Cytotoxic Barrigenol-like Triterpenoids from an Extract of Cyrilla racemiflora Housed in a Repository

Abstract

Two new [(+)-cyrillins A (1) and B (2)] and four known barrigenol-like triterpenoids (3–6), along with betulinic acid and (+)-3β-O-trans-feruloylbetulinic acid, were isolated from a sample-restricted CH2Cl2-soluble extract of the bark of Cyrilla racemiflora, collected in Dominica. The structures of the new compounds were elucidated by interpretation of their spectroscopic data, and the absolute configuration of the cyclic 1,2-diol unit of (+)-cyrillin A (1) was ascertained by analysis of the electronic circular dichroism (ECD) spectrum induced with [Mo2(OAc)4]. In the case of (+)-cyrillin B (2), which was found to contain a di-angeloylated glucose residue, the structure proposed was supported by analysis of its MS2 and MS3 spectra. All compounds isolated were evaluated for their cytotoxicity against HT-29 human colon cancer cells, and the known compound, (+)-barringtogenol B (3), was found to be the most potent, exhibiting an IC50 value of 1.7 µM. This compound also showed inhibitory activity toward the CCD-112CoN human normal colon cell line, with an IC50 value of 5.9 µM, indicating a lack of cytotoxic selectivity.

Cytotoxic and NF-κB and mitochondrial transmembrane potential inhibitory pentacyclic triterpenoids from Syzygium corticosum and their semi-synthetic derivatives

“…To identify the main functional groups responsible for the activities of (+)-ursolic acid (1) , two of its analogues, (+)-oleanolic acid ( 8 , a commercially available sample) and (+)-betulinic acid (9) , 39 were evaluated for their cytotoxic and NF-κB and MTP inhibitory activities. Neither 8 nor 9 showed activity in any of the cytotoxicity assays.…”

The antitumor activity screening of chemical constituents from Camellia nitidissima Chi

“…1 . Finally, 16 compounds, including flavonoids, C-27 steroidal saponins, monoterpenes, and triterpenes were identified as follows: compound 1: 3β-acetoxy-20-lupanol ( 11 ); compound 2: 3β,6α,13β-trihydroxyolean-7-one ( 12 ); compound 3: A1-barrigenol-22a-angelate ( 13 ); compound 4: (3R, 6R, 7E)-3-hydroxy-4,7-megastigmadien-9-one ( 11 ); compound 5: β-D-glucopyranoside, 3-[(1-oxo-9,12,15-octadecadienyl)oxy]-2-[(1-oxo-9,12,15-octadecatrienyl)oxy ( 14 ); compound 6: β-D-glucopyranoside, 2-[[(9Z,12Z,15Z)-1-oxo-9,12,15-octadecatrien-1-yl]oxy]-3-[(1-oxooctyl)oxy]propyl ( 15 ); compound 7: β-D-Glucopyranoside,3-[(1-oxo-9,12-octade-cadienyl)oxy]-2-[(1-oxo-9,12,15-octadecatrienyl)oxy]propyl ( 16 ); compound 8: kaempferol3-O-[2-O-(trans-p-coumaroyl)-3-O-α-D-glucopyranosyl]-α-D-glucopyranoside ( 11 ); compound 9: stigmasta-7,22-diene-3-O-[α-L-arabinopyranosyl(1→2)]-β-D-gala-ctopyranoside ( 11 ); compound 10: β-D-galactopy ranoside, (2S)-2-(acetyloxy)-3-[[(9Z)-1-oxo-9-octadecen-1-yl]oxy]propyl ( 17 ); compound 11: aromadendrin( 11 ); compound 12: α-spinasteryl-β-D-glucopyranoside ( 11 ); compound 13: catechin ( 11 ); compound 14: phlorizin4′-O-β-D-glucopyranoside ( 11 ); compound 15: 3β,6α,13β-trihydroxyolean-7-one ( 11 ); compound 16: dodecanoic acid ( 11 ).…”

Natural Product Triterpenoids and Their Semi-Synthetic Derivatives with Potential Anticancer Activity

“…In our continuing search for anticancer agents from tropical plants, a barrigenol-like triterpenoid, (+)-barringtogenol B (9) (▶ Fig. 2), was isolated as a major cytotoxic component from an extract of the bark of Cyrilla racemiflora L. (Cyrillaceae), collected in Dominica [51]. This compound exhibited an IC 50 value of 1.7 µM for HT-29 human colon cancer cells (the positive control, paclitaxel, showed an IC 50 value of 0.8 nM) [51].…”

“…2), was isolated as a major cytotoxic component from an extract of the bark of Cyrilla racemiflora L. (Cyrillaceae), collected in Dominica [51]. This compound exhibited an IC 50 value of 1.7 µM for HT-29 human colon cancer cells (the positive control, paclitaxel, showed an IC 50 value of 0.8 nM) [51]. A preliminary SAR study showed that an angeloyl group attached at either C-21 or C-22 is necessary for barrigenol-like triterpenoids to mediate their cytotoxicity.…”

“…A preliminary SAR study showed that an angeloyl group attached at either C-21 or C-22 is necessary for barrigenol-like triterpenoids to mediate their cytotoxicity. The presence of a hydroxy group at the C-24 position enhances the cytotoxicity of some barrigenollike triterpenoids, but introducing a hydroxy group at the C-15 position results in the potency being decreased [51].…”