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Article ; Online: Rapid screening of diarylpentanoids from Daphne bholua.

Dong, Shu-Hui / Lian, Mei-Ya / Han, Jin-Ling / Ai, Yun-Fei / Zhou, Xiao-Fang / Bai, Ming / Huang, Xiao-Xiao / Song, Shao-Jiang

Phytochemistry

2023 Volume 209, Page(s) 113614

Abstract: ... led to the isolation of seventeen diarylpentanoids from the whole plant of Daphne bholua Buch.-Ham. ex ...

Abstract	Fractionation motivated by biological activity screening and NMR characteristic signals analysis led to the isolation of seventeen diarylpentanoids from the whole plant of Daphne bholua Buch.-Ham. ex D. Don, among which nine compounds were undescribed. Their structures and stereochemistry were determined by comprehensive spectroscopic data, J-based configurational analysis, and quantum chemical calculations. The inhibitory potentials of all isolates against acetylcholinesterase were evaluated in vitro and in silico.
MeSH term(s)	Daphne/chemistry ; Daphne/metabolism ; Molecular Structure ; Acetylcholinesterase/metabolism ; Magnetic Resonance Spectroscopy
Chemical Substances	Acetylcholinesterase (EC 3.1.1.7)
Language	English
Publishing date	2023-02-18
Publishing country	England
Document type	Journal Article
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2023.113614
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Article ; Online: Exploring the mechanism of daphne-type diterpenes against gastric cancer cells.

Wang, Yu-Jue / Wang, Xin-Ye / Yang, Zi-Nuo / Shang, Xin-Yue / Mi, Si-Hui / Liu, Qingbo / Yao, Guo-Dong / Song, Shao-Jiang

Journal of Asian natural products research

2024 , Page(s) 1–13

Abstract: Gastric cancer is one of the common malignant tumors. It is reported that daphne-type diterpenes ... the detailed mechanism of the anticancer effect of daphne-type diterpenes, we carried out an integrated network ...

Abstract	Gastric cancer is one of the common malignant tumors. It is reported that daphne-type diterpenes have inhibitory effects on gastric cancer cells, but the mechanism is still unknown. To explore the detailed mechanism of the anticancer effect of daphne-type diterpenes, we carried out an integrated network pharmacology prediction study and selected an effective component (yuanhuacine, YHC) for the following validation
Language	English
Publishing date	2024-02-12
Publishing country	England
Document type	Journal Article
ZDB-ID	2077926-4
ISSN	1477-2213 ; 1028-6020
ISSN (online)	1477-2213
ISSN	1028-6020
DOI	10.1080/10286020.2024.2311149
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Article ; Online: Eight structurally diverse components with anti-acetylcholinesterase activity from Daphne bholua.

Lian, Mei-Ya / Dong, Shu-Hui / Ai, Yun-Fei / Duan, Zhi-Kang / Bai, Ming / Huang, Xiao-Xiao / Song, Shao-Jiang

Phytochemistry

2024 Volume 220, Page(s) 114015

Abstract: ... were isolated from the herb of Daphne bholua Buch.-Ham. ex D. Don. Their planar structures were ...

Abstract	Eight structurally diverse components, including six undescribed ones, (±)-daphuarin A (1a/1b), daphuarin B (2), daphuarin D-E (4-6), together with a pair of new natural products (±)-daphuarin C (3a/3b) were isolated from the herb of Daphne bholua Buch.-Ham. ex D. Don. Their planar structures were elucidated by extensive spectroscopic analyses. The configurations were established with the assistance of quantum chemical calculations, together with the Custom DP4+ method. The inhibitory potentials of all isolates against acetylcholinesterase were evaluated.
MeSH term(s)	Daphne/chemistry ; Daphne/metabolism ; Molecular Structure ; Acetylcholinesterase/metabolism
Chemical Substances	Acetylcholinesterase (EC 3.1.1.7)
Language	English
Publishing date	2024-02-14
Publishing country	England
Document type	Journal Article
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2024.114015
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Article ; Online: Guided isolation of daphnane-type diterpenes from Daphne genkwa by molecular network strategies.

Mi, Si-Hui / Zhao, Peng / Li, Qian / Zhang, Hao / Guo, Rui / Liu, Yu-Yang / Lin, Bin / Yao, Guo-Dong / Song, Shao-Jiang / Huang, Xiao-Xiao

Phytochemistry

2022 Volume 198, Page(s) 113144

Abstract: A molecular networking-guided study on the Daphne genkwa Sieb. et Zucc led to the isolation ... of twelve daphnane-type diterpenoids including four undescribed compounds, yuanhuakines A-D ...

Abstract	A molecular networking-guided study on the Daphne genkwa Sieb. et Zucc led to the isolation of twelve daphnane-type diterpenoids including four undescribed compounds, yuanhuakines A-D. Their structures were elucidated by spectroscopic analyses, ECD calculations, and single-crystal X-ray diffraction analysis. All isolates were evaluated for their inhibitory activity against the A549, Hep3B, and MCF-7 cell lines. The majority of compounds inhibited A549 cells with IC
MeSH term(s)	Daphne/chemistry ; Diterpenes/chemistry ; Humans ; MCF-7 Cells ; Molecular Structure ; Structure-Activity Relationship
Chemical Substances	Diterpenes ; mezerein (34807-41-5)
Language	English
Publishing date	2022-03-10
Publishing country	England
Document type	Journal Article
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2022.113144
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Article: First report of Phytophthora blight caused by Phytophthora nicotianae on Daphne odora in China.

Hu, JiangTao / Zhou, Ying / Luo, SuMei / Zhang, YuanFu / Chen, YuanHua / Cai, Lei / Zhou, YongHui / Li, Rong / Zhang, KaiDong / Liu, ShuYuan / Liu, XiaoPing

Plant disease

2022

Abstract: The variegated leaves and fragrant flowers of Daphne odora var. marginata Mak. make it a popular ...

Abstract	The variegated leaves and fragrant flowers of Daphne odora var. marginata Mak. make it a popular garden plant. In May 2020, we found diseased D. odora plants in a greenhouse at the Ganzhou Vegetable and Flower Research Institute, in southeast China; 72% of 1800 plants had Phytophthora blight-like symptoms-shrunken stems, black withered branches, wilted and dropped leaves (Fig 1a), and rotted and dark green roots. The root and stem tissue surfaces were disinfected with 75% ethanol for 30 s followed by 0.1% HgCl2 for 1 min, rinsed thrice with sterile water, and cultured on potato-dextrose agar (PDA) medium at 25°C. Mycelia from the diseased tissue were subcultured on fresh PDA medium, providing three colonies. White colonies (~4.1 mm) were formed after 10 days at 25°C (Fig 1b). Sporangia and chlamydospores were induced by placing actively growing mycelia on PDA medium at 25°C for ~30 days and then at 45°C for ~3 days. Sporangia were ovoid to spherical and 19.33 × 20.99 µm in size (Fig 1c), whereas chlamydospores were spherical and 15.68 × 16.10 µm in size (Fig 1d). All three colonies resembled Phytophthora spp. Genomic DNA was extracted from isolates using the Ezup Column Fungi Genomic DNA Purification Kit (Sangon Biotech [Shanghai] Co. Ltd.), and rDNA-ITS and β-tubulin were amplified and sequenced. BLAST analysis (GenBank) revealed that the ITS (Accession No. MZ676071) and β-tubulin (MZ748503) sequences of isolates shared the highest similarity (99-100%) with those of Phytophthora nicotianae (Duccio et al. 2015). A phylogenetic tree of the relationship between our isolate hjt3 and its close relatives within the P. nicotianae species was constructed using the MEGA X neighbor-joining method (Fig 2). The pathogen was identified as P. nicotianae based on morphological and molecular characteristics. Sequencing results of the three samples were consistent, all indicating P. nicotianae. A specimen (JXAU-H2020245) was deposited in the Herbarium of the College of Agronomy, Jiangxi Agricultural University. To confirm pathogenicity, 9-month-old healthy D. odora plants were used for stem and soil inoculation. Stems were cut ~5 cm from the soil with sterilized scalpels and inoculated with 0.8 cm diameter PDA plugs containing actively growing mycelia of isolate hjt3. The soil was sterilized and 0.8 cm PDA plugs containing actively growing mycelia were buried in the soil at ~5 cm; the mycelia were in contact with the roots. Plants in both groups were treated equally; those inoculated with sterile PDA plugs served as controls. There were six plants in each group, with each experiment performed in triplicate. All plants were incubated in a greenhouse at 25-28°C. The stems shrank and began to rot rapidly after 7 days (Fig 3) and the branches turned black and withered within 2 weeks. After soil inoculation, the stems of the inoculated plants blackened and rotted in ~20 days (Fig 4) and the roots rotted and turned dark green (Fig 5). These symptoms rapidly spread to the branches. The control plants did not exhibit any symptoms. Reisolated colonies showed the same morphological traits as the isolates used for inoculation; no target colonies were isolated from the control plants. Phytophthora blight caused by P. nicotianae on D. odora has been reported in Italy (Garibaldi A, 2009) and Korea (Kwon et al. 2005). This is the first detection in China. Therefore, Phytophthora blight on D. odora caused by P. nicotianae should be monitored and controlled to promote the development of the D. odora industry.
Language	English
Publishing date	2022-11-10
Publishing country	United States
Document type	Journal Article
ZDB-ID	754182-x
ISSN	0191-2917
ISSN	0191-2917
DOI	10.1094/PDIS-08-22-1994-PDN
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Article ; Online: Anti-rheumatoid arthritis effects of flavonoids from Daphne genkwa.

Sun, Yue-Wen / Bao, Yarigui / Yu, Hui / Chen, Qiu-Jing / Lu, Fang / Zhai, Shuo / Zhang, Chun-Feng / Li, Fei / Wang, Chong-Zhi / Yuan, Chun-Su

International immunopharmacology

2020 Volume 83, Page(s) 106384

Abstract: ... of flavonoids from Daphne genkwa Sieb. et Zucc. by anti-inflammatory and immunomodulatory effects in vitro, and ...

Abstract	Objective: This study aims to select the most effective anti-Rheumatoid Arthritis (RA) component of flavonoids from Daphne genkwa Sieb. et Zucc. by anti-inflammatory and immunomodulatory effects in vitro, and to elucidate the mechanism. Methods: The anti-inflammatory and immunomodulatory effects of total flavonoids (TF) and four flavonoid components (genkwanin, hydroxygenkwanin, luteolin and apigenin) were determined by pharmacological approach in LPS-induced RAW 264.7 macrophages and ConA-induced T lymphocytes. Principal component analysis (PCA) was used to obtain the optimal anti-RA component in vitro. Western blot and real-time quantitative PCR (q-PCR) were used to explore the mechanisms. Finally, the in vitro anti-RA effect was verified by human rheumatoid arthritis fibroblast-like synoviocytes (FLSs). Results: TF and four flavonoids significantly reduced the expressions of NO, iNOS, TNF-α, IL-6, IFN-γ and IL-2. PCA showed that genkwanin was the most effective anti-RA component in vitro. Genkwanin inhibited nuclear factor-κB (NF-κB) pathway by decreasing the phosphorylation levels of IKK, IκB and NF-κB, and down-regulated the expressions of iNOS, COX-2 and IL-6 mRNA. Genkwanin also inhibited the abnormal proliferation of FLSs and down-regulated the secretions of NO and IL-6. Conclusion: The most effective anti-RA component was genkwanin. Genkwanin exerts anti-RA effect through down-regulating the activation of NF-κB pathway and mRNA expressions of inflammatory mediators, and also by inhibiting the abnormal proliferation of FLSs and its NO and IL-6 secretion levels.
MeSH term(s)	Animals ; Antirheumatic Agents/therapeutic use ; Arthritis, Rheumatoid/drug therapy ; Cytokines/metabolism ; Daphne/immunology ; Flavonoids/therapeutic use ; Humans ; Immunomodulation ; Inflammation Mediators ; Lipopolysaccharides/metabolism ; Macrophages/immunology ; Mice ; NF-kappa B/metabolism ; Nitric Oxide Synthase Type II/metabolism ; RAW 264.7 Cells ; Signal Transduction ; T-Lymphocytes/immunology
Chemical Substances	Antirheumatic Agents ; Cytokines ; Flavonoids ; Inflammation Mediators ; Lipopolysaccharides ; NF-kappa B ; Nitric Oxide Synthase Type II (EC 1.14.13.39)
Language	English
Publishing date	2020-03-18
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	2043785-7
ISSN	1878-1705 ; 1567-5769
ISSN (online)	1878-1705
ISSN	1567-5769
DOI	10.1016/j.intimp.2020.106384
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Article ; Online: Target isolation of cytotoxic diterpenoid esters and orthoesters from Daphne tangutica maxim based on molecular networking.

Guo, Rui / Li, Qian / Mi, Si-Hui / Jia, Shu-He / Yao, Guo-Dong / Lin, Bin / Huang, Xiao-Xiao / Liu, Yu-Yang / Song, Shao-Jiang

Phytochemistry

2022 Volume 203, Page(s) 113358

Abstract: ... diterpenoids, tanguticanines A-E, and eleven known analogues were discovered from the whole plants of Daphne ... Guiding by LC-MS/MS analysis and the GNPS Molecular Networking, five undescribed daphnane ...

Abstract	Guiding by LC-MS/MS analysis and the GNPS Molecular Networking, five undescribed daphnane diterpenoids, tanguticanines A-E, and eleven known analogues were discovered from the whole plants of Daphne tangutica Maxim. Their structures and absolute configurations were determined via extensive NMR spectroscopic analysis, ECD calculations, and X-ray diffraction crystallography. Tanguticanine E (5) exhibited promising cytotoxicity against the HepG2 cell line with an IC
MeSH term(s)	Antineoplastic Agents/chemistry ; Antineoplastic Agents/pharmacology ; Chromatography, Liquid ; Daphne/chemistry ; Diterpenes/chemistry ; Esters/pharmacology ; Molecular Structure ; Tandem Mass Spectrometry
Chemical Substances	Antineoplastic Agents ; Diterpenes ; Esters
Language	English
Publishing date	2022-08-14
Publishing country	England
Document type	Journal Article
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2022.113358
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Article: Guided isolation of daphnane-type diterpenes from Daphne genkwa by molecular network strategies

Mi, Si-Hui / Zhao, Peng / Li, Qian / Zhang, Hao / Guo, Rui / Liu, Yu-Yang / Lin, Bin / Yao, Guo-Dong / Song, Shao-Jiang / Huang, Xiao-Xiao

Phytochemistry. 2022 June, v. 198

2022

Abstract	A molecular networking-guided study on the Daphne genkwa Sieb. et Zucc led to the isolation of twelve daphnane-type diterpenoids including four undescribed compounds, yuanhuakines A–D. Their structures were elucidated by spectroscopic analyses, ECD calculations, and single-crystal X-ray diffraction analysis. All isolates were evaluated for their inhibitory activity against the A549, Hep3B, and MCF-7 cell lines. The majority of compounds inhibited A549 cells with IC₅₀ values ranging from 7.77 to 20.56 μM, and their structure-activity relationship is preliminarily discussed. Five of these compounds were selected for further experiments, and they appear to inhibit A549 cell lines by inducing apoptosis.
Keywords	Daphne genkwa ; X-ray diffraction ; apoptosis ; diterpenoids ; human cell lines ; plant biochemistry ; spectroscopy ; structure-activity relationships
Language	English
Dates of publication	2022-06
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2022.113144
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Guaiane-type sesquiterpenoids with various ring skeletons from Daphne bholua uncovered by molecular networking and structural revisions of previously reported analogues.

Dong, Shu-Hui / Duan, Zhi-Kang / Ai, Yun-Fei / Zhou, Xiao-Fang / Zhang, Xin / Lian, Mei-Ya / Huang, Xiao-Xiao / Bai, Ming / Song, Shao-Jiang

Bioorganic chemistry

2022 Volume 129, Page(s) 106208

Abstract: The genus Daphne is a treasure-house of secondary metabolites with various biological effects ... which inspired Daphne bholua being fully investigated phytochemically and biologically for the first time. Here ...

Abstract	The genus Daphne is a treasure-house of secondary metabolites with various biological effects, which inspired Daphne bholua being fully investigated phytochemically and biologically for the first time. Here, seven undescribed guaiane-type sesquiterpenoids (1-7) along with thirteen known analogues (8-20) were targeted and isolated from D. bholua using molecular networking. Their chemical structure and configurations were established via NMR spectroscopy analysis, NMR and ECD calculations, Snatzke's method, along with single-crystal X-ray diffraction technique. Moreover, two pairs of sesquiterpene isomers, either with prominent biological properties or with unprecedented skeleton, were revised by means of computer-assisted structure elucidation, chemical shift calculator using deep learning, etc. The inhibitory potentials of all isolates against acetylcholinesterase were evaluated in vitro and in silico.
MeSH term(s)	Acetylcholinesterase/chemistry ; Daphne/chemistry ; Molecular Structure ; Sesquiterpenes, Guaiane/chemistry ; Sesquiterpenes, Guaiane/isolation & purification ; Sesquiterpenes, Guaiane/pharmacology ; Cholinesterase Inhibitors/chemistry ; Cholinesterase Inhibitors/isolation & purification ; Cholinesterase Inhibitors/pharmacology
Chemical Substances	Acetylcholinesterase (EC 3.1.1.7) ; Sesquiterpenes, Guaiane ; Cholinesterase Inhibitors
Language	English
Publishing date	2022-10-17
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	120080-x
ISSN	1090-2120 ; 0045-2068
ISSN (online)	1090-2120
ISSN	0045-2068
DOI	10.1016/j.bioorg.2022.106208
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Article ; Online: Discovery of guaiane-type sesquiterpenoids from the roots of Daphne genkwa with neuroprotective effects.

Wang, Jie / Liu, Qing-Bo / Hou, Zi-Lin / Shi, Shao-Chun / Ren, Hui / Yao, Guo-Dong / Lin, Bin / Huang, Xiao-Xiao / Song, Shao-Jiang

Bioorganic chemistry

2019 Volume 95, Page(s) 103545

Abstract: A phytochemical study on the roots of Daphne genkwa yielded seven new guaiane-type sesquiterpenoids ... 1-7), daphne A-G. Their structures were elucidated through comprehensive spectroscopic analyses ...

Abstract	A phytochemical study on the roots of Daphne genkwa yielded seven new guaiane-type sesquiterpenoids (1-7), daphne A-G. Their structures were elucidated through comprehensive spectroscopic analyses. The absolute configurations were determined by comparison between experimental electronic circular dichroism (ECD) and calculated ECD spectra via time-dependent density functional theory (TDDFT) and the modified Mosher's method. Furthermore, all isolates were evaluated for their neuroprotective activities against H
MeSH term(s)	Cell Line, Tumor ; Daphne/chemistry ; Drug Discovery ; Humans ; Mitochondria/drug effects ; Neuroprotective Agents/chemistry ; Neuroprotective Agents/isolation & purification ; Neuroprotective Agents/pharmacology ; Plant Roots/chemistry ; Sesquiterpenes/chemistry ; Sesquiterpenes/isolation & purification ; Sesquiterpenes/pharmacology
Chemical Substances	Neuroprotective Agents ; Sesquiterpenes
Language	English
Publishing date	2019-12-23
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	120080-x
ISSN	1090-2120 ; 0045-2068
ISSN (online)	1090-2120
ISSN	0045-2068
DOI	10.1016/j.bioorg.2019.103545
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