Sesquiterpenes produced by Pestalotiopsis microspora HF 12440 isolated from Artocarpus heterophyllus

Abstract

A drimane-type sesquiterpene, (+)-dendocarbin L (1) together with two bisabolane-type sesquiterpenes, (+)-sydonic acid (2) and (+)-sydowic acid (3) were isolated from the mycelium of Pestalotiopsis microspora HF 12440, an endophytic fungus from the stem of Artocarpus heterophyllus. The structures of all compounds were elucidated using spectroscopic methods and by comparison with the literature. Compound 1 was isolated from the fungi for the first time, compounds 2 and 3 were firstly obtained from this endophytic fungus. Compound 3 showed cytotoxicity (IC₅₀ 2.56?μg/mL) against murine leukemia P-388 cells.     

菠萝蜜微量元素含量的分析

应用电感耦合等离子体发射光谱仪(ICP—AES)，对菠萝蜜各个部位进行了微量元素成分的测定分析，其结果为菠萝蜜的综合开发利用提供依据。     

New 2-arylbenzofurans from the root bark of Artocarpus gomezianus and their α-glucosidase inhibitory activity

Two new 2-arylbenzofurans, namely 13-O-methyllakoochin B (1) and artogomezianin (2), were isolated from the root bark of Artocarpus gomezianus, along with six known compounds (3–8). The structures of new compounds were determined by spectroscopic and chemical methods. All of the isolates were evaluated for their α-glucosidase inhibitory activity. Artogomezianin (2) and lakoochin A (3) exhibited strong α-glucosidase inhibitory activity with IC₅₀ values of 18.25 and 26.19 µM, respectively, as compared with the positive control acarbose.     

New phenolic compounds from the leaves of Artocarpus heterophyllus

One new 2-arylbenzofuran derivative, artocarstilbene B(1), one new benzaldehyde derivative,(E)-3,5-dihydroxy-4-(3-methylbut-1-enyl)benzaldehyde(2), as well as 18 known compounds(3–20) were obtained from the leaves of Artocarpus heterophyllus. Their structures were elucidated on the basis of extensive spectroscopic techniques including 2D NMR and HR-ESIMS. Many compounds exhibited moderate to weak inhibitory activity against the proliferation of the PC-3, NCI-H460, and A549 cancer cell lines.     

Novel 2‐Arylbenzofuran Derivatives from Artocarpus petelotii

Further phytochemical investigations on the root barks of Artocarpus petelotii Gagnep afforded four novel isoprenylated 2‐arylbenzofuran derivatives, namely artopetelins D–G ( 1 – 4 ). Their structures were elucidated by spectroscopic methods, mainly by 2D‐NMR techniques. The biogenetic origins of artopetelins F and G ( 3 and 4 ) were also postulated.     

Isolation and identification of O- and N-linked glycoproteins in milk from different mammalian species and their roles in biological pathways which support infant growth

Milk serves as the sole nutrition for newborns, as well as a medium for the transfer of immunological components from the mother to the baby. This study reveals different glycoprotein profiles obtained from human, bovine, and caprine milk and their potential roles in supporting infant growth. Proteins from these three milk samples are separated and analyzed using two-dimensional gel electrophoresis (2-DE). Glycosylated proteins from all samples are enriched by affinity chromatography using lectins from the seeds of Artocarpus integer before analysis using LC/MS-QTOF. The glycoproteome profiling demonstrates that glycosylated proteins are higher in caprine milk compared to other samples. Analysis using LC/MS-QTOF identified 42 O-glycosylated and 56 N-glycosylated proteins, respectively. Among those identified, human milk has 17 glycoproteins, which are both O- and N-glycosylated, whereas caprine and bovine have 10 and 1, respectively. Only glycoproteins from human milk have shown positive matching to important human biological pathways, such as vesicle-mediated transport, immune system and hemostasis pathways. Human milk remains unique for human babies with the presence of antibodies in the form of immunoglobulins that are lacking in ruminant milk proteomes.     

Bioactivity of Ethyl Acetate Fraction from the Leaves of “Sukun” (Artocarpus Altilis (Parkinson) Fosberg) in Preventing Atherosclerosis

Artocarpus altilis(Parkinson) Fosberg), a tropical tree, belonging to Moraceae family has been known in folk medicine to have some health benefits in particular for inflammation, infection, diabetes and even some cardiovascular problems. One of risk factors of some cardiovascular diseases is hypercholesterolemia. Previous in vitro works showed that ethyl acetate fraction of A. altilis exhibited cytoprotective effect in human U937 cells treated with oxidized LDL. This current work aimed to investigate the effect of ethyl acetate (EA) fraction from the leaves of Sukun, on serum total cholesterol level and on lipid deposition in aorta in vivo.The EA fraction was administered in 8-weeks-Wistar rats fed with high cholesterol diet for 30 days. The serum total cholesterol was dosed using enzimatic test and lipid accumulation in aorta was examined by histology of parafin-blocked aorta stained with hematoxilin-eosin. Antioxidant capacity of flavonoids contained in EA fraction was examined by 1,1-diphenyl-2-picryl-hydrazyl (DPPH) method. The result showed that EA fractions at doses 150 and 300 mg/kg BW were able to lower significantly serum total cholesterol and to prevent lipid accumulation in rat aorta. DPPH examination of flavonoids which were cyclocommunol, 1-(2,4-dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone or AC-31 and 2-geranyl-2′,3,4,4′-tetrahydroxydihydrochalcone or AC-51 showed IC₅₀ value 1548.8±486.8, 275.3±10.0 and 94.1±1.4 μM respectively. It is concluded that the EA fraction is able to lower serum total cholesterol and to prevent lipid accumulation in rat aorta, therefore, has the potential medicinal effect to prevent atherosclerosis. Furthermore, its content of flavonoid especially 2-geranyl-2′,3,4,4′-tetrahydroxydihydrochalcone is suggested to contribute to this effect by acting as antioxidant.     

Molecular diversity of Artocarpus champeden (Moraceae): A species endemic to Indonesia

A summary of results obtained in the study of natural products isolated from a Moraceae species Artocarpus champeden is presented. The various classes of 3-prenylflavonoids isolated and the biogenetical correlation between the metabolites are discussed. Some of the flavonoids exhibited strong cytotoxicity against murine leukemia P388 cell lines, suggesting that flavonoids derived from moraceous plants represent a plausible unexplored resource of novel antitumor leads.     

In vitro anti-acne activity of phytoactives from the stem bark of Artocarpus hirsutus Lam. and characterisation of pyranocycloartobiloxanthone A as a mixture of two anomers

This study is aimed to isolate the phytoactives from the stem bark of Artocarpus hirsutus and evaluate their in vitro anti-acne activity. The ethanolic stem bark extract of A. hirsutus provided two major phytoactive constituents: (i) pyranocycloartobiloxanthone A, (1) and (ii) Artonine E, (2) whose structures were determined by NMR and MS spectroscopic analysis. The present study is the first to report compound 1 as a mixture of two anomers (α and β), approximately 70:30 ratio. Both compounds 1 and 2 were isolated for the first time from this plant. In vitro anti-acne activity of compounds 1 and 2 were evaluated by agar well diffusion method and the minimum inhibition was determined by broth micro dilution method. The result of anti-microbial activity (MIC = 2.0 μg/mL each) is comparable to antibiotic, Clindamycin (MIC = 0.03 μg/mL) and clearly demonstrate their potential as anti-acne agents.     

Three New Isoprenylated Flavones from Artocarpus chama Stem and Their Bioactivities

Phytochemical investigation of Artocarpus chama stem was performed by chromatographic techniques, resulting from the isolation and structure elucidation of three new compounds, namely 3′-farnesyl-apigenin (1), 3-(hydroxyprenyl) isoetin (2), and 3-prenyl-5,7,2′,5′-tetrahydroxy-4′-methoxyflavone (3), and five known compounds, namely homoeriodictyol (4), isocycloartobilo-xanthone (5), artocarpanone (6), naringenin (7), and artocarpin (8). From the screening result, A. chama extract showed a potent tyrosinase inhibitory effect. Ihe isolated compounds 1, 4 and 6 also exhibited tyrosinase inhibition with IC₅₀ of 135.70, 52.18, and 38.78 µg/mL, respectively. Moreover, compounds 3, 4, 5, 6, and 8 showed strong activity against Staphylococcus epidermidis, S. aureus, methicillin-resistant S. aureus, and Cutibacterium acnes. This study is the first report on phytochemical investigation with new compounds and biological activities of A. chama. Skin infection can cause dark spots or hyperpigmentation. The isolated compounds that showed both anityrosinase and antimicrobial activities will be further studied in in vivo and clinical trials in order to develop treatment for hyperpigmentation, which is caused by infectious diseases by microorganisms.