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GB1493926A - Pentacyclic triterpenes obtainable from terminalia sericea and their derivatives - Google Patents

Pentacyclic triterpenes obtainable from terminalia sericea and their derivatives

Info

Publication number
GB1493926A
GB1493926A GB4042/74A GB404274A GB1493926A GB 1493926 A GB1493926 A GB 1493926A GB 4042/74 A GB4042/74 A GB 4042/74A GB 404274 A GB404274 A GB 404274A GB 1493926 A GB1493926 A GB 1493926A
Authority
GB
United Kingdom
Prior art keywords
acid
free
novel
methyl
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB4042/74A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Inverni Della Beffa SpA
Original Assignee
Inverni Della Beffa SpA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Inverni Della Beffa SpA filed Critical Inverni Della Beffa SpA
Priority to GB4042/74A priority Critical patent/GB1493926A/en
Priority to ZA00750403A priority patent/ZA75403B/en
Priority to AR257368A priority patent/AR211381Q/en
Priority to DE2503135A priority patent/DE2503135C3/en
Priority to CA218,831A priority patent/CA1061777A/en
Priority to JP1145775A priority patent/JPS5418328B2/ja
Priority to ES434246A priority patent/ES434246A1/en
Priority to FR7502779A priority patent/FR2258849B1/fr
Priority to US05/778,458 priority patent/US4103025A/en
Priority to US05/778,457 priority patent/US4147777A/en
Publication of GB1493926A publication Critical patent/GB1493926A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Pain & Pain Management (AREA)
  • Dermatology (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Saccharide Compounds (AREA)
  • Peptides Or Proteins (AREA)

Abstract

1493926 Pentacyclic triterpenes from Terminalia sericea INVERNI DELLA BEFFA SpA 10 Jan 1975 [29 Jan 1974] 04042/74 Heading C2U Novel terpenic compounds have the formulae wherein OR 1 , OR 2 , OR 3 and OR 4 are free or acylated hydroxy groups and COOR 5 is a free, salified or esterified carboxyl group. Also novel is the 18α-epimer of the compound of Formula (II) wherein R 1 , R 2 , R 3 and R 4 are each acetyl and R 5 is methyl. The free tetrol acid and its D-glucosyl ester are isolated from Terminalia sericea plants by extraction with an organic solvent. They may be separated by a fractionation step making use of the fact that the free acid (named sericic acid) is preferentially soluble in chlorinated hydrocarbon solvents while the glucosyl ester (named sericoside) is preferentially soluble in aqueous solutions. Sericic acid and sericoside may be interconverted and converted to other compounds of the above formulae by known methods of esterification, hydrolysis, oxidation and salt formation. The 18α-epimer of methyl tetraacetyl sericate is prepared by treating methyl triacetyl sericate with 40% hydrobromic acid in acetic acid. The novel compounds possess cicatrizing and anti-inflammatory properties, and they may be made up into pharmaceutical compositions with suitable carriers.
GB4042/74A 1974-01-29 1974-01-29 Pentacyclic triterpenes obtainable from terminalia sericea and their derivatives Expired GB1493926A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
GB4042/74A GB1493926A (en) 1974-01-29 1974-01-29 Pentacyclic triterpenes obtainable from terminalia sericea and their derivatives
ZA00750403A ZA75403B (en) 1974-01-29 1975-01-21 Novel terpenes
AR257368A AR211381Q (en) 1974-01-29 1975-01-21 PROCEDURE FOR THE PRODUCTION OF SERICOSIDE (D-GLOCUPYRANOSIDE OF SERICICO ACID), SERICICO ACID AND ETHYLASINE-DIALKYLIC ACID, SALTS AND DERIVATIVES
DE2503135A DE2503135C3 (en) 1974-01-29 1975-01-27 Terpene compounds, processes for their preparation and pharmaceuticals containing these products
CA218,831A CA1061777A (en) 1974-01-29 1975-01-28 Terpenes
JP1145775A JPS5418328B2 (en) 1974-01-29 1975-01-29
ES434246A ES434246A1 (en) 1974-01-29 1975-01-29 Pentacyclic triterpenes obtainable from terminalia sericea and their derivatives
FR7502779A FR2258849B1 (en) 1974-01-29 1975-01-29
US05/778,458 US4103025A (en) 1974-01-29 1977-03-17 Novel terpenes
US05/778,457 US4147777A (en) 1974-01-29 1977-03-17 Sericosides and method of use

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4042/74A GB1493926A (en) 1974-01-29 1974-01-29 Pentacyclic triterpenes obtainable from terminalia sericea and their derivatives

Publications (1)

Publication Number Publication Date
GB1493926A true GB1493926A (en) 1977-11-30

Family

ID=9769654

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4042/74A Expired GB1493926A (en) 1974-01-29 1974-01-29 Pentacyclic triterpenes obtainable from terminalia sericea and their derivatives

Country Status (8)

Country Link
JP (1) JPS5418328B2 (en)
AR (1) AR211381Q (en)
CA (1) CA1061777A (en)
DE (1) DE2503135C3 (en)
ES (1) ES434246A1 (en)
FR (1) FR2258849B1 (en)
GB (1) GB1493926A (en)
ZA (1) ZA75403B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4752606A (en) * 1982-04-27 1988-06-21 501 Noristan Limited Pharmaceutical compositions and preparations thereof
WO2002087534A2 (en) * 2001-04-26 2002-11-07 Beiersdorf Ag Cosmetic or dermatological formulations having a content of sericoside
WO2003026603A1 (en) * 2001-09-21 2003-04-03 Beiersdorf Ag Cosmetic and/or dermatological active ingredient combination of triterpenes and cyclodextrins
WO2007060684A1 (en) * 2005-11-25 2007-05-31 Council Of Scientific & Industrial Research An improved process for the isolation of arjunic acid from the bark of the tree terminalia arjuna and the use of this compound in the treatment of cancer

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4752606A (en) * 1982-04-27 1988-06-21 501 Noristan Limited Pharmaceutical compositions and preparations thereof
WO2002087534A2 (en) * 2001-04-26 2002-11-07 Beiersdorf Ag Cosmetic or dermatological formulations having a content of sericoside
WO2002087532A2 (en) * 2001-04-26 2002-11-07 Beiersdorf Ag Cosmetic or dermatological formulations having a content of sericoside
WO2002087532A3 (en) * 2001-04-26 2003-04-24 Beiersdorf Ag Cosmetic or dermatological formulations having a content of sericoside
WO2002087534A3 (en) * 2001-04-26 2003-10-02 Beiersdorf Ag Cosmetic or dermatological formulations having a content of sericoside
WO2003026603A1 (en) * 2001-09-21 2003-04-03 Beiersdorf Ag Cosmetic and/or dermatological active ingredient combination of triterpenes and cyclodextrins
WO2007060684A1 (en) * 2005-11-25 2007-05-31 Council Of Scientific & Industrial Research An improved process for the isolation of arjunic acid from the bark of the tree terminalia arjuna and the use of this compound in the treatment of cancer

Also Published As

Publication number Publication date
JPS50111213A (en) 1975-09-01
FR2258849B1 (en) 1978-07-21
ZA75403B (en) 1976-01-28
ES434246A1 (en) 1976-12-16
DE2503135B2 (en) 1979-06-21
CA1061777A (en) 1979-09-04
AR211381Q (en) 1977-12-15
DE2503135C3 (en) 1980-02-21
DE2503135A1 (en) 1975-07-31
FR2258849A1 (en) 1975-08-22
JPS5418328B2 (en) 1979-07-06

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years

Effective date: 19950109