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A plausible biogenetic pathway of lupeol
Source publication
Dehaasia is a member Lauraceae. It is locally known as ‘gajus hutan’ or ‘pekan’. A triterpenoid, lupeol was isolated from the bark of Dehaasia cuneate. The structure of the isolated compound was determined using spectroscopic methods, such as UV–vis, FT-IR, 1D and 2D NMR, and mass spectrometer. The isolated compound was tested against Gram-negative...
Contexts in source publication
Context 1
... rearrangement reaction to form bacharenyl cation. A further electrophilic addition of bacharenyl cation results in lupanyl cation, which is converted to lupeol (1) by deprotonation of the methyl group (C-29) by lupeol synthase (LUS) ( Gallo and Sarachine, 2009;Phillips et al., 2006). A plausible biogenetic pathway from lupeol is shown in Fig. 2. ...
Context 2
... rearrangement reaction to form bacharenyl cation. A further electrophilic addition of bacharenyl cation results in lupanyl cation, which is converted to lupeol (1) by deprotonation of the methyl group (C-29) by lupeol synthase (LUS) ( Gallo and Sarachine, 2009;Phillips et al., 2006). A plausible biogenetic pathway from lupeol is shown in Fig. 2. ...
Citations
... When a double bond in a triterpene molecule is formed by methylene and a quarternary carbon, it is confirmed outside the ring system. This skeletal characteristic belongs to the lupane-type triterpene lupeol (Rosandy et al., 2021). See Fig. S1. ...
Context: One approach to cancer therapy medication is exploring medicinal plants that contain one or more compounds specifically targeting cancer cells with fewer side effects. Cascara from coffee fruit (Coffea canephora Pierre ex A.Froehner) is a waste rarely processed but has various chemical contents that can be used in medicine. Aims: To evaluate the in silico and in vitro activity of compounds isolated from ethanolic extract of C. canephora cascara against HeLa and MCF-7 breast cancer cells. Methods: Isolation of the compounds by radial chromatography and thin layer chromatography techniques, and the chemical structures were elucidated by infrared radiation, ultraviolet, nuclear magnetic resonance spectroscopy, and mass spectrometry. In silico study about the compounds binding with the receptor responsibility to cancer (caspases 3 and 9). In vitro study by examining the cytotoxicity of HeLa and MCF-7 cells of the isolated compounds from C. canephora. Results: Four known bioactive compounds, lupeol (1), stigmasterol (2), ursolic acid (3), and caffeic acid (4), were isolated from the ethanol extract of C. canephora cascara. Based on the ESI-MS results, the m/z value for lupeol was 427.50 [M+H]+, stigmasterol was 454.48 [M+ACN+H]+, ursolic acid was 456.51 [M+H]+, and caffeic acid was 179 [M-H]. In silico and in vitro data show that the ursolic acid compound has activity against HeLa and MCF-7 cancer cells with IC50 values of 25.98 ± 0.01 µg/mL and 12.70 ± 0.11 µg/mL, respectively. Conclusions: All isolated compounds from C. canephora cascara have a promising ability to interact with caspases 3 and 9, particularly ursolic acid, which has the smallest IC50 value against HeLa and MCF-7 breast cancer cells.
... Moreover, no report could be seen on the volatile compositions and biological activities of other species in the genus Dehaasia and Caryodaphnopsis. However, a phytochemical study revealed that lupeol isolated from D. cuneata had a moderate inhibition on Serratia marcescens ATCC 14756 and low inhibition of Escherichia coli ATCC 25922, Vibrio fluvialis ATCC 33809, Bacillus subtilis ATCC 6633, and Methicillin-resistant Staphylococcus aureus ATCC 43300 [3]. Alkaloids were previously isolated from several Dehaasia species [4]. ...
... However, D. cuneata leaf oil exhibited lesser inhibitory anti-candidal activity to C. albicans ATCC10231 with MIC value of 56.56 µg/mL. The leaf essential oil of D. cuneata exhibited higher antibacterial action than the non-volatile lupeol which has low inhibition of B. subtilis and S. aureus [3]. However, lupeol [3] was more active against E. coli than the essential oil. ...
... The leaf essential oil of D. cuneata exhibited higher antibacterial action than the non-volatile lupeol which has low inhibition of B. subtilis and S. aureus [3]. However, lupeol [3] was more active against E. coli than the essential oil. On the other hand, the leaf oil of C. tonkinensis exhibited good antibacterial activity towards E. faecalis ATCC299212 with MIC value of 15.99 µg/mL, and anti-candidal action against C. albicans ATCC10231 with MIC value of 33.68 µg/mL. ...
