35 results about "Annonaceous Acetogenins" patented technology

The present invention relates to a plant extract with the action of resisting diabetes, its application and preparation method. The extract is a kind of acetogenins extracted from branck, leaf, trunk, bark, root, seed and fruit skin of annona squamosa plant as raw material. The compound acetogenins can be made into various dosage forms for curing diabetes, and its preparation method can adopt oneor several processes of solvent extraction process, resin adsorption process, supercritical CO2 extraction process and conventional drying process.

The invention relates to the chemical compound of the chiral annonaceous acetogenins of the comformational restriction structure, the synthetic method and the purpose. The compound has the optical activity compound as the above formula: (R or S configuration) (R or S configuration). The compound of the invention has high anti-cancer activity and selectivity and has the IC50 (MuM) of the human breast duct cancer reaching less than 0.04, and the suppressive activity on the cancer cell is about 100 times that of the normal cell and has better selectivity. The compound of the invention can also be used as the anti-cancer drug and has simple preparation method, which is a method suitable for the industrial production.

The invention discloses a new application of an annonaceous acetogenin monomeric compound desacetyluvaricin in preparing medicaments for treating lung cancer and breast cancer. The results of antitumor pharmacological tests in animals indicate that the annonaceous acetogenin monomeric compound desacetyluvaricin has distinct inhibitor action on the growth of lung cancer and breast cancer cells, and has antitumor activity hundreds of times higher than the chemotherapeutic drug 5-flurouracil. The desacetyluvaricin can be used for preparing medicaments for treating lung cancer and breast cancer.

The invention provides an annonaceous acetogenin extract extracted from seeds, leaves and barks of Annona squamosa L., a preparation method thereof, an external preparation taking the annonaceous acetogenin extract as an active ingredient, and medicinal use of the external preparation in cancer resistance and relief of cancerous pain. The preparation method for the annonaceous acetogenin extract has a simple process, common, low-price and low-toxicity reagents are adopted and are environment-friendly and relatively safe for human health, the production cost is lower, and the whole preparation method is easy to implement, can effectively shorten the production cycle and is suitable for mass production. An external patch comprising the annonaceous acetogenin extract serving as the active ingredient is easy to use, and has prominent curative effect on cancerous pain and no side effect.

The invention belongs to the technical field of medicines, and in particular relates to a nanosuspension of annonaceous acetogenin drugs prepared from such amphiphilic stabilizers as mPEG PCL, mPEG PLA, mPEG PLGA, mPEG DSPE, mPEG Chol, SPC, Tween80, BSA, TPGS and the like, as well as a preparation method and an application of the nanosuspension. The annonaceous acetogenin total lactone nanosuspension is prepared by virtue of a solvent precipitation-ultrasonic injection method, and according to a prescription, the proportioning ratio of the annonaceous acetogenin drugs to the stabilizer is at 1 to (0.02-10) (in percentage by weight). The prepared annonaceous acetogenin nanosuspension can reach a load-loading capacity to 90% to the greatest extent and can reach a minimum grain size to 123.2nm, and the nanosuspension is good in polydispersity. The nanosuspension is stable in both gastrointestinal fluid and plasma, and the nanosuspension is applicable to oral administration and injection administration; the nanosuspension has a good in-vitro sustained-release effect and is free from burst release; the nanoparticle, in comparison with a crude drug solution, is more obvious in tumor cell inhibitory rate in vitro; the nanosuspension, in in-vivo tissue distribution, shows tumor passive targeting; therefore, the nanosuspension is beneficial for enhancing efficacy and reducing toxic and side effects. Meanwhile, an in-vivo efficacy experiment shows that the nanosuspension is outstanding in antineoplastic efficacy, and the nanosuspension has a broad development prospect.

The invention discloses application of annonaceous acetogenins polyether analog AA005 and structural analogs thereof to pharmacy, and especially relates to application to prepare medicine for preventing or treating diseases about abnormal lipid metabolism. The inventor firstly discovers that AA005 is capable of inhibiting accumulation of triglycerides in preadipocyte 3T3-L1 and inhibiting accumulation of fat in nematodes, and apoptosis-inducing factor AIF is capable of specifically mutually acting with AA005 and participating the process of AA005 influencing lipid metabolism. AA005 may well provides a treatment method for selectively targeting adipocyte as a small molecule compound taking mitochondrial as target, and has good medicinal prospect to prepare medicines for preventing or treating diseases about abnormal lipid metabolism. The active substance AA005 and the structural analogs thereof are safe, low in toxicity and strong in pharmacological action, have the characteristics of absorption easiness, good stability and the like, and are relatively suitable for exploitation as novel medicines, food, health-care products and / or food additives.

The invention discloses a new mono-tetrahydrofuran type sugar apple lactone compound with anti-tumor activity, through systematic in-depth research of chemical ingredients of sugar apple seeds, the analysis of wave spectrum and mass spectrum data shows that the new mono-tetrahydrofuran type sugar apple lactone compound (Anno Shikemominbing) can be separated from the sugar apple seeds, in vivo and in vitro anti-tumor activity researches show that mono-tetrahydrofuran type sugar apple lactone provided by the invention has very strong anti-tumor activity for a variety of tumor cells, including lung cancer, breast cancer, liver cancer, cervical cancer and gastric cancer, and the toxicity test research shows that the mono-tetrahydrofuran type sugar apple lactone compound with the anti-tumor activity provided by the invention is expected to be developed into new anti-tumor medicaments.

The invention provides pharmaceutical composition with a selective killing or nM level efficient killing effect on drug-resistant tumors and an application of the pharmaceutical composition, and relates to the technical field of tumor therapy. The pharmaceutical composition is prepared from effective component as follows: annona squamosal seed extract, and the annona squamosal seed extract form further comprises an ACGs (annonaceous acetogenins) effective part of or an ACGs monomer. The effective components in the composition have the moderate-intensity killing effect on tumor cells, but havethe selective killing or nM level efficient killing effect on the drug-resistant tumors; after nanoparticles are prepared from the pharmaceutical composition, not only are the problems of insolubilityand difficulty in administration of total lactone solved, but also a strong killing effect of ACGs on the drug-resistant tumors is retained.

The invention discloses an o-bis-tetrahydrofuran type annonaceous acetogenins compound having antitumor activity. Through systemically deep researching on chemical ingredients of seeds of annona squamosa, wave spectrum and mass spectrum data analysis proves that the novel o-bis-tetrahydrofuran type annonaceous acetogenins compound can be separated from the seeds of annona squamosa. In-vivo and in-vitro antitumor activity researching proves that the o-bis-tetrahydrofuran type annonaceous acetogenins has strong antitumor activity on various tumor cells, such as lung cancer cells, breast cancer cells, liver cancer cells, etc., and also has significant inhibition activity on mouse transplanted liver tumor HepG2 and mouse sarcoma S180 solid tumor. Toxicity tests prove that the o-bis-tetrahydrofuran type annonaceous acetogenins compound has low toxicity and is an excellent antitumor compound.

This invention relates to an acetogenin compound linked by amide bonds, its synthesis method and its application. The acetogenin compound is an optically active or racemized compound, whose structural formula is shown in this invention, wherein, Y is C6-20 alkyl; n is 0-3; m is 7-19; R1, R2, R3 and R4 are the same or not, and are H or C1-10 alkyl; when n is 0-2, R3 and R4 are H, Cl, C1-10 alkyl or combined to form fiver-, six- or seven-membered ring shape; when n is 0, R1 and R2 are C1-10 alkyl or combined to form fiver-, six- or seven-membered ring shape. The acetogenin compound has high anticancer activity, and IC50 (mu.M) is lower than 0.04 to breast cancer (MDA-MB-435S). The can be manufactured into anticancer drugs. The synthesis method is simple, and suitable for industrial production.

The invention discloses an application of annona squamosa seed total lactones and annona squamosa pivalolactone monomeric compounds thereof to preparation of medicines for controlling diabetes and diabetic nephropathy thereof. Through massive experimental selection, results show that the annona squamosa seed total lactones and the annona squamosa pivalolactone monomeric compounds thereof have theefficacy of reducing fasting blood sugar of rats suffering from diabetic nephropathy, the content of serum creatinine, the content of urea nitrogen and the content of urine protein of the rats suffering from the diabetic nephropathy can be notably reduced, and the annona squamosa seed total lactones and the annona squamosa pivalolactone monomeric compounds thereof have good effects of reducing blood sugar and protecting the kidney.

The invention discloses an m-bistetrahydrofuran annonaceous acetogenins compound with anti-tumor activity. Shown by the spectral and mass spectral data analysis, the new m-bistetrahydrofuran annonaceous acetogenins compound is separated from seeds of annona squamosa by carrying out systematic in-depth study on the chemical composition of the seeds of annona squamosa; shown by in vivo and in vitro antineoplastic activity studies, the m-bistetrahydrofuran annonaceous acetogenins provided by the invention has strong anti-tumor activity on various tumor cells including lung cancer cells, breast cancer cells, liver cancer cells and the like, and also has obvious inhibition activity on solid tumors such as mice transplanted tumor HepG2 and mice sarcoma S180; and shown by toxicity experimental study, the m-bistetrahydrofuran annonaceous acetogenins compound provided by the invention has lower toxicity and is an excellent anti-tumor compound.

The invention provides a nanoparticle with effect-enhancing and toxicity-reducing effect on synergistic and attenuating effects on annonaceous acetogenins drugs, and belongs to the field of pharmaceutical preparations. The present invention uses poloxamer P188, Poloxamer P407, Poloxamer P124, one or more of poloxamer P237 and poloxamer P338 are adjuvants, By limiting the kinds and dosage of excipients, the problems of insoluble and difficult administration of annonolactone are solved, and more importantly, the anti-tumor effect in vivo is improved, at the same time, it has better safety, breaks through the bottleneck problem of narrow window of treatment of annonolactone, and provides a feasible solution for clinical application.

The invention discloses a novel monotetrahydropyrane annonaceous acetogenins compound with anti-tumor activity. Chemical compounds of an annonaceous seed are systematically and deeply researched; analysis of spectral data mass spectrometric data shows that one novel monotetrahydropyrane annonaceous acetogenins compound is separated from the annonaceous seed; an in-vitro anti-tumor activity research shows that the monotetrahydropyrane annonaceous acetogenins provided by the invention has extremely high anti-tumor activity for cells of various tumors including gastric cancer, intestinal cancer,lung cancer, breast cancer, liver cancer and cervical cancer, and is expected to be developed into an anti-tumor medicine.

The invention discloses a new application of an annonaceous acetogenin monomeric compound annonareticin in preparing medicaments for treating lung cancer and breast cancer. The results of antitumor pharmacological tests in animals indicate that the annonaceous acetogenin monomeric compound annonareticin has distinct inhibitor action on the growth of lung cancer and breast cancer cells, and has antitumor activity hundreds of times higher than the chemotherapeutic drug 5-flurouracil. The annonareticin can be used for preparing medicaments for treating lung cancer and breast cancer.

The invention discloses new single-tetrahydrofuran-type annonaceous acetogenin compounds with antitumor activity. In the invention, based on systemic deep research on the chemical composition of anonaceae seed, wave spectrometric and mass spectrometric data analysis shows that two new single-tetrahydrofuran-type annonaceous acetogenin compounds (Annonacins I and II) are separated from anonaceae seed; in-vivo and in-vitro antitumor activity researches show that the single-tetrahydrofuran-type annonaceous acetogenin compounds provided by the invention have strong antitumor activity on various tumor cells including lung cancer, breast cancer, liver cancer, cervical carcinoma and gastric cancer; toxicity test researches show that the single-tetrahydrofuran-type annonaceous acetogenin compounds with antitumor activity, provided by the invention, have low toxicity and are expected to be developed into new antitumor drugs.

The invention discloses an epoxy type annonaceous acetogenin compound with antitumor activity; through systematic deep research on the chemical composition of Annona squamosa seeds, wave spectral and mass spectral data analysis indicates the novel epoxy annonaceous acetogenin compound is isolated from Annona squamosa seeds, in-vivo and in-vitro antitumor activity researches indicate that epoxy type annonaceous acetogenins provided herein show high antitumor activity to various tumor cells, such as lung cancer cells, breast cancer cells, and liver cancer cells and show significant inhibitory activity to the solid tumors of mouse implanted hepatic tumor HepG2 and mouse sarcoma S180, and toxicity experiment researches indicate that the epoxy type annonaceous acetogenin compound provided herein has low toxicity and is a good antitumor compound.

The invention discloses an R or S-shaped or racemic annonaceous acetogenin compound with a structure of a formula 1. In the formula, R1 is alkane of C2 to C10, five to seven-element naphthenic hydrocarbon or five-element alpha or beta unsaturated lactonic ring, or substituted benzene ring or naphthalene ring compound; R2 is H or OH; x is 0 to 5, y is 1 to 6, n is 3 to 5, and m is 7 to 19; and when x is 0, y is 1 and n is 3, R1 is alkane of C2 to C10, five to seven-element naphthenic hydrocarbon or substituted benzene ring or naphthalene ring, and R2 is H or OH; or when x is 1 to 5 and y is 6,the R1 is five-element alpha or beta unsaturated lactonic ring, and R2 is hydroxy. The preparation raw materials for the compound are cheap and easily obtained; the preparation method is simple and suitable for industrialized production; and the compound has high anti-tumor activity, and can be used for preparing anti-tumor medicaments. Formula 1.

The invention discloses new single-tetrahydrofuran-type annonaceous acetogenin compounds with antitumor activity. In the invention, based on systemic deep research on the chemical composition of anonaceae seed, wave spectrometric and mass spectrometric data analysis shows that two new single-tetrahydrofuran-type annonaceous acetogenin compounds (Annonacins I and II) are separated from anonaceae seed; in-vivo and in-vitro antitumor activity researches show that the single-tetrahydrofuran-type annonaceous acetogenin compounds provided by the invention have strong antitumor activity on various tumor cells including lung cancer, breast cancer, liver cancer, cervical carcinoma and gastric cancer; toxicity test researches show that the single-tetrahydrofuran-type annonaceous acetogenin compounds with antitumor activity, provided by the invention, have low toxicity and are expected to be developed into new antitumor drugs.

The invention provides an annonaceous acetogenin extract extracted from seeds, leaves and barks of Annona squamosa L., a preparation method thereof, an external preparation taking the annonaceous acetogenin extract as an active ingredient, and medicinal use of the external preparation in cancer resistance and relief of cancerous pain. The preparation method for the annonaceous acetogenin extract has a simple process, common, low-price and low-toxicity reagents are adopted and are environment-friendly and relatively safe for human health, the production cost is lower, and the whole preparation method is easy to implement, can effectively shorten the production cycle and is suitable for mass production. An external patch comprising the annonaceous acetogenin extract serving as the active ingredient is easy to use, and has prominent curative effect on cancerous pain and no side effect.

The invention relates to the chemical compound of the chiral annonaceous acetogenins of the comformational restriction structure, the synthetic method and the purpose. The compound has the optical activity compound as the above formula: (R or S configuration) (R or S configuration). The compound of the invention has high anti-cancer activity and selectivity and has the IC50 (MuM) of the human breast duct cancer reaching less than 0.04, and the suppressive activity on the cancer cell is about 100 times that of the normal cell and has better selectivity. The compound of the invention can also be used as the anti-cancer drug and has simple preparation method, which is a method suitable for the industrial production.

The invention discloses a new application of an annonaceous acetogenin monomeric compound annonareticin in preparing medicaments for treating lung cancer and breast cancer. The results of antitumor pharmacological tests in animals indicate that the annonaceous acetogenin monomeric compound annonareticin has distinct inhibitor action on the growth of lung cancer and breast cancer cells, and has antitumor activity hundreds of times higher than the chemotherapeutic drug 5-flurouracil. The annonareticin can be used for preparing medicaments for treating lung cancer and breast cancer.

The invention discloses a preparation method of bubble-shaped annonaceous acetogenins. The method comprises the following steps of: a, taking bubble-shaped sweetsop barks and crushing, adding the crushed bubble-shaped sweetsop barks into a supercritical extraction kettle, and carrying out supercritical CO2 extraction by taking ethanol as an entrainer; b, purifying an extractive by adopting neutral magnesium oxide column chromatography, carry outing gradient elution by utilizing a petroleum ether-acetone mixing agent, collecting an elution solution and decompressing and concentrating to obtain a rough extract; and c, carrying out high-speed countercurrent chromatography separation on the rough extract, monitoring by an ultraviolet detector, collecting target components, refrigerating and crystallizing to obtain the bubble-shaped annonaceous acetogenins. When the preparation method is used for preparing the bubble-shaped annonaceous acetogenins, the process is simple and the efficiency is high, and the content of the obtained products is high, so that the preparation method is suitable for industrial production.

The invention discloses an epoxy type annonaceous acetogenin compound with antitumor activity; through systematic deep research on the chemical composition of Annona squamosa seeds, wave spectral and mass spectral data analysis indicates the novel epoxy annonaceous acetogenin compound is isolated from Annona squamosa seeds, in-vivo and in-vitro antitumor activity researches indicate that epoxy type annonaceous acetogenins provided herein show high antitumor activity to various tumor cells, such as lung cancer cells, breast cancer cells, and liver cancer cells and show significant inhibitory activity to the solid tumors of mouse implanted hepatic tumor HepG2 and mouse sarcoma S180, and toxicity experiment researches indicate that the epoxy type annonaceous acetogenin compound provided herein has low toxicity and is a good antitumor compound.

The invention relates to annonaceous acetogenins nanoparticles, which are prepared by taking cyclodextrin and lecithin as vectors, as well as a preparation method and an application of annonaceous acetogenins nanoparticles. The annonaceous acetogenins (annonaceous acetogenins total lactone or monomer ingredients thereof) nanoparticles are prepared by virtue of a solvent precipitation method; the mass ratio of the annonaceous acetogenins to the cyclodextrin to the lecithin is at 1 to (0.02-20) to (0.02-20); and in accordance with an optimal prescription, the combining proportion of the annonaceous acetogenins to the cyclodextrin to the lecithin is at 4 to 2 to 1 (in percentage by mass). The average grain size of the annonaceous acetogenins nanoparticles is 20-1000nm, and the annonaceous acetogenins nanoparticles are good in dispersity; the annonaceous acetogenins nanoparticles are stable in both gastrointestinal fluid and plasmid, and the annonaceous acetogenins nanoparticles are suitable for both oral administration and intravenous injection; with the application of the nanoparticles, the inhibitory effect of the annonaceous acetogenins on tumor cells can be significantly improved, and meanwhile, in vivo anti-tumor efficacy can be enhanced; and the annonaceous acetogenins nanoparticles have a broad development prospect.

The invention discloses a pesticide composition containing annonaceous acetogenin and pymetrozine. The pesticide composition contains the active ingredients, pymetrozine and annonaceous acetogenin; the mass ratio of the pymetrozine to annonaceous acetogenin is 40:1 to 1:40; within the ratio range, the pymetrozine and annonaceous acetogenin are synergic to the prevention and treatment of cabbage aphids and cotton aphids; the pymetrozine and annonaceous acetogenin can be made into pesticidal preparations; the mass sum of the pymetrozine and annonaceous acetogenin accounts for 0.1-60% by weight of the total weight of the pesticidal preparations, and the otherness is pesticidal aids; the pesticide composition is applicable to the prevention and treatment of cabbage aphids and cotton aphids.

The invention discloses a method for extracting annonaceous acetogenin from atemoya, and belongs to the field of an annonaceous acetogenin extracting processes. The method comprises the following steps: pretreating an extracted raw material; drying the pretreated raw material, and then crushing by using a vacuum crusher to obtain crushed raw material powder; placing the crushed raw material powderinto a quick freezer for quick freezing to obtain ice powder, crushing the ice powder by using a crusher, unfreezing the crushed ice powder, and drying steam to obtain dry fine powder; placing the dried fine powder and water into a vacuum stirring tank for vacuum stirring; filtering to remove filter residues, and pouring filtrate into an extraction kettle for extraction; and collecting the extract after extracting for 2vh, extracting the extract with chloroform for 4 times, combining chloroform layers, carrying out vacuum filtration, recovering a solvent under reduced pressure at the temperature of 45 DEG C, and drying under reduced pressure to obtain the final product. The raw material is crushed for multiple times, and is crushed again after being frozen, so that the effect is good, theextraction efficiency of the raw material in the later period is high, a large amount of organic solvents are avoided, and the extraction efficiency is high.