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11 pages, 912 KiB

Open AccessArticle

Chemical Constituents and Bioactivities of the Plant-Derived Fungus Aspergillus fumigatus

by Zihuan Sang, Yanjiang Zhang, Kaidi Qiu, Yuting Zheng, Chen Chen, Li Xu, Jiaying Lai, Zhenxing Zou and Haibo Tan

Molecules 2024, 29(3), 649; https://doi.org/10.3390/molecules29030649 - 30 Jan 2024

Viewed by 1382

Abstract

A new bergamotane sesquiterpenoid, named xylariterpenoid H (1), along with fourteen known compounds (2–15), were isolated from the crude extract of Aspergillus fumigatus, an endophytic fungus isolated from Delphinium grandiflorum L. Their structures were elucidated mainly [...] Read more.

A new bergamotane sesquiterpenoid, named xylariterpenoid H (1), along with fourteen known compounds (2–15), were isolated from the crude extract of Aspergillus fumigatus, an endophytic fungus isolated from Delphinium grandiflorum L. Their structures were elucidated mainly by extensive analyses of NMR and MS spectroscopic data. In addition, the screening results of antibacterial and cytotoxic activities of compounds 1–15 showed that compound 4 displayed antibacterial activities against Staphylococcus aureus and MRSA (methicillin-resistant S. aureus) with an MIC value of 3.12 µg/mL. Full article

(This article belongs to the Special Issue Natural Products as Inspirations for the Development of Potential Therapeutic Agents)

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32 pages, 9644 KiB

Open AccessArticle

Pleiotropic Potential of Evernia prunastri Extracts and Their Main Compounds Evernic Acid and Atranorin: In Vitro and In Silico Studies

by Elżbieta Studzińska-Sroka, Magdalena Bulicz, Marika Henkel, Natalia Rosiak, Magdalena Paczkowska-Walendowska, Dominik Szwajgier, Ewa Baranowska-Wójcik, Katarzyna Korybalska and Judyta Cielecka-Piontek

Molecules 2024, 29(1), 233; https://doi.org/10.3390/molecules29010233 - 31 Dec 2023

Cited by 4 | Viewed by 1564

Abstract

Evernia prunastri is a lichen widely distributed in the Northern Hemisphere. Its biological properties still need to be discovered. Therefore, our paper focuses on studies of E. prunastri extracts, including its main metabolites evernic acid (EA) or atranorin (ATR). Phytochemical profiles using chromatographic [...] Read more.

Evernia prunastri is a lichen widely distributed in the Northern Hemisphere. Its biological properties still need to be discovered. Therefore, our paper focuses on studies of E. prunastri extracts, including its main metabolites evernic acid (EA) or atranorin (ATR). Phytochemical profiles using chromatographic analysis were confirmed. The antioxidant activity was evaluated using in vitro chemical tests and in vitro enzymatic cells-free tests, namely superoxide dismutase (SOD), glutathione peroxidase (GPx), glutathione reductase (GR), and catalase (CAT). The anti-inflammatory potential using cyclooxygenase-2 (COX-2) and hyaluronidase were determined. The neuroprotective potential using acetylcholinesterase, (AChE), butyrylcholinesterase (BChE), and tyrosinase (Tyr) was estimated. The hypoglycemic activity was also confirmed (α-glucosidase). Principal component analysis was performed to determine the relationship between the biological activity of extracts. The inhibitory effect of EA and ATR on COX-2 AChE, BChE, Tyr, and α-glucosidase was evaluated using molecular docking techniques and confirmed for EA and ATR (besides α-glucosidase). The penetration of EA and ATR from extracts through the blood–brain barrier was confirmed using the parallel artificial membrane permeability assay blood–brain barrier test. In conclusion, depending on chemical surroundings and the concentration, the E. prunastri extracts, EA or ATR, showed attractive pleiotropic properties, which should be further investigated. Full article

(This article belongs to the Special Issue Natural Products as Inspirations for the Development of Potential Therapeutic Agents)

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11 pages, 1412 KiB

Open AccessArticle

Koninginins X-Z, Three New Polyketides from Trichoderma koningiopsis SC-5

by Weiwei Peng, Jianbing Tan, Zihuan Sang, Yuantao Huang, Li Xu, Yuting Zheng, Siyu Qin, Haibo Tan and Zhenxing Zou

Molecules 2023, 28(23), 7848; https://doi.org/10.3390/molecules28237848 - 29 Nov 2023

Cited by 1 | Viewed by 1175

Abstract

Koninginins X-Z (1–3), three novel polyketides, were isolated from the solid fermentation of the endophytic fungus Trichoderma koningiopsis SC-5. Their structures, including the absolute configurations, were comprehensively characterized by a combination of NMR spectroscopic methods, HRESIMS, ¹³C NMR, [...] Read more.

Koninginins X-Z (1–3), three novel polyketides, were isolated from the solid fermentation of the endophytic fungus Trichoderma koningiopsis SC-5. Their structures, including the absolute configurations, were comprehensively characterized by a combination of NMR spectroscopic methods, HRESIMS, ¹³C NMR, DFT GIAO ¹³C NMR, and electronic circular dichroism calculations as well as single crystal X-ray diffraction. In addition, all the compounds were evaluated for antifungal activity against Candida albicans. Full article

(This article belongs to the Special Issue Natural Products as Inspirations for the Development of Potential Therapeutic Agents)

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10 pages, 1991 KiB

Open AccessArticle

Three New Benzophenone Derivatives from Selaginella tamariscina

by Jiayin Long, Qingqing Mao, Yujie Peng, Lei Liu, Yin Hong, Honglin Xiang, Ming Ma, Hui Zou and Junwei Kuang

Molecules 2023, 28(12), 4582; https://doi.org/10.3390/molecules28124582 - 6 Jun 2023

Cited by 1 | Viewed by 1634

Abstract

Six compounds including three new benzophenones, selagibenzophenones D-F (1–3), two known selaginellins (4–5) and one known flavonoid (6), were isolated from Selaginella tamariscina. The structures of new compounds were established by 1D-, [...] Read more.

Six compounds including three new benzophenones, selagibenzophenones D-F (1–3), two known selaginellins (4–5) and one known flavonoid (6), were isolated from Selaginella tamariscina. The structures of new compounds were established by 1D-, 2D-NMR and HR-ESI-MS spectral analyses. Compound 1 represents the second example of diarylbenzophenone from natural sources. Compound 2 possesses an unusual biphenyl-bisbenzophenone structure. Their cytotoxicity against human hepatocellular carcinoma HepG2 and SMCC-7721 cells and inhibitory activities on lipopolysaccharide-induced nitric oxide (NO) production in RAW264.7 cells were evaluated. Compound 2 showed moderate inhibitory activity against HepG2 and SMCC-7721 cells, and compounds 4 and 5 showed moderate inhibitory activity to HepG2 cells. Compounds 2 and 5 also exhibited inhibitory activities on lipopolysaccharide-induced nitric oxide (NO) production. Full article

(This article belongs to the Special Issue Natural Products as Inspirations for the Development of Potential Therapeutic Agents)

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9 pages, 1924 KiB

Open AccessArticle

Two New Compounds from the Fungus Xylaria nigripes

by Hongping Long, Siqian Zhou, Lanqing Li, Jing Li and Jikai Liu

Molecules 2023, 28(2), 508; https://doi.org/10.3390/molecules28020508 - 4 Jan 2023

Cited by 5 | Viewed by 2711

Abstract

In the process of discovering more neural-system-related bioactive compounds from Xylaria nigripes, xylariamino acid A (1), a new amino acid derivative, and a new isovaleric acid phenethyl ester (2) were isolated and identified. Their structures and absolute configurations [...] Read more.

In the process of discovering more neural-system-related bioactive compounds from Xylaria nigripes, xylariamino acid A (1), a new amino acid derivative, and a new isovaleric acid phenethyl ester (2) were isolated and identified. Their structures and absolute configurations were determined by analyses of IR, HRESIMS, NMR spectroscopic data, and gauge-independent atomic orbital (GIAO) NMR calculation, as well as electronic circular dichroism (ECD) calculation. The isolated compounds were evaluated for their neuroprotective effects against damage to PC12 cells by oxygen and glucose deprivation (OGD). Compounds 1 and 2 can increase the viability of OGD-induced PC12 cells at all tested concentrations. Moreover, compound 2 (1 μmol L⁻¹) can significantly reduce the percentage of apoptotic cells. Full article

(This article belongs to the Special Issue Natural Products as Inspirations for the Development of Potential Therapeutic Agents)

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13 pages, 6004 KiB

Open AccessArticle

Neuroprotective Effects of the Psychoactive Compound Biatractylolide (BD) in Alzheimer’s Disease

by Qianmei Hu, Jixiang Wang, Maida Irshad, Siyu Mao, Hongting Chen, Yujiao Song, Xuan Xu and Xing Feng

Molecules 2022, 27(23), 8294; https://doi.org/10.3390/molecules27238294 - 28 Nov 2022

Cited by 3 | Viewed by 2438

Abstract

Mitochondria play a central role in the survival or death of neuronal cells, and they are regulators of energy metabolism and cell death pathways. Many studies support the role of mitochondrial dysfunction and oxidative damage in the pathogenesis of Alzheimer’s disease. Biatractylolide (BD) [...] Read more.

Mitochondria play a central role in the survival or death of neuronal cells, and they are regulators of energy metabolism and cell death pathways. Many studies support the role of mitochondrial dysfunction and oxidative damage in the pathogenesis of Alzheimer’s disease. Biatractylolide (BD) is a kind of internal symmetry double sesquiterpene novel ester compound isolated from the Chinese medicinal plant Baizhu, has neuroprotective effects in Alzheimer’s disease. We developed a systematic pharmacological model based on chemical pharmacokinetic and pharmacological data to identify potential compounds and targets of Baizhu. The neuroprotective effects of BD in PC12 (rat adrenal pheochromocytoma cells) and SH-SY5Y (human bone marrow neuroblastoma cells) were evaluated by in vitro experiments. Based on the predicted results, we selected 18 active compounds, which were associated with 20 potential targets and 22 signaling pathways. Compound-target, target-disease and target-pathway networks were constructed using Cytoscape 3.2.1. And verified by in vitro experiments that BD could inhibit Aβ by reducing oxidative stress and decreasing CytC release induced mPTP opening. This study provides a theoretical basis for the development of BD as an anti-Alzheimer’s disease drug. Full article

(This article belongs to the Special Issue Natural Products as Inspirations for the Development of Potential Therapeutic Agents)

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18 pages, 4517 KiB

Open AccessArticle

Polygonatum cyrtonema Hua Polysaccharides Protect BV2 Microglia Relief Oxidative Stress and Ferroptosis by Regulating NRF2/HO-1 Pathway

by Jiayu Li, Xifan Wang, Rongrong Zhou, Fei Cheng, Xueyang Tang, Jia Lao, Linben Xu, Wei He, Dan Wan, Hongliang Zeng and Shuihan Zhang

Molecules 2022, 27(20), 7088; https://doi.org/10.3390/molecules27207088 - 20 Oct 2022

Cited by 21 | Viewed by 3263

Abstract

Neuronal-regulated cell death (RCD) due to the accumulation of ROS within the central nervous system (CNS) is one of the crucial causes of central system diseases. Caspase-dependent apoptosis is the only form of RCD. As research progressed, several nonapoptotic cell death pathway RCDs [...] Read more.

Neuronal-regulated cell death (RCD) due to the accumulation of ROS within the central nervous system (CNS) is one of the crucial causes of central system diseases. Caspase-dependent apoptosis is the only form of RCD. As research progressed, several nonapoptotic cell death pathway RCDs were identified. Ferroptosis is a nonapoptotic RCD characterized by lipid peroxidation and plasma membrane damage. Polygonatum cyrtonema Hua. Polysaccharides (PCP) are an effective antioxidant. Based on this, the protective effect and mechanism of PCP against H₂O₂-induced microglial injury were investigated. Furthermore, the protective mechanism of PCP against ferroptosis in microglia was explored. Our results indicated that PCP could reduce oxidative stress-induced ROS accumulation by activating the NRF2/HO-1 signaling pathway, thus attenuating RCD in microglia. Subsequent studies have revealed that PCP alleviates ferroptosis in microglia due to protein levels of ERASTIN/RSL3 inhibitor SLC7A11/GPX4 by activating the NRF2/HO-1 signaling pathway. Therefore, we hypothesized that PCP exerts antioxidative and anti-ferroptosis effects by activating the expression of the NRF2/HO-1 pathway. This facilitates new ideas for clinically effective prevention and treatment of diseases due to accumulated reactive oxygen species in the CNS. Simultaneously, PCP has the development potential as a new drug candidate for treating CNS diseases. Full article

(This article belongs to the Special Issue Natural Products as Inspirations for the Development of Potential Therapeutic Agents)

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9 pages, 1080 KiB

Open AccessArticle

Brasesquilignan A–E, Five New Furofurans Lignans from Selaginella braunii Baker

by Fei Cheng, Jianping Wu, Yan Zhang, Yuyan Wang, Guihua Li, Hongliang Zeng, Xiaoai He, Guiming Deng, Jianbin Tan, Hongping Long, Puhua Zeng, Yiheng Liu, Gangzhi Zhu, Zuhui Chen and Kangping Xu

Molecules 2022, 27(19), 6349; https://doi.org/10.3390/molecules27196349 - 26 Sep 2022

Cited by 1 | Viewed by 1462

Abstract

Five new furofurans lignans, Brasesquilignan A–E (1–5), were isolated from the aqueous ethanol extract of Selaginella braunii Baker. Their structures were elucidated by extensive analysis of NMR and HRESIMS data. Their absolute configurations were determined by CD spectra, enzymatic hydrolysis, and [...] Read more.

Five new furofurans lignans, Brasesquilignan A–E (1–5), were isolated from the aqueous ethanol extract of Selaginella braunii Baker. Their structures were elucidated by extensive analysis of NMR and HRESIMS data. Their absolute configurations were determined by CD spectra, enzymatic hydrolysis, and GCMS analysis. Furthermore, all compounds were evaluated for anti-proliferative activities against various human cancer cellsin vitro. Compounds 2 and 3 exhibited weak inhibitorypotency against five human cancer cells. Full article

(This article belongs to the Special Issue Natural Products as Inspirations for the Development of Potential Therapeutic Agents)

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8 pages, 1325 KiB

Open AccessArticle

Two New Seco-Labdane Diterpenoids from the Leaves of Callicarpa nudiflora

by Xia Guo, Yao Zhang, Yin Xiao, Lu Zhou, Shaoyang Yin, Xifeng Sheng, Hongling Xiang and Hui Zou

Molecules 2022, 27(13), 4018; https://doi.org/10.3390/molecules27134018 - 22 Jun 2022

Cited by 1 | Viewed by 1742

Abstract

Two new seco-labdane diterpenoids, nudiflopene N (1) and nudiflopene O (2), and four known compounds were isolated from the leaves of Callicarpa nudiflora. The structures of the new compounds were established by 1D-, 2D-NMR, and HR-ESI-MS spectral analyses. Compounds 1–3 [...] Read more.

Two new seco-labdane diterpenoids, nudiflopene N (1) and nudiflopene O (2), and four known compounds were isolated from the leaves of Callicarpa nudiflora. The structures of the new compounds were established by 1D-, 2D-NMR, and HR-ESI-MS spectral analyses. Compounds 1–3 showed inhibitory activities on lipopolysaccharide-induced nitric oxide (NO) production in RAW264.7 cells, and new compounds 1–2 exhibited more potent inhibitory activity than compound 3. The cytotoxicity of compounds 1–3 against human hepatocellular carcinoma HepG2 cells and human gastric carcinoma SGC-7901 cells were evaluated, while all of them exhibited no cytotoxicity. Full article

(This article belongs to the Special Issue Natural Products as Inspirations for the Development of Potential Therapeutic Agents)

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Review

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14 pages, 2175 KiB

Open AccessReview

Veratrum parviflorum: An Underexplored Source for Bioactive Steroidal Alkaloids

by Jared T. Seale and Owen M. McDougal

Molecules 2022, 27(16), 5349; https://doi.org/10.3390/molecules27165349 - 22 Aug 2022

Cited by 8 | Viewed by 2998

Abstract

Plants of the Veratrum genus have been used throughout history for their emetic properties, rheumatism, and for the treatment of high blood pressure. However, inadvertent consumption of these plants, which resemble wild ramps, induces life-threatening side effects attributable to an abundance of steroidal [...] Read more.

Plants of the Veratrum genus have been used throughout history for their emetic properties, rheumatism, and for the treatment of high blood pressure. However, inadvertent consumption of these plants, which resemble wild ramps, induces life-threatening side effects attributable to an abundance of steroidal alkaloids. Several of the steroidal alkaloids from Veratrum spp. have been investigated for their ability to antagonize the Hedgehog (Hh) signaling pathway, a key pathway for embryonic development and cell proliferation. Uncontrolled activation of this pathway is linked to the development of various cancers; most notably, basal cell carcinoma and acute myeloid leukemia. Additional investigation of Veratrum spp. may lead to the identification of novel alkaloids with the potential to serve as chemotherapeutics. V. parviflorum is a relatively uncommon species of Veratrum that resides in the southeastern regions of North America. The phytochemical profile of this plant remains largely unexplored; however, bioactive steroidal alkaloids, including cyclopamine, veratramine, veratridine, and verazine were identified in its extract. The structural elucidation and bioactivity assessment of steroidal alkaloids in lesser abundance within the extract of V. parviflorum may yield potent Hh pathway inhibitors. This review seeks to consolidate the botanical and phytochemical information regarding V. parviflorum. Full article

(This article belongs to the Special Issue Natural Products as Inspirations for the Development of Potential Therapeutic Agents)

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