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Five new limonoids isolated from Walsura robusta
Collect
Li Hou, Cui-Xuan Mei, Chun-Mao Yuan, Gui-Hua Tang, Duo-Zhi Chen, Qing Zhao, Hong-Ping He, Ming-Ming Cao, Xiao-Jiang Hao
Natural Products and Bioprospecting. 2023, 13 (2): 7-7.
DOI: 10.1007/s13659-023-00371-6
Five new toosendanin limonoids with highly oxidative furan ring walsurobustones A-D (1-4), and one new furan ring degraded limonoid walsurobustone E (5) together with one known compound toonapubesic acid B (6) were isolated from the leaves of Walsura robusta. Their structures were elucidated by NMR and MS data. Especially, the absolute configuration of toonapubesic acid B (6) was confirmed by X-ray diffraction study. Compounds 1-6 exhibited good cytotoxicity against the cancer cell lines HL-60, SMMC-7721, A-549, MCF-7, and SW480.
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Anti-inflammatory maistemonine-class alkaloids of Stemona japonica
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Cheng-Yong Tan, Bao-Bao Shi, Mei-Fen Bao, Xiang-Hai Cai
Natural Products and Bioprospecting. 2023, 13 (2): 8-8.
DOI: 10.1007/s13659-023-00372-5
Three hitherto undescribed Stemona alkaloids, named stemajapines A-C (1-3), along with six known alkaloids (4-9), were isolated and identified from the roots of Stemona japonica (Blume) Miq. (Stemonaceae). Their structures were established by the analysis of the mass data, NMR spectra, and computational chemistry. Stemjapines A and B were degraded maistemonines without spiro-lactone ring and skeletal methyl from maistemonine. Concurrence of alkaloids 1 and 2 revealed an undescribed way to form diverse Stemona alkaloids. Bioassay results disclosed the anti-inflammatory natural constituents stemjapines A and C with IC50 values of 19.7 and 13.8 μM, respectively, compared to positive control dexamethasone with 11.7 μM. The findings may point out a new direction of Stemona alkaloids inaddition to its traditional antitussive and insecticide activities.
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Antifungal activity against Fusarium oxysporum of quinolizidines isolated from three controlled-growth Genisteae plants: structure–activity relationship implications
Collect
Willy Cely-Veloza, Lydia Yamaguchi, Diego Quiroga, Massuo J. Kato, Ericsson Coy-Barrera
Natural Products and Bioprospecting. 2023, 13 (2): 9-9.
DOI: 10.1007/s13659-023-00373-4
The Genisteae tribe belongs to the Fabaceae family. The wide occurrence of secondary metabolites, explicitly highlighting the quinolizidine alkaloids (QAs), characterizes this tribe. In the present study, twenty QAs (1-20), including lupanine (1-7), sparteine (8-10), lupanine (11), cytisine and tetrahydrocytisine (12-17), and matrine (18-20)-type QAs were extracted and isolated from leaves of three species (i.e., Lupinus polyphyllus ('rusell' hybrid), Lupinus mutabilis, and Genista monspessulana) belonging to the Genisteae tribe. These plant sources were propagated under greenhouse conditions. The isolated compounds were elucidated by analyzing their spectroscopical data (MS, NMR). The antifungal effect on the mycelial growth of Fusarium oxysporum (Fox) of each isolated QA was then evaluated through the amended medium assay. The best antifungal activity was found to be for compounds 8 (IC50=16.5 μM), 9 (IC50=7.2 μM), 12 (IC50=11.3 μM), and 18 (IC50=12.3 μM). The inhibitory data suggest that some QAs could efficiently inhibit Fox mycelium growth depending on particular structural requirements deduced from structure-activity relationship scrutinies. The identified quinolizidine-related moieties can be involved in lead structures to develop further antifungal bioactives against Fox.
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Antifungal alkaloids from Mahonia fortunei against pathogens of postharvest fruit
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Xiao-Na Wang, Zhao-Jie Wang, Yun Zhao, Huan Wang, Mei-Ling Xiang, Yang-Yang Liu, Li-Xing Zhao, Xiao-Dong Luo
Natural Products and Bioprospecting. 2023, 13 (2): 10-10.
DOI: 10.1007/s13659-023-00374-3
Postharvest pathogens can affect a wide range of fresh fruit and vegetables, including grapes, resulting in significant profit loss. Isoquinoline alkaloids of Mahonia fortunei, a Chinese herbal medicine, have been used to treat infectious microbes, which might be effective against postharvest pathogens. The phytochemical and bioactive investigation of this plant led to the isolation of 18 alkaloids, of which 9 compounds inhibited the growth of Botrytis cinerea and 4 compounds against Penicillium italicum. The antifungal alkaloids could change the mycelium morphology, the total lipid content, and leak the cell contents of B. cinerea. Furthermore, the two most potent antifungal alkaloids, berberine (13) completely inhibited effect on gray mold of table grape at 512 mg L-1, while jatrorrhizine (18) exhibited an inhibition rate > 90% on grape rot at the same concentration, with lower cytotoxicity and residue than chlorothalonil, which suggested that ingredients of M. fortunei might be a low-toxicity, low-residue, eco-friendly botanical fungicide against postharvest pathogens.
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Protective effect and mechanism insight of purified Antarctic krill phospholipids against mice ulcerative colitis combined with bioinformatics
Collect
Rong Huang, Jiaxu Yao, Li Zhou, Xiang Li, Jinrui Zhu, Yueqi Hu, Jikai Liu
Natural Products and Bioprospecting. 2023, 13 (2): 11-11.
DOI: 10.1007/s13659-023-00375-2
Antarctic krill oil is functional oil and has a complex phospholipids composition that poses difficulties in elucidating its effect mechanism on ulcerative colitis (UC). The mechanism of UC action was studied by bioinformatics, and the therapeutic effect of Antarctic krill phospholipids (APL) on dextran sulfate sodium (DSS)-induced colitis mice was verified. GO functional enrichment analysis uncovered an enrichment of these genes in the regulation of cell-cell adhesion, membrane region, signaling receptor activator activity, and cytokine activity. Meanwhile, the KEGG results revealed the genes were enriched in the TNF signaling pathway, pathogenic Escherichia coli infection, inflammatory bowel disease and tight junction. Animal experiments showed that APL treatment alleviated the UC symptoms and reduced inflammatory damage. Meanwhile, the expressions of the tight junction (TJ) proteins, ZO-1 and occludin, were restored, and the levels of IL-6 and TNF-α were reduced. Moreover, Firmicutes/Bacteroidetes ratio in the intestinal microbiota was regulated, and the contents of short-chain fatty acids metabolites were raised. These findings would provide an insight for the beneficial effects of APL and dietary therapy strategies for UC.
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Four new lanostane triterpenoids featuring extended π-conjugated systems from the stems of Kadsura coccinea
Collect
Qi-Qi Zhang, Kun Hu, Han-Dong Sun, Pema-Tenzin Puno
Natural Products and Bioprospecting. 2023, 13 (2): 12-12.
DOI: 10.1007/s13659-023-00376-1
Four new 14(13 → 12)-abeolanostane triterpenoids featuring extended π-conjugated systems, kadcoccitanes E-H (1-4), were obtained from the stems of Kadsura coccinea through using a HPLC - UV-guided approach. Their structural and configurational determination was accomplished through extensive spectroscopic analysis coupled with quantum chemical calculations. Kadcoccitanes E-H were tested for their cytotoxic activities against five human tumor cell lines (HL-60, A-549, SMMC-7721, MDA-MB-231, SW-480) but none of them exhibited activities at the concentration 40 μM.
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Uncarialines A-E, new alkaloids from Uncaria rhynchophylla and their anticoagulant activity
Collect
Ke-Pu Huang, Li-Li Xu, Sheng Li, Yin-Ling Wei, Lian Yang, Xiao-Jiang Hao, Hong-Ping He, Yu Zhang
Natural Products and Bioprospecting. 2023, 13 (2): 13-13.
DOI: 10.1007/s13659-023-00377-0
Uncarialines A-E (1-5), five undescribed monoterpene indole alkaloids, together with five known analogues were obtained from the stems of Uncaria rhynchophylla. Alkaloids 1-3 were unique 3,4-seco-tricyclic alkaloids with a 6/5/10 ring system, while 4 and 5 possessed a rare rearranged scaffold originated from corynantheine-type alkaloids with C-2/C-7 oxidation. Their structures were characterized by a comprehensive analysis of MS, NMR, and ECD. Their effects on blood clotting times of human plasma were evaluated and alkaloid 5 had a slight prolongation effect on both thrombin time and activated partial thromboplastin time (p<0.001).
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