Two new aromatic compounds and a new d-arabinitol ester from the mushroom Hericium erinaceum

Two new aromatic compounds (1, 2), new d-arabinitol ester (3), and two known compounds (4, 5) were isolated from mushroom Hericium erinaceum. The structures of 1–5 were elucidated on the basis of spectral data. Compounds 1, 2, 4, and 5 exhibited α-glucosidasae inhibitory activity.     

Two new aromatic compounds from Hericium erinaceum (BULL.: FR.) PERS(1)

Two new aromatic compounds, erinacerins A (1) and B (2), were isolated from the fruiting bodies of Hericium erinaceum (BULL.: FR.) PERS. (Hericiaceae) together with a known compound, hericenone A (3). The structures of the new compounds were elucidated on the basis of their spectral data. It was found that 1 occurred as a racemate.     

Herinase: A Novel Bi-functional Fibrinolytic Protease from the Monkey Head Mushroom, Hericium erinaceum

Herinase, a new bi-functional fibrinolytic metalloprotease, was purified from a medicinal and edible mushroom Hericium erinaceum. The enzyme was monomeric with a molecular mass of 51 kDa. Analysis of fibrin zymography showed an active band with a similar molecular mass. The N-terminal sequence of herinase VPSSFRTTITDAQLRG was highly distinguished from known fibrinolytic enzymes. Moreover, the enzyme activity was strongly inhibited by EDTA and EGTA, indicating that herinase is a metalloprotease. Herinase exhibited high specificity for the substrate t-PA followed by plasmin. The K _m and V _max values for H-D-Ile-Pro-Arg-PNA were found to be 4.7 mg and 26.7 U/ml respectively. Similarly, fibrin plate assays revealed that it was able to degrade fibrin clot directly and also able to activate plasminogen. Herinase provoked a rapid degradation of fibrin and fibrinogen α chains and slower degradation of γ chains. It had no activity on the β chains of fibrin and fibrinogen. This result suggests that herinase could possibly contain higher amount of α-fibrinogenase. The activity of herinase was stimulated by metal ions such as Ca²⁺, Mg²⁺, and Mn²⁺, but inhibited by Cu²⁺, Fe²⁺, and Zn²⁺. Herinase exhibited maximum activity at 30 °C and pH 7.0. These results demonstrate that herinase could be a novel fibrinolytic enzyme.     

A geranylated biphenyl derivative from Garcinia malvgostana

Extracts of root bark, stem bark and the latex collected from the green fruits of Garcinia mangostana gave alpha-mangostin, beta-mangostin, gamma-mangostin, garcinone-E, methoxy-beta-mangostin and a new geranylated biphenyl derivative 3-hydroxy-4-geranyl-5-methoxybiphenyl. The latex of G. mangostana consists of more than 75% of xanthones which have strong antibacterial (anti-MRSA and -VRE), anti-inflammatory, antifungal and a number of other biological activities. Hence the presence of the above highly bioactive compounds in large quantities should be the causative factor for G. mangostana's medicinal value in indigenous medicine.     

Reaction of allyltrimethylsilane with an aromatic compound using hypervalent organoiodine compound: A new allylation of aromatic compounds

New general method for the allylation of aromatic compounds from allyltrimethylsilane utilizing the combination of iodosylbenzene and BF₃ OEt₂ are described, which is based upon the umpolung of allyltrimethylsilane by way of cationic allylphenyliodonium (III) salt complex as an intermediate.     

Novel prenylated and geranylated aromatic compounds isolated from Polysphondylium cellular slime molds

We have studied the diversity of secondary metabolites of cellular slime molds to utilize them as new biological resources for natural product chemistry. From the methanol extract of fruiting bodies of Polysphondylium tenuissimum, we obtained five prenylated and geranylated aromatic compounds, Pt-1-5 (1-5). An additional aromatic compound, Ppc-1 (6), was isolated from Polysphondylium pseudo-candidum. The structures of these compounds were determined by spectral analysis, and synthetic routes to 4, 5, and 6 were developed. Compound 5 showed the glucose consumption-promotive activity on 3T3-L1 cells.     

Leccinine A, an endoplasmic reticulum stress-suppressive compound from the edible mushroom Leccinum extremiorientale

Leccinine A (1) along with a known compound (2), were isolated from the edible mushroom Leccinum extremiorientale. The structure of 1 was determined by the interpretation of spectral data. Leccinine A showed protective activity against endoplasmic reticulum stress-dependent cell death. Seven analogues (3-9) of 1 were synthesized in order to evaluate the structure-activity relationship, and the result indicated that the formamide group of 1 was indispensable for the activity.     

A new fatty acid ester from an edible mushroom Rhizopogon luteolus

Phytochemical investigation of the Rhizopogon luteolus Fr. led to the isolation of one new fatty acid ester, 3-hydroxy-2,4-dimethylheptacosyl acetate (1) together with two known compounds tetracosanoic acid (2) and ergosterol (3). 1D and 2D NMR, and MS techniques were used for structural elucidation. Phenolic and fatty acid compositions were identified using HPLC–DAD and GC–MSD, respectively. Fumaric acid was the major phenolic acid, whereas linoleic, stearic and oleic acids were the most abundant fatty acids. Antioxidant and anticholinesterase activities of the extracts and compounds (1–3) were tested spectrophotometrically. Among the extracts, hexane extract showed the highest activity in all tests, particularly in β-carotene-linoleic acid assay (IC₅₀: 16.65 ± 1.12 μg/mL). Furthermore, compound 3 exhibited higher antioxidant and anticholinesterase activities. The study indicates that R. luteolus can be used in food, cosmetic and pharmaceutical industries.     

A new heterocyclic compound from Cyathula officinalis Kuan

<正>A new heterocyclic compound,named 5,5'-diisobutoxy-2,2'-bifuran(1),and four known compounds(2-5) were isolated from the roots of Cyathula officinalis Kuan.Their structures were elucidated by spectroscopic methods.Among these compounds,5,5'- dibutoxy-2,2'-bifuran(2) was isolated for the first time from this plant.     

A new and efficient one-pot synthesis of aromatic alkynyl ketones from aromatic esters

The reaction of aromatic esters with alkynyllithiums in the presence of lithium morpholinide and BF₃·OEt₂ gave aromatic alkynyl ketones in good yield (78-87%).     

Russuphelin A, a new cytotoxic substance from the mushroom Russula subnigricans Hongo.

A new cytotoxic substance, designated russuphelin A (1), has been isolated from the mushroom Russula subnigricans Hongo (Basidiomycetes). The structure was elucidated as 2,6-bis(2,6-dichloro-4-hydroxyphenyloxy)-1,4-dimethoxy-benzene on the basis of spectroscopic data and confirmed by total synthesis.     

A new phenolic compound from Crinum asiaticum L.

A new phenolic compound was isolated from the ethanol extract of the bulbs of Crinum asiaticum L.var.sinicum Baker.Its structure was defined as 1-（2-hydroxy-4-hydroxymethyl）phenyl-6-O-caffeoyl-β-D-gluco-pyranoside on the basis of spectroscopic evidences.     

A new compound against Peries rapae from Stellera chamaejasme

The ethanol extract of Stellera chamaejasme roots exhibited significant bioactivity against Peries rapae. In the course of a search for the active compounds, S-(+)-1,5-diphenly-3-hydroxy-1-pentanone (1) was isolated and this compound has never been found before in S. chamaejasme as far as we known. The structure was established on the basis of various spectral data, including IR, UV, 1H NMR, 13C NMR, EIMS, and chemical synthesis. Mortality against P. rapae was also determined.     

A new isoprenyl phenyl ether compound from mangrove fungus

A new isoprenyl phenyl ether, 3-hydroxy-4-(3-methylbut-2-enyloxy)benzoic acid methyl ester (1), together with 4-hydroxybenzoic acid (2), 2-hydroxy-6-methylbenzoic acid (3), and 4-hydroxy-3-methoxybenzoic acid (4) were isolated from Mangrove fungus (No. B60) from the South China Sea. The structures of the compounds were established on the basis of NMR spectroscopic and mass spectrometric data. In the preliminary bioassay, compound 1 exhibited antibacterial and antifungal activities. Compound 1 also inhibited cytotoxicity to the hepG2 cell line with an IC₅₀ value of 10.0 μg/mL. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 313–314, July–August, 2007.     

A new organic far-red mechanofluorochromic compound derived from cyano-substituted diarylethene

A new cyano-substituted diarylethene derivative (R-NH₂) with reversible far-red mechanofluorochromic property was synthesized and confirmed by standard spectroscopic methods. To the best of our knowledge, the 684 nm red-shifted wavelength of the ground R-NH₂ is the longest wavelength that has appeared in the literature. The mechanofluorochromic mechanism was investigated by small and wide-angle X-ray scattering and was ascribed to the destruction of crystalline structure. More in-depth study by infrared spectra and time-resolved emission-decay behaviors showed that the changes of C–H out-of-plane bending vibrations in aryl group of the compound and the obvious increase of fluorescence lifetime might be the fundamental reasons. The synthetic strategy reported here can be extended to prepare more and more long-wavelength emission mechanofluorochromic materials, which can broaden the scope of application of such materials and for thoroughly understanding the mechanofluorochromic mechanism.     

A new phenolic compound from Phedimus middendorffianus with antiproliferative activity

Abstract

A new phenolic compound (1) and together with 12 known compounds–eight flavonoids (2?～?9), two phenolic compounds (10 and 11) and two benzoic acid (12 and 13)–were isolated from Phedimus middendorffianus (Maxim.). The structures of all compound were determined on the basis of spectroscopic (MS and NMR) analyses. Compounds 4, 5, 7 and 11?～?13 were showed anti-proliferative activities against MCF-7 than PC-3 cell line. Also compound 12 and 13 showed the significant cytotoxic activities against two cancer cell lines, PC-3 and MCF-7.     

Ganoderic acid Sz, a new lanostanoid from the mushroom Ganoderma lucidum

A new lanostanoid, ganoderic acid SZ (1), isolated from a lipophilic extract of the fruiting body of Ganoderma lucidum, is a geometric Z-isomer of the known ganoderic acid S (2). The structure of ganoderic SZ (1) was deduced mainly by 1D and 2D NMR studies. During the course of this study, 12 known lanostanoids have also been isolated and characterized.     

A new synthesis of aromatic thiolis

Benzenoid and heterocylic lithio derivatives react smoothly with tetraisopropyl-thiuram disulfide to give highly crystalline and readily purified S-aryl-N, N-diisopropyldi-thiocarbamates, which yield aromatic thiols on alkaline hydrolysis.