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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: A new flavanol from the roots of Daphne genkwa

Wang, Rui / Tong, Ling / Liu, Cai-Yun / Guo, Cong

Journal of Asian natural products research. 2019 Dec. 2, v. 21, no. 12

2019

Abstract: The phytochemical investigation of the roots of Daphne genkwa yielded six secondary metabolites ...

Abstract	The phytochemical investigation of the roots of Daphne genkwa yielded six secondary metabolites, including a new flavanol derivative, (2R, 3S)-5,7,4′-trihydroxy-8-methoxycarbonylflavanol (1), and five known compounds (2–6). The molecular structures of the isolated constituents were elucidated on the basis of extensive spectroscopic analysis, including UV, IR, NMR, and MS, and comparison with literature data. Furthermore, the cytotoxic activity of 1 and 2 against A549, HL-60, SMMC-7721, MCF-7, and SW480 cell lines was also described.
Keywords	Daphne genkwa ; anticarcinogenic activity ; cell lines ; chemical structure ; cytotoxicity ; flavanols ; mass spectrometry ; neoplasm cells ; nuclear magnetic resonance spectroscopy ; roots ; secondary metabolites ; spectral analysis
Language	English
Dates of publication	2019-1202
Size	p. 1215-1220.
Publishing place	Taylor & Francis
Document type	Article
ZDB-ID	2077926-4
ISSN	1477-2213 ; 1028-6020
ISSN (online)	1477-2213
ISSN	1028-6020
DOI	10.1080/10286020.2018.1530222
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Article ; Online: Prenylated flavans from Daphne giraldii and their cytotoxic activities.

Sun, Qian / Shang, Xin-Yue / Wang, Yu-Xi / Yao, Guo-Dong / Li, Fei-Fei / Li, Ling-Zhi / Zhang, Yan / Huang, Xiao-Xiao / Song, Shao-Jiang

Fitoterapia

2018 Volume 132, Page(s) 68–74

Abstract: ... isolated from the stem and root bark of Daphne giraldii. Their structures were established by extensive NMR ...

Abstract	Nine new prenylated flavan compounds with multi-chiral centers including two pairs of epimers were isolated from the stem and root bark of Daphne giraldii. Their structures were established by extensive NMR and HR-ESIMS spectroscopic data analyses. The in vitro cytotoxicity experiments indicated that compound 6 showed the most significant cytotoxicity against Hep3B cells, with an IC
MeSH term(s)	Antineoplastic Agents, Phytogenic/chemistry ; Antineoplastic Agents, Phytogenic/isolation & purification ; Apoptosis ; Cell Line, Tumor ; China ; Daphne/chemistry ; Humans ; Molecular Structure ; Plant Bark/chemistry ; Plant Stems/chemistry ; Poly(ADP-ribose) Polymerases/metabolism ; Polyphenols/chemistry ; Polyphenols/isolation & purification ; Prenylation ; Proto-Oncogene Proteins c-bcl-2/metabolism ; Up-Regulation ; bcl-2-Associated X Protein/metabolism
Chemical Substances	Antineoplastic Agents, Phytogenic ; BAX protein, human ; BCL2 protein, human ; Polyphenols ; Proto-Oncogene Proteins c-bcl-2 ; bcl-2-Associated X Protein ; Poly(ADP-ribose) Polymerases (EC 2.4.2.30)
Language	English
Publishing date	2018-11-27
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	412385-2
ISSN	1873-6971 ; 0367-326X
ISSN (online)	1873-6971
ISSN	0367-326X
DOI	10.1016/j.fitote.2018.11.011
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Article ; Online: Isolation and structure elucidation of antioxidant compounds from stem and root barks of Daphne giraldii

Zhang, Jie / Chu, Wan-Chun / Li, Ling-Zhi

Journal of Asian Natural Products Research. 2023 Nov. 2, v. 25, no. 11 p.1058-1067

2023

Abstract: ... by phytochemical work on EtOAc-soluble ingredients extracted from stem and root barks of Daphne giraldii ...

Abstract	Two new compounds, aphegiractin A₁/A₂ (1a/1b), and seven known compounds were isolated by phytochemical work on EtOAc-soluble ingredients extracted from stem and root barks of Daphne giraldii. Their structures were established based on extensive spectroscopic methods, including HRESIMS, CD experiments, 1D and 2D NMR. All compounds were evaluated for their antioxidant activity to DPPH, ABTS radical scavenging activity and inhibitory activity on tyrosinase. Of these compounds, compound 3 exhibited significant antioxidant activities.
Keywords	Daphne ; antioxidant activity ; antioxidants ; phytochemicals ; spectroscopy ; Thymelaeaceae ; Daphne giraldii ; coumarins
Language	English
Dates of publication	2023-1102
Size	p. 1058-1067.
Publishing place	Taylor & Francis
Document type	Article ; Online
ZDB-ID	2077926-4
ISSN	1477-2213 ; 1028-6020
ISSN (online)	1477-2213
ISSN	1028-6020
DOI	10.1080/10286020.2023.2195106
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Article ; Online: Daphne giraldii Nitsche (Thymelaeaceae): Phytochemistry, pharmacology and medicinal uses.

Han, Shuang / Li, Ling-Zhi / Song, Shao-Jiang

Phytochemistry

2019 Volume 171, Page(s) 112231

Abstract: Daphne giraldii Nitsche., a member of the genus Daphne (Thymelaeaceae), is a deciduous shrub ...

Abstract	Daphne giraldii Nitsche., a member of the genus Daphne (Thymelaeaceae), is a deciduous shrub with mild toxicity. Its rhizome bark, generally called 'Zushima' in Chinese, has many medicinal folkloric uses and good therapeutic effects. Previous studies investigating the chemical constituents and pharmacological activities of D. giraldii have focused on several major classes of compounds, such as coumarins, lignans and flavonoids, especially the interesting enantiomeric flavans. Extracts and pure compounds of D. giraldii were found to possess anti-inflammatory, anti-nociceptive, cytotoxicity, antimalarial, immunomodulating, sedative and hypnotic effects. They have also been reported to influence the cardiovascular functions and blood activities. This comprehensive review will describe the advances in the phytochemistry, pharmacology, medicinal uses and clinical applications of D. giraldii and its formulations covering the literature published from 1970 to 2018. Almost half of the reviewed studies were originally published in non-English languages (mainly in Chinese). Collectively, the aim of this article is to open new avenues for further in-depth pharmacological studies on D. giraldii.
MeSH term(s)	Animals ; Anti-Inflammatory Agents, Non-Steroidal/chemistry ; Anti-Inflammatory Agents, Non-Steroidal/isolation & purification ; Anti-Inflammatory Agents, Non-Steroidal/pharmacology ; Anti-Obesity Agents/chemistry ; Anti-Obesity Agents/isolation & purification ; Anti-Obesity Agents/pharmacology ; Antimalarials/chemistry ; Antimalarials/isolation & purification ; Antimalarials/pharmacology ; Antineoplastic Agents, Phytogenic/chemistry ; Antineoplastic Agents, Phytogenic/isolation & purification ; Antineoplastic Agents, Phytogenic/pharmacology ; Humans ; Hypnotics and Sedatives/chemistry ; Hypnotics and Sedatives/isolation & purification ; Hypnotics and Sedatives/pharmacology ; Immunologic Factors/chemistry ; Immunologic Factors/isolation & purification ; Immunologic Factors/pharmacology ; Phytochemicals/chemistry ; Phytochemicals/isolation & purification ; Phytochemicals/pharmacology ; Thymelaeaceae/chemistry
Chemical Substances	Anti-Inflammatory Agents, Non-Steroidal ; Anti-Obesity Agents ; Antimalarials ; Antineoplastic Agents, Phytogenic ; Hypnotics and Sedatives ; Immunologic Factors ; Phytochemicals
Language	English
Publishing date	2019-12-31
Publishing country	England
Document type	Journal Article ; Review
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2019.112231
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Article ; Online: Chiral Separation of Cytotoxic Flavan Derivatives from Daphne giraldii.

Li, Fei-Fei / Sun, Qian / Wang, Di / Liu, Sen / Lin, Bin / Liu, Chun-Ting / Li, Ling-Zhi / Huang, Xiao-Xiao / Song, Shao-Jiang

Journal of natural products

2016 Volume 79, Issue 9, Page(s) 2236–2242

Abstract: ... isolated from the stem bark and roots of Daphne giraldii. Their structures were elucidated using ...

Abstract	Twelve new flavan derivatives including four pairs of enantiomers, daphnegiralins A1-A4 (1) and daphnegiralins B1-B4 (2), and two pairs of epimers, daphnegiralins C1/C2 (3) and daphnegiralins D1/D2 (4), were isolated from the stem bark and roots of Daphne giraldii. Their structures were elucidated using spectroscopic analyses, computational approaches, and chemical methods. Separation of the enantiomeric mixtures (1a, 1b, 2a, and 2b) was achieved using chiral HPLC. The compounds were evaluated against a small panel of human cancer cell lines, and 1b-2, 2a, and 2b were cytotoxic against Hep3B human hepatoma cells.
MeSH term(s)	Antineoplastic Agents/chemistry ; Antineoplastic Agents/isolation & purification ; Antineoplastic Agents/pharmacology ; Chromatography, High Pressure Liquid ; Daphne/chemistry ; Drug Screening Assays, Antitumor ; Drugs, Chinese Herbal/chemistry ; Flavonoids/chemistry ; Flavonoids/isolation & purification ; Flavonoids/pharmacology ; Humans ; Molecular Structure ; Plant Roots/chemistry ; Polyphenols/chemistry ; Polyphenols/isolation & purification ; Polyphenols/pharmacology ; Stereoisomerism
Chemical Substances	Antineoplastic Agents ; Drugs, Chinese Herbal ; Flavonoids ; Polyphenols
Language	English
Publishing date	2016-09-23
Publishing country	United States
Document type	Journal Article
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.6b00305
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Article: Daphne giraldii Nitsche (Thymelaeaceae): Phytochemistry, pharmacology and medicinal uses

Han, Shuang / Li, Ling-zhi / Song, Shao-jiang

Phytochemistry. 2020 Mar., v. 171

2020

Abstract: Daphne giraldii Nitsche., a member of the genus Daphne (Thymelaeaceae), is a deciduous shrub ...

Abstract	Daphne giraldii Nitsche., a member of the genus Daphne (Thymelaeaceae), is a deciduous shrub with mild toxicity. Its rhizome bark, generally called ‘Zushima’ in Chinese, has many medicinal folkloric uses and good therapeutic effects. Previous studies investigating the chemical constituents and pharmacological activities of D. giraldii have focused on several major classes of compounds, such as coumarins, lignans and flavonoids, especially the interesting enantiomeric flavans. Extracts and pure compounds of D. giraldii were found to possess anti-inflammatory, anti-nociceptive, cytotoxicity, antimalarial, immunomodulating, sedative and hypnotic effects. They have also been reported to influence the cardiovascular functions and blood activities. This comprehensive review will describe the advances in the phytochemistry, pharmacology, medicinal uses and clinical applications of D. giraldii and its formulations covering the literature published from 1970 to 2018. Almost half of the reviewed studies were originally published in non-English languages (mainly in Chinese). Collectively, the aim of this article is to open new avenues for further in-depth pharmacological studies on D. giraldii.
Keywords	Daphne ; antimalarials ; bark ; blood ; chemical composition ; coumarins ; cytotoxicity ; flavonoids ; languages ; lignans ; medicinal properties ; rhizomes ; sedatives ; shrubs ; therapeutics
Language	English
Dates of publication	2020-03
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.2019.112231
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Article ; Online: Yuanhuatine from Daphne genkwa selectively induces mitochondrial apoptosis in estrogen receptor α-positive breast cancer cells in vitro.

Zhang, Ying-Ying / Shang, Xin-Yue / Hou, Xue-Wen / Li, Ling-Zhi / Wang, Wei / Hayashi, Toshihiko / Zhang, Yan / Yao, Guo-Dong / Song, Shao-Jiang

Planta medica

2019 Volume 85, Issue 16, Page(s) 1275–1286

Abstract: Breast cancer is one of the most common cancers diagnosed among women worldwide. Estrogen receptor alpha ( ... ...

Abstract	Breast cancer is one of the most common cancers diagnosed among women worldwide. Estrogen receptor alpha (ER
MeSH term(s)	Antineoplastic Agents, Phytogenic/chemistry ; Antineoplastic Agents, Phytogenic/pharmacology ; Apoptosis/drug effects ; Breast Neoplasms/drug therapy ; Cell Proliferation/drug effects ; Daphne/chemistry ; Down-Regulation/drug effects ; Female ; Humans ; MCF-7 Cells ; Mitochondria/metabolism ; Molecular Docking Simulation ; Tamoxifen/chemistry ; Tamoxifen/pharmacology
Chemical Substances	Antineoplastic Agents, Phytogenic ; Tamoxifen (094ZI81Y45)
Language	English
Publishing date	2019-10-18
Publishing country	Germany
Document type	Journal Article
ZDB-ID	123545-x
ISSN	1439-0221 ; 0032-0943
ISSN (online)	1439-0221
ISSN	0032-0943
DOI	10.1055/a-1013-1439
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Article: A new coumarin from Daphne pedunculata

Du, Jing-ling / Xu, Wen-zheng / Cheng, Xiang-Rong / Jin, Hui-zi

Chemistry of natural compounds. 2013 July, v. 49, no. 3

2013

Abstract: ... isolated from the stems and branches of Daphne pedunculata. The structure was elucidated on the basis ...

Abstract	A new coumarin, 3-[(3-hydroxy-4-ethylpropanpicatephenyl)oxy]-6-methoxy-7-hydroxycoumarin (1), was isolated from the stems and branches of Daphne pedunculata. The structure was elucidated on the basis of spectroscopic and 2D NMR spectral analysis.
Keywords	Daphne ; branches ; coumarin ; nuclear magnetic resonance spectroscopy ; spectral analysis
Language	English
Dates of publication	2013-07
Size	p. 426-427.
Publishing place	Springer-Verlag
Document type	Article
ZDB-ID	213866-9
ISSN	0009-3130
ISSN	0009-3130
DOI	10.1007/s10600-013-0629-6
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Article ; Online: Cytotoxic prenylated flavones from the stem and root bark of Daphne giraldii.

Sun, Qian / Wang, Di / Li, Fei-Fei / Yao, Guo-Dong / Li, Xue / Li, Ling-Zhi / Huang, Xiao-Xiao / Song, Shao-Jiang

Bioorganic & medicinal chemistry letters

2016 Volume 26, Issue 16, Page(s) 3968–3972

Abstract: ... from the stem and root bark of Daphne giraldii. Their structures were determined by comprehensive NMR and ...

Abstract	Three new prenylated flavones (1-3), along with three known analogues (4-6), were isolated from the stem and root bark of Daphne giraldii. Their structures were determined by comprehensive NMR and HRESIMS spectroscopic data analyses. The absolute configurations of compounds 2 and 3 were assigned by optical rotation comparison, CD and [Rh2(OCOCF3)4]-induced CD spectral methods. The in vitro cytotoxicity experiments carried out involving five cancer cell lines (U251, A549, HepG2, MCF-7 and Bcap37) showed that 2 markedly inhibited the proliferation of all tested cells with IC50 values ranging from 4.26 to 20.82μM. The preliminary structure-activity relationships of these flavones are discussed. In addition, compound 2 was found to effectively induce apoptosis in HepG2 cells according to a flow cytometry analysis.
MeSH term(s)	A549 Cells ; Antineoplastic Agents, Phytogenic/chemistry ; Antineoplastic Agents, Phytogenic/isolation & purification ; Antineoplastic Agents, Phytogenic/toxicity ; Apoptosis/drug effects ; Cell Line, Tumor ; Cell Proliferation/drug effects ; Daphne/chemistry ; Daphne/metabolism ; Drug Screening Assays, Antitumor ; Flavones/chemistry ; Flavones/isolation & purification ; Flavones/toxicity ; Hep G2 Cells ; Humans ; MCF-7 Cells ; Magnetic Resonance Spectroscopy ; Molecular Conformation ; Plant Bark/chemistry ; Plant Bark/metabolism ; Plant Roots/chemistry ; Plant Roots/metabolism ; Plant Stems/chemistry ; Plant Stems/metabolism ; Structure-Activity Relationship
Chemical Substances	Antineoplastic Agents, Phytogenic ; Flavones
Language	English
Publishing date	2016--15
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/j.bmcl.2016.07.002
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