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New halimane and clerodane diterpenoids from Croton cnidophyllus
Xun Wei, Jia-Luo Huang, Hua-Hua Gao, Fang-Yu Yuan, Gui-Hua Tang, Sheng Yin
Natural Products and Bioprospecting    2023, 13 (3): 21-21.   DOI: 10.1007/s13659-023-00386-z
Abstract   PDF (1782KB)  
Three new halimane furanoditerpenoids (1-3) and three new clerodane furanoditerpenoids (4-6), along with seven known terpenoids including four pimarane diterpenoids (7-10) and three norisoprenoids (11-13) were isolated from the 95% EtOH extracts of the plants of Croton cnidophyllus. The 2D structures including absolute configuration of new furanoditerpenoids (1-6) were elucidated by analysis of their HRMS and NMR data as well as comparison of experimental and calculated ECD curves. Bioassay revealed that two compounds (8 and9) possessed certain inhibitory effects against NO production stimulated by LPS, with IC50 values of 19.00±1.76 and 21.61±1.11 μM, respectively.
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Protective effect and mechanism insight of purified Antarctic krill phospholipids against mice ulcerative colitis combined with bioinformatics
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
Abstract   PDF (2016KB)  
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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Antifungal alkaloids from Mahonia fortunei against pathogens of postharvest fruit
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
Abstract   PDF (3294KB)  
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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Antifungal activity against Fusarium oxysporum of quinolizidines isolated from three controlled-growth Genisteae plants: structure–activity relationship implications
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
Abstract   PDF (2094KB)  
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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Five new limonoids isolated from Walsura robusta
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
Abstract   PDF (1304KB)  
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
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
Abstract   PDF (2288KB)  
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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Four undescribed pyrethrins from seeds of Pyrethrum cinerariifolium and their aphidicidal activity
Hao-Ran Zhou, Li-Wu Lin, Zhong-Rong Li, Xing-Rong Peng, Ming-Hua Qiu
Natural Products and Bioprospecting    2023, 13 (3): 22-22.   DOI: 10.1007/s13659-023-00385-0
Abstract   PDF (1211KB)  
Four undescribed pyrethrins C-F (1-4) as well as four known pyrethrins (5-8) were isolated from seeds of Pyrethrum cinerariifolium Trev. The structures of compounds1-4 were elucidated by UV, HRESIMS, and NMR (1H and 13C NMR, 1H-1H COSY, HSQC, HMBC and ROESY), among which the stereostructure of compound4 was determined by calculated ECD. Furthermore, compounds1-4 were evaluated for their aphidicidal activities. The insecticidal assay results showed that1-4 exhibited moderate aphidicidal activities at the concentration of 0.1 mg/mL with the 24 h mortality rates ranging from 10.58 to 52.98%. Among them, pyrethrin D (2) showed the highest aphidicidal activity, with the 24 h mortality rate of 52.98%, which was slightly lower than the positive control (pyrethrin II, 83.52%).
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Four new lanostane triterpenoids featuring extended π-conjugated systems from the stems of Kadsura coccinea
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
Abstract   PDF (1580KB)  
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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Effects of combined cannabidiol (CBD) and hops (Humulus lupulus) terpene extract treatment on RAW 264.7 macrophage viability and inflammatory markers
Inga Dammann, Claudia Keil, Iris Hardewig, Elżbieta Skrzydlewska, Michał Biernacki, Hajo Haase
Natural Products and Bioprospecting    2023, 13 (3): 19-19.   DOI: 10.1007/s13659-023-00382-3
Abstract   PDF (1803KB)  
This study investigates the potential of cannabidiol (CBD), one major cannabinoid of the plant Cannabis sativa, alone and in combination with a terpene-enriched extract from Humulus lupulus (“Hops 1”), on the LPS-response of RAW 264.7 macrophages as an established in vitro model of inflammation. With the present study, we could support earlier findings of the anti-inflammatory potential of CBD, which showed a dose-dependent [0-5 μM] reduction in nitric oxide and tumor necrosis factor-alpha (TNF-α) released by LPS-stimulated RAW 264.7 macrophages. Moreover, we observed an additive anti-inflammatory effect after combined CBD [5 μM] and hops extract [40 μg/mL] treatment. The combination of CBD and Hops 1 showed effects in LPS-stimulated RAW 264.7 cells superior to the single substance treatments and akin to the control hydrocortisone. Furthermore, cellular CBD uptake increased dose-dependently in the presence of terpenes from Hops 1 extract. The anti-inflammatory effect of CBD and its cellular uptake positively correlated with terpene concentration, as indicated by comparison with a hemp extract containing both CBD and terpenes. These findings may contribute to the postulations for the so-called “entourage effect” between cannabinoids and terpenes and support the potential of CBD combined with phytomolecules from a non-cannabinoid source, such as hops, for the treatment of inflammatory diseases.
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The medicinal chemistry of Urtica dioica L.: from preliminary evidence to clinical studies supporting its neuroprotective activity
Prabhakar Semwal, Abdur Rauf, Ahmed Olatunde, Pooja Singh, Mohamed Y. Zaky, Md. Mozahidul Islam, Anees Ahmed Khalil, Abdullah S. M. Aljohani, Waleed Al Abdulmonem, Giovanni Ribaudo
Natural Products and Bioprospecting    2023, 13 (3): 16-16.   DOI: 10.1007/s13659-023-00380-5
Abstract   PDF (3424KB)  
Urtica dioica is a perennial herb from the family of Urticaceae that is commonly known as stinging nettle. This plant is widespread in Europe, Africa, America, and a part of Asia, as it adapts to different environments and climatic conditions. The leaves, stalk, and bark of U. dioica found applications in the field of nutrition, cosmetics, textile, pest control and pharmacology. In this connection, bioactive chemical constituents such as flavonoids, phenolic acids, amino acids, carotenoids, and fatty acids have been isolated from the plant. With this review, we aim at providing an updated and comprehensive overview of the contributions in literature reporting computational, in vitro, pre-clinical and clinical data supporting the therapeutic applications of U. dioica. Experimental evidence shows that U. dioica constituents and extracts can provide neuroprotective effects by acting through a combination of different molecular mechanisms, that are discussed in the review. These findings could lay the basis for the identification and design of more effective tools against neurodegenerative diseases.
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