# US 8,785,376 B2 · Isolation, identification, and uses of antifungal compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,785,376 B2 - Document ID: US8785376B2 - Status: Granted - Kind: B2 - Application number: 13/332,345 - Filed: 2011-12-20 - Published: 2013-04-11 - Granted: 2014-07-22 - Earliest claimed: 2010-12-20 - Assignees: Virginia Tech Intellectual Properties, Inc.; University of Utah Research Foundation - Applicants: Eric W. Schmidt; Joseph O. Falkinham; Peter W. Jeffs - Inventors: Eric W. Schmidt; Joseph O. Falkinham; Peter W. Jeffs - Web page: https://patentgrep.com/patent/US8785376B2 ## CPC - C07K 7/64: Cyclic peptides containing only normal peptide links - C07K 7/56: the cyclisation not occurring through 2,4-diamino-butanoic acid - C07K 9/00: Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof - C07K 9/006: {the peptide sequence being part of a ring structure} - A61K 38/12: Cyclic peptides {, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C (A61K38/043 - A61K38/046 take precedence)} - A61K 38/14: Peptides containing saccharide radicals; Derivatives thereof {, e.g. bleomycin, phleomycin, muramylpeptides or vancomycin} - C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00) - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) ## Abstract In one aspect, the invention relates to isolated compounds useful as antifungal agents, for example, compounds having a structure represented by a formula: wherein R1 is hydrogen or hydroxyl; wherein R2 is hydrogen or xylose; and wherein R3 and R4 are each hydrogen or together oxygen, or a pharmaceutically acceptable salt thereof; methods of isolating and purifying same; pharmaceutical compositions comprising same; agricultural compositions comprising same; and methods of treating and/or preventing fungal infections using same. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention. ## Claims ### Claim 1 An isolated compound having a structure represented by a formula: wherein R1 is hydrogen or hydroxyl; wherein R2 is hydrogen or xylose; and wherein R3 and R4 are each hydrogen or together oxygen, or a pharmaceutically acceptable salt thereof. ### Claim 2 (depends on 1) The compound of claim 1, wherein R3 and R4 are each hydrogen. ### Claim 3 (depends on 1) The compound of claim 1, wherein R3 and R4 are together oxygen. ### Claim 4 (depends on 1) The compound of claim 1, wherein R1 is hydrogen. ### Claim 5 (depends on 1) The compound of claim 1, wherein R1 is hydroxyl. ### Claim 6 (depends on 1) The compound of claim 1, wherein R2 is hydrogen. ### Claim 7 (depends on 1) The compound of claim 1, wherein R2 has a structure represented by a formula: ### Claim 8 (depends on 1) The compound of claim 1, wherein R2 has a structure represented by a formula: ### Claim 9 (depends on 1) The compound of claim 1, wherein the compound exhibits inhibition of fungal growth with a MIC of less than about 12.5 μg/ml against Aspergillus. ### Claim 10 (depends on 1) The compound of claim 1, wherein the compound exhibits of about at least 90% inhibition of fungal growth with an IC of less than about 2000 ppm against Botrytis. ### Claim 11 (depends on 1) The compound of claim 1, wherein the compound is cytotoxic. ### Claim 12 (depends on 1) The compound of claim 1, wherein the compound exhibits antifungal activity against Aspergillus, Botrytis, Cercospora, Cercosporidium, Erysiphe, Geotrichum, Mycosphaerella, Mucor, Penicillium, Phoma, Phytophthora, Plasmopora, Pseudopeziza, Puccinia, Pythium, Rhizoctonia, Rhizopus, Septoria, Sporothrix, Stemphylium, Trichophyton, or Verticillium. ### Claim 13 (depends on 1) The compound of claim 1, wherein the compound is isolated from a culture of Burkholderia ambifaria. ### Claim 14 A pharmaceutical composition comprising a compound having a structure represented by a formula: wherein R1 is hydrogen or hydroxyl; wherein R2 is hydrogen or xylose; and wherein R3 and R4 are each hydrogen or together oxygen, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier. ### Claim 15 (depends on 1) The pharmaceutical composition of claim 1, wherein R3 and R4 are together oxygen. ### Claim 16 (depends on 1) The pharmaceutical composition of claim 1, wherein R1 is hydroxyl. ### Claim 17 (depends on 1) The pharmaceutical composition of claim 1, wherein R2 is hydrogen. ### Claim 18 (depends on 1) The pharmaceutical composition of claim 1, wherein R2 is xylose. ### Claim 19 An agricultural composition comprising a compound having a structure represented by a formula: wherein R1 is hydrogen or hydroxyl; wherein R2 is hydrogen or xylose; and wherein R3 and R4 are each hydrogen or together oxygen, or a pharmaceutically acceptable salt thereof, and an agriculturally acceptable carrier. ### Claim 20 (depends on 1) The agricultural composition of claim 1, wherein R3 and R4 are together oxygen. ### Claim 21 (depends on 1) The agricultural composition of claim 1, wherein R1 is hydroxyl. ### Claim 22 (depends on 1) The agricultural composition of claim 1, wherein R2 is hydrogen. ### Claim 23 (depends on 1) The agricultural composition of claim 1, wherein R2 is xylose.