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(12) Patent Application Publication (10) Pub. No.: US 2012/0296073 A1 Baird Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2012/0296073 A1 Baird Et Al US 20120296073A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2012/0296073 A1 Baird et al. (43) Pub. Date: Nov. 22, 2012 (54) COMPOSITION AND METHOD Publication Classification (75) Inventors: Mark Stephen Baird, Gwynedd (51) E",M6 (2006.01) (GB); David Preskett, Gwynedd C07C 67/00 (2006.01) (GB) C7H I/00 (2006.01) CIIC I/04 2006.O1 (73) Assignee: BANGOR UNIVERSITY, CIIB I/00 388 Gwynedd (GB) (52) U.S. Cl. ............. 536/18.1:554/160:554/8:554/124 (21) Appl. No.: 13/469,470 (57) ABSTRACT 1-1. A process of obtaining a saponin-rich component from a plant (22) Filed: May 11, 2012 of the Araliaceae family, the process comprising the steps of O O (a) treating a portion of the plant with an extraction solvent in Related U.S. Application Data which saponin-containing compounds are soluble; and (b) (62) Division of application No. 12/810,010, filed on Sep. treating the portion of plant or the extract obtained therefrom 13, 2010, filed as application No. PCT/GB2008/ to remove fatty acid residues from said portion of plant or 051224 on Dec. 22, 2008. extract thereof. Patent Application Publication Nov. 22, 2012 Sheet 1 of 28 US 2012/0296073 A1 §§§ {}{} Patent Application Publication Nov. 22, 2012 Sheet 3 of 28 US 2012/0296073 A1 s „...(tutu) Patent Application Publication Nov. 22, 2012 Sheet 4 of 28 US 2012/0296073 A1 {} Roc ?“’qawwao |__(unu) Patent Application Publication Nov. 22, 2012 Sheet 5 of 28 US 2012/0296073 A1 qax****** {{??a) Patent Application Publication Nov. 22, 2012 Sheet 6 of 28 US 2012/0296073 A1 X& txtaendwa???e?ti, Patent Application Publication Nov. 22, 2012 Sheet 7 of 28 US 2012/0296073 A1 %,§§§§ **********.*). x, t Patent Application Publication Nov. 22, 2012 Sheet 8 of 28 US 2012/0296073 A1 ºººuwono„(unu) Patent Application Publication Nov. 22, 2012 Sheet 9 of 28 US 2012/0296073 A1 tan??ødsoffi?3 8: .(tutu) Patent Application Publication Nov. 22, 2012 Sheet 10 of 28 US 2012/0296073 A1 Patent Application Publication Nov. 22, 2012 Sheet 11 of 28 US 2012/0296073 A1 Patent Application Publication Nov. 22, 2012 Sheet 13 of 28 US 2012/0296073 A1 Patent Application Publication Nov. 22, 2012 Sheet 14 of 28 US 2012/0296073 A1 Patent Application Publication Nov. 22, 2012 Sheet 15 of 28 US 2012/0296073 A1 s Patent Application Publication Nov. 22, 2012 Sheet 16 of 28 US 2012/0296073 A1 Patent Application Publication Nov. 22, 2012 Sheet 17 of 28 US 2012/0296073 A1 Patent Application Publication Nov. 22, 2012 Sheet 18 of 28 US 2012/0296073 A1 **************************************************************** § ?gðað?tættätaeae Patent Application Publication Nov. 22, 2012 Sheet 19 of 28 US 2012/0296073 A1 8õ?? §§ *{}{ {}{ Patent Application Publication Nov. 22, 2012 Sheet 20 of 28 US 2012/0296073 A1 Patent Application Publication Nov. 22, 2012 Sheet 21 of 28 US 2012/0296073 A1 Patent Application Publication Nov. 22, 2012 Sheet 22 of 28 US 2012/0296073 A1 E. six k & 8 : & Patent Application Publication Nov. 22, 2012 Sheet 23 of 28 US 2012/0296073 A1 xxxx {}{} ·## Patent Application Publication Nov. 22, 2012 Sheet 24 of 28 US 2012/0296073 A1 s Patent Application Publication Nov. 22, 2012 Sheet 25 of 28 US 2012/0296073 A1 Patent Application Publication Nov. 22, 2012 Sheet 26 of 28 US 2012/0296073 A1 Ys & Patent Application Publication Nov. 22, 2012 Sheet 27 of 28 US 2012/0296073 A1 Patent Application Publication Nov. 22, 2012 Sheet 28 of 28 US 2012/0296073 A1 US 2012/0296073 A1 Nov. 22, 2012 COMPOSITION AND METHOD bitanes and lanostanes. The pentacyclic structure forms the largest single group, the oleananes. Other major pentacyclic CROSS-REFERENCE TO RELATED triterpene classes are ursanes and lupanes while minor classes APPLICATIONS of taraxeranes, taraxastanes and friedolanes are also recogn 0001. This application is a divisional application of co ised. pending U.S. patent application Ser. No. 12/810,010, filed 21 0011. The core skeleton molecules are termed aglycones Jun. 2010, which is a U.S. National Stage Application of (also referred to as genins or Sapogenins) and are not usually International Patent Application No. PCT/GB2008/051224, found without substituents attached. The carbon skeleton of filed 22 Dec. 2008, which in turn claims the benefit of UK the most common aglycones of the oleanane class are shown Patent Application No. 0724967.5, filed 21 Dec. 2007. in Formula 1. 0002 The present invention relates to compounds obtain Formula 1 able from the Araliaceae family of plants, to compositions comprising the same and to uses therefor. 0003. The Araliaceae family of plants comprises two sub families, the Araliodideae and the Hydrocotyloideae sub families. The genera of plants covered by the Araliodideae Subfamily include Anakasia, Apiopetalum, Aralia, Arthro phyllum, Astrotricha, Boninofatsia, Brassaiopsis, Ceph alaralia, Chemodendron, Cromapanax, Cuphocarpus, Cus Sonia, Dendropanax, Eleutherococcus, XFatshedera, Fatsia, Gamblea, Gastonia, Harmsiopanax, Hedera, Heteropanax, Hunaniopanax, Kalopanax, Mackinlaya, Macropanax, Megalopanax, Merrilliopanax, Meryta, Metapanax, Mother wellia, Munroidendron, Oplopanax, Oreopanax, Osmoxylon, Panax, Polyscias, Pseudopanax, Pseudosciadium, Raukaua, Reynoldsia, Schefflera, Sciadodendron, Seemannaralia, 0012 Formula 1 shows the carbon skeleton of the olean Sinopanax, Stilbocarpa, Tetrapanax, Tetraplasandra, Treve 12-en aglycone structure. Principal attachments are most sia and Woodburnia. commonly found at the C3 and C28 positions. Other attach 0004. The subfamily Hydrocotyloideae includes the gen ment points are usually linked to an OH group, typically at the era Azorella, Centella, Hydrocotyle, Platysace and Xantho C2, C23 or C24 positions. SC. 0013. Of the oleananes, which occur in most orders of the 0005 Of the genera of species in the Araliaceae plant plant kingdom, the aglycones most commonly found are ole family, the present invention relates in particular to those of anolic acid shown in Formula 2, followed by hederagenin the Hedera genus. Species of the Hedera genus include Hed shown in Formula 3. era algeriensis, Hedera azorica, Hedera Canariensis, Hedera caucasigena, Hedera Colchica, Hedera cypria, Hedera helix, Formula 2 Hedera hibernica, Hedera maderensis, Hedera maroccana, Hedera nepalensis, Hedera pastuchowii, Hedera rhombea, Hedera sinensis and Hedera taurica. 0006 A wide variety of plant extracts are commonly used in numerous medicinal and industrial applications. 0007. One class of useful compounds obtainable from a number of plants are saponins. 0008 Saponins are so named due to their ability to form stable, soap-like foams at low concentrations (Latin Sapo-Soap); this ability was used as a quantitative assay of saponins and forms the basis of much literature on the Subject. 0009. The nomenclature of saponins was reviewed by Formula 3 Hostettmann and Marston in Saponins, p 10-17, in Phillipson, J. D. (ed.) Chemistry and Pharmacology of Natural Products (series), CUP Cambridge, 1995, starting with two basic skel etons; steroidal, having 27 carbon atoms or triterpenoid, with 30 carbon atoms. The less widely distributed steroidal forms are further divided into two classes, the spirostanes, found principally in monocotyledons such as lilies, onions, yucca and agave and the furostanes. This lattersteroidal group are of considerable commercial importance as a platform molecule for the manufacture of steroid hormones, principally from Dioscorea. A recent review has classified dammaranes, lupanes, hopanes, oleananes, ursanes and steroids according to their biosynthetic pathways. 0010. The triterpenes are a larger group consisting of two principal structural classes; either tetracyclic or pentacyclic. 0014. In broad terms, sugars are the principal substituents Tetracyclic structures are sub-divided as dammaranes, cucur found generally either as monosaccharides or as polysaccha US 2012/0296073 A1 Nov. 22, 2012 ride chains, although in Calendula officianalis (marigolds), 0033. The plant may be selected from any saponin-con saturated fatty acids are sometimes bound to the aglycone at taining plant of the Araliaceae family including all of the the C3 position. It will be appreciated however that natural generalisted above. Preferably the plant is selected from the Sources of Saponins comprise complex mixtures of com Hedera genus. Most preferably the plant is Hedera helix. pounds and that the amounts of different compounds present 0034. The inventors have found that a saponin-rich com in a sample will vary considerably from species to species. ponent can be obtained from the leaves, the fruit (including They also vary within the different parts of the plant. the seed) and other parts of the Hedera helix plant, for example the stems or the bark. However the process provides BRIEF DESCRIPTION OF THE SEVERAL particularly favourable results when carried out using fruits VIEWS OF THE DRAWINGS and/or leaves of the plant. It may also be carried out on only 00.15 Aspects and embodiments of the invention will be the seeds. more readily understood from the following detailed descrip 0035. In especially preferred embodiments the portion of tion of the various aspects of the invention taken in conjunc plant comprises fruits of the plant. It may comprise the whole tion with the accompanying drawings, which depict various fruit, including the fleshy pulp and the seed or it may comprise embodiments of the invention, in which: only the fleshy pulp part of the fruit. 0016 FIGS. 1a-i show graphs of the results of fungistatic 0036. In some embodiments the portion of plant consists action on timber decay for various species of fungi. essentially of fruit, which may be whole fruit including seeds 0017 FIG. 2 shows a plot of lesion development of P or only the fleshy portion of the fruit. infestans. 0037. The portion of plant may be harvested by any suit 0018 FIG. 3 shows a graph of the rates of tubers infected able means. It may be harvested by hand or by mechanical by blight for a control group and those treated according to means, for example using flails, combined harvesting, by embodiments of the invention.
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