WO2020068004A3 - Antituberculosis lanostane triterpenoid and method of making the compounds - Google Patents

Antituberculosis lanostane triterpenoid and method of making the compounds Download PDF

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Publication number
WO2020068004A3
WO2020068004A3 PCT/TH2019/000037 TH2019000037W WO2020068004A3 WO 2020068004 A3 WO2020068004 A3 WO 2020068004A3 TH 2019000037 W TH2019000037 W TH 2019000037W WO 2020068004 A3 WO2020068004 A3 WO 2020068004A3
Authority
WO
WIPO (PCT)
Prior art keywords
thx
trien
strain
oic acid
xdr
Prior art date
Application number
PCT/TH2019/000037
Other languages
French (fr)
Other versions
WO2020068004A2 (en
Inventor
Masahiko Isaka
Panida CHINTHANOM
Vanicha VICHAI
Kanchana DOKLADDA
Malipan SAPPAN
Chawanee Thongpanchang
Original Assignee
National Science And Technology Development Agency
The Thai Land Research Fund (Trf)
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 National Science And Technology Development Agency, The Thai Land Research Fund (Trf) filed Critical National Science And Technology Development Agency
Publication of WO2020068004A2 publication Critical patent/WO2020068004A2/en
Publication of WO2020068004A3 publication Critical patent/WO2020068004A3/en

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Classifications

    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • 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
    • A61K36/06—Fungi, e.g. yeasts
    • A61K36/07—Basidiomycota, e.g. Cryptococcus
    • A61K36/074—Ganoderma
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A61P31/06—Antibacterial agents for tuberculosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Mycology (AREA)
  • Epidemiology (AREA)
  • Oncology (AREA)
  • Biotechnology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Engineering & Computer Science (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Botany (AREA)
  • Medical Informatics (AREA)
  • Microbiology (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

A new lanostane triterpenoid (24E)-3β-acetoxy-15α-propionyloxylanosta-7,9( 11 ),24-trien-26-oic acid (GA003), is synthesized by acylation reaction of a naturally occurring fungal metabolite, (24E)-3β-acetoxy-15α-hydroxylanosta-7,9( 11 ),24-trien-26-oic acid (ganoderic acid T-O). GA003 is identified as the most potent antimycobacterial against Mycobacterium tuberculosis H37Ra (MIC 0.0977 μg/ml) through a series of structural modifications (semi-synthesis) of a lead natural product, (24E)-3β,15α diacetoxylanosta-7,9(1 1),24-trien-26-oic acid. GA003 exhibits potent growth inhibitory activity against Mycobacterium tuberculosis strains H37Rv (virulent strain), THX-0001 (pre-XDR strain), THX-0002 (XDR strain), and THX-0003 (XDR strain), with MIC values of 0.3125, <0.156, 0.625, and 1.25 μg/ml, respectively, while showing very weak cytotoxicity to Vero cells (African green monkey kidney fibroblasts). Therefore, GA003 and pharmaceutical compositions containing GA003 may be useful for the treatment of tuberculosis.
PCT/TH2019/000037 2018-09-28 2019-08-30 Antituberculosis lanostane triterpenoid and method of making the compounds WO2020068004A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TH1801006027 2018-09-28
TH1801006027 2018-09-28

Publications (2)

Publication Number Publication Date
WO2020068004A2 WO2020068004A2 (en) 2020-04-02
WO2020068004A3 true WO2020068004A3 (en) 2020-06-25

Family

ID=69952023

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/TH2019/000037 WO2020068004A2 (en) 2018-09-28 2019-08-30 Antituberculosis lanostane triterpenoid and method of making the compounds

Country Status (1)

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WO (1) WO2020068004A2 (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140294753A1 (en) * 2013-03-29 2014-10-02 Double Crane Biotechnology Co. LTD Novel use of ganodermic acids for treating cancer

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140294753A1 (en) * 2013-03-29 2014-10-02 Double Crane Biotechnology Co. LTD Novel use of ganodermic acids for treating cancer

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ARPHA ,C.PHOSRI, N. SUWANNASAI, W. MONGKOLTHANARUK, S. SODNGAM: "Astraodoric Acids A-D: New Lanostane Triterpenes from Edible Mushroom Astraeus odoratus and Their Anti-Mycobacterium tuberculosis H37Ra and Cytotoxic Activity", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 60, no. 39, 10 September 2012 (2012-09-10), pages 9834 - 9841, XP055721231 *
ISAKA, P. CHINTANOM, M. SAPPAN, S. SUPOTHINA, V. VICHAI, K. DANWISWTKANJANA, T. BOONPRATUANG, K. D. HYDE, R. CHOEYKLIN: "Antitubercular Activity of Mycelium-Associated Ganoderma Lanostanoids", JOURNAL OF NATURAL PRODUCTS, vol. 80, 15 May 2017 (2017-05-15), pages 1361 - 1369, XP055721228 *

Also Published As

Publication number Publication date
WO2020068004A2 (en) 2020-04-02

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