Isolation of hopane triterpenes and other constituents from Machaerium brasiliense vogel (Fabaceae)

• Published in: Biochemical systematics and ecology 2020-12, Vol.93, p.104182, Article 104182
• Main Authors: Silva, Juliana F., Ximenez, Gabriel R., Bianchin, Mirelli, Jasper, Jaqueline O., Pastorini, Lindamir H., Carvalho, João E., Ruiz, Ana L.T.G., Pomini, Armando M., Santin, Silvana M.O.
• Format: Article
• Language: English
• Subjects: Antioxidant activity; Cytostatic activity; Hopane triterpenes; Machaerium brasiliense
• ISSN: 0305-1978; 1873-2925
• DOI: 10.1016/j.bse.2020.104182

Phytochemical study of Machaerium brasiliense leaves extract afforded three hopane triterpenes 3,4-seco-21β-H-hop-22 (29)-en-3-oic acid (1), hopenone B (2), hopene B (3). In addition, lupeol (4), stigmasterol (5), β-sitosterol (6), daucosterol (7), uracil (8), allantoin (9) and trans-4-hydroxy-N-methylproline (10) were isolated. The structures of these compounds were established based on spectroscopic data in comparison to those described in literature. Considering the chemotaxonomic relevance of the isolated compounds, this is the first report of triterpenes 1, 2 and 3 in Fabaceae family and compounds 7, 8 and 9 in the genus Machaerium. Besides, preliminary screening on antiproliferative and antioxidant activities was performed for MBEB and its fractions. [Display omitted] •Around 50 species of Machaerium genus (Fabaceae) are endemic in Brazil.•This is the first report on chemical composition of Machaerium brasiliense leaves.•First report of daucosterol, uracil and allantoin in Machaerium genus.•First report of three hopane triterpenes in Fabaceae family.•Low polar M. brasiliense fractions showed cytostatic effect might due to steroids.