# US 2010/0168223 A1 · 7-Hydroxy Chromones As Potent Antioxidants

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- Number: US 2010/0168223 A1
- Document ID: US20100168223A1
- Status: Published application
- Kind: A1
- Application number: 12/721,371
- Filed: 2010-03-10
- Published: 2010-07-01
- Earliest claimed: 2002-05-03
- Assignees: Unigen Pharmaceuticals, Inc.
- Inventors: Qi Jia; Thomas M. Farrow
- Web page: https://patentgrep.com/patent/US20100168223A1

## CPC

- A61K 36/48: Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
- A61K 31/353: 3,4-Dihydrobenzopyrans, e.g. chroman, catechin
- A61K 31/7034: attached to a carbocyclic compound, e.g. phloridzin
- A61K 31/7048: having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin {, digitoxin or digoxin}
- A61K 36/185: Magnoliopsida (dicotyledons)
- A61K 36/282: Artemisia, e.g. wormwood or sagebrush
- A61K 36/296: Epimedium
- A61K 36/38: Clusiaceae, Hypericaceae or Guttiferae (Hypericum or Mangosteen family), e.g. common St. Johnswort
- A61K 36/489: Sophora, e.g. necklacepod or mamani
- A61K 36/704: Polygonum, e.g. knotweed
- A61K 36/886: Aloeaceae (Aloe family), e.g. aloe vera
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/08: Vasodilators for multiple indications
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/14: Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 27/12: for cataracts
- A61P 35/00: Antineoplastic agents
- A61P 39/06: Free radical scavengers or antioxidants
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention describes the identification and purification of 7-hydroxychromes that exhibit potent antioxidant activity. In one embodiment the present invention includes a method for providing an antioxidant to a host in need thereof, comprising administering an effective amount of a 7-hydroxychrome or a mixture of 7-hydroxychromones. The present invention includes methods that are effective in inhibiting free radical and oxidation caused damage through the simultaneous suppression of free radical generation and the suppression of the production of reactive oxygen species (ROS). The present invention also includes methods for preventing and treating ROS mediated diseases and conditions and diseases and conditions associated with other oxidative processes. The method for preventing and treating ROS mediated diseases and conditions and diseases and conditions associated with other oxidative processes is comprised of administering to a host in need thereof an effective amount of a composition comprised of a 7-hydroxychrome or a mixture of 7-hydroxychromones and a pharmaceutically acceptable carrier. Included in this invention is an improved method to isolate and purify 7-hydroxychromones from plant sources.

## Claims

### Claim 1

A method for preventing and treating ROS mediated diseases and conditions comprising administering to a host in need thereof an effective amount of a composition having a 7-hydroxychrome or a mixture of 7-hydroxychromones and a pharmaceutically acceptable carrier.

### Claim 2 (depends on 1)

The method of claim 1 wherein said 7-hydroxychrome is selected from the group of compounds having the following structure:
wherein
R1, R2 and R3 are independently selected from the group consisting of —H, —OH, —SH, alkyl, alkenyl, oxoalkyl, oxoalkenyl, hydroxylalkyl, hydroxylalkenyl, —OR, —SR, —NH2, —NRH, —NR2, —NR3+X−, an ester selected from the group consisting of gallate, acetate, cinnamoyl and hydroxyl-cinnamoyl esters, trihydroxybenzoyl esters and caffeoyl esters; and a hexose or pentose, wherein said hexose or pentose is linked to the 7-hydroxychromone by a carbon, nitrogen sulfur or oxygen and wherein said hexose or pentose is selected from the group consisting of aldopentoses, methyl aldopentose, aldohexoses, ketohexose and their chemical derivatives thereof; including a dimer, trimer and other polymerized chromones;
wherein said alkyl and/or alkenyl group is a straight and/or branched chain having between 1-20 carbon atoms with and/or without double bonds in different positions;
X is selected from the group of pharmaceutically acceptable counter anions including hydroxyl, chloride, iodide, sulfate, phosphate, acetate, fluoride, carbonate, etc.; and
R is an alkyl group having between 1-20 carbon atoms and a pharmaceutically acceptable carrier.

### Claim 3 (depends on 2)

The method of claim 2 wherein said 7-hydroxychrome is selected from aloesin or aloeresin A.

### Claim 4 (depends on 1)

The method of claim 1 wherein said compound is obtained by organic synthesis.

### Claim 5 (depends on 1)

The method of claim 1 wherein said compound is from a plant part.

### Claim 6 (depends on 5)

The method of claim 5 wherein said plant is selected from the group consisting of the genus of Acacia, Adina, Aloe, Alternaria, Amoora, Antidesma, Artemisia, Baeckia, Cassia, Clusea, Cnidium, Convolvulus, Epimedium, Eriosema, Eriostemon, Eugenia, Garcinia, Hypericum, Lindenbergia, Pancratium, Penicillium, Polygonum, Ptaeroxylon, Rheum, Sophora, Stephanitis, Syzygium, Talaromyces and Zonaria.

### Claim 7 (depends on 5)

The method of claim 5 wherein said plant is selected from the group consisting of Acacia catechu, Acacia concinna, Aloe arborescens, Aloe barbadensis, Aloe cremnophila, Aloe ferox, Aloe saponaria, Aloe vera, Aloe vera var. chinensis, Antidesma membranaceum, Artemisia capillaries, Baeckia frutescens, Epimedium sagittatum, Garcinia dulcis, Hypericum japonicum, Polygonum cuspidatum, Sophora tomentosa, and Stephanitis rhododendri.

### Claim 8 (depends on 5)

The method of claim 5 wherein said plant part is selected from the group consisting of stems, stem barks, trunks, trunk barks, twigs, tubers, roots, root barks, young shoots, seeds, rhizomes, flowers and other reproductive organs, leaves and other aerial parts.

### Claim 9 (depends on 1)

The method of claim 1 wherein the ROS mediated diseases and conditions are selected from the group consisting of atherosclerosis, coronary heart diseases, cataracts, dementia, Alzheimer's disease, cognitive dysfunction, diabetes mellitus, cancer, skin photo aging, skin wrinkles, sun burns, melanoma, and other degenerative processes associated with aging.

### Claim 10 (depends on 1)

The method of claim 1 wherein the composition is comprised of 0.01% to 100% of the 7-hydroxychrome.

### Claim 11 (depends on 1)

The method of claim 1 wherein the composition is administered in a dosage selected from 0.01 to 200 mg/kg of body weight.

### Claim 12 (depends on 1)

The method of claim 1 wherein the routes of the administration are selected from the group consisting of oral, topical, suppository, intravenous, and intradermic, intragaster, intramusclar, intraperitoneal and intravenous administration in an appropriate pharmaceutical formula.

### Claim 13

A method for isolating and purifying a composition of 7-hydroxychromones from plants containing said compounds, said method comprising:
a) extracting the ground biomass of the plant with a solvent;
b) neutralizing and concentrating said extract; and
c) purifying said extract from step b) by polyamide or LH-20 chromatography.

### Claim 14 (depends on 13)

The method of claim 13 wherein the composition of chromones is extracted with a solvent selected from the group consisting of water, alcohol, an organic solvent and/or a combination thereof.

### Claim 15 (depends on 13)

The method of claim 13 wherein the extract is further purified using a method selected from the group consisting of recrystallization, solvent partition, precipitation, sublimation, and/or chromatographic separation.