559-74-0Relevant articles and documents
Dominguez et al.
, p. 224 (1973)
FRIEDELIN, D:A-FRIEDO-OLEAN-3,21-DONE AND 21α-HYDROXY-D:A-FREDO-OLEAN-3-ONE FROM KOKOONA ZEYLANICA
Gunatilaka, A. A. Leslie,Nanayakkara, N. P. Dhammika,Sultanbawa, M. Uvais S.,Balasubramaniam, Sinnathamby
, p. 2061 - 2064 (1982)
Three triterpenes obtained from inner bark of Kokoona zeylanica have been identified as friedelin, D:A-friedo-olean-3,21-dione and 21α-hydroxy-D:A-friedo-olean-3-one by spectroscopic propertiesand chemical interconversions.Their chemotaxanomic significance is emphasized.Key Word Index - Kokoona zeylanica; Celastraceae; friedelin; D:A-friedo-olean-3,21-dione; 21α-hydroxy-D:A-friedo-olean-3-one; structure elucidation; triterpenoids; chemotaxonomy.
Extraction and purification of friedelin
-
, (2009/07/10)
Friedelin is a natural compound with promising proprieties. On its own or with chemical modification it is possible to introduce relevant biological activities, e.g. anti-cancer, anti-aging and agrochemical. Its availability in significant amounts has been a major drawback on its regular use and in the pursuit of different applications. Cork and cork-derived materials (e.g. black condensate) are the most relevant sources of Friedelin in nature (up to 10% in concentration). The present invention reports straightforward procedures to extract and purify Friedelin from cork and cork-derived materials (e.g. black condensate). It uses solvent extraction and (re)crystallization techniques easy to scale up to an industrial level, with a low solvent and low time consumption, high yields, up to 2.9%, and high purity degrees, up to 96%.
Biovalorization of friedelane triterpenes derived from cork processing industry byproducts
Moiteiro, Cristina,Marcelo Curto, Maria Joao,Mohamed, Nagla,Bailen, Maria,Martinez-Diaz, Rafael,Gonzalez-Coloma, Azucena
, p. 3566 - 3571 (2007/10/03)
Here, we describe the synthesis, bioactivity screening, and structure-activity relationships of various synthetic triterpenoids prepared from the cork processing byproducts friedelin (1) and 3-hydroxyfriedel-3-en-2- one (2) via oxidative procedures. The synthesis of compounds 2α-trimethylsiloxyfriedelan-3-one (17), friedelin-2,3-lactone (18), friedelin-3-oxime (19), and friedelin-3,4-lactam (20) is also described. We have studied the insecticidal and phytotoxic potential of these compounds, their selective cytotoxic effects on insect and mammalian cells, and their antiparasitic effects. Structural modifications of the A-ring of friedelin (1) improved its insecticidal activity with derivatives 5, 2,3-secofriedelan-2-al-3- oic acid (6), its acetylated derivative 6a, 3β- and 3α- hydroxyfriedelane (9 and 10), 3α-hydroxyfriedel-2-one (11), 4β-hydroxyfriedel-3-one (16), the acetylated 10a, 3,4-secofriedelan-4-oxo- 3-oic-acid (14), lactone 18, and the oxime 19 being stronger insecticides than the parent compound. Methyl-3-nor-2,4-secofriedelan-4-oxo-2-oic acid (12) and its acetylated derivative 12a also showed insecticidal activity in contrast to their inactive parent compound 2. The postingestive effects and cytotoxicity of these compounds suggest a multifaceted insecticidal mode of action. These structural modifications did not result in better phytotoxic agents than the parent compounds except for lactam 20 and yielded several moderately active antiparasite derivatives (seco acids 6, 12, 14, and 4β -hydroxyfriedel-3- one 16) with cytotoxic effects on mammalian cells.
