Guaiane Sesquiterpenes from the Rhizome of Curcuma xanthorrhiza and Their Inhibitory Effects on UVB-induced MMP-1 Expression in Human Keratinocytes

A new guaiane sesquiterpene, (1 R,4 S,5 S,10 R)-10-methyl guaianediol (1), along with five known compounds, 10-methylalismoxide (2), (+)-alismoxide (3), isozedoarondiol (4), zedoarondiol (5), and zedoalactone B (6), were isolated from the rhizomes of Curcuma xanthorrhiza Roxb. Compounds 1-6 were isolated from this plant for the first time. Chemical structures were determined using nuclear magnetic resonance (NMR), electron ionization mass spectrometry (EI/MS), polarimetry, circular dichroism (CD), and infrared spectroscopy (IR). Compounds 3 and 4 decreased MMP-1 expression in UVB-treated human keratinocytes by about 8.9-fold and 7.6-fold at the mRNA level, and by about 9.2-fold and 6.6-fold at the protein level, respectively. Results indicate that the isolated compounds have anti-aging effects by inhibiting MMP-1 expression in skin cells.

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Natalenamides A–C, Cyclic Tripeptides from the Termite-Associated Actinomadura sp. RB99

Molecules ◽

10.3390/molecules23113003 ◽

2018 ◽

Vol 23 (11) ◽

pp. 3003 ◽

Cited By ~ 4

Author(s):

Seoung Rak Lee ◽

Dahae Lee ◽

Jae Sik Yu ◽

René Benndorf ◽

Sullim Lee ◽

...

Keyword(s):

Mass Spectrometry ◽

Cyclic Peptides ◽

Culture Broth ◽

Resonance Spectroscopy ◽

Ionization Mass ◽

Inhibitory Effects ◽

Associated Bacteria ◽

Chemical Structures ◽

New Compounds ◽

Powerful Strategy

In recent years, investigations into the biochemistry of insect-associated bacteria have increased. When combined with analytical dereplication processes, these studies provide a powerful strategy to identify structurally and/or biologically novel compounds. Non-ribosomally synthesized cyclic peptides have a broad bioactivity spectrum with high medicinal potential. Here, we report the discovery of three new cyclic tripeptides: natalenamides A–C (compounds 1–3). These compounds were identified from the culture broth of the fungus-growing termite-associated Actinomadura sp. RB99 using a liquid chromatography (LC)/ultraviolet (UV)/mass spectrometry (MS)-based dereplication method. Chemical structures of the new compounds (1–3) were established by analysis of comprehensive spectroscopic methods, including one-dimensional (1H and 13C) and two-dimensional (1H-1H-COSY, HSQC, HMBC) nuclear magnetic resonance spectroscopy (NMR), together with high-resolution electrospray ionization mass spectrometry (HR-ESIMS) data. The absolute configurations of the new compounds were elucidated using Marfey’s analysis. Through several bioactivity tests for the tripeptides, we found that compound 3 exhibited significant inhibitory effects on 3-isobutyl-1-methylxanthine (IBMX)-induced melanin production. The effect of compound 3 was similar to that of kojic acid, a compound extensively used as a cosmetic material with a skin-whitening effect.

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Antioxidant and Hepatoprotective Activity of Phenyl Glycosides Isolated From Heliciopsis lobata

Natural Product Communications ◽

10.1177/1934578x20946255 ◽

2020 ◽

Vol 15 (8) ◽

pp. 1934578X2094625

Author(s):

Bui Van Trung ◽

Do Thi Thao ◽

Duong Hong Anh ◽

Phan Van Kiem ◽

Pham Hung Viet

Keyword(s):

Barbituric Acid ◽

Multiple Bond ◽

Radical Scavenging ◽

Hepatoprotective Activity ◽

Ionization Mass ◽

Chemical Structures ◽

Heteronuclear Single Quantum Correlation ◽

First Time ◽

C Nmr

A new macrocyclic glycoside named helilobatoside A (1) and 5 known phenyl glycosides as 3,5-dimethoxy-4-hydroxyphenyl-1- O-β-d-glucopyranoside (2), tachioside (3), isotachioside (4), 1-(4-hydroxy-3-methoxyphenyl)-1-propanone-3- O-β-d-glucopyranoside (5), and 1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone-3- O-β-d-glucopyranoside (6), were isolated from the wood of Heliciopsis lobata (Merr.) Sleumer. Their chemical structures were elucidated using a combination of high-resolution electrospray ionization mass spectrometry, 1-dimensional (1D) and 2D nuclear magnetic resonance (NMR) spectral data as well as by comparison with data in the previous literature. This is the first time the 13C NMR data of compounds 5 and 6 were reported and also were assigned by heteronuclear single quantum correlation and heteronuclear multiple bond correlation spectra. Compounds 2-6 were first isolated from Heliciopsis genus. The isolated compounds were evaluated for their antioxidant and hepatoprotective activities in vitro. Compound 2 showed potential as an antioxidant in a 2,2-diphenyl-1-picryl-hydrazyl-hydrate assay (half-maximal inhibitory concentration [IC50] = 6.07 ± 0.17 µg/mL) and in thio-barbituric acid reactive substances assay (IC50 = 89.55 ± 8.26 µg/mL). This compound could also reduce the toxic effects of carbon tetrachloride on HepG2 survival and significantly protect the viability of cells up to 52.25 ± 4.36% at the 100 µg/mL treatment ( P < 0.05). Thus, with obtained results, the hepatoprotective activity of compound 2 could be related to radical scavenging and limited the lipid peroxidative activities.

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ChemInform Abstract: New Bisabolane Sesquiterpenes from the Rhizomes of Curcuma xanthorrhiza Roxb. and Their Inhibitory Effects on UVB-Induced MMP-1 Expression in Human Keratinocytes.

ChemInform ◽

10.1002/chin.201436193 ◽

2014 ◽

Vol 45 (36) ◽

pp. no-no

Author(s):

Ji-Hae Park ◽

Ye-Jin Jung ◽

Mohamed Antar Aziz Mohamed ◽

Tae Hoon Lee ◽

Chang-Ho Lee ◽

...

Keyword(s):

Human Keratinocytes ◽

Inhibitory Effects ◽

Curcuma Xanthorrhiza

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Cordidepsine is A Potential New Anti-HIV Depsidone from Cordia millenii, Baker

Molecules ◽

10.3390/molecules24173202 ◽

2019 ◽

Vol 24 (17) ◽

pp. 3202

Author(s):

Rostanie Dongmo Zeukang ◽

Xavier Siwe-Noundou ◽

Maurice Tagatsing Fotsing ◽

Turibio Tabopda Kuiate ◽

Joseph Tanyi Mbafor ◽

...

Keyword(s):

Mass Spectrometry ◽

2D Nmr ◽

Ionization Mass Spectrometry ◽

Ionization Mass ◽

Hiv Integrase ◽

Etoac Extract ◽

X Ray Crystallography ◽

Chemical Structures ◽

First Time ◽

Anti Hiv

Chemical investigation of Cordia millenii, Baker resulted in the isolation of a new depsidone, cordidepsine (1), along with twelve known compounds including cyclooctasulfur (2), lup-20(29)-en-3-triacontanoate (3), 1-(26-hydroxyhexacosanoyl)glycerol (4), glyceryl-1-hexacosanoate (5) betulinic acid (6), lupenone (7), β-amyrone (8), lupeol (9), β-amyrin (10), allantoin (11), 2′-(4-hydroxyphenyl)ethylpropanoate (12) and stigmasterol glycoside (13). Hemi-synthetic reactions were carried out on two isolated compounds (5 and 6) to afford two new derivatives, that is, cordicerol A (14) and cordicerol B (15), respectively. The chemical structures of all the compounds were established based on analysis and interpretation of spectroscopic data such as electron ionization mass spectrometry (EI–MS), high resolution electrospray ionization mass spectrometry (HR-ESI–MS), fast atom bombardment mass spectrometry (FAB–MS), one dimension and two dimension nuclear magnetic resonance (1D and 2D-NMR) spectral data as well as X-ray crystallography (XRC). Lupeol ester derivatives [Lup-20(29)-en-3-triacontanoate (3)], monoglycerol derivatives [1-(26-hydroxyhexacosanoyl)glycerol (4) and glyceryl-1 hexacosanoate (5)] were isolated for the first time from Cordia genus while sulfur allotrope [cyclooctasulfur (2)] was isolated for the first time from plant origin. Biological assays cordidepsine (1) exhibited significant anti-HIV integrase activity with IC50 = 4.65 μM; EtOAc extract of stem barks, EtOAc fraction of roots and leaves were not toxic against 3T3 cells.

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New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of Aster koraiensis

Plants ◽

10.3390/plants9121811 ◽

2020 ◽

Vol 9 (12) ◽

pp. 1811

Author(s):

Ji-Young Kim ◽

Young Hye Seo ◽

Im-Ho Lee ◽

He Yun Choi ◽

Hak Cheol Kwon ◽

...

Keyword(s):

Spectroscopic Data ◽

2D Nmr ◽

Isolation Procedure ◽

Pge2 Production ◽

Raw 264.7 Cells ◽

Inhibitory Effects ◽

Etoh Extract ◽

Chemical Structures ◽

New Compounds ◽

First Time

Four new eudesmane-type sesquiterpenoids, (1R,5S,6R,7S,9S,10S)-1,6,9-trihydroxy-eudesm-3-ene-1,6-di-O-β-d-glucopyranoside (1), (1R,5S,6S,7R,9S,10S)-1,6,9,11-tetrahydroxy-eudesm-3-ene-1,6-di-O-β-d-glucopyranoside (3), (1R,5S,6R,7S,9S,10R)-9-O-(Z-p-coumaroyl)-1,6,9-trihydroxy-eudesm-3-ene-6-O-β-d-glucopyranoside (6), and (1R,5S,6R,7S,9S,10R)-9-O-(E-feruloyl)-1,6,9-trihydroxy-eudesm-3-ene-6-O-β-d-glucopyranoside (7), were isolated from a 95% EtOH extract of the leaves of Aster koraiensis by repeated chromatography. Moreover, three sesquiterpenoids (2, 4, and 5) and two caffeoylquinic acids (8 and 9) having previously known chemical structures were isolated during the isolation procedure. The four new compounds (1, 3, 6, and 7) were elucidated by spectroscopic data (1D- and 2D-NMR, MS, and ECD) interpretation and hydrolysis. Moreover, the absolute configurations of 2, 4, and 5 were determined for the first time in this study. The compounds isolated were tested for their viability on nitric oxide (NO) and prostaglandin E2 (PGE2) production on LPS-stimulated RAW 264.7 cells. Among them, only 7 presented weak inhibitory effects on both NO and PGE2 production.

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Purification of Four Caffeoylquinic Acid Derivatives from the Flowers of Gynura Procumbens by HSCCC

Journal of Chromatographic Science ◽

10.1093/chromsci/bmab036 ◽

2021 ◽

Author(s):

Ming-yuan Cao ◽

Ju-wu Hu ◽

Zhen Gu ◽

Wei Xiong ◽

Lei Wu ◽

...

Keyword(s):

High Speed ◽

High Performance ◽

Solvent System ◽

Ionization Mass ◽

Preparative Scale ◽

Complex Samples ◽

Chemical Structures ◽

Caffeoylquinic Acid ◽

One Step ◽

First Time

Abstract Four caffeoylquinic acid derivatives from the Gunura procumbens flowers (GPF) were successfully isolated and purified by high-speed counter-current chromatography (HSCCC). Ethyl acetate–methanol–water (3:1:3, v/v/v) was the optimum biphasic solvent system, which was selected by high-performance liquid chromatography (HPLC) and run on a preparative scale where the lower aqueous phase was used as the mobile phase with a head-to-tail elution mode. Chlorogenic acid (3.83 mg), Isochlorogenic acid A (6.51 mg), Isochlorogenic acid B (4.38 mg) and Isochlorogenic acid C (4.47 mg) were obtained for the first time in an one-step HSCCC separation from 800 mg of the crude extracts. The purities of four compounds were determined to be >95% by HPLC. Chemical structures of each isolated compounds were identified by nuclear magnetic resonance and electrospray ionization mass spectrometry methods. It is worth noting that all the four compounds were isolated here for the first time from GPF and this work confirms the effectiveness of HSCCC for the separation of compounds contained in complex samples, and provides a foundation for further exploitation of G. procumbens.

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Reduction Reactions in the Ion Source in Electron Ionization Mass Spectrometry

Journal of Analytical Chemistry ◽

10.1134/s1061934820130092 ◽

2020 ◽

Vol 75 (13) ◽

pp. 1685-1692

Author(s):

D. M. Mazur ◽

M. E. Zimens ◽

Th. B. Latkin ◽

N. V. Ul’yanovskii ◽

V. B. Artaev ◽

...

Keyword(s):

Mass Spectrometry ◽

Ion Source ◽

Electron Ionization ◽

Electron Ionization Mass Spectrometry ◽

Ionization Mass Spectrometry ◽

Ionization Mass ◽

Reduction Reactions

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High-resolution AP-SMALDI MSI as a tool for drug imaging in Schistosoma mansoni

Analytical and Bioanalytical Chemistry ◽

10.1007/s00216-021-03230-w ◽

2021 ◽

Author(s):

Annika S. Mokosch ◽

Stefanie Gerbig ◽

Christoph G. Grevelding ◽

Simone Haeberlein ◽

Bernhard Spengler

Keyword(s):

Schistosoma Mansoni ◽

Egg Production ◽

Drug Repurposing ◽

Cancer Drug ◽

Ionization Mass ◽

Parasitic Flatworm ◽

Paired Female ◽

First Time ◽

Organ Tropism

AbstractSchistosoma mansoni is a parasitic flatworm causing schistosomiasis, an infectious disease affecting several hundred million people worldwide. Schistosomes live dioeciously, and upon pairing with the male, the female starts massive egg production, which causes pathology. Praziquantel (PZQ) is the only drug used, but it has an inherent risk of resistance development. Therefore, alternatives are needed. In the context of drug repurposing, the cancer drug imatinib was tested, showing high efficacy against S. mansoni in vitro. Besides the gonads, imatinib mainly affected the integrity of the intestine in males and females. In this study, we investigated the potential uptake and distribution of imatinib in adult schistosomes including its distribution kinetics. To this end, we applied for the first time atmospheric-pressure scanning microprobe matrix-assisted laser desorption/ionization mass spectrometry imaging (AP-SMALDI MSI) for drug imaging in paired S. mansoni. Our results indicate that imatinib was present in the esophagus and intestine of the male as early as 20 min after in vitro exposure, suggesting an oral uptake route. After one hour, the drug was also found inside the paired female. The detection of the main metabolite, N-desmethyl imatinib, indicated metabolization of the drug. Additionally, a marker signal for the female ovary was successfully applied to facilitate further conclusions regarding organ tropism of imatinib. Our results demonstrate that AP-SMALDI MSI is a useful method to study the uptake, tissue distribution, and metabolization of imatinib in S. mansoni. The results suggest using AP-SMALDI MSI also for investigating other antiparasitic compounds and their metabolites in schistosomes and other parasites. Graphical abstract

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The Assessment of IL-21 and IL-22 at the mRNA Level in Tumor Tissue and Protein Concentration in Serum and Peritoneal Fluid in Patients with Ovarian Cancer

Journal of Clinical Medicine ◽

10.3390/jcm10143058 ◽

2021 ◽

Vol 10 (14) ◽

pp. 3058

Author(s):

Aleksandra Mielczarek-Palacz ◽

Celina Kruszniewska-Rajs ◽

Marta Smycz-Kubańska ◽

Jarosław Strzelczyk ◽

Wojciech Szanecki ◽

...

Keyword(s):

Ovarian Cancer ◽

Peritoneal Fluid ◽

Tumor Tissue ◽

Mrna Level ◽

Enzyme Linked Immunosorbent Assay ◽

Control Group ◽

Expression Of Genes ◽

Genes Encoding ◽

First Time ◽

Ovarian Serous Cancer

The aim of the analysis was for the first time to assess the expression of genes encoding IL-21 and IL-22 at the mRNA level in ovarian tumor specimens and the concentration of these parameters in serum and peritoneal fluid in patients with ovarian serous cancer. The levels of IL-21 and IL-22 transcripts were evaluated with the use of the real-time RT-qPCR. Enzyme-linked immunosorbent assay (ELISA) was used to determine the concentration of proteins. Quantitative analysis of IL-21 gene mRNA in the tumor tissue showed the highest activity in the G1 degree of histopathological differentiation and was higher in G1 compared to the control group. The concentration of IL-21 and IL-22 in the serum and in the peritoneal fluid of women with ovarian cancer varied depending on the degree of histopathological differentiation of the cancer and showed statistical variability compared to controls. The conducted studies have shown that the local and systemic changes in the immune system involving IL-21 and IL-22 indicate the participation of these parameters in the pathogenesis of ovarian cancer, and modulation in the IL-21/IL-22 system may prove useful in the development of new diagnostic and therapeutic strategies used in patients, which require further research.

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Highly Oxygenated Triterpenoids and Diterpenoids from Fructus Rubi (Rubus Chingii Hu) and Their NF-kappa B Inhibitory Effects

Molecules ◽

10.3390/molecules26071911 ◽

2021 ◽

Vol 26 (7) ◽

pp. 1911

Author(s):

Jiang Wan ◽

Xiao-Juan Wang ◽

Nan Guo ◽

Xi-Ying Wu ◽

Juan Xiong ◽

...

Keyword(s):

Inhibitory Effects ◽

Nf Kappa B ◽

Pentacyclic Triterpenoids ◽

Chemical Structures ◽

Phytochemical Investigation ◽

Ic50 Values ◽

Rubus Chingii ◽

Rubus Chingii Hu ◽

Type 3

During a phytochemical investigation of the unripe fruits of Rubus chingii Hu (i.e., Fructus Rubi, a traditional Chinese medicine named “Fu-Pen-Zi”), a number of highly oxygenated terpenoids were isolated and characterized. These included nine ursane-type (1, 2, and 4–10), five oleanane-type (3, 11–14), and six cucurbitane-type (15–20) triterpenoids, together with five ent-kaurane-type diterpenoids (21–25). Among them, (4R,5R,8R,9R,10R,14S,17S,18S,19R,20R)-2,19α,23-trihydroxy-3-oxo-urs-1,12-dien-28-oic acid (rubusacid A, 1), (2R*,4S*,5R*,8R*,9R*,10R*,14S*,17S*, 18S*,19R*,20R*)-2α,19α,24-trihydroxy-3-oxo-urs-12-en-28-oic acid (rubusacid B, 2), (5R,8R,9R,10R, 14S,17R,18S,19S)-2,19α-dihydroxy-olean-1,12-dien-28-oic acid (rubusacid C, 3), and (3S,5S,8S,9R, 10S,13R,16R)-3α,16α,17-trihydroxy-ent-kaur-2-one (rubusone, 21) were previously undescribed. Their chemical structures and absolute configurations were elucidated on the basis of spectroscopic data and electronic circular dichroism (ECD) analyses. Compounds 1 and 3 are rare naturally occurring pentacyclic triterpenoids featuring a special α,β-unsaturated keto-enol (diosphenol) unit in ring A. Cucurbitacin B (15), cucurbitacin D (16), and 3α,16α,20(R),25-tetrahydroxy-cucurbita-5,23- dien-2,11,22-trione (17) were found to have remarkable inhibitory effects against NF-κB, with IC50 values of 0.08, 0.61, and 1.60 μM, respectively.

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