydroxyphenyl)-9-[4-hydroxy-3-(p-menth-1-en-8-oxy)-phenyl]-1-nonanone ( 1) and (7 R,8 R)-7,8-dihydro-7-(3,4-dihydroxyphenyl)-3'-methoxy-8-methyl-1'-( E-propenyl)benzofuran (2). In addition, the absolute configuration of (+)-Delta8'-7-acetoxy-3,4,3',5'-tetramethoxy-8- O-4'-neolignan (3) was determined for the first time through spectroscopic and chemical methods. Their antioxidative activities against 2,2-diphenyl-1-picrylhydrazyl radical and cytotoxicity against K-562 cells were tested, and (7 S,8 S,7' R,8' S)-4,5'-dihydroxy-3,3'-dimethoxy-7,7'-epoxylignan (4) showed the corresponding activities with IC(50) values of 39.4 and 2.11 microM, respectively.

Resin glycoside constituents of Ipomoea pes-caprae (beach morning glory).

Eight new resin glycosides, pescapreins X-XVII (1-8), were isolated from a lipophilic fraction of an ethanol extract of the entire plant of beach morning glory, Ipomoea pes-caprae. Their structures were elucidated by spectroscopic data analysis and by chemical transformation. These compounds were evaluated biologically in terms of cancer cell line cytotoxicity, antibacterial and antifungal activity, and effects on the mu-opioid receptor.

GPR12 selections of the metabolites from an endophytic Streptomyces sp. associated with Cistanches deserticola.

An endophytic Streptomyces sp. (AC-2) was isolated from the root of Cistanches deserticola Y.C.Ma.. Chemical investigations of the culture broth of AC-2 afforded fifteen compounds including K1115 A (1), tyrosol (2), phenylethylamine derivatives (3, 4), cyclic dipeptides (5-8), nucleosides and their aglycones (9-13), N-acetyltryptamine (14), and pyrrole-2-carboxylic acid (15). Only tyrosol can promote an increase of intracellular cAMP special on GPR12 transfected cells, such as CHO and HEK293, which means it may be a possible ligand for GPR12.

Minor furofurano lignans from the Tibetan herb, Lancea tibetica.

Four new furofurano lignans, lantibesides B - D ( 1 - 3) and lantibetin ( 4), along with nine known phenolic compounds were isolated from the EtOH extract of the traditional Tibetan medicinal plant, Lancea tibetica. By means of spectroscopic and chemical methods, the structures of the new compounds were elucidated as (1 R,2 S,5 R,6 S)-2-(3,4-methylenedioxyphenyl)-6-[(3-methoxy-4-beta- D-xylopyranosyloxy(1-->6)-beta- D-glucopyranosyloxy)phenyl]-3,7-dioxabicyclo[3.3.0]octane ( 1), (1 R,2 R,5 R,6 S)-2-(3,4-methylenedioxyphenyl)-6-[(3-methoxy-4-beta- D-xylopyranosyloxy(1-->6)-beta- D-glucopyranosyloxy)phenyl]-3,7-dioxabicyclo [3.3.0]octane ( 2), (1 R,2 R,5 R,6 S)-2-(3,4-methylenedioxyphenyl)-6-(3-methoxy-4-beta- D-glucopyranosyloxy)phenyl-3,7-dioxabicyclo[3.3.0]octane ( 3), and (1 R,2 R,5 R,6 S)-2-(3,4-dimethoxyphenyl)-6-(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3.3.0] octane ( 4). Compounds 2 and 3 showed weak cytotoxicity against the HL-60 cell line with IC (50) values of 61 and 99 microM, respectively.

Chrysogenamide A from an endophytic fungus associated with Cistanche deserticola and its neuroprotective effect on SH-SY5Y cells.

Chrysogenamide A (1), a new member of the macfortine group of alkaloids, along with four known compounds (2 approximately 5) were identified from Penicillium chrysogenum No. 005, an endophytic fungus associated with Cistanche deserticola Y. C. Ma. The new structure was elucidated on the basis of comprehensive spectral analysis. 1 exhibited a neurocyte protection effect against oxidative stress-induced cell death in SH-SY5Y cells.