Eight new annonaceous acetogenins, squamotin A-D (1-4), annosquatin IV-V (5 and 6), muricin O (7) and squamosten B (8), together with four known ones (9-12) were isolated from the seeds of Annona squamosa. Their structures were elucidated by chemical methods and spectral data. The inhibitory activities of compound 1-9 against three multidrug resistance cell lines were evaluated. All tested compounds showed strong cytotoxicity.
Acetogenins ; chemistry ; isolation & purification ; pharmacology ; toxicity ; Annona ; chemistry ; Antineoplastic Agents, Phytogenic ; chemistry ; isolation & purification ; pharmacology ; toxicity ; Cell Line, Tumor ; Cell Survival ; drug effects ; Drug Resistance, Neoplasm ; drug effects ; Drug Screening Assays, Antitumor ; Humans ; Molecular Structure ; Plant Extracts ; chemistry ; pharmacology ; toxicity ; Seeds ; chemistry

To investigate the secondary metabolites of endophytic fungi Pericinia sp. F-31. Column chromatography on silica gel, Sephadex LH-20 and semi-preparative HPLC were used to separate and purify the compounds. Two compounds were isolated from the fermentation broth of Periconia sp. Their structures were identified as 5-(1-hydroxyhexyl) -6-methyl-2H-pyran-2-one (1) and 2-(3-hydroxy-4-methylphenyl) -propanoic acid (2). Compound 1 was a new lactone compound, compound 2 was new natural product, and the NMR data of compound 2 was reported for the first time.
Annona ; microbiology ; Ascomycota ; chemistry ; genetics ; isolation & purification ; metabolism ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; metabolism ; Endophytes ; chemistry ; genetics ; isolation & purification ; metabolism ; Lactones ; chemistry ; isolation & purification ; metabolism ; Mass Spectrometry ; Molecular Structure

Women's health has been threatened by various diseases mainly including heart disease, breast cancer, osteoporosis, depression, and autoimmune disease. But development of medication for these diseases has been restricted by high development costs and low success rates. Herein the attempt to develop valid bioactive materials from a traditional natural material has been made. Resveratrol has been reported to be effective in treatment of breast cancer and heart disease. Goji berry has received attention as a natural based therapeutic material to treat a diabetes, cardiovascular disease, and osteoporosis. Leonurus family has been reported to be effective particularly in pregnant women due to high contents of vitamin as well as stimulation of uterine contraction. Annona family has effects such as anti-anxiety, anticonvulsant and recently it is proposed to be as a therapeutic material to cure depression based on its strong antidepressant effect. Shiraia bambusicola has been utilized to cure angiogenesis-related disease from ancient China and furthermore recently it was proved to be effective in rheumatoid arthritis. Getting an understanding of utilization of these traditional natural materials not only enhances the interest in development of therapeutic materials for preventing and treating various women's diseases, but also makes it possible to develop novel therapeutic materials.
Annona ; Antioxidants ; Arthritis, Rheumatoid ; Autoimmune Diseases ; Breast Neoplasms ; Cardiovascular Diseases ; China ; Depression ; Female ; Fruit ; Heart Diseases ; Humans ; Leonurus ; Osteoporosis ; Pregnant Women ; Uterine Contraction ; Vitamin A ; Women's Health

OBJECTIVETo confirm the anticancer effect of total annonaceous acetogenins (TAAs) abstracted from Annona squamosa Linn. on human hepatocarcinoma.

METHODSThe inhibitory effect of TAAs was demonstrated in H22-bearing mice. The potency of TAAs was confirmed as its 50% inhibiting concentration (IC50) on Bel-7402 cell under Sulfur Rhodamine B staining. Both underlying mechanisms were explored as cellular apoptosis and cell cycle under flow cytometry. Mitochondrial and recipient apoptotic pathways were differentiated as mitochondrial membrane potential under flow cytometry and caspases activities under fluorescence analysis.

RESULTSThe inhibitory rate of TAAs in mice was 50.98% at 4 mg/kg dose. The IC50 of TAAs on Bel-7402 was 20.06 µg/mL (15.13-26.61µg/mL). Effective mechanisms of TAAs were confirmed as both of arresting cell cycle at G1 phase and inducing apoptosis dose- and time-dependently. Mitochondrial and recipient pathways involved in apoptotic actions of TAAs.

CONCLUSIONTAAs is effective for hepatocarcinoma, via inhibiting proliferation and inducing apoptosis.

Acetogenins ; chemistry ; pharmacology ; therapeutic use ; Animals ; Annona ; chemistry ; Antineoplastic Agents, Phytogenic ; chemistry ; pharmacology ; therapeutic use ; Apoptosis ; drug effects ; Carcinoma, Hepatocellular ; drug therapy ; enzymology ; pathology ; Caspases ; metabolism ; Cell Cycle ; drug effects ; Cell Line, Tumor ; Cell Proliferation ; drug effects ; Chromatography, High Pressure Liquid ; Dose-Response Relationship, Drug ; Humans ; Liver Neoplasms ; drug therapy ; enzymology ; pathology ; Male ; Membrane Potential, Mitochondrial ; drug effects ; Mice ; Organ Specificity ; drug effects ; Spleen ; drug effects ; Thymus Gland ; drug effects ; Xenograft Model Antitumor Assays

OBJECTIVETo investigate the constituents of the Annona squamosa and evaluate their anti-tumor activity.

METHODThe compounds were isolated and purified by various column chromatography. Their structures were elucidated by spectral data analysis. Their anti-tumor activity was assayed by SRB method.

RESULTEleven compounds were obtained from the 95% EtOH extract. The structures were determined as: annosquamosin C(1),15, 16-epoxy-17-hydroxy-ent-kau-ran-19-oic acid (2),16,17-dihydroxy-ent-kau-ran-19-oic acid(3), annosquamosin A(4), ent-kaur-16-en-19-oic acid (5), 19-nor-ent-kauran4-ol-17-oic acid (6),16-hydroxy ent-kau ran-19-oic acid (7), ent-15beta-hydroxy-kaur-16-en-19-oic acid (8), annosquamosin B (9), ent-16beta, 17-dihydroxykauran-19-al (10), 16, 17-dihydroxy-ent-kauran-19-oic acid me thyl ester (11). Compounds 1,2,3,5,9 showed different inhibitory activities against 95-D lung cancer cells,the effect of compound 5 was strongest with the IC50 value 7.78 micromol x L(-1); Compounds 2, 5, 9 showed inhibitory activities against A2780 ovarian cancer cells, the effects of compounds 2 and 9 were strong with the IC50 values being 0.89, 3.10 micromol x L(-1), respectively.

CONCLUSIONCompound 2 was firstly isolated from this family, while compound 8 and 10 were first found from this genus and the title species, respectively. The in vitro anti-tumor test showed compound 5 significantly inhibited 95-D lung cancer cells and compounds 2 and 9 exhibited remarkbale activity against A2780 ovarian cancer cells.

Annona ; chemistry ; Antineoplastic Agents, Phytogenic ; analysis ; pharmacology ; Cell Line, Tumor ; Humans ; Plant Bark ; chemistry

BACKGROUND: The use of natural bioactive compounds in conventional chemotherapy is a new direction in cancer treatment that is gaining more research attention recently. Bioactive polysaccharides and polysaccharide-protein complexes from some fungi (edible mushrooms) have been identified as sources of effective and non-toxic antineoplastic agents. Selected oyster mushrooms (Pleurotus pulmonarius and P. ostreatus being local [Nigeria] and exotic strains, respectively) were cultured on a novel medium of yeast extract supplemented with an ethanolic extract of Annona senegalensis, and the antileukemic potential of their metabolites was studied. METHODS: Leukemia was successfully induced in Wister rats by intravenous injection (0.2 mL) of a benzene solution every 2 days for 3 consecutive weeks. The aqueous solution of fungal metabolites (20 mg/mL) produced by submerged fermentation was orally administered (0.2 mL) before, during, and after leukemia induction. Leukemia burden was assessed by comparing the hematological parameters at baseline and after leukemia induction. The immunomodulatory potential of the metabolites was assessed by using a phagocytic assay (carbon clearance method). The ability to enhance leukopoiesis was assessed by using the total leukocyte count. RESULTS: Leukemia induction resulted in significant anemia indices and leukocytosis (P<0.05) in the experimental rats. Both metabolites equally enhanced leukopoiesis and demonstrated phagocytic actions; P. ostreatus activity was significantly higher than that of P. pulmonarius (P<0.05). CONCLUSION: The metabolites exhibited profound antileukemic potential by suppressing leukemia and demonstrating immunotherapeutic activities on animals after oral administration in various experimental groups.
Administration, Oral ; Anemia ; Animals ; Annona ; Antineoplastic Agents ; Benzene ; Ethanol ; Fermentation ; Fungi ; Immunotherapy ; Injections, Intravenous ; Leukemia ; Leukocytes ; Leukocytosis ; Leukopoiesis ; Pleurotus ; Polysaccharides ; Rats ; Yeasts

Many major neurodegenerative diseases are associated with proteins misfolding and aggregation, which are also called "neurodegenerative conformational disease". The interaction of gene mutation and environmental factors are probably primary events resulting in oligomer and aggregate formations of proteins. Moreover, the dysfunctions of protein control systems, i.e. the ubiquitin-proteasome system and autophagy-lysosomal system, also contribute to the neurodegenerative process. The present review mainly summarizes protein misfolding and aggregation in the development of neurodegenerative conformational disease and the underling mechanisms, as well as upregulation of heatshock proteins as a promising treatment method for this kind of disease.
Alzheimer Disease ; drug therapy ; genetics ; metabolism ; pathology ; Animals ; Annona ; chemistry ; Autophagy ; Benzeneacetamides ; isolation & purification ; therapeutic use ; Heat-Shock Proteins ; metabolism ; physiology ; Humans ; Mutation ; Neurodegenerative Diseases ; drug therapy ; genetics ; metabolism ; pathology ; Parkinson Disease ; drug therapy ; genetics ; metabolism ; pathology ; Phenols ; isolation & purification ; therapeutic use ; Plants, Medicinal ; chemistry ; Proteasome Endopeptidase Complex ; metabolism ; Protein Folding ; Ubiquitin ; metabolism

OBJECTIVETo investigate the chemical constituents of an endophytic fungus, F-31, from Annona muricata and search antitumor natural products.

METHODAfter scaling up, the fermentation broth and mycelia were extracted by macroporous resin and chromatographied by silica gel column, Sephadex LH-20 gel column and semi-preparative HPLC. The structures of compounds were determined by the means of extensive spectroscopic data The activity of the compounds were evaluated through MTT assay.

RESULTSix compounds were isolated from the fermentation broth and mycelia of this fungus, their structures were identified as 5-(3-hydroxybutyl)furan-2(5H)-one(1), chloranthalactone E(2), 5, 7-dimethyl-6-hydroxycoumarin(3), 1, 2, 4-triazole-(1'R, 2'R, 3'R, 4'R)-nucleosides(4), L-tryptophan(5), L-phenylalanine(6). The in vitro pharmalogical evaluation results displayed that the above compounds exhibited no inhibitory effects on the proliferation of six tumor cell lines (HCT-8, Bel-7402, BGC-823, A549, A2780 and MCF-7).

CONCLUSIONAmong these obtained compounds, compound 1 was a new compound.

Annona ; microbiology ; physiology ; Ascomycota ; chemistry ; physiology ; Cell Line, Tumor ; Fermentation ; Humans ; Symbiosis

In the present study, antioxidant activities of the fruits of A. heterophyllus, A. squamosa, T. bellirica, S. samarangense, A. carambola and O. europa were investigated. For this, at first matured fruits of them were sliced into small pieces and dried in the sun and finally crushed in a grinder to make powder. Ethanolic extracts of fruit powder were prepared using 99.99% ethanol. The antioxidative activities of these extracts were determined according to their abilities of scavenging 1, 1-diphenyl-2-picrylhydrazyl (DPPH) free radical. It was demonstrated that all the ethanolic extracts of A. heterophyllus, A. squamosa, T. bellirica, S. samarangense, A. caranbola and O. europa showed antioxidant activities. The IC50 of the ethanolic extracts of A. heterophyllus, A. squamosa, T. bellirica, S. samarangense, A. carambola and O. europa were 410, 250, 34, 200, 30 and 76 microg/mL, respectively. Among them, A. carambola showed the highest antioxidant activities followed by T. bellirica, O. europa, S. samarangense, A. squamosa and A. heterophyllus indicating that fruits of A. carambola, T. bellirica and O. europa are very beneficial to human health.
Annona ; chemistry ; Antioxidants ; metabolism ; pharmacology ; Artocarpus ; chemistry ; Biphenyl Compounds ; chemistry ; Dose-Response Relationship, Drug ; Ethanol ; chemistry ; Fruit ; chemistry ; Magnoliopsida ; chemistry ; Olea ; chemistry ; Oxidation-Reduction ; drug effects ; Picrates ; chemistry ; Plant Extracts ; metabolism ; pharmacology ; Spectrophotometry, Ultraviolet ; Syzygium ; chemistry ; Terminalia ; chemistry

AIMTo study the antitumor active constituents of the seeds from Annona squamosa L. (Annonaceae).

METHODSVarious chromatographic techniques were used to isolate and purify the constituents. Their physico-chemical properties and spectral data were determined to elucidate the structures.

RESULTSEleven compounds were isolated and identified as annonaceous acetogenins: squamocenin (1), annotemoyin-2 (2), reticulatain-2 (3), squamocin-I (4), squamocin-B (5), squamocin (6), motrilin (7), squamostatin-D (8), squamostatin-E (9), cherimolin-1 (10), cherimolin-2 (11) from the ethyl alcohol extract of A. squamosa L.

CONCLUSIONSquamocenin (1) is a new acetogenin. Annotemoyin-2 (2) and reticulatain-2 (3) were isolated from this plant for the first time.

Annona ; chemistry ; Furans ; chemistry ; isolation & purification ; Lactones ; chemistry ; isolation & purification ; Molecular Conformation ; Molecular Structure ; Plants, Medicinal ; chemistry ; Seeds ; chemistry