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Article ; Online: Isoflavones isolated from the fruits of Ficus altissima and their anti-proliferative activities.

Liu, Yiliang / Pu, Yajing / Shen, Liyuan / Li, Dan / Xu, Jingwen / He, Xiangjiu / Wang, Yihai

2024 Volume 175, Page(s) 105966

Abstract: Ficus altissima, also known as lofty fig, is a monoecious plant from the Moraceae family commonly found in southern China. In this study, we isolated and identified one new isoflavone (1), three new hydroxycoumaronochromones (2a, 2b and 3a) and 12 known ... ...

Abstract	Ficus altissima, also known as lofty fig, is a monoecious plant from the Moraceae family commonly found in southern China. In this study, we isolated and identified one new isoflavone (1), three new hydroxycoumaronochromones (2a, 2b and 3a) and 12 known compounds from the fruits of F. altissima. Their chemical structures were determined using spectroscopic analysis methods. We also tested all the isolated compounds for their anti-proliferative activities against eight human tumour cell lines (A-549, AGS, K562, K562/ADR, HepG2, HeLa, SPC-A-1 and CNE2) using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. Our experiments showed that compound 6 exhibited obvious anti-proliferative activity against the K562 cell line with an IC
Language	English
Publishing date	2024-04-16
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.2024.105966
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Article ; Online: Anti-inflammatory steroids from the stems of Solanum nigrum L

Deng, Junru / Wang, Lin / Jin, Qingyu / Zeng, Jia / Xu, Jingwen / He, Xiangjiu / Wang, Yihai

Phytochemistry. 2023 June, v. 210 p.113667-

2023

Abstract: Sixteen previously undescribed steroidal sapogenins along with two known ones were isolated from the stems of Solanum nigrum L. (Solanaceae). Their structures were identified using a combination of 1D and 2D NMR, HR-ESI-MS spectroscopy, the Mosher method, ...

Abstract	Sixteen previously undescribed steroidal sapogenins along with two known ones were isolated from the stems of Solanum nigrum L. (Solanaceae). Their structures were identified using a combination of 1D and 2D NMR, HR-ESI-MS spectroscopy, the Mosher method, and X-ray diffraction analysis. Compounds 1–8 have an unusual F ring and 9–12 have a derived A ring, both of which are rare skeletons found in natural products. The biological evaluation showed that the isolated steroids exhibited inhibition of nitric oxide in the LPS-induced RAW 264.7 macrophages with IC₅₀ values from 7.4 to 41.3 μM. Further studies revealed that compounds 6 and 10 exhibited anti-inflammatory activity by blocking the nuclear translocation of NF-κB, and down-regulating the expression of iNOS, COX-2, IL-1β, and IL-6 in a concentration-dependent manner. These results suggest that the stems of S. nigrum may serve as a source of anti-inflammatory agents for use in healthy or medicinal products.
Keywords	Solanum nigrum ; X-ray diffraction ; anti-inflammatory activity ; biological assessment ; interleukin-6 ; macrophages ; nitric oxide ; plant biochemistry ; sapogenins ; spectroscopy ; Solanum nigrum L. ; Solanaceae ; steroid ; 23,26-epoxyfurostanoids ; 4-oxa-A-homo-5α-spirostan-3-one ; anti-inflammatory
Language	English
Dates of publication	2023-06
Publishing place	Elsevier Ltd
Document type	Article ; Online
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2023.113667
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Article ; Online: Anti-proliferative and anti-inflammatory eudesmanolides from the flowers of Sphagneticola trilobata (L.) Pruski

Zhang, Bei / Wang, Lutong / Wang, Lin / Wang, Yihai / Xu, Jingwen / He, Xiangjiu

Phytochemistry. 2023 June, v. 210 p.113666-

2023

Abstract: Twenty-six eudesmanolides including six undescribed compounds were isolated from the flowers of Sphagneticola trilobata (L.) Pruski. Their structures were elucidated based on the interpretation of spectroscopic techniques, NMR calculation, and DP4+ ... ...

Abstract	Twenty-six eudesmanolides including six undescribed compounds were isolated from the flowers of Sphagneticola trilobata (L.) Pruski. Their structures were elucidated based on the interpretation of spectroscopic techniques, NMR calculation, and DP4+ analysis. The stereochemistry of (1S,4S,5R,6S,7R,8S,9R,10S,11S)-1,4,8- trihydroxy-6-isobutyryloxy-11-methyleudesman-9,12-olide (1) was demonstrated by single crystal X-ray diffraction. All eudesmanolides were evaluated for their anti-proliferative activities against four human tumor cell lines (HepG2, HeLa, SGC-7901, and MCF-7). 1α,4β-Dihydroxy-6α-methacryloxy-8β-isobutyryloxyeudesman-9,12-olide (3) and wedelolide B (8) showed pronounced cytotoxic effects against AGS cell line with IC₅₀ values of 1.31 and 0.89 μM, respectively. Their anti-proliferative activities against AGS cells were exerted through a dose-dependent apoptosis pathway, as verified by cell and nucleus morphological assessment, clone formation assay, and Western blot analysis. Furthermore, 1α,4β,8β-trihydroxy-6β-methacryloxyeudesman-9,12-olide (2) and 1α,4β,9β-trihydroxy-6α-isobutyryloxy- 11α-13-methacryloxyprostatolide (7) performed significant inhibitory effects on lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 macrophages with IC₅₀ values of 11.82 and 11.05 μM, respectively. Moreover, compounds 2 and 7 could block the nuclear translocation of NF-κB and reduce the expression of iNOS, COX-2, IL-1β, and IL-6 to exert anti-inflammatory effects. This study provides evidence for the utilization of the eudesmanolides from S. trilobata as lead compounds for further research due to their cytotoxic potential.
Keywords	Sphagneticola trilobata ; Western blotting ; X-ray diffraction ; apoptosis ; cell lines ; cytotoxicity ; dose response ; eudesmanolides ; humans ; interleukin-6 ; macrophages ; neoplasm cells ; nitric oxide ; plant biochemistry ; spectroscopy ; stereochemistry ; Sphagneticola trilobata (L.) Pruski ; Asteraceae ; Anti-proliferation ; Anti-inflammation
Language	English
Dates of publication	2023-06
Publishing place	Elsevier Ltd
Document type	Article ; Online
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2023.113666
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Article ; Online: Total steroidal saponins from black nightshade (Solanum nigrum L.) overcome tumor multidrug resistance by inducing autophagy‐mediated cell death in vivo and in vitro

Wang, Yi / Wang, Siyu / Xu, Jingwen / Wang, Yihai / Xiang, Limin / He, Xiangjiu

Phytotherapy Research. 2023 July, v. 37, no. 7 p.3009-3024

2023

Abstract: Multiple drug resistance (MDR) often occurs after prolonged chemotherapy, leading to refractory tumors and cancer recurrence. In this study, we demonstrated that the total steroidal saponins from Solanum nigrum L. (SN) had broad‐spectrum cytotoxic ... ...

Abstract	Multiple drug resistance (MDR) often occurs after prolonged chemotherapy, leading to refractory tumors and cancer recurrence. In this study, we demonstrated that the total steroidal saponins from Solanum nigrum L. (SN) had broad‐spectrum cytotoxic activity against various human leukemia cancer cell lines, especially in adriamycin (ADR)‐sensitive and resistant K562 cell lines. Moreover, SN could effectively inhibit the expression of ABC transporter in K562/ADR cells in vivo and in vitro. In vivo, by establishing K562/ADR xenograft tumor model, we demonstrated that SN might overcome drug resistance and inhibit the proliferation of tumors by regulating autophagy. In vitro, the increased LC3 puncta, the expression of LC3‐II and Beclin‐1, and the decreased expression of p62/SQSTM1 in SN‐treated K562/ADR and K562 cells demonstrated autophagy induced by SN. Moreover, using the autophagy inhibitors or transfecting the ATG5 shRNA, we confirmed that autophagy induced by SN was a key factor in overcoming MDR thereby promoting cell death in K562/ADR cells. More importantly, SN‐induced autophagy through the mTOR signaling pathway to overcome drug resistance and ultimately induced autophagy‐mediated cell death in K562/ADR cells. Taken together, our findings suggest that SN has the potential to treat multidrug‐resistant leukemia.
Keywords	ABC transporters ; Solanum nigrum ; autophagy ; cancer recurrence ; cytotoxicity ; doxorubicin ; drug therapy ; humans ; leukemia ; models ; multiple drug resistance ; neoplasm cells ; phytotherapy ; research ; steroid saponins ; xenotransplantation
Language	English
Dates of publication	2023-07
Size	p. 3009-3024.
Publishing place	John Wiley & Sons, Ltd.
Document type	Article ; Online
Note	JOURNAL ARTICLE
ZDB-ID	639136-9
ISSN	1099-1573 ; 0951-418X
ISSN (online)	1099-1573
ISSN	0951-418X
DOI	10.1002/ptr.7796
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: S-20, a steroidal saponin from the berries of black nightshade, exerts anti-multidrug resistance activity in K562/ADR cells through autophagic cell death and ERK activation.

Wang, Yi / Xu, Jingwen / Wang, Yihai / Xiang, Limin / He, Xiangjiu

Food & function

2022 Volume 13, Issue 4, Page(s) 2200–2215

Abstract: Multidrug resistance (MDR) is a major cause of chemotherapy failure. Adriamycin (ADR) has been widely used to treat cancer, however, as a substrate of the adenosine triphosphate binding cassette (ABC) transporter, it is easy to develop drug resistance ... ...

Abstract	Multidrug resistance (MDR) is a major cause of chemotherapy failure. Adriamycin (ADR) has been widely used to treat cancer, however, as a substrate of the adenosine triphosphate binding cassette (ABC) transporter, it is easy to develop drug resistance during the treatment. Here, we demonstrated that steroidal saponin S-20 isolated from the berries of black nightshade has comparable cytotoxicity in ADR-sensitive and resistant K562 cell lines. Autophagy is generally considered to be a protective mechanism to mediate MDR during treatment. However, we found that S-20-induced cell death in K562/ADR is associated with autophagy. We further explored the underlying mechanisms and found that S-20 induces caspase-dependent apoptosis in ADR-sensitive and resistant K562 cell lines. Most importantly, S-20-induced autophagy activates the ERK pathway and then inhibits the expression of drug resistance protein, which is the main reason to overcome K562/ADR resistance, rather than apoptosis. Taken together, our findings emphasize that S-20 exerts anti-multidrug resistance activity in K562/ADR cells through autophagic cell death and ERK activation, which may be considered as an effective strategy.
MeSH term(s)	Cell Death/drug effects ; Drug Resistance, Multiple/drug effects ; Drug Resistance, Neoplasm/drug effects ; Fruit ; Humans ; Inhibitory Concentration 50 ; K562 Cells/drug effects ; MAP Kinase Signaling System/drug effects ; Saponins/pharmacology ; Saponins/therapeutic use ; Solanum nigrum
Chemical Substances	Saponins
Language	English
Publishing date	2022-02-21
Publishing country	England
Document type	Journal Article
ZDB-ID	2612033-1
ISSN	2042-650X ; 2042-6496
ISSN (online)	2042-650X
ISSN	2042-6496
DOI	10.1039/d1fo03191k
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Article ; Online: Antiproliferative piperidine alkaloids from the leaves of Alocasia macrorrhiza.

Deng, Wenjie / Shen, Liyuan / Zeng, Jia / Gao, Jianxin / Luo, Jiachun / Xu, Jingwen / Wang, Yihai / He, Xiangjiu

Phytochemistry

2024 Volume 222, Page(s) 114069

Abstract: Seventeen piperidine alkaloids, including 15 previously undescribed 2-substituted-6-(9-phenylnonyl)-piperidine-3,4-diol alkaloids and a previously undescribed 2-substituted-6-(9-phenylnonyl)-piperidine-3-ol alkaloid, were isolated from the leaves of ... ...

Abstract	Seventeen piperidine alkaloids, including 15 previously undescribed 2-substituted-6-(9-phenylnonyl)-piperidine-3,4-diol alkaloids and a previously undescribed 2-substituted-6-(9-phenylnonyl)-piperidine-3-ol alkaloid, were isolated from the leaves of Alocasia macrorrhiza (L.) Schott. Their planar structures and configurations were elucidated based on HR-ESI-MS, 1D and 2D NMR, Snatzke's method, modified Mosher method, single-crystal X-ray crystallography, as well as quantum chemical calculation. It was found that Δδ
Language	English
Publishing date	2024-03-27
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.2024.114069
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Article ; Online: Anti-inflammatory monoterpenes from morinda (Morinda officinalis How.).

Jiang, Yan / Chen, Lu / Zeng, Jia / Wang, Yihai / Chen, Yuanyuan / Chen, Siting / Xu, Jingwen / He, Xiangjiu

Phytochemistry

2024 Volume 220, Page(s) 114034

Abstract: Morinda (Morinda officinalis How.) is widely consumed as a functional food owing to its potential to promote health. This study investigated the anti-inflammatory phytochemicals of morinda and isolated 30 monoterpenes, including 6 undescribed iridoids (1, ...

Abstract	Morinda (Morinda officinalis How.) is widely consumed as a functional food owing to its potential to promote health. This study investigated the anti-inflammatory phytochemicals of morinda and isolated 30 monoterpenes, including 6 undescribed iridoids (1, 6, 9-11 and 25), 2 undescribed acyclic monoterpenoids (28, 29), a known acyclic monoterpenoid and 21 known iridoids. Their chemical and stereo-structures were elucidated based on HR-ESI-MS, NMR,
MeSH term(s)	Morinda/chemistry ; Health Promotion ; Anti-Inflammatory Agents/pharmacology ; NF-kappa B/metabolism ; Iridoids/pharmacology ; Nitric Oxide ; Lipopolysaccharides/pharmacology ; Nitric Oxide Synthase Type II/metabolism
Chemical Substances	Anti-Inflammatory Agents ; NF-kappa B ; Iridoids ; Nitric Oxide (31C4KY9ESH) ; Lipopolysaccharides ; Nitric Oxide Synthase Type II (EC 1.14.13.39)
Language	English
Publishing date	2024-02-19
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.2024.114034
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Article ; Online: Total steroidal saponins from black nightshade (Solanum nigrum L.) overcome tumor multidrug resistance by inducing autophagy-mediated cell death in vivo and in vitro.

Wang, Yi / Wang, Siyu / Xu, Jingwen / Wang, Yihai / Xiang, Limin / He, Xiangjiu

Phytotherapy research : PTR

2023 Volume 37, Issue 7, Page(s) 3009–3024

Abstract	Multiple drug resistance (MDR) often occurs after prolonged chemotherapy, leading to refractory tumors and cancer recurrence. In this study, we demonstrated that the total steroidal saponins from Solanum nigrum L. (SN) had broad-spectrum cytotoxic activity against various human leukemia cancer cell lines, especially in adriamycin (ADR)-sensitive and resistant K562 cell lines. Moreover, SN could effectively inhibit the expression of ABC transporter in K562/ADR cells in vivo and in vitro. In vivo, by establishing K562/ADR xenograft tumor model, we demonstrated that SN might overcome drug resistance and inhibit the proliferation of tumors by regulating autophagy. In vitro, the increased LC3 puncta, the expression of LC3-II and Beclin-1, and the decreased expression of p62/SQSTM1 in SN-treated K562/ADR and K562 cells demonstrated autophagy induced by SN. Moreover, using the autophagy inhibitors or transfecting the ATG5 shRNA, we confirmed that autophagy induced by SN was a key factor in overcoming MDR thereby promoting cell death in K562/ADR cells. More importantly, SN-induced autophagy through the mTOR signaling pathway to overcome drug resistance and ultimately induced autophagy-mediated cell death in K562/ADR cells. Taken together, our findings suggest that SN has the potential to treat multidrug-resistant leukemia.
MeSH term(s)	Humans ; Solanum nigrum ; Drug Resistance, Neoplasm ; Drug Resistance, Multiple ; Doxorubicin/pharmacology ; K562 Cells ; Saponins/pharmacology ; Leukemia ; Cell Death ; Autophagy
Chemical Substances	Doxorubicin (80168379AG) ; Saponins
Language	English
Publishing date	2023-03-06
Publishing country	England
Document type	Journal Article
ZDB-ID	639136-9
ISSN	1099-1573 ; 0951-418X
ISSN (online)	1099-1573
ISSN	0951-418X
DOI	10.1002/ptr.7796
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Article ; Online: Diterpenoid WT-29 isolated from Wedelia exerted anti-inflammatory and anti-allergic activities.

Wang, Ru / Zeng, Jia / Chen, Lu / Sun, Lianlian / Wang, Yihai / Xu, Jingwen / He, Xiangjiu

Journal of ethnopharmacology

2023 Volume 319, Issue Pt 2, Page(s) 117265

Abstract: Ethnopharmacological relevance: Wedelia (Sphagneticola trilobata) is a traditional anti-inflammatory herb native to tropical America. It is commonly used to treat some inflammatory related diseases clinically, such as pertussis, pharyngitis, etc. ... ...

Abstract	Ethnopharmacological relevance: Wedelia (Sphagneticola trilobata) is a traditional anti-inflammatory herb native to tropical America. It is commonly used to treat some inflammatory related diseases clinically, such as pertussis, pharyngitis, etc. However, its specific anti-inflammatory mechanism is still unclear. Aim of the study: WT-29 (3α-angeloyloxy-9β-hydroxyent-kaura-16-en-19-oic acid) is a main bioactive diterpenoid isolated and purified from Wedelia. This study aims to explore the potential anti-inflammatory and anti-allergic properties of WT-29 on RAW264.7 cells stimulated with LPS and P815 cells induced by C48/80, as well as investigating their underlying molecular mechanisms. Methods: The anti-inflammatory mechanism of WT-29 was analyzed and predicted using network pharmacology, and then verified through experiments. The Griess reagent assay was employed to evaluate the impact of WT-29 on the generation of nitric oxide (NO) in RAW264.7 cells induced by LPS, the expression of various inflammatory cytokines and the release of histamine in cells were measured through qRT-PCR and ELISA techniques. The impact of WT-29 on the translocation of the NF-κB p65 protein to the nucleus was assessed through immunofluorescence staining. Western blot technique was utilized to investigate protein expression in inflammation, allergy, and autophagy pathways. Results: The study found that WT-29 can reduce the secretion of inflammatory factors (NO, iNOS, COX-2, IL-6, IL-1β and TNF-α), inhibit NF-κB activation and MAPK family phosphorylation, and induce autophagy in RAW264.7 cells stimulated with LPS. In addition, it demonstrated that WT-29 could inhibit histamine release and degranulation, as well as inhibit the MAPK family in C48/80-induced P815 cells. Conclusion: WT-29 isolated from Wedelia exerts anti-inflammatory and anti-allergic effects mainly through NF-κB, Nrf2/Keap-1, MAPK pathways and regulating of autophagy, suggesting that it might be a potential anti-inflammatory and anti-allergic agent and could be used as medicine or health benefit product.
MeSH term(s)	Animals ; Mice ; NF-kappa B/metabolism ; Wedelia/metabolism ; Lipopolysaccharides/pharmacology ; Anti-Allergic Agents/therapeutic use ; Anti-Inflammatory Agents/therapeutic use ; Inflammation/drug therapy ; RAW 264.7 Cells ; Nitric Oxide/metabolism
Chemical Substances	NF-kappa B ; Lipopolysaccharides ; Anti-Allergic Agents ; Anti-Inflammatory Agents ; Nitric Oxide (31C4KY9ESH)
Language	English
Publishing date	2023-09-30
Publishing country	Ireland
Document type	Journal Article
ZDB-ID	134511-4
ISSN	1872-7573 ; 0378-8741
ISSN (online)	1872-7573
ISSN	0378-8741
DOI	10.1016/j.jep.2023.117265
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Article ; Online: Anti-inflammatory steroids from the stems of Solanum nigrum L.

Deng, Junru / Wang, Lin / Jin, Qingyu / Zeng, Jia / Xu, Jingwen / He, Xiangjiu / Wang, Yihai

Phytochemistry

2023 Volume 210, Page(s) 113667

Abstract	Sixteen previously undescribed steroidal sapogenins along with two known ones were isolated from the stems of Solanum nigrum L. (Solanaceae). Their structures were identified using a combination of 1D and 2D NMR, HR-ESI-MS spectroscopy, the Mosher method, and X-ray diffraction analysis. Compounds 1-8 have an unusual F ring and 9-12 have a derived A ring, both of which are rare skeletons found in natural products. The biological evaluation showed that the isolated steroids exhibited inhibition of nitric oxide in the LPS-induced RAW 264.7 macrophages with IC
MeSH term(s)	Animals ; Mice ; Solanum nigrum/chemistry ; Anti-Inflammatory Agents/pharmacology ; Anti-Inflammatory Agents/metabolism ; Macrophages/metabolism ; NF-kappa B/metabolism ; Steroids/chemistry ; Lipopolysaccharides/pharmacology ; Nitric Oxide ; Nitric Oxide Synthase Type II/metabolism ; RAW 264.7 Cells
Chemical Substances	Anti-Inflammatory Agents ; NF-kappa B ; Steroids ; Lipopolysaccharides ; Nitric Oxide (31C4KY9ESH) ; Nitric Oxide Synthase Type II (EC 1.14.13.39)
Language	English
Publishing date	2023-04-01
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.2023.113667
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