Hunterines A–C, Three Unusual Monoterpenoid Indole Alkaloids from <i>Hunteria zeylanica</i>

Zhang, Jian; Liu, Zhiwen; Ao, Yun-Lin; Hu, Lijun; Cui, Wei; Zhang, Qinghua; Yuan, Mengfei; Wang, Ying; Zhang, Qingwen; Ye, Wen‐Cai; Zhang, Xiaoqi

doi:10.1021/acs.joc.9b01835

Cited by 21 publications

(8 citation statements)

References 36 publications

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“…Alashanine A ( 1 ) was tested for antibacterial effect against Bacillus subtilis and anti- Candida albicans by the established bioassay methods. , The results showed that 1 exhibited significant inhibition against Bacillus subtilis with a MIC value of 5.31 μg/mL. In addition, the cytotoxic activity of 1 against the growth of HepG2 and MCF-7 human cancer cell lines was tested by the MTT method. − Alashanine A ( 1 ) was found to possess moderate cytotoxic activity in vitro . The IC 50 values of 1 against HepG2 and MCF-7 cells were 9.16 and 5.01 μM, respectively (taxol as the positive control, Table S6).…”

Section: Resultsmentioning

confidence: 99%

Alashanines A–C, Three Quinone-Terpenoid Alkaloids from Syringa pinnatifolia with Cytotoxic Potential by Activation of ERK

Jiao,

Huang,

Wang

et al. 2023

J. Org. Chem.

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Three quinone-terpenoid alkaloids, alashanines A–C (1–3), possessing an unprecedented 6/6/6 tricyclic conjugated backbone and quinone–quinoline-fused characteristic, were isolated from the peeled stems of Syringa pinnatifolia. Their structures were elucidated by analysis of extensive spectroscopic data and quantum chemical calculations. A hypothesis of biosynthesis pathways for 1–3 was proposed on the basis of the potential precursor iridoid and benzoquinone. Compound 1 exhibited antibacterial activities against Bacillus subtilis and cytotoxicity against HepG2 and MCF-7 human cancer cell lines. The results of the cytotoxic mechanism revealed that compound 1 induced apoptosis of HepG2 cells through activation of ERK.

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Section: Resultsmentioning

confidence: 99%

Alashanines A–C, Three Quinone-Terpenoid Alkaloids from Syringa pinnatifolia with Cytotoxic Potential by Activation of ERK

Jiao,

Huang,

Wang

et al. 2023

J. Org. Chem.

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“…Whereas the first observation indicated the need for cautiousness in the interpretation of experimental data, the second observation provided hope that semi-synthetic transformations ( e.g. , Mosher ester formation) could be adequately controlled to create a series of differentially esterified products for analysis. − …”

Section: Resultsmentioning

confidence: 99%

Resolving a Natural Product Cold Case: Elucidation of Fusapyrone Structure and Absolute Configuration and Demonstration of Their Fungal Biofilm Disrupting Properties

et al. 2023

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Fusapyrones are fungal metabolites, which have been reported to have broad-spectrum antibacterial and antifungal properties. Despite the first members of this chemical class being described three decades prior, many aspects of their structures have remained unresolved, thereby constraining efforts to fully understand structure–activity relationships within this metabolite family and impeding the design of streamlined syntheses. Among the main challenges posed by fusapyrones is the incorporation of several single and groups of stereocenters separated by atoms with freely rotating bonds, which have proven unyielding to spectroscopic analyses. In this study, we obtained a series of new (2–5 and 7–9) and previously reported fusapyrones (1 and 6), which were subjected to a combination of spectroscopic, chemical, and computational techniques enabling us to offer proposals for their full structures, as well as provide a pathway to reinterpreting the absolute configurations of other published fusapyrone metabolites. Biological testing of the fusapyrones revealed their abilities to inhibit and disrupt biofilms made by the human fungal pathogen, Candida albicans. These results show that fusapyrones reduce hyphae formation in C. albicans, as well as decrease the surface adherence capabilities of planktonic cells and cells transitioning into early-stage biofilm formation.

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“…Colorless crystals of 1 and 2 were obtained from MeOH at room temperature. The X-ray crystallographic data were collected on a Super Nova (Dual, Cu at zero, AtlasS2) diffractometer with Cu Kα radiation (λ = 1.54184 Å) at 100.00 (10) K. After we used Olex2, the structures were solved with the ShelXT structure solution program using intrinsic phasing and refined with the ShelXL refinement package using least-squares minimization. − Crystallographic data of compound 1 (CIF 1 and Table S1) and compound 2 (CIF 2 and Table S2) have been deposited at the Cambridge Crystallographic Data Center, and the deposition numbers of 1 and 2 were CCDC 1916494 and CCDC 1916493, respectively. Copies of the data can be obtained on application to the CDCC free of charge, 12 Union Road, Cambridge, CB21EZ, United Kingdom [Phone: + 44 (0) 1223 336408; Fax: + 44 (0) 1223 336033; Email: deposit@ccdc.ac.uk].…”

Section: Methodsmentioning

confidence: 99%

Bioactive Limonoids and Triterpenoids from the Fruits of Melia azedarach

et al. 2020

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Nine new limonoids, meliazedarines A−I (1−9), seven known analogues (10−16), and five known triterpenoids (17−21) were isolated from the fruits of Melia azedarach. Their structures were determined by analysis of 1D and 2D NMR, HRESIMS, X-ray diffraction, and electronic circular dichroism (ECD) data. Compound 7 showed significant cytotoxicity against the HCT116 cell line with IC 50 values of 0.3 ± 0.1 μM.A deciduous tree of the Meliaceae family, Melia azedarach, is widely distributed in tropical and subtropical regions of Asia. 1 The fruits, twigs, and bark of M. azedarach have been used for the treatment of anthelmintic, ulcer, leprosy, and helminthiasis in China for a long time. 2−4 Previous phytochemical investigations of plants from this genus led to the isolation of triterpenoids, limonoids, steroids, flavonoids, lignans, and fatty acids. 4−6 The triterpenoids and limonoids exhibited diverse bioactivities, such as antifeedant, insecticidal, antiviral, antifungal, antibacterial, and cytotoxicity activities. 3−5,7−9 In a search for structurally unique and biologically interesting natural products from traditional Chinese medicines, nine new limonoids, meliazedarines A−I (1−9), seven known analogues (10−16), and five known triterpenoids (17− 21), were isolated from the EtOAc extract of the fruits of M. azedarach (Figure 1). The new structures and their absolute configurations were elucidated by comprehensive spectroscopic, X-ray diffraction, and ECD data. The compounds were evaluated for their cytotoxicity against BEL7402, HCT116, A549, U251, and HT29 cell lines. Compounds 7 and 17 displayed significant cytotoxicity against the HCT116 cell line with IC 50 values of 0.3 ± 0.1 and 5.9 ± 0.4 μM, respectively. Herein, we report the isolation, structural elucidation, and cytotoxicity of these compounds.

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Hunterines A–C, Three Unusual Monoterpenoid Indole Alkaloids from Hunteria zeylanica

Cited by 21 publications

References 36 publications

Alashanines A–C, Three Quinone-Terpenoid Alkaloids from Syringa pinnatifolia with Cytotoxic Potential by Activation of ERK

Alashanines A–C, Three Quinone-Terpenoid Alkaloids from Syringa pinnatifolia with Cytotoxic Potential by Activation of ERK

Resolving a Natural Product Cold Case: Elucidation of Fusapyrone Structure and Absolute Configuration and Demonstration of Their Fungal Biofilm Disrupting Properties

Bioactive Limonoids and Triterpenoids from the Fruits of Melia azedarach

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