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Cytotoxic Activity of Triterpenoids from Cheiloclinium cognatum Branches against Chronic and Acute Leukemia Cell Lines
Author(s) -
Gonçalves Pereira Rafael César,
Gontijo Evangelista Fernanda Cristina,
Santos Júnior Valtair Severino,
Paula Sabino Adriano,
Gonçalves Maltarollo Vinícius,
Freitas Rossimiriam Pereira,
Pains Duarte Lucienir
Publication year - 2020
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.202000773
Subject(s) - friedelin , celastraceae , k562 cells , chronic leukemia , phytochemical , cytotoxic t cell , apoptosis , chemistry , leukemia , cell culture , traditional medicine , myeloid leukemia , stereochemistry , triterpenoid , biology , biochemistry , cancer research , in vitro , acute leukemia , immunology , genetics , medicine
Cheiloclinium cognatum (Miers) A.C.Sm. is an endemic species of Brazilian Cerrado that belongs to Celastraceae family. The phytochemical study of C. cognatum branches led to the identification of ten triterpenoids (TPs), 3 β ‐acyloxyurs‐12‐ene ( 1 ), friedelin ( 2 ), β ‐friedelinol ( 3 ), glut‐5‐en‐3 β ‐ol ( 4 ), α ‐amyrin ( 5 ), β ‐amyrin ( 6 ), β ‐sitosterol ( 7 ), canophyllol ( 8 ), 29‐hydroxyfriedelan‐3‐one ( 9 ) and friedelane‐3 β ,29‐diol ( 10 ). TPs 4 , 5 and 6 are described for the first Cheiloclinium genus and TPs 8 and 9 were isolated in expressive amounts. Their cytotoxic activities were evaluated against THP‐1 and K562 leukemia cell lines. TPs 3 and 5 were the most active, exhibiting lower or similar IC 50 against both cell lines when compared to the controls. Their mechanisms of action were investigated suggesting an intrinsic mitochondrial pathway of apoptosis evidenced by up‐regulation of BAK mRNA expression. Chemometric studies indicated that their activities may be related to their molecular size and shape as well as electronic interactions of C‐3 hydroxy group with molecular targets.