The Absolute Configuration of Leiocarpin B

Mu, Quanquan; Tang, Weidong; Li, Chaoming; Xu, Yongping; Sun, Han‐Dong; Lou, Liguang; Hao, Xiao‐Jiang; Xu, Bei; Hu, Chun

doi:10.3987/com-01-9399

Cited by 4 publications

(12 citation statements)

References 2 publications

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“…Unlike 1−6, compound 7 comprises a styrylpyrone connected to a dihydroflavone through an oxygen atom, similar to the previously reported compound leiocarpin B. 16 Besides the common fragments at m/z 341 and 241, the fragments at m/z 256 (75), 179 (61), and 152 (41) were more abundant in the EI-MS of 7 (Figure 6). Thus, compound 7 was elucidated as a positional isomer with a linkage between C-5′ and C-8 through a C−O bond.…”

Section: ■ Results and Discussionsupporting

confidence: 81%

“…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: 63%

“…15 The absolute configuration of C-7 in 1 was determined as S by the Mosher's ester method (Tables 2 and S4). 16 Accordingly, the chiral center of C-8 was assigned as R. ECD spectroscopy analysis was used to determine the absolute configuration of C-6. A positive n → π* Cotton effect (CE) for the α,βunsaturated-δ-lactone was observed at λ max 250 nm (Figure 3), confirming the R-configuration for the stereogenic center at C-6.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Uncovering the Power of HSCCC: Separation of Diastereomeric and Regioisomeric Styrylpyrones from the Stem Bark of Goniothalamus leiocarpus

Liu,

Li,

Zhang

et al. 2024

J. Nat. Prod.

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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.

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Section: ■ Results and Discussionsupporting

confidence: 81%

Section: ■ Results and Discussionsupporting

confidence: 63%

Section: ■ Results and Discussionmentioning

confidence: 99%

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Uncovering the Power of HSCCC: Separation of Diastereomeric and Regioisomeric Styrylpyrones from the Stem Bark of Goniothalamus leiocarpus

Liu,

Li,

Zhang

et al. 2024

J. Nat. Prod.

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“…Goniothalamus leiocarpus (Annonaceae) (Mu et al, 1996;Li et al, 1997;Li et al, 1998;Mu et al, 1998;Mu et al, 1999a;Mu et al, 1999b;Mu et al, 2002;Mu et al, 2003;Mu et al, 2004), and the absolute configuration of leiocarpin B was determined by Mosher ester method (Mu et al, 2002). In this paper, the absolute configuration of five styryllactone compounds were determined by single-crystal X-ray diffraction analysis, using Cu Ka radiation.…”

Section: Discussionmentioning

confidence: 99%

“…In our previous work, styryllactone compounds were extracted from Goniothalamus griffithii (Annonaceae) and Goniothalamus leiocarpus (Annonaceae) (Mu et al, 1996;Li et al, 1997;Li et al, 1998;Mu et al, 1998;Mu et al, 1999a;Mu et al, 1999b;Mu et al, 2002;Mu et al, 2003;Mu et al, 2004). Their relative configurations were initially established on the basis of spectroscopic data (Li et al, 1997;Li et al, 1998;Mu et al, 1999a;Mu et al, 1999b;Mu et al, 2002;Mu et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

Hydroxypropyl-β-Cyclodextrin Complexes of Styryllactones Enhance the Anti-Tumor Effect in SW1116 Cell Line

Chen

et al. 2020

Front. Pharmacol.

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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-diphenyl-tetrazolium bromide staining in four tumor cell lines. The induced apoptosis activity of leiocarpin E-7ʹ-Monoacetate was studied by an annexin V fluorescein isothiocyanate/propidium iodide double-staining experiment, and the caspase activity was tested in the SW1116 cell line. The results demonstrated that the antitumor activities of cheliensisin A and goniodiol-7-monoacetate were limited by their poor water solubility. To address this issue, hydroxypropyl-b-cyclodextrin (HP-b-CD) complexes of the compounds were synthesized by the saturated aqueous method. The complexes were then analyzed using a differential scanning calorimeter. The IC 50 of cheliensisin A was reduced by 45% and 58% against SW1116 and SMMC-7721 cell lines, respectively. Similarly, the IC 50 of goniodiol-7-monoacetate was reduced by 55% and 34% against the two tumor cell lines, respectively. To further evaluate whether the styryllactones and complexes possessed selectivity against cancer cell lines and normal cell lines, toxicity against human normal cell line (HEK293T) was evaluated. The results demonstrated that the HP-b-CD complexes displayed more cytotoxicity than the respective pristine compounds against the HEK293T cell line. However, there existed a therapeutic window when the complexes were applied against cancer cell lines. In summary, the synthesis of several styryllactone compounds complexed with HP-b-CD was reported for the first time. These complexes could significantly enhance the cytotoxic effects of styryllactone compounds.

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ChemInform Abstract: The Absolute Configuration of Leiocarpin B.

Tang

et al. 2002

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The Absolute Configuration of Leiocarpin B

Cited by 4 publications

References 2 publications

Uncovering the Power of HSCCC: Separation of Diastereomeric and Regioisomeric Styrylpyrones from the Stem Bark of Goniothalamus leiocarpus

Uncovering the Power of HSCCC: Separation of Diastereomeric and Regioisomeric Styrylpyrones from the Stem Bark of Goniothalamus leiocarpus

Hydroxypropyl-β-Cyclodextrin Complexes of Styryllactones Enhance the Anti-Tumor Effect in SW1116 Cell Line

ChemInform Abstract: The Absolute Configuration of Leiocarpin B.

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