scholarly journals Bioactive Capnosanes and Cembranes from the Soft Coral Klyxum flaccidum

Marine Drugs ◽  
2019 ◽  
Vol 17 (8) ◽  
pp. 461
Author(s):  
Tseng ◽  
Ahmed ◽  
Huang ◽  
Tsai ◽  
Tai ◽  
...  
Keyword(s):  
Superoxide Anion ◽  
Spectroscopic Data ◽  
Cytochalasin B ◽  
Soft Coral ◽  
Biological Activities ◽  
Human Neutrophils ◽  
Data Comparison ◽  
Spectroscopic Analyses ◽  
New Compounds ◽  
First Time

Two new capnosane-based diterpenoids, flaccidenol A (1) and 7-epi-pavidolide D (2), two new cembranoids, flaccidodioxide (3) and flaccidodiol (4), and three known compounds 5 to 7 were characterized from the marine soft coral Klyxum flaccidum, collected off the coast of the island of Pratas. The structures of the new compounds were determined by extensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and spectroscopic data comparison with related structures. The rare capnosane diterpenoids were isolated herein from the genus Klyxum for the first time. The cytotoxicity of compounds 1 to 7 against the proliferation of a limited panel of cancer cell lines was assayed. The isolated diterpenoids also exhibited anti-inflammatory activity through suppression of superoxide anion generation and elastase release in the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-stimulated human neutrophils. Furthermore, 1 and 7 also exhibited cytotoxicity toward the tested cancer cells, and 7 could effectively inhibit elastase release. It is worth noting that the biological activities of 7 are reported for the first time in this paper.

Four New 2-(2-Phenylethyl)-4H-chromen-4-one Derivatives from the Resinous Wood of Aquilaria sinensis and Their Inhibitory Activities on Neutrophil Pro-Inflammatory Responses

Planta Medica ◽  
2018 ◽  
Vol 84 (18) ◽  
pp. 1340-1347 ◽  
Author(s):  
Sin-Ling Wang ◽  
Hsiang-Ruei Liao ◽  
Ming-Jen Cheng ◽  
Chih-Wen Shu ◽  
Chun-Lin Chen ◽  
...  
Keyword(s):  
Superoxide Anion ◽  
Inflammatory Responses ◽  
2D Nmr ◽  
Human Neutrophils ◽  
Aquilaria Sinensis ◽  
Superoxide Anion Generation ◽  
Spectroscopic Analyses ◽  
Inhibitory Activities ◽  
New Compounds ◽  
First Time

AbstractFour new 2-(2-phenylethyl)-4H-chromen-4-one derivatives, 6-hydroxy-5-methoxy-2-[2-(4′-methoxyphenyl)ethyl]chromone (1), 6,7-dimethoxy-2-[2-(2′-hydroxyphenyl)ethyl]chromone (2), 5-hydroxy-6-methoxy-2-[2-(3′-methoxyphenyl)ethyl]-chromone (3), and 7-chloro-8-hydroxy-2-[2-(4′-methoxyphenyl)ethyl]chromone (4), have been isolated from the resinous wood of Aquilaria sinensis, together with 16 known compounds (5–20). Among these, 7-methoxy-2-[2-(4′-methoxyphenyl)ethyl]chromone (5) was isolated from a natural source for the first time. The structures of the new compounds were established by spectroscopic analyses (1D and 2D NMR, HR-ESI-MS, IR, UV). Nine compounds, including 1 showed more than 80% inhibition of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine at 50 µM.

scholarly journals Cherbonolides M and N from a Formosan Soft Coral Sarcophyton cherbonnieri

Marine Drugs ◽  
2021 ◽  
Vol 19 (5) ◽  
pp. 260
Author(s):  
Chia-Chi Peng ◽  
Tzu-Yin Huang ◽  
Chiung-Yao Huang ◽  
Tsong-Long Hwang ◽  
Jyh-Horng Sheu
Keyword(s):  
Superoxide Anion ◽  
Cytochalasin B ◽  
Soft Coral ◽  
2D Nmr ◽  
Human Neutrophils ◽  
Cd Spectra ◽  
Ether Linkage ◽  
Relative Configuration ◽  
Nmr Data ◽  
New Compounds

Two new isosarcophine derivatives, cherbonolides M (1) and N (2), were further isolated from a Formosan soft coral Sarcophyton cherbonnieri. The planar structure and relative configuration of both compounds were established by the detailed analysis of the IR, MS, and 1D and 2D NMR data. Further, the absolute configuration of both compounds was determined by the comparison of CD spectra with that of isosarcophine (3). Notably, cherbonolide N (2) possesses the unique cembranoidal scaffold of tetrahydrooxepane with the 12,17-ether linkage fusing with a γ-lactone. In addition, the assay for cytotoxicity of both new compounds revealed that they showed to be noncytotoxic toward the proliferation of A549, DLD-1, and HuCCT-1 cell lines. Moreover, the anti-inflammatory activities of both metabolites were carried out by measuring the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced generation of superoxide anion and elastase release in the primary human neutrophils. Cherbonolide N (2) was found to reduce the generation of superoxide anion (20.6 ± 6.8%) and the elastase release (30.1 ± 3.3%) in the fMLF/CB-induced human neutrophils at a concentration of 30 μM.

scholarly journals Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral Lobophytum varium

Marine Drugs ◽  
2020 ◽  
Vol 18 (4) ◽  
pp. 223
Author(s):  
Chuan-Hsiang Chang ◽  
Atallah F. Ahmed ◽  
Tian-Sheng Yang ◽  
You-Cheng Lin ◽  
Chiung-Yao Huang ◽  
...  
Keyword(s):  
Superoxide Anion ◽  
Soft Coral ◽  
2D Nmr ◽  
Human Neutrophils ◽  
Etoac Extract ◽  
1H And 13C Nmr ◽  
Spectroscopic Analyses ◽  
Complete Assignment ◽  
First Time ◽  
New Metabolites

Further chemical investigation of the EtOAc extract of the soft coral Lobophytum varium resulted in the discovery of eleven new diterpenoids lobovarols F–P (1–11) of lobane– and prenyleudesmane–types, along with two known metabolites (12 and 13). The structures of the new metabolites were established by spectroscopic analyses, including 2D NMR experiments. The absolute configuration of 1 was determined using Mosher’s method. The complete assignment of 1H and 13C NMR spectroscopic data of 12 and 13 and the identification of pyran-derived moieties in the prenyleudesmanes were reported for the first time. Anti-inflammatory activities of the isolated compounds in suppressing elastase release and superoxide anion generation in human neutrophils were disclosed for 1, 2, 4, 12, and 13. A stereospecific biosynthesis for lobanes and prenyleudesmanes from the related prenylgermacranes could explain the coexistence of lobanes and prenylgermacranes in L. varium.

scholarly journals Cembranoid-Related Metabolites and Biological Activities from the Soft Coral Sinularia flexibilis

Marine Drugs ◽  
2018 ◽  
Vol 16 (8) ◽  
pp. 278 ◽  
Author(s):  
Chia-Hua Wu ◽  
Chih-Hua Chao ◽  
Tzu-Zin Huang ◽  
Chiung-Yao Huang ◽  
Tsong-Long Hwang ◽  
...  
Keyword(s):  
Spectral Analysis ◽  
Cell Lines ◽  
Cancer Cell ◽  
Superoxide Anion ◽  
Cytochalasin B ◽  
Soft Coral ◽  
Biological Activities ◽  
Human Neutrophils ◽  
Sinularia Flexibilis ◽  
Anti Inflammatory

Five new cembranoid-related diterpenoids, namely, flexibilisins D and E (1 and 2), secoflexibilisolides A and B (3 and 4), and flexibilisolide H (5), along with nine known compounds (6–14), were isolated from the soft coral Sinularia flexibilis. Their structures were established by extensive spectral analysis. Compound 3 possesses an unusual skeleton that could be biogenetically derived from cembranoids. The cytotoxicity and anti-inflammatory activities of the isolates were investigated, and the results showed that dehydrosinulariolide (7) and 11-epi-sinulariolide acetate (8) exhibited cytotoxicity toward a limited panel of cancer cell lines and 14-deoxycrassin (9) displayed anti-inflammatory activity by inhibition of superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced human neutrophils.

scholarly journals New Anti-Inflammatory Aporphine and Lignan Derivatives from the Root Wood of Hernandia nymphaeifolia

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2286 ◽  
Author(s):  
Chuan-Yen Wei ◽  
Shih-Wei Wang ◽  
Jin-Wang Ye ◽  
Tsong-Long Hwang ◽  
Ming-Jen Cheng ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Superoxide Anion ◽  
Cytochalasin B ◽  
Human Neutrophils ◽  
Superoxide Anion Production ◽  
Natural Sources ◽  
Spectroscopic Analyses ◽  
Anion Production ◽  
Ic50 Values ◽  
Anti Inflammatory

A new aporphine, 3-hydroxyhernandonine (1) and a new lignin, 4′-O-demethyl-7-O-methyldehydropodophyllotoxin (2), have been isolated from the root wood of Hernanadia nymphaeifolia, together with thirteen known compounds (3–15). The structures of these compounds were determined through mass spectrometry (MS) and spectroscopic analyses. The known isolate, 2-O-methyl-7-oxolaetine (3), was first isolated from natural sources. Among the isolated compounds, 3-hydroxyhernandonine (1), 4′-O-demethyl-7-O-methyldehydropodophyllotoxin (2), hernandonine (4), oxohernangerine (5), and oxohernagine (6) displayed inhibition (IC50 values ≤5.72 μg/mL) of superoxide anion production by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). In addition, 3-hydroxyhernandonine (1), 4′-O-demethyl-7-O-methyldehydropodophyllotoxin (2), oxohernangerine (5), and oxohernagine (6) suppressed fMLP/CB-induced elastase release with IC50 values ≤5.40 μg/mL.

Flavonolignan 2, 3-dehydroderivatives from Oenanthe javanica and their anti inflammatory activities

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Rong-Rui Wei ◽  
Qin-Ge Ma
Keyword(s):  
Data Analysis ◽  
Spectroscopic Data ◽  
Biological Activities ◽  
Inflammatory Activity ◽  
Macrophage Cells ◽  
Oenanthe Javanica ◽  
Anti Inflammatory ◽  
New Compounds ◽  
First Time ◽  
Raw264.7 Macrophage

Abstract Flavonolignans, for example, silymarin and silybin, have interesting biological activities. For the first time, three new flavonolignans named oenanthenoid A-C (1–3) and nine known flavonolignan derivatives (4–12) were isolated from Oenanthe javanica. Comprehensive spectroscopic data analysis and references were used to identify all of the compounds. The anti inflammatory activities of these isolates (1–12) on RAW264.7 macrophage cells were investigated. Three new compounds (1–3) demonstrated anti inflammatory activity with IC50 values ranging from 6.5 ± 0.6 to 14.7 ± 1.6 µM. Furthermore, two compounds (11 and 12) demonstrated moderate anti inflammatory activity, with IC50 values ranging from 24.1 ± 1.2 to 62.5 ± 1.9 µM.

scholarly journals Cytochalasins from Xylaria sp. CFL5, an Endophytic Fungus of Cephalotaxus fortunei

2020 ◽  
Author(s):  
Kai-Liang Ma ◽  
Shi-Hui Dong ◽  
Hang-Ying Li ◽  
Wen-Jun Wei ◽  
Yong-Qiang Tu ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
Spectroscopic Data ◽  
Biological Activities ◽  
Optical Rotation ◽  
Ags Cells ◽  
Mhc Ii ◽  
Chemical Structures ◽  
Data Analyses ◽  
Binding Inhibition ◽  
New Compounds

Abstract Three previously undescribed cytochalasins, named xylariasins A‒C (1‒3), together with six known ones (4‒9) were isolated from Xylaria sp. CFL5, an endophytic fungus of Cephalotaxus fortunei. The chemical structures of all new compounds were elucidated on the basis of extensive spectroscopic data analyses and electronic circular dichroism calculation, as well as optical rotation calculation. Biological activities of compounds 1, 4‒9 were evaluated, including cytotoxic, LAG3/MHC II binding inhibition and LAG3/FGL1 binding inhibition activities. Compounds 6 and 9 possessed cytotoxicity against AGS cells at 5 μM, with inhibition rates of 94% and 64%, respectively. In addition, all tested isolates, except compound 6, exhibited obvious inhibitory activity against the interaction of both LAG3/MHC II and LAG3/FGL1. Compounds 1, 5, 7, and 8 inhibited LAG3/MHC II with IC50 values ranging from 2.37 to 4.74 μM. Meanwhile, the IC50 values of compounds 1, 7, and 8 against LAG3/FGL1 were 11.78, 4.39, and 7.45 μM, respectively. Graphic Abstract

scholarly journals Phytochemical Study of Stem and Leaf of Clausena lansium

Molecules ◽  
2019 ◽  
Vol 24 (17) ◽  
pp. 3124 ◽  
Author(s):  
Wenwen Peng ◽  
Xiaoxiang Fu ◽  
Yuyan Li ◽  
Zhonghua Xiong ◽  
Xugen Shi ◽  
...  
Keyword(s):  
Biological Activities ◽  
Healthcare Systems ◽  
Water Soluble ◽  
Phytochemical Analysis ◽  
Phytochemical Study ◽  
Spectroscopic Analyses ◽  
First Time ◽  
Local Healthcare ◽  
Carbazole Alkaloids ◽  
Aromatic Glycoside

Clausena lansium Lour. Skeels (Rutaceae) is widely distributed in South China and has historically been used as a traditional medicine in local healthcare systems. Although the characteristic components (carbazole alkaloids and coumarins) of C. lansium have been found to possess a wide variety of biological activities, little attention has been paid toward the other components of this plant. In the current study, phytochemical analysis of isolates from a water-soluble stem and leaf extract of C. lansium led to the identification of 12 compounds, including five aromatic glycosides, four sesquiterpene glycosides, two dihydrofuranocoumarin glycosides, and one adenosine. All compounds were isolated for the first time from the genus Clausena, including a new aromatic glycoside (1), a new dihydrofuranocoumarin glycoside (6), and two new sesquiterpene glycosides (8 and 9). The phytochemical structures of the isolates were elucidated using spectroscopic analyses including NMR and MS. The existence of these compounds demonstrates the taxonomic significance of C. lansium in the genus Clausena and suggests that some glycosides from this plant probably play a role in the anticancer activity of C. lansium to some extent.

scholarly journals Bioactivity-Guided Purification of Novel Herbal Antioxidant and Anti-NO Compounds from Euonymus laxiflorus Champ.

Molecules ◽  
2018 ◽  
Vol 24 (1) ◽  
pp. 120 ◽  
Author(s):  
Van Nguyen ◽  
San-Lang Wang ◽  
Anh Nguyen ◽  
Zhi-Hu Lin ◽  
Chien Doan ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Natural Products ◽  
Biological Activities ◽  
The Novel ◽  
Health Food ◽  
Ic50 Values ◽  
Comparable Activity ◽  
New Compounds ◽  
First Time ◽  
Antidiabetic Effects

Euonymus laxiflorus Champ., a medicinal herb collected in Vietnam, has been reported to show several potent bioactivities, including anti-NO, enzyme inhibition, hypoglycemic and antidiabetic effects. Recently, the antioxidant activity of Euonymus laxiflorus Champ. trunk bark (ELCTB) has also been reported. However, the active antioxidant and anti-NO constituents existing in ELCTB have not been reported in the literature. The objective of this study was to purify the active antioxidants from ELCTB and investigate the anti-NO effect of the major constituents. Twenty-two phenolics isolated from ELCTB, including 12 compounds newly isolated in this study (1–12) and 10 constituents obtained from our previous work, were evaluated for their antioxidant activity. Of these, 12 compounds (4–6, 9, 13–15, 18–22) showed a potent antioxidant capacity (FRS50 = 7.8–58.11 µg/mL), in comparison to α-tocopherol (FRS50 = 23 µg/mL). In the anti-NO activity tests, Walterolactone A (1a) and B (1b) β-d-glucopyranoside (13) demonstrated the most effective and comparable activity to that of quercetin with max inhibition and IC50 values of 100%, 1.3 µg/mL, and 100%, 1.21 µg/mL, respectively. The crude extract and its major compounds showed no cytotoxicity on normal cells. Notably, three constituents (9, 11, and 12) were identified as new compounds, another three constituents, including 1, 7, and 8, were found to be new natural products, constituents 9 and 13 were determined to be new antioxidants, and compound 13 was reported to have novel potent anti-NO activity for the first time. The results of this study contribute to the enrichment of new natural products and compounds, as well as the novel biological activity of constituents isolated from Euonymus laxiflorus Champ. The current study also indicates ELCTB as a rich natural source of active phenolics. It is suggested that ELCTB could be developed as a health food with promising antioxidant and anti-NO effects, as well as other beneficial biological activities.

scholarly journals New Cembranoids and a Biscembranoid Peroxide from the Soft Coral Sarcophyton cherbonnieri

Marine Drugs ◽  
2018 ◽  
Vol 16 (8) ◽  
pp. 276 ◽  
Author(s):  
Chia-Chi Peng ◽  
Chiung-Yao Huang ◽  
Atallah Ahmed ◽  
Tsong-Long Hwang ◽  
Chang-Feng Dai ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Cytochalasin B ◽  
Soft Coral ◽  
Human Neutrophils ◽  
Superoxide Anions ◽  
Chemical Methods ◽  
Peroxide Group ◽  
Molecular Skeleton ◽  
Phenyl Alanine

Six new cembranoids, cherbonolides A−E (1–5) and bischerbolide peroxide (6), along with one known cembranoid, isosarcophine (7), were isolated from the Formosan soft coral Sarcophyton cherbonnieri. The structures of these compounds were elucidated by detailed spectroscopic analysis and chemical methods. Compound 6 was discovered to be the first example of a molecular skeleton formed from two cembranoids connected by a peroxide group. Compounds 1–7 were shown to have the ability of inhibiting the production of superoxide anions and elastase release in N-formyl-methionyl-leucyl-phenyl-alanine/cytochalasin B (fMLF/CB)-induced human neutrophils.

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