Botanical Extracts and Compounds from Castanea Plants and Methods of Use

Patent metadata

Field	Value
Publication number	US-2016375074-A1
Application number	US-201615192514-A
Country	US
Kind code	A1
Filing date	Jun 24, 2016
Priority date	Jun 26, 2015
Publication date	Dec 29, 2016
Grant date	—

Abstract

This disclosure relates to extracts from chestnut plants and compositions comprising compounds contained therein. In certain embodiments, the extracts are derived from the leaves of a Castanea plant. In certain embodiments, the disclosure relates to methods of treating or preventing bacterial infections, acne, and other related uses.

First claim

1 . An extract comprising a leaf derived mixture of compounds from a Castanea plant wherein the extracting process comprises the steps of:
mixing a leaf with methanol under conditions such that leaf compounds dissolves in the methanol and removing the methanol providing a methanol derived mixture of compounds, partitioning the methanol derived mixture of compounds in hexane and water providing a water derived mixture of compounds, partitioning the water derived mixture of compounds by mixing the water with ethyl acetate under conditions such that leaf compounds dissolve in the ethyl acetate and removing the ethyl acetate providing an ethyl acetate derived mixture of compounds; and purifying the ethyl acetate derived mixture of compounds by liquid chromatography through silica with a mobile phase comprising hexane and ethyl acetate; wherein the mobile phase comprises increasing amounts of ethyl acetate, and a mobile phase fraction is isolated comprising a leaf derived mixture of compounds which does not contain chlorogenic acid, ellagic acid, hyperoside, isoquercitrin, or rutin.

2 . The extract of claim 1 , wherein the mixture of compounds comprises components having the following formulas and relative abundance,
C 39 H 59 O 8 or C 38 H 55 O 9 , or mixture, with a relative abundance of 0.1 to 0.9%; C 35 H 59 O 6 with a relative abundance of 0.1 to 0.9%; C 31 H 49 O 6 with a relative abundance of 1.0 to 2.0%; C 32 H 51 O 7 with a relative abundance of 0.1 to 0.9%; C 30 H 48 O 5 with a relative abundance of 3.0 to 5.0%; C 30 H 48 O 6 with a relative abundance of 6.0 to 8.0%; and C 30 H 45 O 5 with a relative abundance of 2.0 to 4.0%.

3 . The extract of claim 3 , further comprises additional components of different compounds having the following formula and relative abundance,
C 35 H 59 O 6 with a relative abundance of 0.2 to 0.4; C 27 H 23 O 18 with a relative abundance of 0.05 to 0.30; C 39 H 31 O 15 with a relative abundance of 0.50 to 0.80; C 17 H 11 O 8 or C 20 H 11 O 4 N 2 , or mixture, with a relative abundance of 0.5 to 1.0; and C 34 H 29 O 15 with a relative abundance of 0.2 to 0.4%.

4 . The extract of claims 1 , wherein the mixture comprises at least one component from each of the following groups a) to g):
a) a compound selected from escigenin tetraacetate (6CI); tetraacetate (7CI,8CI) 16α,21α-epoxy-olean-9(11)-ene-3β,22β,24,28-tetrol; tetraacetate aescigenin; triacetate (8CI) cyclic 16,22-acetal-olean-12-ene-3β,16α,21β,22α,28-pentol; and triacetate (8CI) cyclic 22,28-acetal-olean-12-ene-3β,16α,21β,22α,28-pentol, or mixture of two, three, four or all; b) a compound selected from stigmastane and (3β,4β,16α,21β,22α)-16,21,22,23,28-pentamethoxy (9CI) olean-12-en-3-ol, or mixture; c) amirinic acid; d) a compound selected from 21-acetate protoescigenin, 16-acetate protoescigenin, 22-acetate protoescigenin and 28-acetate protoescigenin, or mixture of two, three, four or all; e) a compound selected from 16,21-epoxy-(3β,4β,16α,21α,22β)-olean-12-ene-3,22,24,28-tetrol (9CI); asiatic acid; arjunolic acid; and isoescigenin, or mixture of two, three, or all; f) a compound selected from camelliagenin E; brahmic acid; sericic acid; belleric acid; and 2,3,23,24-tetrahydroxy-(2α,3β)-urs-12-en-28-oic acid, or mixture of two, three, four or all; and g) ouillaic acid.

5 . The extract of claim 4 , wherein the mixture comprises at least one component from each of the following groups a) to d):
a) a compound selected from stigmastane and (3β,4β,16α,21β,22α)-16,21,22,23,28-pentamethoxy (9CI) olean-12-en-3-ol or a mixture; b) a compound selected from 1,3,6-tri-O-galloylglucose; 1,2,6-tri-galloyl-β-D-glucose; 1,2,3 -tri-O-gall oylglucose; 1,2,3 -tri-O-galloyl-β-D-glucopyranose; 2′,3,5-tri-O-galloyl-D-hamamelose; 2-C-[[(3 ,4, 5-trihydroxyb enzoyl)oxy]methyl]-1,5-bis(3 ,4, 5-trihydroxybenzoate) D-ribofuranose; kurigalin; and 3,4,6-tri-O-galloyl-D-glucose, or mixture of two, three, four, five, six, seven, or all; c) castanoside B; and d) a compound selected from 3,4,3′-tri-O-methylellagic acid and 3,3′,4′-tri-O-methylellagic acid, or a mixture.

6 . A pharmaceutical or cosmetic formulation comprising the extract or one or more compounds in the extract of claim 1 and a pharmaceutically acceptable excipient or cosmetically acceptable excipient.

7 . A liquid or gel formulation of claim 6 , optionally further comprising an antibiotic agent, a topical steroid, an anti-inflammatory agent, a promoter of skin barrier function, a skin moisturizer or combinations thereof.

8 . The formulation of claim 6 comprising an enteric coating.

9 . A solid or liquid soap or lotion comprising the extract or one or more compounds in the extract of claim 1 and a fatty acid.

10 . A medical device comprising a coating comprising the extract or one or more compounds in the extract of claim 1 .

11 . A wound dressings or wound rinse comprising the extract or one or more compounds in the extract of claim 1 wherein the wound dress comprises an absorbent pad and optionally an adhesive.

12 . A tampon comprising the extract or one or more compounds in the extract of claim 1 wherein the tampon comprises an absorbent material.

13 . A method of treating or preventing a bacterial infections comprising administering or contacting a formula comprising the extract or one or more compounds in the extract as in claim 1 to a subject in need thereof.

14 . The method of claim 13 , wherein the subject is at risk of, exhibiting symptoms of, or diagnosed with toxic shock syndrome, scalded skin syndrome, abscesses, furuncles, cellulitis, folliculitis, bloodstream infections, medical device infections, pneumonia, osteomyelitis, staphylococcal food poisoning, skin and soft tissue infections, endocarditis, eczema, atopic dermatitis, psoriasis, impetigo, septic arthritis, brain abscess, burn wounds, venous ulcers, diabetic foot ulcers, surgical wounds, post-operation infections, carbuncles, meningitis, bacteremia, necrotizing pneumonia, or necrotizing fasciitis.

15 . The method of claim 13 , wherein the formula is administered in combination with an antibiotic agent.

16 . A method of treating acne comprising administering a composition comprising an extract the extract or one or more compounds in the extract as in claim 1 to a subject at risk of, exhibiting symptoms of, or diagnosed with abnormal acne.

Assignees

• Univ Emory
• Univ Iowa Res Found

Inventors

• Quave Cassandra L
• Lyles James
• Horswill Alexander R

Classifications

• A61K9/0036

  Devices retained in the vagina or cervix for a prolonged period, e.g. intravaginal rings, medicated tampons, medicated diaphragms · CPC title

• A61L15/44

  Medicaments · CPC title

• A61K36/49 Primary

  Fagaceae (Beech family), e.g. oak or chestnut · CPC title

• A61K45/06

  Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca · CPC title

• A61Q19/10

  Washing or bathing preparations · CPC title