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1.
Biosci Biotechnol Biochem ; 88(5): 529-537, 2024 Apr 22.
Article in English | MEDLINE | ID: mdl-38509025

ABSTRACT

Four ethanol fractionated crude extracts (EFCEs [A-D]) purified from the leaves of Cinnamomum macrostemon Hayata were screened for antioxidative effects and mitochondrial function in HaCaT cells. The higher cell viability indicated that EFCE C was mildly toxic. Under the treatment of 50 ng/mL EFCE C, the hydrogen peroxide (H2O2)-induced cytosolic and mitochondrial reactive oxygen species levels were reduced as well as the H2O2-impaired cell viability, mitochondrial membrane potential (MMP), ATP production, and mitochondrial mass. The conversion of globular mitochondria to tubular mitochondria is coincident with EFCE C-restored mitochondrial function. The mitophagy activator rapamycin showed similar effects to EFCE C in recovering the H2O2-impaired cell viability, MMP, ATP production, mitochondrial mass, and also mitophagic proteins such as PINK1, Parkin, LC3 II, and biogenesis protein PGC-1α. We thereby propose the application of EFCE C in the prevention of oxidative stress in skin cells.


Subject(s)
Cell Survival , Cinnamomum , Hydrogen Peroxide , Keratinocytes , Membrane Potential, Mitochondrial , Mitochondria , Mitophagy , Oxidative Stress , Plant Extracts , Reactive Oxygen Species , Humans , Mitophagy/drug effects , Keratinocytes/drug effects , Keratinocytes/metabolism , Keratinocytes/cytology , Oxidative Stress/drug effects , Plant Extracts/pharmacology , Plant Extracts/chemistry , Membrane Potential, Mitochondrial/drug effects , Reactive Oxygen Species/metabolism , Hydrogen Peroxide/metabolism , Cell Survival/drug effects , Cinnamomum/chemistry , Mitochondria/drug effects , Mitochondria/metabolism , Adenosine Triphosphate/metabolism , Plant Leaves/chemistry , Antioxidants/pharmacology , Ubiquitin-Protein Ligases/metabolism , Sirolimus/pharmacology , HaCaT Cells , Protein Kinases/metabolism , Peroxisome Proliferator-Activated Receptor Gamma Coactivator 1-alpha/metabolism , Peroxisome Proliferator-Activated Receptor Gamma Coactivator 1-alpha/genetics
2.
Mar Drugs ; 21(4)2023 Mar 24.
Article in English | MEDLINE | ID: mdl-37103340

ABSTRACT

The mold Monascus, also called red yeast rice, anka, or koji, has been used as the natural food coloring agent and food additives for more than 1000 years in Asian countries. It has also been used in Chinese herbology and traditional Chinese medicine due to its easing digestion and antiseptic effects. However, under different culture conditions, the ingredients in Monascus-fermented products may be changed. Therefore, an in-depth understanding of the ingredients, as well as the bioactivities of Monascus-derived natural products, is important. Here, through the thorough investigation into the chemical constituents of M. purpureus wmd2424, five previously undescribed compounds, monascuspurins A-E (1-5), were isolated from the EtOAc extract of mangrove-derived fungus Monascus purpureus wmd2424 cultured in RGY medium. All the constituents were confirmed via HRESIMS and 1D- and 2D-NMR spectroscopy. Their antifungal activity was also evaluated. Our results showed that four constituents (compounds 3-5) possessed mild antifungal activity against Aspergillus niger, Penicillium italicum, Candida albicans, and Saccharomyces cerevisiae. It is worth mentioning that the chemical composition of the type strain Monascus purpureus wmd2424 has never been studied.


Subject(s)
Monascus , Oryza , Antifungal Agents/pharmacology , Antifungal Agents/metabolism , Monascus/metabolism , Fungi , Food Additives/metabolism , Coloring Agents , Fermentation , Oryza/microbiology
3.
Antibiotics (Basel) ; 12(1)2023 Jan 05.
Article in English | MEDLINE | ID: mdl-36671296

ABSTRACT

In our continued search for bioactive metabolites from cultures of rare Actinobacteria resources from all over Taiwan and various natural ecological environments, an active antimicrobial strain of Acrocarpospora punica 04107M was collected in Taitung County in Taiwan and prepared from soil. The bioassay-guided fractionation of the BuOH extract of a culture broth from A. punica 04107M led to the isolation of five previously undescribed compounds: Acrocarposporins A−E (Compounds 1−5). All the constituents were confirmed by HRESIMS and 1D- and 2D-NMR spectroscopy. Their antifungal activity was also evaluated. Our results showed that four constituents (Compounds 1, 2, 4, and 5) possessed mild antifungal activity against Aspergillus niger, Penicillium italicum, Candida albicans, and Saccharomyces cerevisiae. It is worth mentioning that the chemical composition of Acrocarpospora punica 04107M has never been studied. This is the first report on diterpenoid metabolites from the genus Acrocarpospora.

4.
Nat Prod Res ; 37(1): 47-55, 2023 Jan.
Article in English | MEDLINE | ID: mdl-34519597

ABSTRACT

Two new chromones named cnidimol G (1) and cnidimol H (2), one new coumarin, 7-methoxy-8-(3-methoxy-3-methyl-2-oxobutyl)coumarin (3), and twenty known compounds were isolated from MeOH extract of the fruit of Cnidium monnieri (L.) Cusson. The structures of compounds were elucidated by extensive spectroscopic analyses including 1 D and 2 D NMR, HRESIMS, IR and UV. Anti-inflammatory activity of the selected isolated compounds were evaluated. Compounds 1 and 8 exhibited inhibitory activities against nitric oxide production.


Subject(s)
Cnidium , Fruit , Cnidium/chemistry , Fruit/chemistry , Chromones/pharmacology , Chromones/analysis , Plant Extracts/chemistry , Coumarins/chemistry
5.
Molecules ; 27(22)2022 Nov 17.
Article in English | MEDLINE | ID: mdl-36432083

ABSTRACT

In an effort to explore bioactive anti-inflammatory compounds from natural Actinobacteria resources from all over Taiwan and various ecological environments, an active strain of Acrocarpospora punica was collected at Taitung County in Taiwan, prepared from soil origin. A bioassay-guided fractionation of the BuOH extract of a culture broth of a new strain of the actinomycete Acrocarpospora punica led to the isolation of five previously undescribed compounds: acrocarpunicains A-F (1-6). The structures were elucidated by 1D and 2D Nuclear Magnetic Resonance (NMR) spectroscopy and mass spectrometry. Furthermore, the isolated compounds were subjected to in vitro testing to evaluate their anti-inflammatory activity. Of these isolates, acrocarpunicains A (1), B (2), C (3) and F (6) showed NO inhibitory activity with IC50 values of 9.36 ± 0.25, 10.11 ± 0.47, 5.15 ± 0.18, and 27.17 ± 1.87 µM, stronger than the positive control, quercetin (IC50 = 35.95 ± 2.34 µM). To the best of our knowledge, this is the first report on azaphilone and phenanthrene-type metabolites from the genus Acrocarpospora.


Subject(s)
Actinobacteria , Actinomycetales , Actinobacteria/metabolism , Actinomycetales/chemistry , Anti-Inflammatory Agents , Magnetic Resonance Spectroscopy , Taiwan
6.
Bioorg Chem ; 129: 106166, 2022 Dec.
Article in English | MEDLINE | ID: mdl-36191429

ABSTRACT

From the anti-inflammatory screening of Formosan Lauraceous plants, the methanolic extract of the root of Machilus zuihoensis var. mushaensis stood out for its potent inhibitory activity toward superoxide anion and elastase release in human neutrophils. Bioassay-guided fractionation of the root of M. zuihoensis var. mushaensis led to eight new compounds, including two butanolides (1-2), five lignanoids (3-7), and one sesquiterpenoid (8), along with 50 known compounds (9-58). Structures of these compounds were elucidated by NMR, UV, IR, CD, and MS analyses. Thirty-two isolates were evaluated for their anti-inflammatory activity. Among them, 9, 20, 27, 28, 30, 31, 35, and 40 exhibited significant superoxide anion generation inhibition selectively (IC50 value < 7.4 µM), 15 and 19 showed selective inhibition toward elastase release (IC50 value < 8.0 µM). Moreover, 3, 16, 21, and 22 simultaneously displayed superoxide anion generation and elastase release inhibition. It is worth mentioning that 21 and 22 showed more potent inhibitory activities (IC50 < 1.0 µM) on superoxide anion than the positive control, LY294002. Further quantitative HPLC analysis indicated the content of 21 and 22 were 0.90 and 3.04 mg/g (w/w) in the ethyl-acetate layer of the root of M. zuihoensis var. mushaensis, respectively. Altogether, M. zuihoensis var. mushaensis revealed a potential for developing the botanical new drug against inflammation-related disease.


Subject(s)
Lauraceae , Superoxides , Humans , Lauraceae/chemistry , Anti-Inflammatory Agents/pharmacology , Pancreatic Elastase
7.
Molecules ; 27(18)2022 Sep 16.
Article in English | MEDLINE | ID: mdl-36144871

ABSTRACT

The authors wish to make the following changes to their paper [...].

9.
Molecules ; 27(18)2022 Sep 16.
Article in English | MEDLINE | ID: mdl-36144873

ABSTRACT

The authors wish to make the following changes to their paper [...].

10.
Phytochemistry ; 204: 113347, 2022 Dec.
Article in English | MEDLINE | ID: mdl-36027968

ABSTRACT

One undescribed C40 terpenoid, calomacroquinoic acid; four undescribed diterpenes, 5α,6α-epoxy-7α-hydroxyferruginol, 15-ethoxysugiol, 7-methoxy-6,7-secoabieta-8,11,13-triene-6,12-diol, and ethyl 7,8-secoabieta-11,14-dioxo-7-ate; two compounds isolated from Nature for the first time, 6ß,7α-dihydroxyferruginol and 12-O-methyltaxochinon; and six known compounds were successfully identified from the bark of Taiwan incense cedar Calocedrus formosana. Structures of all isolates were elucidated by physical data (appearance, ultraviolet, infrared, specific rotation, and X-ray) and spectroscopic data (1D and 2D nuclear magnetic resonance, and high-resolution electron ionization mass spectrometry). The biosynthetic pathway of calomacroquinoic acid is also described in the current study. Nitric oxide production in lipopolysaccharide (LPS)-stimulated BV-2 microglia cells was inhibited by 6,7-dehydroferruginol, 7α,11-dihydroxy-12-methoxy-8,11,13-abietriene, and trans-communic acid. Altogether, the bark of C. formosana possessed several potential natural therapeutics against inflammation-related neuronal diseases.

11.
Phytochemistry ; 202: 113312, 2022 Oct.
Article in English | MEDLINE | ID: mdl-35830940

ABSTRACT

To explore valuable endophytic fungus from Formosan Lauraceous plants as natural medicinal products, the fungus, Diaporthe caulivora isolated from leaves of Neolitsea daibuensis, was investigated. Through a thorough investigation of the ethanolic extract of the solid fermentation of D. caulivora 09F0132, six undescribed alkyne-geranylcyclohexenetriols, caulivotrioloxins A-F, one undescribed trichopyrone, diapopyrone, two undescribed sesquiterpenes, caulibysins A-B, one compound firstly isolated from the natural source, 3-O-desmethyl phomentrioloxin, and eight known compounds have been successfully identified. The absolute configuration of caulibysin A was confirmed by single-crystal X-ray diffraction, and those of (3R,8S)-5,7-dihydroxy-3-(1-hydroxyethyl)phthalide and (3S,8S)-5,7-dihydroxy-3-(1-hydroxyethyl)phthalide were determined by circular dichroism (CD) spectra. Among the isolated compounds, caulivotrioloxin A concentration-dependently decreased the cellular melanin contents and tyrosinase activities in mouse melanoma B16-F10 cells, suggesting the anti-melanogenic potentials. The anti-melanogenic effects of caulivotrioloxin A involved the decrease in the protein expressions of melanogenic enzymes, including tyrosinase, tyrosinase-related protein (TRP)-1, and TRP-2. Taken together, these results suggested that the isolates from D. caulivora could be served as natural melanogenesis inhibitors for cosmeceutical applications.


Subject(s)
Melanins , Melanoma, Experimental , Alkynes , Animals , Ascomycota , Endophytes , Mice , Monophenol Monooxygenase , Plant Extracts/chemistry
12.
Molecules ; 27(5)2022 03 02.
Article in English | MEDLINE | ID: mdl-35268758

ABSTRACT

The genus Cimicifuga is one of the smallest genera in the family Ranunculaceae. Cimicifugae Rhizoma originated from rhizomes of Cimicifuga simplex, and C. dahurica, C. racemosa, C. foetida, and C. heracleifolia have been used as anti-inflammatory, analgesic and antipyretic remedies in Chinese traditional medicine. Inflammation is related to many diseases. Cimicifuga taiwanensis was often used in folk therapy in Taiwan for inflammation. Phytochemical investigation and chromatographic separation of extracts from the roots of Cimicifuga taiwanensis has led to the isolation of six new compounds: cimicitaiwanins A-F (1-6, respectively). The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic data analysis (1D- and 2D-NMR, MS, and UV) and comparison with the literature data. The effect of some isolates on the inhibition of NO production in lipopolysaccharide-activated RAW 264.7 murine macrophages was evaluated. Of the isolates, 3-6 exhibited potent anti-NO production activity, with IC50 values ranging from 6.54 to 24.58 µM, respectively, compared with that of quercetin, an iNOS inhibitor with an IC50 value of 34.58 µM. This is the first report on metabolite from the endemic Taiwanese plant-C. taiwanensis.


Subject(s)
Cimicifuga
13.
Molecules ; 27(6)2022 Mar 14.
Article in English | MEDLINE | ID: mdl-35335250

ABSTRACT

Bioassay-guided fractionation of extracts derived from solid cultures of a Herbidospora daliensis originating from Taiwan led to the isolation of five new compounds, for which we propose the name herbidosporadalins A−E (1−5), one isolated for the first time, herbidosporadalin F (6), together with two known compounds (7 & 8). Their structures were elucidated by spectroscopic analyses, including 1D- and 2D-NMR experiments with those of known analogues, and on the basis of HR-EI-MS mass spectrometry, their anti-inflammatory activities were also evaluated. Of these isolates, herbidosporadalin A (1), B (2), F (6) and G (8) showed NO inhibitory activity, with IC50 values of 11.8 ± 0.9, 7.1 ± 2.9, 17.8 ± 1.7, and 13.3 ± 6.5 µM, stronger than the positive control quercetin (IC50 = 36.8 ± 1.3 µM). To the best of our knowledge, this is the first report on 3,4-seco-friedelane metabolites (5, 6 & 8) from the genus Herbidospora.


Subject(s)
Actinobacteria , Actinomycetales , Anti-Inflammatory Agents/pharmacology , Taiwan
14.
Environ Monit Assess ; 194(3): 219, 2022 Feb 24.
Article in English | MEDLINE | ID: mdl-35201445

ABSTRACT

In the context of extreme climate due to global climate transition, rainwater adaptation in resilient cities is a key issue for countries. The purpose of this study is to identify the rainfall hotspots in urban areas and investigate whether these hotspots have environmental conditions for rainfall adaptation. The study site is located in the Taichung area. This study collects rainfall data from rainfall stations at elevations below 500 m, employs QGIS (quantum GIS) to create an inverse distance weighted graphical distribution of rainfall to determine the hotspots where the maximum and minimum rainfalls occur, identifies the topography, green spaces, water areas, and buildings in the catchment, integrates the coverage area in the project, and estimates the amount of rainwater that could be directly absorbed by the land within the catchment. The results of this study show that, among the rainfall stations at an elevation below 100 m where most urban areas are located, the Taichung rainfall station is the area with the highest number of rainfall events from May to August. Without reliance on gully or river drainage, the natural infiltration of the land in the catchment could only adjust to 80 mm of heavy precipitation within 24 h of the rainfall warning level of the Central Weather Bureau.


Subject(s)
Rain , Water , Cities , Environmental Monitoring/methods , Taiwan
15.
Antioxidants (Basel) ; 11(2)2022 Feb 06.
Article in English | MEDLINE | ID: mdl-35204203

ABSTRACT

Crataegus pinnatifida is used to treat various diseases, including indigestion, congestive heart failure, hypertension, atherosclerosis, and myocardial dysfunction. We evaluated antioxidant and anti-α-glucosidase activities of various solvent extracts and major bioactive components from the fruit of C. pinnatifida. Ethyl acetate extracts showed potent antioxidant activities with IC50 values of 23.26 ± 1.97 and 50.73 ± 8.03 µg/mL, respectively, in DPPH and ABTS radical scavenging assays. Acetone extract exhibited significant anti-α-glucosidase activity with IC50 values of 42.35 ± 2.48 µg/mL. HPLC analysis was used to examine and compare the content of active components in various solvent extracts. We isolated four active compounds and evaluated their antioxidant and anti-α-glucosidase properties. Among the isolated compounds, chlorogenic acid and hyperoside showed potential antioxidant activities in ABTS and superoxide radical scavenging assays. Moreover, hyperoside also displayed stronger anti-α-glucosidase activity than other isolates. The molecular docking model and the hydrophilic interactive mode of anti-α-glucosidase assay revealed that hyperoside might have a higher antagonistic effect than positive control acarbose. The present study suggests that C. pinnatifida and its active extracts and components are worth further investigation and might be expectantly developed as the candidates for the treatment or prevention of oxidative stress-related diseases and hyperglycemia.

16.
Antioxidants (Basel) ; 11(2)2022 Feb 14.
Article in English | MEDLINE | ID: mdl-35204266

ABSTRACT

The rhizome of Anemarrhena asphodeloides Bunge (AA, family Liliaceae) is a famous and frequently used herbal drug in the traditional medicine of Northeast Asia, under vernacular name "zhimu". A. asphodeloides has been used as an anti-inflammatory, antipyretic, anti-platelet aggregation, anti-depressant, and anti-diabetic agent in traditional Chinese medicine. We examined the antioxidant, anti-acetylcholinesterase (AChE), and anti-α-glucosidase activities of various solvent extracts and the main bioactive compounds from the rhizome of A. asphodeloides. Acetone extract exhibited comparatively high antioxidant activities by 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging, and ferric-reducing antioxidant power (FRAP) assays. A water extract exhibited relatively strong antioxidant activity by superoxide radical scavenging test. Furthermore, dichloromethane, chloroform, and n-hexane extracts showed significant anti-α-glucosidase activities. Finally, ethanol and dichloromethane extracts exhibited relatively strong AChE inhibitory activity. HPLC analysis was used to examine and compare various solvent extracts for their compositions of isolates. We isolated four major chemical constituents and analyzed their antioxidant, anti-α-glucosidase, and AChE inhibitory activities. The bioactivity assays showed that mangiferin displayed the most potential antioxidant activities via FRAP, ABTS, DPPH, and superoxide assays and also exhibited the most effective anti-AChE and anti-α-glucosidase activities among all the isolates. The present study suggests that A. asphodeloides and its active extracts and components are worth further investigation and might be expected to develop as a candidate for the treatment or prevention of oxidative stress-related diseases, AChE inhibition, and hyperglycemia.

17.
Molecules ; 27(2)2022 01 10.
Article in English | MEDLINE | ID: mdl-35056744

ABSTRACT

Seven new compounds, including one dimer novel skeleton, chamaecyformosanin A (1); three diterpenes, chamaecyformosanins B-D (2-4); one sesquiterpene, chamaecyformosanin E (5); and two monoterpenes, chamaecyformosanins F and G (6 and 7) were isolated from the methanol extract of the bark of Chamaecyparis obtusa var. formosana. Their structures were established by the mean of spectroscopic analysis and the comparison of NMR data with those of known analogues. Their structures were elucidated on the basis of physicochemical evidence, in-depth NMR spectroscopic analysis, and high-resolution mass spectrometry. Furthermore, the isolated compounds were subjected to an evaluation of their antimicrobial activity. Metabolites 1, 3, and 4 present antibacterial activities. It is worth mentioning that the chemical composition of the bark of C. obtusa var. formosana has never been studied in the past. This is the first time the barks from C. obtusa var. formosana were studied and two new skeleton compounds, 1 and 7, were obtained.


Subject(s)
Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Chamaecyparis/chemistry , Chamaecyparis/metabolism , Diterpenes/chemistry , Drug Evaluation, Preclinical , Magnetic Resonance Spectroscopy , Mass Spectrometry , Microbial Sensitivity Tests , Molecular Structure , Secondary Metabolism , Sesquiterpenes/chemistry , Taiwan
18.
Molecules ; 27(2)2022 01 10.
Article in English | MEDLINE | ID: mdl-35056749

ABSTRACT

Five new dimer compounds, namely Taiwaniacryptodimers A-E (1-5), were isolated from the methanol extract of the roots of Taiwania cryptomerioides. Their structures were established by mean of spectroscopic analysis and comparison of NMR data with those of known analogues. Their antifungal activities were also evaluated. Our results indicated that metabolites 1, 2, 4, and 5 displayed moderate antifungal activities against Aspergillus niger, Penicillium italicum, Candida albicans, and Saccharomyces cerevisiae.


Subject(s)
Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Cupressaceae/chemistry , Plant Roots/chemistry , Antifungal Agents/isolation & purification , Aspergillus niger/drug effects , Candida albicans/drug effects , Dimerization , Drug Evaluation, Preclinical , Magnetic Resonance Spectroscopy , Methanol/chemistry , Microbial Sensitivity Tests , Molecular Structure , Penicillium/drug effects , Plant Extracts/chemistry
19.
Molecules ; 26(19)2021 Sep 23.
Article in English | MEDLINE | ID: mdl-34641311

ABSTRACT

Phytochemical investigation and chromatographic separation of extracts from one new actinobacteria strain Amycolatopsis taiwanensis that was isolated from soil of Yilan township, in the north of Taiwan, led to the isolation of nine new compounds, amycolataiwanensins A-I (1-9, resp.), and one new natural product, namely amycolataiwanensin J (10). The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic-data analysis (1D- and 2D-NMR, MS, and UV) and comparison with literature data. The effect of some isolates on the inhibition of NO production in lipopolysaccharide-activated RAW 264.7 murine macrophages was evaluated. Of the isolates, 3, 5, 7 and 8 exhibited potent anti-NO production activity, with IC50 values of 17.52, 12.31, 17.81 and 13.32 µM, respectively, compared to that of quercetin, an iNOS inhibitor with an IC50 value of 35.94 µM. This is the first report on indole metabolite from the genus Amycolatopsis.


Subject(s)
Anti-Inflammatory Agents/chemistry , Biological Products/chemistry , Lipopolysaccharides/adverse effects , Amycolatopsis/chemistry , Amycolatopsis/isolation & purification , Animals , Anti-Inflammatory Agents/pharmacology , Biological Products/isolation & purification , Biological Products/pharmacology , Inhibitory Concentration 50 , Mice , Molecular Structure , Nitric Oxide/metabolism , RAW 264.7 Cells , Secondary Metabolism , Soil Microbiology , Taiwan
20.
Molecules ; 26(20)2021 Oct 15.
Article in English | MEDLINE | ID: mdl-34684816

ABSTRACT

The cultivation of one actinobacteria strain, Herbidospora yilanensis, was isolated from sediment samples collected from Yilan County City in Taiwan, resulting in the isolation of five previously undescribed compounds: herbidosporayilanensins A-E (1-5), and four compounds isolated from nature for the first time: herbidosporayilanensins F-I (6-9). Their structures were elucidated by spectroscopic analyses, including 1D- and 2D-NMR experiments with those of known analogues, and on the basis of HR-EI-MS mass spectrometry, their antimycobacterial activities were also evaluated.


Subject(s)
Actinobacteria/metabolism , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/metabolism , Actinobacteria/isolation & purification , Anti-Bacterial Agents/pharmacology , Antitubercular Agents/chemistry , Antitubercular Agents/metabolism , Antitubercular Agents/pharmacology , Geologic Sediments/microbiology , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Molecular Structure , Mycobacterium tuberculosis/drug effects , Soil Microbiology , Taiwan
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