Cytotoxic Steroidal Alkaloids from Kibatalia laurifolia

Abstract

Four new steroids, 3-epi-gitingensine (1), N-acetylgitingensine (6), kibalaurifoline (7) and kibalaurifenone (8), along with the known paravallarine (2), 7α-hydroxyparavallarine (3), gitingensine (4), and N-methylgitingensine (5) were isolated from the leaves of Kibatalia laurifolia. Their structures were determined primarily from mass spectrometry and 2D NMR analyses. On the basis of the known absolute configurations of 2 and 4, the absolute configurations of the new compounds were proposed. Due to the structural relationships of compounds 1-8, a biosynthetic pathway was suggested. Compound 2 was cytotoxic to KB cells (IC50 12.8 μM), followed by 1 with IC50 21.2 μM.

Cytotoxic Steroids from the Trunk ofBerberis koreana

“…1,2) Many of them showed interesting oxygenation patterns and structural modifications of both the side chain and polycyclic core. These steroids have attracted strong interest for cell biology and pathophysiology because of their wide range of biological activities, in particular their cytotoxicity.…”

“…These steroids have attracted strong interest for cell biology and pathophysiology because of their wide range of biological activities, in particular their cytotoxicity. [1][2][3] As part of our efforts to screen the bioactive constituents of Korean medicinal plants with potential anti-tumor activities, we found that an MeOH extract of the trunk of Berberis koreana exhibited considerable cytotoxic activity against cultured human tumor cell lines in vitro. 4,5) B. koreana (Berberidaceae), one of the endemic Korean plants, is used as a traditional Korean medicine for treating fever, gastroenteritis, sore throats, and conjunctivitis.…”

Antimalarial and cytotoxic activities of pregnene-type steroidal alkaloids from Holarrhena pubescens roots

“…In the HMBC spectrum, the correlations from H-3 (δ H 6.22) to C-1 (δ C 33.1), C-2 (δ C 23.5) and C-5 (δ C 161.5), of H-4 (δ H 6.13) to C-2 (δ C 23.5), C-5 (δ C 161.5), C-6 (δ C 124.0) and C-10 (δ C 36.6), of H-6 (δ H 5.66) to C-4 (δ C 127.8), C-8 (δ C 47.5) and C-10 (δ C 36.6), of H-8 (δ H 2.65) to C-6 (δ C 124.0), C-7 (δ C 200.6), C-9 (δ C 49.9), C-10 (δ C 36.6) and C-14 (δ C 49.1), and of H 3 -19 (δ H 1.18) to C-1 (δ C 33.1), C-5 (δ C 161.5), C-9 (δ C 49.9) and C-10 (δ C 36.6) confirmed the location of the two conjugated double bonds at C-3-C-4-C-5-C6 and the ketone group at C-7. Comparison of the 1 H and 13 C NMR spectral data between compound 1 and kibalaurifenone (Phi et al 2011) revealed a close structural similarity, except for the replacement of a lactone ring with a 1pyrroline ring, in which the imino proton (δ H 7.59) at C-18 was determined from the HMBC correlations of H-18 to C-13 (δ C 67.1), and C-20 (δ C 68.…”

Potential of Steroidal Alkaloids in Cancer: Perspective Insight Into Structure–Activity Relationships

“…It was observed that the acetylation of C-3 amino reduced the cytotoxic activity against KB cells ( 16 ). Since paravallarine (16) was more active than methylgitingensine (19), allowing a conclusion that the configuration of C-3 can influence cytotoxic activity ( 16 ). Minorics et al.…”

“…Paravallarine ( 16), 7Rhydroxyparavallarine (17), gitingensine (18), methylgitingensine (19), and N-acetylgitingensine (20) were isolated from Kibatalia laurifolia and tested for cytotoxic activity against KB cell lines by Phi et al The results showed that paravallarine (16) presented cytotoxicity with IC 50 of 12.8 mM, gitingensine (18) and methylgitingensine (19) displayed weak cytotoxicity with IC 50 ranged from 21 to 42 mM, and N-acetylgitingensine (20) showed no cytotoxicity (IC 50 > 50 mM) (Figure S1). It was observed that the acetylation of C-3 amino reduced the cytotoxic activity against KB cells (16). Since paravallarine (16) was more active than methylgitingensine (19), allowing a conclusion that the configuration of C-3 can influence cytotoxic activity (16).…”