Alkohol betulinowy i jego pochodne

Tomaszkiewicz-Potępa, A.; Piękoś, M.

Artykuł - szczegóły

Tytuł artykułu

Alkohol betulinowy i jego pochodne

Autorzy

Tomaszkiewicz-Potępa A. , Piękoś M.

Wybrane pełne teksty z tego czasopisma

Identyfikatory

Warianty tytułu

Betulinic alcohol and its derivatives

Języki publikacji

Abstrakty

Betulinic alkohol (lup-20(29)-en-3,28-diol) is a naturally occuring triterpene compound forming the principal extractive substance of the birch bark. The content of betulinol in the outer bark varies between 10-30% depending on the growth condition, age, season etc. Chemically, betulinol is a pentacyclic triterpene alcohol belonging to a lupane series of compouds. The characteristic feature of the lupane group is the five membered ring E and a-isopropyl group at C-19. Suberin and triterpenoids, the two major component groups in the outer bark of birch, have been investigated by many workers. Analytical procedures, starting with sample extraction and hydrolysis with ethanolic alkali, were developed for routine analysis, which triterpenoids to be identified by the chromatographic and spectroscopic methods. The functional groups in the betulinol molecule comprise primary and secondary hydroxyl groups and a double bond. Methods of synthesis and use of the chemical modification of betulinol has been investigated by many workers. The most investigated products from betulinol now are betulinic acid and his derivatives. It was isolated for the first time from many of plants. Betulin was convert to betulinic acid using two different synthetic routes. The first approach involved an oxidation of betulin using Jones reagent to betulonic acid and subsequent NaBH4 reduction to betulinic acid. The second approach involved steps utilizing different protecting groups on the alcohol functional groups of betulin and Jones’ oxidation to circumvent the isomerization of the secondary alcohol of betulinic acid. Betulinic acid was identified as a highly selective inhibitor of human melanoma. It has recently been reported to possess antitumor activity against cultured human melanoma cells. Betulinic acid has been modified at C-3, C-20 and C-28 positions. A series of w-undecanoic amides of betulinic acid derivatives were synthesized and evaluated for activity in human immunodeficiency virus type 1 (HIV-1). A novel series of w - aminoalkanoic acid derivatives of betulinic acid were synthesized and evaluated for their activity against human immunodeficiency virus (HIV). Effect of betulinic acid and radiotherapy on survival was demonstrated by autors.

Słowa kluczowe

triterpeny betulina kwas betulinowy metoda syntezy leczenie

triterpene betulinic acid synthesis

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2002

Tom

[Z] 56, 11-12

Strony

983--1001

Opis fizyczny

wykr., bibliogr. 58 poz.

Twórcy

autor

Tomaszkiewicz-Potępa A.

autor

Piękoś M.

Zakład Technologii Organicznej, Wydział Inżynierii i Technologii Chemicznej Politechniki Krakowskiej ul. Warszawska 24, 31-155 Kraków

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Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUS1-0010-0091