Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
  • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
  • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
  • C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
  • A61K31/05—Phenols
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01D—SEPARATION
  • B01D11/00—Solvent extraction
  • B01D11/02—Solvent extraction of solids
  • B01D11/028—Flow sheets
  • B01D11/0284—Multistage extraction
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01D—SEPARATION
  • B01D11/00—Solvent extraction
  • B01D11/02—Solvent extraction of solids
  • B01D11/0288—Applications, solvents
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01D—SEPARATION
  • B01D9/00—Crystallisation
  • B01D9/0004—Crystallisation cooling by heat exchange
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
  • A61K2236/30—Extraction of the material
  • A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
  • A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
  • A61K2236/30—Extraction of the material
  • A61K2236/37—Extraction at elevated pressure or temperature, e.g. pressurized solvent extraction [PSE], supercritical carbon dioxide extraction or subcritical water extraction
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
  • A61K36/18—Magnoliophyta (angiosperms)
  • A61K36/185—Magnoliopsida (dicotyledons)
  • A61K36/60—Moraceae (Mulberry family), e.g. breadfruit or fig

Definitions

• the present invention relates to a method for extraction of Oxyresveratrol from Artocarpus hirsutus (A. hirsutus).
• Oxyresveratrol is a hydroxyl-substituted stilbene found in the roots, leaves, stem and fruit of many widely distributed plants including Moraceae, Liliaceae, Gnetaceae, etc. The biological activity of this compound is well documented in the following scientific articles;
• Oxyresveratrol has been isolated from several Artocarpus species (A. lakoocha Roxb.; A. champlasha Roxb.; A. champlasha Roxb.; A. heterophy!lus; A. gomeziamis Wall.).
• Nasapon Povichit Ampai Plrnitivorapongkul, Maitree Suttajit and Pimpora Leelapornpisid, Antiglycation and antioxidant activities of Oxyresveratrol extracted from the heartwood of Artocarpus lakoocha Roxb., Maejo Int. J. Sci. Technol. 2010, 4(03), 454-461) using chromatographic techniques like HPLC, Column chromatography etc.
• [Para0008] Disclosed is method for extraction of Oxyresveratrol from A. hirsutus. More specifically, the invention discloses a novel method for extraction of Oxyresveratrol from A. hirsutus using a simple solvent-solvent purification method,
• FIG. 2 shows 13 C NMR of Oxyresveratrol (DMSO-d 6 , 75 MHz): ⁇ 158.75 (C-3 ' and 5 ' ), 158.37 (C-4), 156.30 (C-2), 140.36 (C-V), 127.60 (C-6), 124.97 (C- ⁇ ), 123.57 (C-a), 115.61 (C-1), 107.60 (C-5), 104.34 (C-2 ' and 6 ' ), 102.87 (C-4 ' ), 101.70 (C-3).
• Fig. 3a and 3b shows Liquid Chromatography Mass Spectrometry (LCMS) of compound Oxyresveratrol obtained from A. hirsutus
• Fig. 4 shows High Performance Liquid Chromatography (HPLC) of compound Oxyresveratrol obtained from A. hirsutus
• the present invention discloses a novel method for extraction of Oxyresveratrol from Artocarpus hirsutus, said method comprising steps of: a) Cutting, drying the wood of A. hirsutus and pulverising to coarse powder;
• step d Concentrating the extract from step c under vacuum at 50 55 °C to thick paste; SUBSTITUTE SHEET (RULE 26) e) Drying the extract from step d completely in vacuum tray dryer at 65-70 °C to get powder;
• step f Dissolving the powder from step e in ethanol (2 volumes); g) Addition of the ethanolic extract from step f slowly into 10 volumes of water under continuous stirring;
• step h Separating the insolubles obtained from step g to get clear layer by filtration;
• step k Drying the concentrated extract from step k to get powder m vacuum tray dryer at 65-70
• step n Cool the water layer from step m to 10- 15 °C for 8 h and allowed for crystallization; o) Filtering the crystals obtained from step n; p) Drying the crystals from step o in a vacuum at 70-75 °C;
• Oxyresveratrol This filtered crystallised material was characterized as Oxyresveratrol from its [ H and l3 C NMR spectra as well as from its LCMS spectrum and was comparable with the reported values.
• the isolated Oxyresveratrol shows the following values: C 14H12O4. m. p.: 191-194 °C. Color: pale brown fine powder, APCI-MS m/z 245.00 (M+H 4 ) and 245.05 (M-H " ) (Ci 4 H 12 0 4 requires 244.2426). Purity of the compound was further verified by HPLC.

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• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Natural Medicines & Medicinal Plants (AREA)
• Veterinary Medicine (AREA)
• Pharmacology & Pharmacy (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Public Health (AREA)
• General Health & Medical Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• Crystallography & Structural Chemistry (AREA)
• Epidemiology (AREA)
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• Biotechnology (AREA)
• Alternative & Traditional Medicine (AREA)
• Engineering & Computer Science (AREA)
• Mycology (AREA)
• Thermal Sciences (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
• Coloring Foods And Improving Nutritive Qualities (AREA)
• Medicines Containing Plant Substances (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Extraction Or Liquid Replacement (AREA)

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• 2016
  • 2016-12-22 CA CA3047702A patent/CA3047702C/en active Active
  • 2016-12-22 WO PCT/US2016/068161 patent/WO2018118059A1/en not_active Ceased
  • 2016-12-22 US US16/471,148 patent/US20200039907A1/en not_active Abandoned
  • 2016-12-22 JP JP2019555560A patent/JP6920462B2/ja not_active Expired - Fee Related
  • 2016-12-22 EP EP16924736.8A patent/EP3558283B1/en not_active Not-in-force

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