scholarly journals Dimacrolide Sesquiterpene Pyridine Alkaloids from the Stems of Tripterygium regelii

2016 ◽  
Author(s):  
Dongsheng Fan ◽  
Guo-Yuan Zhu ◽  
Ting Li ◽  
Zhi-Hong Jiang ◽  
Li-Ping Bai
Keyword(s):  
Furan Ring ◽  
Fibroblast Cell ◽  
2D Nmr ◽  
Ring System ◽  
Human Rheumatoid Arthritis ◽  
Inhibitory Effects ◽  
Macrocyclic Ring ◽  
Spectroscopic Analyses ◽  
Tripterygium Regelii ◽  
Sesquiterpene Pyridine Alkaloids

Two new dimacrolide sesquiterpene pyridine alkaloids (DMSPAs), dimacroregelines A (1) and B (2), were isolated from the stems of Tripterygium regelii. The structures of both compounds were characterized by extensive 1D and 2D NMR spectroscopic analyses, as well as HRESIMS data. Compounds 1 and 2 are two rare DMSPAs possessing unique 2-(3′-carboxybutyl)-3-furanoic acid units forming the second macrocyclic ring, representing the first example of DMSPAs bearing an extra furan ring in their second macrocyclic ring system. Compound 2 showed inhibitory effects on the proliferation of human rheumatoid arthritis synovial fibroblast cell (MH7A) at a concentration of 20 μM.

scholarly journals Two triterpenoids from Rubus fraxinifolius leaves and their tyrosinase and elastase inhibitory activities

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Yesi Desmiaty ◽  
Muhammad Hanafi ◽  
Fadlina Chany Saputri ◽  
Berna Elya ◽  
Eko Aditya Rifai ◽  
...  
Keyword(s):  
Biological Activities ◽  
2D Nmr ◽  
Skin Aging ◽  
Protective Effects ◽  
Inhibitory Effects ◽  
Dioic Acid ◽  
Spectroscopic Analyses ◽  
Reported Data ◽  
Therapeutic Compounds ◽  
Organic Resources

AbstractNumerous therapeutic compounds have been isolated from naturally abundant organic resources, which may offer economical and sustainable sources of compounds with safe and efficacious biological activities. In the cosmetics industry, natural compounds with anti-aging activities are eagerly sought. Thus, we prepared various extracts from Rubus fraxinifolius leaves and used enzyme inhibition assays to isolate compounds with protective effects against skin aging. Two triterpenoids were isolated from Rubus fraxinifolius Poir. leaves. The structures were characterized by spectroscopic analyses (LC-ESI-MS, 1D/2D NMR) and comparison to reported data. Compound 1 and 2 were determined as 2,3-O-ethyleneglycol, 19-hydroxyurs-12-en-23,28-dioic acid and 2,3-O-propanediol,19-hydroxyurs-12-en-28-oic acid. Methanol extract and isolates were assessed for their inhibitory effects on elastase and tyrosinase. Compounds 1 and 2 inhibited elastase with IC50 122.199 µg/mL and 98.22 µg/mL, and also inhibited tyrosinase with IC50 207.79 µg/mL and 221.51 µg/mL, respectively. The molecular docking proved that both compounds have affinities toward the enzymes.

scholarly journals Aspidoptoids A–D: Four New Diterpenoids from Aspidopterys obcordata Vine

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 529
Author(s):  
Sun ◽  
Cao ◽  
Xiao ◽  
Zhang ◽  
Wang ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Circular Dichroism ◽  
Absolute Configuration ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
No Production ◽  
Inhibitory Effects ◽  
Electronic Circular Dichroism ◽  
Spectroscopic Analyses ◽  
Circular Dichroïsm

Four new diterpenoids, named aspidoptoids A–D (1–4), together with two known analogues (5–6) were isolated from Aspidopterys obcordata vine. Aspidoptoids A–B (1–2) are the first examples of phenylethylene-bearing 20-nor-diterpenoids of which aspidoptoid B (2) possesses a rare 3,10-oxybridge. Their structures and absolute configuration were determined by extensive spectroscopic analyses (IR, HRESIMS, 1D and 2D NMR) and electronic circular dichroism (ECD) calculation. In addition, all the isolates were evaluated for their cytotoxic activities and inhibitory effects on the nitric oxide (NO) production.

scholarly journals Targeted Isolation of Xenicane Diterpenoids from Taiwanese Soft Coral Asterospicularia laurae

Marine Drugs ◽  
2021 ◽  
Vol 19 (3) ◽  
pp. 123
Author(s):  
Yu-Chi Lin ◽  
Yi-Jen Chen ◽  
Shu-Rong Chen ◽  
Wan-Ju Lien ◽  
Hsueh-Wei Chang ◽  
...  
Keyword(s):  
Cytotoxic Effect ◽  
Soft Coral ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Ionization Mass ◽  
Spectroscopic Analyses ◽  
Potential Source ◽  
First Case ◽  
The Family ◽  
Mcf 7

Application of LC-MS/MS-based molecular networking indicated the ethanol extract of octocoral Asterospicularia laurae is a potential source for the discovery of new xenicane derivatives. A natural product investigation of this soft coral resulted in the isolation of four new xenicane diterpenoids, asterolaurins O‒R (1‒4), together with six known compounds, xeniolide-A (5), isoxeniolide-A (6), xeniolide-B (7), 7,8-epoxyxeniolide-B (8), 7,8-oxido-isoxeniolide-A (9), and 9-hydroxyxeniolide-F (10). The structures of isolated compounds were characterized by employing spectroscopic analyses, including 2D-NMR (COSY, HMQC, HMBC, and NOESY) and high-resolution electrospray ionization mass spectrometry (HRESIMS). Asterolaurin O is the first case of brominated tricarbocyclic type floridicin in the family Xeniidae. Concerning bioactivity, the cytotoxic activity of those isolates was evaluated. As a result, compounds 1 and 2 demonstrated a selective cytotoxic effect against the MCF-7 cell line at IC50 of 14.7 and 25.1 μM, respectively.

Antifungal and allelopathic activities of sesquiterpenes from Solidago canadensis

2021 ◽  
Vol 25 ◽  
Author(s):  
Na Liu ◽  
Meina Song ◽  
Yulin Sun ◽  
Fengying Yang ◽  
Haina Yu ◽  
...  
Keyword(s):  
Candida Albicans ◽  
Seed Germination ◽  
Invasive Plant ◽  
2D Nmr ◽  
Solidago Canadensis ◽  
Significant Activity ◽  
Inhibitory Effects ◽  
Ic50 Values ◽  
Allelopathic Effects

: One new eudesmane sesquiterpene (1) and one new chromolaevane sesquiterpene (2), along with 19 known compounds, have been isolated from the invasive plant Solidago canadensis. Their structures were established by spectroscopic means including 1D/2D-NMR and HR-ESIMS analyses. Compounds 10 and 12, in combination with fluconazole, showed significant activity in an in vitro synergistic antifungal assay against Candida albicans, with FIC values of <0.15625 and <0.28125, respectively. Meanwhile, the allelopathic effects of these sesquiterpenes on Arabidopsis seed germination were also tested. Compounds 5, 7, 17 and 18 retarded the seed germination of Arabidopsis with IC50 values ranging from 9.1 to 41 μg/mL, while other compounds showed no obvious inhibitory effects.

Aggregation Behavior of a Six‐Membered Cyclic Frustrated Phosphane/Borane Lewis Pair: Formation of a Supramolecular Cyclooctameric Macrocyclic Ring System

2019 ◽  
Vol 58 (3) ◽  
pp. 882-886 ◽  
Author(s):  
Xiaoming Jie ◽  
Constantin G. Daniliuc ◽  
Robert Knitsch ◽  
Michael Ryan Hansen ◽  
Hellmut Eckert ◽  
...  
Keyword(s):  
Pair Formation ◽  
Ring System ◽  
Aggregation Behavior ◽  
Macrocyclic Ring

scholarly journals Secondary Metabolites with Nitric Oxide Inhibition from Marine-Derived Fungus Alternaria sp. 5102

Marine Drugs ◽  
2020 ◽  
Vol 18 (8) ◽  
pp. 426 ◽  
Author(s):  
Senhua Chen ◽  
Yanlian Deng ◽  
Chong Yan ◽  
Zhenger Wu ◽  
Heng Guo ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
2D Nmr ◽  
X Ray ◽  
X Ray Crystallography ◽  
Spectroscopic Analyses ◽  
Structure Activity ◽  
Ic50 Values ◽  
Alternaria Sp ◽  
Modified Mosher’S Method ◽  
Oxide Inhibition

Two new benzofurans, alternabenzofurans A and B (1 and 2) and two new sesquiterpenoids, alternaterpenoids A and B (3 and 4), along with 18 known polyketides (5−22), were isolated from the marine-derived fungus Alternaria sp. 5102. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HR-ESIMS, and ECD) and X-ray crystallography, as well as the modified Mosher’s method. Compounds 2, 3, 5, 7, 9–18, and 20–22 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50 values in the range from 1.3 to 41.1 μM. Structure-activity relationships of the secondary metabolites were discussed.

Macrolide sesquiterpene pyridine alkaloids from the stems of Tripterygium regelii

2018 ◽  
Vol 73 (1) ◽  
pp. 23-33 ◽  
Author(s):  
Dongsheng Fan ◽  
Ting Li ◽  
Zhiyuan Zheng ◽  
Guo-Yuan Zhu ◽  
Xiaojun Yao ◽  
...  
Keyword(s):  
Tripterygium Regelii ◽  
Sesquiterpene Pyridine Alkaloids

scholarly journals tert-Butylphenolic Derivatives from Paenibacillus odorifer—A Case of Bioconversion

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 1951 ◽  
Author(s):  
Thi-Bach-Le Nguyen ◽  
Olivier Delalande ◽  
Isabelle Rouaud ◽  
Solenn Ferron ◽  
Laura Chaillot ◽  
...  
Keyword(s):  
Bacterial Strain ◽  
2D Nmr ◽  
One Dimensional ◽  
Spectroscopic Analyses ◽  
Human Keratinocyte ◽  
Rhizocarpon Geographicum ◽  
Ionisation Mass Spectrometry ◽  
Keratinocyte Cell ◽  
Ic50 Values ◽  
First Time

Two compounds (1) and (2) containing tert-butylphenol groups were, for the first time, produced during the culture of Paenibacillus odorifer, a bacterial strain associated with the crustose lichen, Rhizocarpon geographicum. Their entire structures were identified by one-dimensional (1D) and two-dimensional (2D) NMR and high-resolution electrospray ionisation mass spectrometry (HRESIMS) spectroscopic analyses. Among them, Compound 1 exhibited significant cytotoxicity against B16 murine melanoma and HaCaT human keratinocyte cell lines with micromolar half maximal inhibitory concentration (IC50) values. Furthermore, after supplementation studies, a putative biosynthesis pathway was proposed for Compound 1 throughout a bioconversion by this bacterial strain of butylated hydroxyanisole (BHA), an antioxidant polymer additive.

scholarly journals Six New 3,5-Dimethylcoumarins from Chelonopsis praecox, Chelonopsis odontochila and Chelonopsis pseudobracteata

2021 ◽  
Author(s):  
Chang-An Geng ◽  
Zhen-Tao Deng ◽  
Qian Huang ◽  
Chun-Lei Xiang ◽  
Ji-Jun Chen
Keyword(s):  
Protein Tyrosine Phosphatase ◽  
Tyrosine Phosphatase ◽  
2D Nmr ◽  
Cell Protein ◽  
Protein Tyrosine Phosphatase 1B ◽  
Protein Tyrosine ◽  
Aerial Parts ◽  
Spectroscopic Analyses ◽  
New Compounds

AbstractTen 3,5-dimethylcoumarins (1–6 and 8‒11) involving six new ones (1–6), together with a known 3-methylcoumarin (7), were isolated from the aerial parts of three Chelonopsis plants, C. praecox, C. odontochila, and C. pseudobracteata. The structures of the new compounds were determined by extensive HRESIMS, 1D and 2D NMR spectroscopic analyses. According to the substitution at C-5, these coumarins were classified into 5-methyl, 5-hydroxymethyl, 5-formyl, and 5-nor types. All the isolates were assayed for their inhibition on α-glucosidase, protein tyrosine phosphatase 1B, and T-cell protein tyrosine phosphatase in vitro. Graphic Abstract

scholarly journals Mono- and Dimeric Xanthones with Anti-Glioma and Anti-Inflammatory Activities from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722

Marine Drugs ◽  
2022 ◽  
Vol 20 (1) ◽  
pp. 51
Author(s):  
Senhua Chen ◽  
Heng Guo ◽  
Minghua Jiang ◽  
Qilin Wu ◽  
Jing Li ◽  
...  
Keyword(s):  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
Crystallographic Analysis ◽  
Selective Cytotoxicity ◽  
X Ray ◽  
Planar Structures ◽  
Spectroscopic Analyses ◽  
Ic50 Values ◽  
Anti Inflammatory ◽  
Resolution Mass

Seven new xanthones, diaporthones A−G (1−7), together with 13 known analogues, including five mono- (8−14) and six dimeric xanthones (15−20), were obtained from the ascidian-derived fungus Diaporthe sp. SYSU-MS4722. Their planar structures were established by extensive spectroscopic analyses, including 1D and 2D NMR and high-resolution mass spectrometry (HR-ESIMS). The absolute configurations of 1−7 were clearly identified by X-ray crystallographic analysis and calculation of the ECD Spectra. Compounds 15−20 showed significant anti-inflammatory activity with IC50 values between 6.3 and 8.0 μM. In addition, dimeric xanthones (15−20) showed selective cytotoxicity against T98G cell lines with IC50 values ranging from 19.5 to 78.0 μM.

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