Abstract:Styryllactones, a class of compounds obtained from the genus Goniothalamus (Annonaceae), have demonstrated in vitro antitumor activity. However, the aqueous solubility of these compounds is poor. In this study, we identified the absolute configurations of the previously isolated compounds, which were first isolated in our laboratory, by single-crystal X-ray diffraction analysis using Cu Ka radiation. Subsequently, the antitumor activities of the compounds were evaluated by 3-(4,5dimethylthiazol-2-yl)-2,5-diphe… Show more
“…C-6 was assigned as R based on the analysis of the ECD spectrum of 7 (Figure S65), which was consistent with the spectrum of leiocarpin B. 16 This, combined with the NMR data (Table 4), led us to assign the absolute configuration of 7 as 6R,7R,8R,2′S and to name it 6R,7R,8R,2′S-goniolactone G (7).…”
Section: ■ Results and Discussionsupporting
confidence: 65%
“…Bioassays of Human Colorectal Cancer Cells and Hepatocellular Carcinoma Cell Lines. 7 Different human colorectal cancer cells and hepatocellular carcinoma cell lines, including COLO205, LS513, SW620, HCCLM3, MHCC97H, HepG2, and HuH7, were obtained from Zhongshan Hospital, Fudan University. All cell lines were cultured in complete Dulbecco's modified Eagle's medium (DMEM) containing 10% fetal bovine serum (FBS), 100 U/mL penicillin, and 0.1% streptomycin.…”
Section: ■ Experimental Sectionmentioning
confidence: 99%
“…2,3 In G. leiocarpus, previously isolated styryllactones include 7-epi-goniodiol 4 and leiocarpins A−E, 5,6 which exhibit significant cytotoxic activities against several human cancer cell lines. 7 In our recent bioactivity screening, a fraction from G. leiocarpus exhibited antibacterial and synergistic activity against strains of antibiotic-resistant Staphylococcus aureus. The active fraction GL-5-19 showed only a single spot in the TLC analysis (Figure S90) and three major peaks in the HPLC chromatogram.…”
The
plant Goniothalamus leiocarpus of the Annonaceae
family is used as an alternative medicine in tropical regions. Applying
high-speed counter current chromatography (HSCCC), eight new bioactive
styrylpyrone isomers, including 6R,7S,8R,2′S-goniolactone B (1), 6S,7S,8S,2′S-goniolactone B (2), 6R,7R,8R,2′S-goniolactone B (3), 6R,7S,8S,2′S-goniolactone
C (4), 6R,7S,8R,2′S-goniolactone C (5), 6S,7R,8S,2′S-goniolactone C (6), and two positional isomers,
6R,7R,8R,2′S-goniolactone G (7) and 6S,7R,8R,2′S-goniolactone G (8), were isolated from a chloroform
fraction (2.1 g) of G. leiocarpus, which had a prominent
spot by TLC analysis. The structures of the new compounds were elucidated
by MS, NMR, IR, and UV spectra, and their absolute configurations
were determined by Mosher’s method, ECD, and X-ray diffraction
analysis. The isolates are characteristic components found in plants
of the genus Goniothalamus and consist of two structural
moieties: a styrylpyrone and a dihydroflavone unit. The isolation
of the eight new compounds demonstrates the effectiveness of HSCCC
in separating the isomers of natural styrylpyrone. In a bioactivity
assessment, compounds 1 and 6 exhibited
cytotoxic effects against the human colon carcinoma cell lines LS513
and SW620 with IC50 values ranging from 1.6 to 3.9 μM.
Compounds 1, 2, 7, and 8 showed significant synergistic activity against antibiotic-resistant Staphylococcus aureus strains.
“…C-6 was assigned as R based on the analysis of the ECD spectrum of 7 (Figure S65), which was consistent with the spectrum of leiocarpin B. 16 This, combined with the NMR data (Table 4), led us to assign the absolute configuration of 7 as 6R,7R,8R,2′S and to name it 6R,7R,8R,2′S-goniolactone G (7).…”
Section: ■ Results and Discussionsupporting
confidence: 65%
“…Bioassays of Human Colorectal Cancer Cells and Hepatocellular Carcinoma Cell Lines. 7 Different human colorectal cancer cells and hepatocellular carcinoma cell lines, including COLO205, LS513, SW620, HCCLM3, MHCC97H, HepG2, and HuH7, were obtained from Zhongshan Hospital, Fudan University. All cell lines were cultured in complete Dulbecco's modified Eagle's medium (DMEM) containing 10% fetal bovine serum (FBS), 100 U/mL penicillin, and 0.1% streptomycin.…”
Section: ■ Experimental Sectionmentioning
confidence: 99%
“…2,3 In G. leiocarpus, previously isolated styryllactones include 7-epi-goniodiol 4 and leiocarpins A−E, 5,6 which exhibit significant cytotoxic activities against several human cancer cell lines. 7 In our recent bioactivity screening, a fraction from G. leiocarpus exhibited antibacterial and synergistic activity against strains of antibiotic-resistant Staphylococcus aureus. The active fraction GL-5-19 showed only a single spot in the TLC analysis (Figure S90) and three major peaks in the HPLC chromatogram.…”
The
plant Goniothalamus leiocarpus of the Annonaceae
family is used as an alternative medicine in tropical regions. Applying
high-speed counter current chromatography (HSCCC), eight new bioactive
styrylpyrone isomers, including 6R,7S,8R,2′S-goniolactone B (1), 6S,7S,8S,2′S-goniolactone B (2), 6R,7R,8R,2′S-goniolactone B (3), 6R,7S,8S,2′S-goniolactone
C (4), 6R,7S,8R,2′S-goniolactone C (5), 6S,7R,8S,2′S-goniolactone C (6), and two positional isomers,
6R,7R,8R,2′S-goniolactone G (7) and 6S,7R,8R,2′S-goniolactone G (8), were isolated from a chloroform
fraction (2.1 g) of G. leiocarpus, which had a prominent
spot by TLC analysis. The structures of the new compounds were elucidated
by MS, NMR, IR, and UV spectra, and their absolute configurations
were determined by Mosher’s method, ECD, and X-ray diffraction
analysis. The isolates are characteristic components found in plants
of the genus Goniothalamus and consist of two structural
moieties: a styrylpyrone and a dihydroflavone unit. The isolation
of the eight new compounds demonstrates the effectiveness of HSCCC
in separating the isomers of natural styrylpyrone. In a bioactivity
assessment, compounds 1 and 6 exhibited
cytotoxic effects against the human colon carcinoma cell lines LS513
and SW620 with IC50 values ranging from 1.6 to 3.9 μM.
Compounds 1, 2, 7, and 8 showed significant synergistic activity against antibiotic-resistant Staphylococcus aureus strains.
“…As a result, cell cytotoxicity and inclusion complex uptake studies revealed that HPβ-CD/PA NFs drug deliveries exhibited promising anti-cancer drug release and can be suggested for human colon cancer treatment. 66 According to the above characterizations, HPβ-CD/PA NFs inclusion complex was synthesized and showed much better chemical and biological properties. To our best knowledge, it is the first time to synthesis HPβ-CD/PA NFs inclusion complex and targeted modification was also carried out.Figure 8.(a) Cell viability of PA, HPβ-CD, and the inclusion complex HPβ-CD/PA (20–100 μg/mL) on HCT-116 cells after 24 h. Data are presented as mean ± standard deviation ( n =3).…”
The electrospinning of nanofibers (NFs) from 2-hydroxypropyl β-cyclodextrin supramolecular inclusion complexes (150% HPβ-CD, w/v) with vitamin B5 (pantothenic acid [PA]) was achieved without using any carrier polymeric matrix. The presence of PA and the formation of the HPβ-CD/PA inclusion complex within the NFs structure were confirmed by SEM, FTIR, XRD, and TGA analysis. SEM images depicted the bead-free uniform NFs and confirmed the incorporation of HPβ-CD/PA NFs did not alter the fiber morphology having an average fiber diameter of 512 ± 24 nm, 328 ± 18 nm, and 150 ± 19 nm, respectively. Fourier transform infrared (FTIR) spectrum indicated inclusion complex from the shifting of the peaks of each component in HPβ-CD/PA NFs, whereas XRD pattern revealed that HPβ-CD/PA NFs was achieved due to the formation of a new amorphous structure. TGA studies showed that the stability of PA after HPβ-CD encapsulation was improved. Molecular docking was used to simulate the positions and interactions of the binding sites of the HPβ-CD/PA inclusion complex. The phase solubility test showed enhanced solubility of PA due to the inclusion complexation; in addition, the stoichiometry of HPβ-CD/PA was determined to be 1:1. The release of PA from HPβ-CD/PA NFs prevented the colonization of Escherichia coli (5.0 ± 0.3%) and Staphylococcus aureus (2.0 ± 0.5%) bacteria to a great extent, as observed in the antibacterial activity results. The cell viability of HCT-116 cells treated with 100 μg/mL of HPβ-CD/PA NFs was registered at 97.5 ± 2.1%. It was observed that HPβ-CD/PA NFs had higher anticancer activity compared to pure PA and HPβ-CD due to the solubility increase. In brief, our results suggested that polymer-free HPβ-CD/PA inclusion complex NFs could have potential applications in food, pharmaceuticals, and healthcare thanks to its efficient antibacterial and anticancer activities.
“…On the other hand, only the 2D structure was proposed for cheliensisine; however, pinocembrin and its derivatives isolated from Goniothalamus sp. had been reported to have (2 S ) configurations. − Therefore, the absolute structure of cheliensisine was presumed to be the same as that of aquiledine ( 6 ). The specific rotations of 9 and 10 were calculated to assign the absolute structure of isoaquiledine in a similar manner.…”
Aquiledine and cheliensisine are flavoalkaloids isolated from Aquilegia ecalcarata and Goniothalamus cheliensis, respectively. Different structures have been proposed for these
flavoalkaloids; however, their 1H and 13C NMR
spectroscopic data were virtually identical. In this study, the structures
of aquiledine and cheliensisine were revised on the basis of the DFT
calculation of NMR data including DP4+ and J-DP4
analysis, as well as specific rotations. Similarly, the structure
of isoaquiledine, a regioisomer of aquiledine, was also revised. A
biosynthetic pathway of these flavoalkaloids is proposed.
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