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Open AccessArticle Sterols from the Octocoral Nephthea columnaris
Mar. Drugs 2017, 15(7), 212; doi:10.3390/md15070212
Received: 23 May 2017 / Revised: 26 June 2017 / Accepted: 1 July 2017 / Published: 4 July 2017
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Abstract
Two new sterols, columnaristerols B (1) and C (2), along with two known analogues, 5,6-epoxylitosterol (3) and litosterol (4), were obtained from the octocoral Nephthea columnaris. The structures of new sterols 1 and 2
[...] Read more.
Two new sterols, columnaristerols B (1) and C (2), along with two known analogues, 5,6-epoxylitosterol (3) and litosterol (4), were obtained from the octocoral Nephthea columnaris. The structures of new sterols 1 and 2 were elucidated by using spectroscopic methods and comparing the spectroscopic data with those of known related metabolites. Sterol 3 was found to suppress superoxide anion production and elastase secretion by human neutrophils. Full article
(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)
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Open AccessArticle Discovery of Indeno[1,2-c]quinoline Derivatives as Potent Dual Antituberculosis and Anti-Inflammatory Agents
Molecules 2017, 22(6), 1001; doi:10.3390/molecules22061001
Received: 17 May 2017 / Revised: 9 June 2017 / Accepted: 12 June 2017 / Published: 16 June 2017
Cited by 1 | Viewed by 340 | PDF Full-text (2274 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A series of indeno[1,2-c]quinoline derivatives were designed, synthesized and evaluated for their anti-tuberculosis (anti-TB) and anti-inflammatory activities. The minimum inhibitory concentration (MIC) of the newly synthesized compound was tested against Mycobacterium tuberculosis H37RV. Among the tested compounds,
[...] Read more.
A series of indeno[1,2-c]quinoline derivatives were designed, synthesized and evaluated for their anti-tuberculosis (anti-TB) and anti-inflammatory activities. The minimum inhibitory concentration (MIC) of the newly synthesized compound was tested against Mycobacterium tuberculosis H37RV. Among the tested compounds, (E)-N′-[6-(4-hydroxypiperidin-1-yl)-11H-indeno[1,2-c]quinolin-11-ylidene]isonicotino-hydrazide (12), exhibited significant activities against the growth of M. tuberculosis (MIC values of 0.96 μg/mL) with a potency approximately equal to that of isoniazid (INH), an anti-TB drug. Important structure features were analyzed by quantitative structure–activity relationship (QSAR) analysis to give better insights into the structure determinants for predicting the anti-TB activity. The anti-inflammatory activity was induced by superoxide anion generation and neutrophil elastase (NE) release using the formyl-l-methionyl-l-leucyl-l-phenylalanine (fMLF)-activated human neutrophils method. Results indicated that compound 12 demonstrated a potent dual inhibitory effect on NE release and superoxide anion generation with IC50 values of 1.76 and 1.72 μM, respectively. Our results indicated that compound 12 is a potential lead compound for the discovery of dual anti-TB and anti-inflammatory drug candidates. In addition, 6-[3-(hydroxymethyl)piperidin-1-yl]-9-methoxy-11H-indeno[1,2-c]quinolin-11-one (4g) showed a potent dual inhibitory effect on NE release and superoxide anion generation with IC50 values of 0.46 and 0.68 μM, respectively, and is a potential lead compound for the discovery of anti-inflammatory drug candidates. Full article
(This article belongs to the Special Issue Frontiers in Antimicrobial Drug Discovery and Design)
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Open AccessArticle Anti-Inflammatory and Neuroprotective Constituents from the Peels of Citrus grandis
Molecules 2017, 22(6), 967; doi:10.3390/molecules22060967
Received: 19 April 2017 / Revised: 8 June 2017 / Accepted: 8 June 2017 / Published: 9 June 2017
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Abstract
A series of chromatographic separations performed on the ethanol extracts of the peels of Citrus grandis has led to the characterization of forty compounds, including seventeen coumarins, eight flavonoids, two triterpenoids, four benzenoids, two steroids, one lignan, one amide, and five other compounds,
[...] Read more.
A series of chromatographic separations performed on the ethanol extracts of the peels of Citrus grandis has led to the characterization of forty compounds, including seventeen coumarins, eight flavonoids, two triterpenoids, four benzenoids, two steroids, one lignan, one amide, and five other compounds, respectively. The chemical structures of the purified constituents were identified on the basis of spectroscopic elucidation, including 1D- and 2D-NMR, UV, IR, and mass spectrometric analysis. Most of the isolated compounds were examined for their inhibition of superoxide anion generation and elastase release by human neutrophils. Among the isolates, isomeranzin (3), 17,18-dihydroxybergamottin (12), epoxybergamottin (13), rhoifolin (19), vitexicarpin (22) and 4-hydroxybenzaldehyde (29) displayed the most significant inhibition of superoxide anion generation and elastase release with IC50 values ranged from 0.54 to 7.57 μM, and 0.43 to 4.33 μM, respectively. In addition, 7-hydroxy-8-(2′-hydroxy-3′-methylbut-3′-enyl)coumarin (8) and 17,18-dihydroxybergamottin (12) also exhibited the protection of neurons against A-mediated neurotoxicity at 50 μM. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle Briarenols C–E, New Polyoxygenated Briaranes from the Octocoral Briareum excavatum
Molecules 2017, 22(3), 475; doi:10.3390/molecules22030475
Received: 16 February 2017 / Revised: 10 March 2017 / Accepted: 15 March 2017 / Published: 17 March 2017
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Abstract
Three new polyoxygenated briarane diterpenoids, briarenols C–E (13), were isolated from the octocoral Briareum excavatum. The structures of briaranes 13 were elucidated by interpretation of spectroscopic data, and the methylenecyclohexane ring in 1 was found to
[...] Read more.
Three new polyoxygenated briarane diterpenoids, briarenols C–E (13), were isolated from the octocoral Briareum excavatum. The structures of briaranes 13 were elucidated by interpretation of spectroscopic data, and the methylenecyclohexane ring in 1 was found to exist in a twisted boat conformation. Briarenol D (2) displayed an inhibitory effect on the release of elastase by human neutrophils with an IC50 value of 4.65 μM. Briarenol E (3) was found to inhibit the protein expression of pro-inflammatory inducible nitric oxide synthase (iNOS) in a murine macrophage-like cell line, RAW 264.7, stimulated with lipopolysaccharides (LPS). Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle New Marine Sterols from a Gorgonian Pinnigorgia sp.
Molecules 2017, 22(3), 393; doi:10.3390/molecules22030393
Received: 19 January 2017 / Revised: 27 February 2017 / Accepted: 28 February 2017 / Published: 3 March 2017
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Abstract
Continuous chemical investigation of the gorgonian coral Pinnigorgia sp. resulted in the isolation of two new sterols, 5α,6α-epoxy-(22E,24R)-3β,11-dihydroxy-9,11-secoergosta-7-en-9-one (1) and (22R)-acetoxy-(24ξ)-ergosta-5-en-3β,25-diol (2). The structures of sterols 1 and 2 were elucidated
[...] Read more.
Continuous chemical investigation of the gorgonian coral Pinnigorgia sp. resulted in the isolation of two new sterols, 5α,6α-epoxy-(22E,24R)-3β,11-dihydroxy-9,11-secoergosta-7-en-9-one (1) and (22R)-acetoxy-(24ξ)-ergosta-5-en-3β,25-diol (2). The structures of sterols 1 and 2 were elucidated using spectroscopic methods. Sterol 1 displayed inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils with IC50 values of 8.65 and 5.86 μM, respectively. The structure of a known metabolite, pubinernoid A (3), is revised as (+)-loliolide (4). Full article
(This article belongs to the Section Natural Products)
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Open AccessReview Briarane Diterpenoids Isolated from Octocorals between 2014 and 2016
Mar. Drugs 2017, 15(2), 44; doi:10.3390/md15020044
Received: 27 January 2017 / Revised: 14 February 2017 / Accepted: 15 February 2017 / Published: 17 February 2017
Cited by 1 | Viewed by 867 | PDF Full-text (1937 KB) | HTML Full-text | XML Full-text
Abstract
The structures, names, bioactivities, and references of 124 briarane-type natural products, including 66 new metabolites, isolated between 2014 and 2016 are summarized in this review article. All of the briarane diterpenoids mentioned in this review were isolated from octocorals, mainly from Briareum violacea
[...] Read more.
The structures, names, bioactivities, and references of 124 briarane-type natural products, including 66 new metabolites, isolated between 2014 and 2016 are summarized in this review article. All of the briarane diterpenoids mentioned in this review were isolated from octocorals, mainly from Briareum violacea, Dichotella gemmacea, Ellisella dollfusi, Junceella fragilis, Junceella gemmacea, and Pennatula aculeata. Some of these compounds exhibited potential biomedical activities, including anti-inflammatory activity, antibacterial activity, and cytotoxicity towards cancer cells. Full article
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Open AccessArticle Pinnisterols D–J, New 11-Acetoxy-9,11-secosterols with a 1,4-Quinone Moiety from Formosan Gorgonian Coral Pinnigorgia sp. (Gorgoniidae)
Mar. Drugs 2017, 15(1), 11; doi:10.3390/md15010011
Received: 20 November 2016 / Revised: 11 December 2016 / Accepted: 28 December 2016 / Published: 6 January 2017
Cited by 1 | Viewed by 996 | PDF Full-text (1790 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Seven new marine 11-acetoxy-9,11-secosterols, pinnisterols D–J (17), with a 1,4-quinone moiety, were discovered from the gorgonian coral Pinnigorgia sp. In this study, the structures of secosterols 17 were revealed by spectroscopic analysis. Bioactivity study showed that secosterol
[...] Read more.
Seven new marine 11-acetoxy-9,11-secosterols, pinnisterols D–J (17), with a 1,4-quinone moiety, were discovered from the gorgonian coral Pinnigorgia sp. In this study, the structures of secosterols 17 were revealed by spectroscopic analysis. Bioactivity study showed that secosterol 1 treatment inhibited cell viability in a hepatic stellate cell line, HSC-T6, with an IC50 value of 3.93 μM; and secosterols 2, 5, and 7 reduced elastase enzyme release, and 3, 5, and 7 decreased the production of superoxide anions from human neutrophils. Full article
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Open AccessArticle New Anti-Inflammatory 9,11-Secosterols with a Rare Tricyclo[5,2,1,1]decane Ring from a Formosan Gorgonian Pinnigorgia sp.
Mar. Drugs 2016, 14(12), 218; doi:10.3390/md14120218
Received: 24 October 2016 / Revised: 8 November 2016 / Accepted: 16 November 2016 / Published: 26 November 2016
Cited by 3 | Viewed by 1389 | PDF Full-text (1160 KB) | HTML Full-text | XML Full-text
Abstract
Pinnigorgiols D (1) and E (2), two new 9,11-secosterols with a rearranged carbon skeleton, were isolated from a Taiwan gorgonian Pinnigorgia sp. The structures of these two compounds were elucidated on the basis of spectroscopic methods and were proven
[...] Read more.
Pinnigorgiols D (1) and E (2), two new 9,11-secosterols with a rearranged carbon skeleton, were isolated from a Taiwan gorgonian Pinnigorgia sp. The structures of these two compounds were elucidated on the basis of spectroscopic methods and were proven to possess a tricyclo[5,2,1,1]decane ring. The new secosterols 1 and 2 displayed significant inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils. Full article
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Open AccessArticle Bioactive Steroids from the Formosan Soft Coral Umbellulifera petasites
Mar. Drugs 2016, 14(10), 180; doi:10.3390/md14100180
Received: 31 August 2016 / Revised: 19 September 2016 / Accepted: 21 September 2016 / Published: 11 October 2016
Cited by 4 | Viewed by 1415 | PDF Full-text (1500 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Three new steroids, petasitosterones A and B (1 and 2) and a spirosteroid petasitosterone C (3), along with eight known steroids (411), were isolated from a Formosan marine soft coral Umbellulifera petasites. The structures
[...] Read more.
Three new steroids, petasitosterones A and B (1 and 2) and a spirosteroid petasitosterone C (3), along with eight known steroids (411), were isolated from a Formosan marine soft coral Umbellulifera petasites. The structures of these compounds were elucidated by extensive spectroscopic analysis and comparison of spectroscopic data with those reported. Compound 3 is a marine steroid with a rarely found A/B spiro[4,5]decane ring system. Compounds 13 and 5 displayed inhibitory activity against the proliferation of a limited panel of cancer cell lines, whereas 2 and 5 exhibited significant anti-inflammatory activity to inhibit nitric oxide (NO) production. The inhibitory activities for superoxide anion generation and elastase release of compounds 111 were also examined to evaluate the anti-inflammatory potential, and 24 were shown to exhibit significant activities. Full article
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Open AccessArticle Tetranortriterpenes and Limonoids from the Roots of Aphanamixis polystachya
Molecules 2016, 21(9), 1167; doi:10.3390/molecules21091167
Received: 22 June 2016 / Revised: 12 August 2016 / Accepted: 26 August 2016 / Published: 2 September 2016
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Abstract
Phytochemical investigation of the acetone extract from the roots of Aphanamixis polystachya resulted in isolation of four new tetranortriterpenes (14) in addition to one protolimonoid (methyl-1ξ,7R-diacetoxy-23R,25-dihydroxy-20S,24R-21,24-epoxy-3,4-seco-apotirucall-4(28),14(15)-diene-3-oate (5)), five known
[...] Read more.
Phytochemical investigation of the acetone extract from the roots of Aphanamixis polystachya resulted in isolation of four new tetranortriterpenes (14) in addition to one protolimonoid (methyl-1ξ,7R-diacetoxy-23R,25-dihydroxy-20S,24R-21,24-epoxy-3,4-seco-apotirucall-4(28),14(15)-diene-3-oate (5)), five known limonoids (rohituka 3 (6), rohituka 7 (7), nymania 1 (8), rubrin G (9), prieurianin (10)) and a steroid (2,3-dihydroxy-5-pregnan-16-one (11)). Their structures were determined by spectroscopic analyses, including 2D-NMR (COSY, HMQC, HMBC, and NOESY) and high-resolution electrospray ionization mass spectrometry (HRESIMS). Cytotoxic and anti-inflammatory activities of these compounds were evaluated. Compounds 4 and 5 showed significant inhibition against superoxide generation and elastase release by human neutrophils in response to (formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B) (FMLP/CB). Full article
(This article belongs to the Special Issue Triterpenes and Triterpenoids 2016)
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Open AccessReview Marine Natural Product Inhibitors of Neutrophil-Associated Inflammation
Mar. Drugs 2016, 14(8), 141; doi:10.3390/md14080141
Received: 29 March 2016 / Revised: 31 May 2016 / Accepted: 7 July 2016 / Published: 26 July 2016
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Abstract
Neutrophils are widely recognized to play an important role in acute inflammatory responses, and recent evidence has expanded their role to modulating chronic inflammatory and autoimmune diseases. Reactive oxygen species (ROS) and microbicidal compounds released from neutrophils that are recruited to the site
[...] Read more.
Neutrophils are widely recognized to play an important role in acute inflammatory responses, and recent evidence has expanded their role to modulating chronic inflammatory and autoimmune diseases. Reactive oxygen species (ROS) and microbicidal compounds released from neutrophils that are recruited to the site of inflammation contribute to the pathogenesis of multiple inflammation-associated diseases such as chronic obstructive pulmonary disease, atherosclerosis, and hepatitis. Marine organisms are a valuable source of bioactive compounds with potential for industrial and pharmaceutical application. Marine natural products that inhibit neutrophil activation could be used as drugs for the treatment of inflammatory diseases. Numerous studies investigating marine natural products have reported novel anti-inflammatory agents. Nevertheless, the detailed mechanisms underlying their actions, which could facilitate our understanding of the molecular events occurring in neutrophils, have not been reported in most of the associated research studies. Therefore, in this review, we will present marine products that inhibit neutrophil-associated inflammation. Furthermore, we will be limiting the detailed discussion to agents with well-investigated molecular targets. Full article
(This article belongs to the Special Issue Drug Design Based on Marine Natural Product Scaffolds)
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Open AccessArticle Antiallergic Phorbol Ester from the Seeds of Aquilaria malaccensis
Int. J. Mol. Sci. 2016, 17(3), 398; doi:10.3390/ijms17030398
Received: 21 January 2016 / Revised: 2 March 2016 / Accepted: 10 March 2016 / Published: 21 March 2016
Cited by 3 | Viewed by 1033 | PDF Full-text (1037 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The Aquilaria malaccensis (Thymelaeaceae) tree is a source of precious fragrant resin, called agarwood, which is widely used in traditional medicines in East Asia against diseases such as asthma. In our continuous search for active natural products, A. malaccensis seeds ethanolic extract demonstrated
[...] Read more.
The Aquilaria malaccensis (Thymelaeaceae) tree is a source of precious fragrant resin, called agarwood, which is widely used in traditional medicines in East Asia against diseases such as asthma. In our continuous search for active natural products, A. malaccensis seeds ethanolic extract demonstrated antiallergic effect with an IC50 value less than 1 µg/mL. Therefore, the present research aimed to purify and identify the antiallergic principle of A. malaccensis through a bioactivity-guided fractionation approach. We found that phorbol ester-rich fraction was responsible for the antiallergic activity of A. malaccensis seeds. One new active phorbol ester, 12-O-(2Z,4E,6E)-tetradeca-2,4,6-trienoylphorbol-13-acetate, aquimavitalin (1) was isolated. The structure of 1 was assigned by means of 1D and 2D NMR data and high-resolution mass spectrometry (HR-MS). Aquimavitalin (1) showed strong inhibitory activity in A23187- and antigen-induced degranulation assay with IC50 values of 1.7 and 11 nM, respectively, with a therapeutic index up to 71,000. The antiallergic activities of A. malaccensis seeds and aquimavitalin (1) have never been revealed before. The results indicated that A. malaccensis seeds and the pure compound have the potential for use in the treatment of allergy. Full article
(This article belongs to the Special Issue The Mechanism of Action of Food Components in Disease Prevention)
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Open AccessArticle Pinnisterols A–C, New 9,11-Secosterols from a Gorgonian Pinnigorgia sp.
Mar. Drugs 2016, 14(1), 12; doi:10.3390/md14010012
Received: 12 December 2015 / Revised: 26 December 2015 / Accepted: 4 January 2016 / Published: 7 January 2016
Cited by 5 | Viewed by 944 | PDF Full-text (1037 KB) | HTML Full-text | XML Full-text
Abstract
Three new 9,11-secosterols, pinnisterols A–C (13), were isolated from a gorgonian coral Pinnigorgia sp., collected off the waters of Taiwan. The structures of these compounds were elucidated on the basis of spectroscopic methods. The new sterols 1 and 3
[...] Read more.
Three new 9,11-secosterols, pinnisterols A–C (13), were isolated from a gorgonian coral Pinnigorgia sp., collected off the waters of Taiwan. The structures of these compounds were elucidated on the basis of spectroscopic methods. The new sterols 1 and 3 displayed significant inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils, and sterol 1 was found to show moderate cytotoxicity in hepatic stellate cells (HSCs). Full article
Open AccessArticle New Flavones, a 2-(2-Phenylethyl)-4H-chromen-4-one Derivative, and Anti-Inflammatory Constituents from the Stem Barks of Aquilaria sinensis
Molecules 2015, 20(11), 20912-20925; doi:10.3390/molecules201119736
Received: 14 October 2015 / Revised: 13 November 2015 / Accepted: 16 November 2015 / Published: 24 November 2015
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Abstract
In the current study, two new flavones, 4′-O-geranyltricin (1) and 3′-O-geranylpolloin (2), and a new 2-(2-phenylethyl)-4H-chromen-4-one derivative, 7-hydroxyl-6-methoxy-2-(2-phenylethyl)chromone (3), have been isolated from the stem barks of A. sinensis, together
[...] Read more.
In the current study, two new flavones, 4′-O-geranyltricin (1) and 3′-O-geranylpolloin (2), and a new 2-(2-phenylethyl)-4H-chromen-4-one derivative, 7-hydroxyl-6-methoxy-2-(2-phenylethyl)chromone (3), have been isolated from the stem barks of A. sinensis, together with 21 known compounds 424. The structures of new compounds 13 were determined through spectroscopic and MS analyses. Compounds 2, 3, 5, 6, and 810 exhibited inhibition (IC50 ≤ 12.51 μM) of superoxide anion generation by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). Compounds 3, 6, 8, 10, and 19 inhibited fMLP/CB-induced elastase release with IC50 values ≤ 15.25 μM. This investigation reveals bioactive isolates (especially 2, 3, 5, 6, 8, 9, 10, and 19) could be further developed as potential candidates for the treatment or prevention of various inflammatory diseases. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle Eunicellin-Based Diterpenoids, Hirsutalins S–V, from the Formosan Soft Coral Cladiella hirsuta
Mar. Drugs 2015, 13(5), 2757-2769; doi:10.3390/md13052757
Received: 24 March 2015 / Revised: 20 April 2015 / Accepted: 20 April 2015 / Published: 30 April 2015
Cited by 8 | Viewed by 1176 | PDF Full-text (555 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Four new eunicellin-type hirsutalins S–V (14), along with a known compound (–)-6α-hydroxy polyanthellin A (5), were isolated from the soft coral Cladiella hirsuta. The structures of the metabolites were determined by extensive spectroscopic analysis. Cytotoxity of
[...] Read more.
Four new eunicellin-type hirsutalins S–V (14), along with a known compound (–)-6α-hydroxy polyanthellin A (5), were isolated from the soft coral Cladiella hirsuta. The structures of the metabolites were determined by extensive spectroscopic analysis. Cytotoxity of compounds 15 against the proliferation of a limited panel of cancer cell lines was measured. Anti-inflammatory activity of compounds 15 was evaluated by measuring their ability in suppressing superoxide anion generation and elastase release in fMLP/ CB-induced human neutrophils. Full article
Open AccessArticle New Coumarin Derivatives and Other Constituents from the Stem Bark of Zanthoxylum avicennae: Effects on Neutrophil Pro-Inflammatory Responses
Int. J. Mol. Sci. 2015, 16(5), 9719-9731; doi:10.3390/ijms16059719
Received: 17 March 2015 / Revised: 10 April 2015 / Accepted: 14 April 2015 / Published: 29 April 2015
Cited by 2 | Viewed by 1263 | PDF Full-text (746 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Three new coumarin derivatives, 8-formylalloxanthoxyletin (1), avicennone (2), and (Z)-avicennone (3), have been isolated from the stem bark of Zanthoxylum avicennae (Z. avicennae), together with 15 known compounds (418).
[...] Read more.
Three new coumarin derivatives, 8-formylalloxanthoxyletin (1), avicennone (2), and (Z)-avicennone (3), have been isolated from the stem bark of Zanthoxylum avicennae (Z. avicennae), together with 15 known compounds (418). The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1, 4, 9, 12, and 15 exhibited inhibition (half maximal inhibitory concentration (IC50) values ≤7.65 µg/mL) of superoxide anion generation by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). Compounds 1, 2, 4, 8 and 9 inhibited fMLP/CB-induced elastase release with IC50 values ≤8.17 µg/mL. This investigation reveals bioactive isolates (especially 1, 2, 4, 8, 9, 12 and 15) could be further developed as potential candidates for the treatment or prevention of various inflammatory diseases. Full article
(This article belongs to the Special Issue Plant Molecular Biology)
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Open AccessArticle Discovery of Benzo[f]indole-4,9-dione Derivatives as New Types of Anti-Inflammatory Agents
Int. J. Mol. Sci. 2015, 16(3), 6532-6544; doi:10.3390/ijms16036532
Received: 5 December 2014 / Revised: 6 February 2015 / Accepted: 13 March 2015 / Published: 23 March 2015
Cited by 4 | Viewed by 1029 | PDF Full-text (1741 KB) | HTML Full-text | XML Full-text
Abstract
Certain benzo[f]indole-4,9-dione derivatives were synthesized and evaluated for their inhibitory effects on superoxide anion generation and neutrophil elastase (NE) release in formyl-l-methionyl-l-leucyl-l-phenylalanine (fMLF)-activated human neutrophils. Results indicated that (Z)-1-benzyl-4-(hydroxyimino)-1H-benzo[f]indol-9(4H)-one (10) showed
[...] Read more.
Certain benzo[f]indole-4,9-dione derivatives were synthesized and evaluated for their inhibitory effects on superoxide anion generation and neutrophil elastase (NE) release in formyl-l-methionyl-l-leucyl-l-phenylalanine (fMLF)-activated human neutrophils. Results indicated that (Z)-1-benzyl-4-(hydroxyimino)-1H-benzo[f]indol-9(4H)-one (10) showed a potent dual inhibitory effect on NE release and superoxide anion generation with IC50 value of 2.78 and 2.74 μM respectively. The action mechanisms of 10 in human neutrophils were further investigated. Our results showed that compound 10 did not alter fMLF-induced phosphorylation of Src (Src family Y416). Notably, phosphorylation of Akt (S473) and mobilization of [Ca2+]i caused by fMLF was inhibited by compound 10. Further structural optimization of 10 is ongoing. Full article
(This article belongs to the Section Biochemistry, Molecular and Cellular Biology)
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Open AccessArticle Briarenolides K and L, New Anti-Inflammatory Briarane Diterpenoids from an Octocoral Briareum sp. (Briareidae)
Mar. Drugs 2015, 13(2), 1037-1050; doi:10.3390/md13021037
Received: 5 January 2015 / Revised: 5 February 2015 / Accepted: 6 February 2015 / Published: 13 February 2015
Cited by 7 | Viewed by 1327 | PDF Full-text (710 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Two new briarane-type diterpenoids, briarenolides K (1) and L (2), were isolated from an octocoral identified as Briareum sp. The structures of new briaranes 1 and 2 were elucidated by spectroscopic methods. In the in vitro anti-inflammatory effects test,
[...] Read more.
Two new briarane-type diterpenoids, briarenolides K (1) and L (2), were isolated from an octocoral identified as Briareum sp. The structures of new briaranes 1 and 2 were elucidated by spectroscopic methods. In the in vitro anti-inflammatory effects test, briaranes 1 and 2 were found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein of the lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. Full article
Open AccessArticle Bioactive Chemical Constituents from the Brown Alga Homoeostrichus formosana
Int. J. Mol. Sci. 2015, 16(1), 736-746; doi:10.3390/ijms16010736
Received: 18 November 2014 / Accepted: 17 December 2014 / Published: 30 December 2014
Cited by 6 | Viewed by 1482 | PDF Full-text (743 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A new chromene derivative, 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-hydroxy-2,6-dimethyl-2H-chromene (1) together with four known natural products, methylfarnesylquinone (2), isololiolide (3), pheophytin a (4), and β-carotene (5) were isolated from the brown alga Homoeostrichus
[...] Read more.
A new chromene derivative, 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-hydroxy-2,6-dimethyl-2H-chromene (1) together with four known natural products, methylfarnesylquinone (2), isololiolide (3), pheophytin a (4), and β-carotene (5) were isolated from the brown alga Homoeostrichus formosana. The structure of 1 was determined by extensive 1D and 2D spectroscopic analyses. Acetylation of 1 yielded the monoacetylated derivative 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-acetyl-2,6-dimethyl-2H-chromene (6). Compounds 16 exhibited various levels of cytotoxic, antibacterial, and anti-inflammatory activities. Compound 2 was found to display potent in vitro anti-inflammatory activity by inhibiting the generation of superoxide anion (IC50 0.22 ± 0.03 μg/mL) and elastase release (IC50 0.48 ± 0.11 μg/mL) in FMLP/CB-induced human neutrophils. Full article
(This article belongs to the Section Biochemistry, Molecular and Cellular Biology)
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Open AccessCommunication Rumphellaoic Acid A, a Novel Sesquiterpenoid from the Formosan Gorgonian Coral Rumphella antipathies
Mar. Drugs 2014, 12(12), 5856-5863; doi:10.3390/md12125856
Received: 9 September 2014 / Revised: 4 November 2014 / Accepted: 21 November 2014 / Published: 4 December 2014
Cited by 5 | Viewed by 1418 | PDF Full-text (410 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A novel sesquiterpenoid, rumphellaoic acid A (1), was isolated from the gorgonian coral Rumphella antipathies, and was found to possess a carbon skeleton that was obtained for the first time from a natural sources. The structure of 1 was elucidated
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A novel sesquiterpenoid, rumphellaoic acid A (1), was isolated from the gorgonian coral Rumphella antipathies, and was found to possess a carbon skeleton that was obtained for the first time from a natural sources. The structure of 1 was elucidated by spectroscopic methods and this compound and was found to exert a moderate inhibitory effect on the release of elastase by human neutrophils. Full article
(This article belongs to the Special Issue Terpenoids of Marine Origin)
Open AccessArticle Krempfielins Q and R, Two New Eunicellin-Based Diterpenoids from the Soft Coral Cladiella krempfi
Int. J. Mol. Sci. 2014, 15(12), 21865-21874; doi:10.3390/ijms151221865
Received: 23 September 2014 / Revised: 12 November 2014 / Accepted: 21 November 2014 / Published: 27 November 2014
Cited by 4 | Viewed by 1260 | PDF Full-text (953 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Two new eunicellin-based diterpenoids, krempfielins Q and R (1 and 2), and one known compound cladieunicellin K (3) have been isolated from a Formosan soft coral Cladiella krempfi. The structures of these two new metabolites were elucidated by
[...] Read more.
Two new eunicellin-based diterpenoids, krempfielins Q and R (1 and 2), and one known compound cladieunicellin K (3) have been isolated from a Formosan soft coral Cladiella krempfi. The structures of these two new metabolites were elucidated by extensive spectroscopic analysis. Anti-inflammatory activity of new metabolites to inhibit the superoxide anion generation and elastase release in N-formyl-methionyl-leucyl phenylalanine/cytochalasin B (FMLP/CB)-induced human neutrophil cells and cytotoxicity of both new compounds toward five cancer cell lines were reported. Full article
(This article belongs to the Section Biochemistry, Molecular and Cellular Biology)
Open AccessArticle Rumphellols A and B, New Caryophyllene Sesquiterpenoids from a Formosan Gorgonian Coral, Rumphella antipathies
Int. J. Mol. Sci. 2014, 15(9), 15679-15688; doi:10.3390/ijms150915679
Received: 3 July 2014 / Revised: 21 August 2014 / Accepted: 26 August 2014 / Published: 4 September 2014
Cited by 6 | Viewed by 1149 | PDF Full-text (771 KB) | HTML Full-text | XML Full-text
Abstract
Two new marine-derived caryophyllene-type sesquiterpenoids, rumphellols A and B (1 and 2), were obtained from the gorgonian coral, Rumphella antipathies, collected off the waters of Taiwan. Although caryophyllene-type sesquiterpenes are rarely found in marine organisms, compounds of this type could
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Two new marine-derived caryophyllene-type sesquiterpenoids, rumphellols A and B (1 and 2), were obtained from the gorgonian coral, Rumphella antipathies, collected off the waters of Taiwan. Although caryophyllene-type sesquiterpenes are rarely found in marine organisms, compounds of this type could be principal components of R. antipathies. The structures of new Compounds 1 and 2 were determined by analysis of their spectroscopic data, including 1D and 2D NMR experiments. Caryophyllene 1 and 2 were evaluated in terms of their anti-inflammatory activity by examining their inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils. Full article
(This article belongs to the Section Biochemistry, Molecular and Cellular Biology)
Open AccessArticle New Briarane Diterpenoids from Taiwanese Soft Coral Briareum violacea
Mar. Drugs 2014, 12(8), 4677-4692; doi:10.3390/md12084677
Received: 28 May 2014 / Revised: 24 July 2014 / Accepted: 24 July 2014 / Published: 22 August 2014
Cited by 4 | Viewed by 1560 | PDF Full-text (1198 KB) | HTML Full-text | XML Full-text
Abstract
Ten new briarane diterpenoids, briaviolides A–J (110), together with six known briaranes, solenolides A and D, excavatolide A, briaexcavatolide I, 4β-acetoxy-9-deacetystylatulide lactone and 9-deacetylstylatulide lactone, were isolated from the Taiwanese soft coral, Briareum violacea. Their structures were determined
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Ten new briarane diterpenoids, briaviolides A–J (110), together with six known briaranes, solenolides A and D, excavatolide A, briaexcavatolide I, 4β-acetoxy-9-deacetystylatulide lactone and 9-deacetylstylatulide lactone, were isolated from the Taiwanese soft coral, Briareum violacea. Their structures were determined on the basis of spectroscopic data (1H- and 13C-NMR, 1H–1H COSY, HSQC, HMBC and NOESY), HR-MS and chemical methods. The absolute configuration of briaviolide A (1) was determined by X-ray crystallographic analysis. Compounds 5, 9 and derivative 11 showed moderate inhibitory activities on superoxide-anion generation and elastase release by human neutrophils in response to N-formyl-methionyl-leucyl-phenylalanine/ Cytochalasin B (fMLP/CB). Full article
(This article belongs to the collection Bioactive Compounds from Marine Invertebrates)
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Open AccessArticle Rumphellaones B and C, New 4,5-Seco-Caryophyllane Sesquiterpenoids from Rumphella
Molecules 2014, 19(8), 12320-12327; doi:10.3390/molecules190812320
Received: 14 July 2014 / Revised: 11 August 2014 / Accepted: 11 August 2014 / Published: 14 August 2014
Cited by 6 | Viewed by 1439 | PDF Full-text (779 KB) | HTML Full-text | XML Full-text
Abstract
Two new 4,5-seco-caryophyllane sesquiterpenoids, rumphellaones B (1) and C (2), which were found to possess unprecedented γ-lactone moieties, were obtained from the gorgonian coral Rumphella antipathies. The structures of 1 and 2 were elucidated by spectroscopic
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Two new 4,5-seco-caryophyllane sesquiterpenoids, rumphellaones B (1) and C (2), which were found to possess unprecedented γ-lactone moieties, were obtained from the gorgonian coral Rumphella antipathies. The structures of 1 and 2 were elucidated by spectroscopic methods and compound 2 was found to display modest inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils at a concentration of 10 μg/mL Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Two Diterpenoids and a Cyclopenta[c]pyridine Derivative from Roots of Salvia digitaloids
Int. J. Mol. Sci. 2014, 15(7), 11566-11577; doi:10.3390/ijms150711566
Received: 2 April 2014 / Revised: 28 May 2014 / Accepted: 29 May 2014 / Published: 27 June 2014
Cited by 3 | Viewed by 1318 | PDF Full-text (305 KB) | HTML Full-text | XML Full-text
Abstract
Two new glucosides, salviadigitoside A (1) and salviatalin A-19-O-β-glucoside (2), belonging to the salviatalin type diterpenoids, and a new cyclopenta[c]pyridine, salviadiginine A (3), were isolated from the roots of Salvia digitaloids. Structures
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Two new glucosides, salviadigitoside A (1) and salviatalin A-19-O-β-glucoside (2), belonging to the salviatalin type diterpenoids, and a new cyclopenta[c]pyridine, salviadiginine A (3), were isolated from the roots of Salvia digitaloids. Structures of these compounds were determined on the basis of spectroscopic analysis. In addition, compounds 13 were evaluated for their anti-inflammatory activity, but the results showed a weak anti-inflammatory activity. Full article
(This article belongs to the Section Green Chemistry)
Open AccessArticle New Coumarins and Anti-Inflammatory Constituents from the Fruits of Cnidium monnieri
Int. J. Mol. Sci. 2014, 15(6), 9566-9578; doi:10.3390/ijms15069566
Received: 3 March 2014 / Revised: 7 May 2014 / Accepted: 13 May 2014 / Published: 28 May 2014
Cited by 3 | Viewed by 1960 | PDF Full-text (278 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The fruit of Cnidium monnieri is commercially used as healthcare products for the improvement of impotence and skin diseases. Three new coumarins, 3'-O-methylmurraol (1), rel-(1'S,2'S)-1'-O-methylphlojodicarpin (2), and (1'S,2'
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The fruit of Cnidium monnieri is commercially used as healthcare products for the improvement of impotence and skin diseases. Three new coumarins, 3'-O-methylmurraol (1), rel-(1'S,2'S)-1'-O-methylphlojodicarpin (2), and (1'S,2'S)-1'-O-methylvaginol (3), have been isolated from the fruits of C. monnieri, together with 14 known compounds (417). The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1, 412, and 1417 exhibited inhibition (IC50 ≤ 7.31 µg/mL) of superoxide anion generation by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). Compounds 7, 911, 15, and 17 inhibited fMLP/CB-induced elastase release with IC50 values ≤7.83 µg/mL. This investigation reveals that bioactive isolates (especially 6, 7, 14, and 17) could be further developed as potential candidates for the treatment or prevention of various inflammatory diseases. Full article
(This article belongs to the Section Biochemistry, Molecular and Cellular Biology)
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Open AccessArticle Eunicellin-Based Diterpenoids, Hirsutalins N–R, from the Formosan Soft Coral Cladiella hirsuta
Mar. Drugs 2014, 12(5), 2446-2457; doi:10.3390/md12052446
Received: 13 February 2014 / Revised: 24 March 2014 / Accepted: 31 March 2014 / Published: 30 April 2014
Cited by 9 | Viewed by 1409 | PDF Full-text (777 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
New eunicellin-type hirsutalins N–R (15), along with two known eunicellins, (6 and 7) were isolated from the soft coral Cladiella hirsuta. The structures of the metabolites were determined by extensive spectroscopic analysis. Cytotoxic activity of compounds
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New eunicellin-type hirsutalins N–R (15), along with two known eunicellins, (6 and 7) were isolated from the soft coral Cladiella hirsuta. The structures of the metabolites were determined by extensive spectroscopic analysis. Cytotoxic activity of compounds 17 against the proliferation of a limited panel of cancer cell lines was measured. The in vitro anti-inflammatory activity of compounds 17 was evaluated by measuring their ability in suppressing superoxide anion generation and elastase release in fMLP/CB-induced human neutrophils. Full article
(This article belongs to the collection Bioactive Compounds from Marine Invertebrates)
Open AccessShort Note 5-(6-Hydroxy-2,5,7,8-tetramethylchroman-2-yl)-2-methyl-pentanoic Acid Methyl Ester
Molbank 2014, 2014(2), M822; doi:10.3390/M822
Received: 10 February 2014 / Accepted: 14 April 2014 / Published: 21 April 2014
Viewed by 1514 | PDF Full-text (212 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A natural diastereomeric mixture of 5-(6-hydroxy-2,5,7,8-tetramethyl-chroman-2-yl)-2-methyl-pentanoic acid methyl ester (1), was isolated from the soft coral Sinularia arborea. The structure of 1 was elucidated by spectroscopic methods and 1 displayed a significantly inhibitory effect on the generation of superoxide anion
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A natural diastereomeric mixture of 5-(6-hydroxy-2,5,7,8-tetramethyl-chroman-2-yl)-2-methyl-pentanoic acid methyl ester (1), was isolated from the soft coral Sinularia arborea. The structure of 1 was elucidated by spectroscopic methods and 1 displayed a significantly inhibitory effect on the generation of superoxide anion by human neutrophils. Full article
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Open AccessArticle Anti-Inflammatory Triterpenoids from the Stems of Microtropis Fokienensis
Molecules 2014, 19(4), 4608-4623; doi:10.3390/molecules19044608
Received: 3 March 2014 / Revised: 9 April 2014 / Accepted: 9 April 2014 / Published: 14 April 2014
Cited by 5 | Viewed by 1693 | PDF Full-text (445 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Three new ursane- and four new oleanane- type triterpenoids 17 were isolated, along with six known compounds 813, from the methanolic extract of Microtropis fokienensis. All structures were elucidated by mass and NMR spectroscopic methods. The isolates
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Three new ursane- and four new oleanane- type triterpenoids 17 were isolated, along with six known compounds 813, from the methanolic extract of Microtropis fokienensis. All structures were elucidated by mass and NMR spectroscopic methods. The isolates 410 and known compounds 1417 that were previously isolated from this material were evaluated for anti-inflammatory activity based on effects against superoxide anion generation and elastase release by neutrophils in response to fMLP/CB. 11α,30-Dihydroxy-2,3-seco-olean-12-en-2,3-dioic anhydride (7) was the first triterpene anhydride from the genus of Microtropis to have the ring A expanded to a seven-membered ring; it showed significant anti-inflammatory activity against superoxide anion generation and elastase release. Unexpectedly, 30-hydroxy-2,3-seco-lup-20(29)-ene-2,3-dioic acid (17) showed the best effect against superoxide anion generation and elastase release with IC50 values of 0.06 ± 0.01 and 1.03 ± 0.35 µg/mL, respectively. Compound 17 had a dioic acid function, and compound 7 had an anhydride function modification in ring A; both showed promising activity in the target assays. Full article
(This article belongs to the Section Natural Products)
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Open AccessArticle Intracellular Glutathione Depletion by Oridonin Leads to Apoptosis in Hepatic Stellate Cells
Molecules 2014, 19(3), 3327-3344; doi:10.3390/molecules19033327
Received: 17 February 2014 / Revised: 4 March 2014 / Accepted: 13 March 2014 / Published: 18 March 2014
Cited by 25 | Viewed by 2276 | PDF Full-text (1785 KB) | HTML Full-text | XML Full-text
Abstract
Proliferation of hepatic stellate cells (HSCs) plays a key role in the pathogenesis of liver fibrosis. Induction of HSC apoptosis by natural products is considered an effective strategy for treating liver fibrosis. Herein, the apoptotic effects of 7,20-epoxy-ent-kaurane (oridonin), a diterpenoid
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Proliferation of hepatic stellate cells (HSCs) plays a key role in the pathogenesis of liver fibrosis. Induction of HSC apoptosis by natural products is considered an effective strategy for treating liver fibrosis. Herein, the apoptotic effects of 7,20-epoxy-ent-kaurane (oridonin), a diterpenoid isolated from Rabdosia rubescens, and its underlying mechanisms were investigated in rat HSC cell line, HSC-T6. We found that oridonin inhibited cell viability of HSC-T6 in a concentration-dependent manner. Oridonin induced a reduction in mitochondrial membrane potential and increases in caspase 3 activation, subG1 phase, and DNA fragmentation. These apoptotic effects of oridonin were completely reversed by thiol antioxidants, N-acetylcysteine (NAC) and glutathione monoethyl ester. Moreover, oridonin increased production of reactive oxygen species (ROS), which was also inhibited by NAC. Significantly, oridonin reduced intracellular glutathione (GSH) level in a concentration- and time-dependent fashion. Additionally, oridonin induced phosphorylations of extracellular signal-regulated kinase (ERK), c-Jun N-terminal kinase (JNK), and p38 mitogen-activated protein kinase (MAPK). NAC prevented the activation of MAPKs in oridonin-induced cells. However, selective inhibitors of MAPKs failed to alter oridonin-induced cell death. In summary, these results demonstrate that induction of apoptosis in HSC-T6 by oridonin is associated with a decrease in cellular GSH level and increase in ROS production. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Krempfielins N–P, New Anti-Inflammatory Eunicellins from a Taiwanese Soft Coral Cladiella krempfi
Mar. Drugs 2014, 12(2), 1148-1156; doi:10.3390/md12021148
Received: 11 December 2013 / Revised: 22 January 2014 / Accepted: 7 February 2014 / Published: 21 February 2014
Cited by 10 | Viewed by 2105 | PDF Full-text (869 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Three new eunicellin-type diterpenoids, krempfielins N–P (13), were isolated from a Taiwanese soft coral Cladiella krempfi. The structures of the new metabolites were elucidated by extensive spectroscopic analysis and by comparison with spectroscopic data of related known compounds.
[...] Read more.
Three new eunicellin-type diterpenoids, krempfielins N–P (13), were isolated from a Taiwanese soft coral Cladiella krempfi. The structures of the new metabolites were elucidated by extensive spectroscopic analysis and by comparison with spectroscopic data of related known compounds. Compound 3 exhibited activity to inhibit superoxide anion generation. Both 1 and 3, in particular 1, were shown to display significant anti-inflammatory activity by inhibiting the elastase release in FMLP/CB-induced human neutrophils. Full article
Open AccessArticle Discovery of Novel Diterpenoids from Sinularia arborea
Mar. Drugs 2014, 12(1), 385-393; doi:10.3390/md12010385
Received: 5 November 2013 / Revised: 23 November 2013 / Accepted: 3 January 2014 / Published: 17 January 2014
Cited by 5 | Viewed by 1736 | PDF Full-text (649 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Two novel diterpenoids, sinularbols A (1) and B (2), which were found to possess a new carbon skeleton were isolated from the soft coral Sinularia arborea. The structures of compounds 1 and 2 were elucidated by spectroscopic methods
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Two novel diterpenoids, sinularbols A (1) and B (2), which were found to possess a new carbon skeleton were isolated from the soft coral Sinularia arborea. The structures of compounds 1 and 2 were elucidated by spectroscopic methods and 2 displayed a moderately inhibitory effect on the generation of superoxide anion by human neutrophils. Full article
Open AccessArticle Triterpenoids and Steroids from Ganoderma mastoporum and Their Inhibitory Effects on Superoxide Anion Generation and Elastase Release
Molecules 2013, 18(11), 14285-14292; doi:10.3390/molecules181114285
Received: 27 September 2013 / Revised: 6 November 2013 / Accepted: 15 November 2013 / Published: 19 November 2013
Cited by 2 | Viewed by 1749 | PDF Full-text (212 KB) | HTML Full-text | XML Full-text
Abstract
The methanol extracts of the fruiting bodies of Ganoderma mastoporum collected in Vietnam was purified to afford eight compounds, including three triterpenoids and five steroids. The purified compounds were examined for their inhibitory effects against superoxide anion generation and elastase release. Among the
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The methanol extracts of the fruiting bodies of Ganoderma mastoporum collected in Vietnam was purified to afford eight compounds, including three triterpenoids and five steroids. The purified compounds were examined for their inhibitory effects against superoxide anion generation and elastase release. Among the tested compounds, ergosta-4,6,8(14),22-tetraen-3-one (3) exhibited the most significant inhibition towards superoxide anion generation and elastase release with IC50 values of 2.30 ± 0.38 and 1.94 ± 0.50 µg/mL, respectively. Full article
Open AccessArticle New Benzo[c]phenanthridine and Benzenoid Derivatives, and Other Constituents from Zanthoxylum ailanthoides: Effects on Neutrophil Pro-Inflammatory Responses
Int. J. Mol. Sci. 2013, 14(11), 22395-22408; doi:10.3390/ijms141122395
Received: 6 August 2013 / Revised: 24 October 2013 / Accepted: 25 October 2013 / Published: 13 November 2013
Cited by 1 | Viewed by 1900 | PDF Full-text (395 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A new benzo[c]phenanthridine, oxynorchelerythrine (1), and two new benzenoid derivatives, methyl 4-(2-hydroxy-4-methoxy-3-methyl-4-oxobutoxy)benzoate (2) and (E)-methyl 4-(4-((Z)-3-methoxy-3-oxoprop-1-enyl)phenoxy)-2-methylbut-2-enoate (3), have been isolated from the twigs of Zanthoxylum ailanthoides, together with 11 known
[...] Read more.
A new benzo[c]phenanthridine, oxynorchelerythrine (1), and two new benzenoid derivatives, methyl 4-(2-hydroxy-4-methoxy-3-methyl-4-oxobutoxy)benzoate (2) and (E)-methyl 4-(4-((Z)-3-methoxy-3-oxoprop-1-enyl)phenoxy)-2-methylbut-2-enoate (3), have been isolated from the twigs of Zanthoxylum ailanthoides, together with 11 known compounds (414). The structures of these new compounds were determined through spectroscopic and MS analyses. Among the isolated compounds, decarine (4), (−)-syringaresinol (6), (+)-episesamin (8), glaberide I (9), (−)-dihydrocubebin (10), and xanthyletin (11) exhibited potent inhibition (IC50 values ≤ 4.79 µg/mL) of superoxide anion generation by human nutrophils in response to N-formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 4, 8, and 11 also inhibited fMLP/CB-induced elastase release with IC50 values ≤ 5.48 µg/mL. Full article
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Open AccessArticle Krempfielins J-M, New Eunicellin-Based Diterpenoids from the Soft Coral Cladiella krempfi
Mar. Drugs 2013, 11(8), 2741-2750; doi:10.3390/md11082741
Received: 17 June 2013 / Revised: 9 July 2013 / Accepted: 11 July 2013 / Published: 2 August 2013
Cited by 15 | Viewed by 1847 | PDF Full-text (506 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
New four eunicellin-based diterpenoids, krempfielins J–M (14) were isolated from the organic extract of a Taiwanese soft coral Cladiella krempfi. The structures of the new metabolites were elucidated on the basis of extensive spectroscopic analysis. The structure of
[...] Read more.
New four eunicellin-based diterpenoids, krempfielins J–M (14) were isolated from the organic extract of a Taiwanese soft coral Cladiella krempfi. The structures of the new metabolites were elucidated on the basis of extensive spectroscopic analysis. The structure of compound 2 is rare due to the presence of the highly oxygenated pattern. Anti-inflammatory activity of 16 to inhibit the superoxide anion generation and elastase release in FMLP/CB-induced human neutrophils was also evaluated, and 2 and 4 were shown to possess the ability to inhibit the elastase release. Full article
(This article belongs to the Special Issue Marine Compounds and Inflammation)
Open AccessArticle Two Anti-inflammatory Steroidal Saponins from Dracaena angustifolia Roxb.
Molecules 2013, 18(8), 8752-8763; doi:10.3390/molecules18088752
Received: 18 June 2013 / Revised: 11 July 2013 / Accepted: 21 July 2013 / Published: 24 July 2013
Cited by 5 | Viewed by 2523 | PDF Full-text (316 KB) | HTML Full-text | XML Full-text
Abstract
Two new steroidal saponins, named drangustosides A–B (12), together with eight known compounds 310 were isolated and characterized from the MeOH extract of Dracaena angustifolia Roxb. The structures of compounds were assigned based on 1D and 2D
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Two new steroidal saponins, named drangustosides A–B (12), together with eight known compounds 310 were isolated and characterized from the MeOH extract of Dracaena angustifolia Roxb. The structures of compounds were assigned based on 1D and 2D NMR spectroscopic analyses, including HMQC, HMBC, and NOESY. Compounds 1 and 2 showed anti-inflammatory activity by superoxide generation and elastase release by human neutrophils in response to fMLP/CB. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle New Labdane-Type Diterpenoids and Anti-Inflammatory Constituents from Hedychium coronarium
Int. J. Mol. Sci. 2013, 14(7), 13063-13077; doi:10.3390/ijms140713063
Received: 16 April 2013 / Revised: 3 June 2013 / Accepted: 8 June 2013 / Published: 25 June 2013
Cited by 8 | Viewed by 2055 | PDF Full-text (313 KB) | HTML Full-text | XML Full-text
Abstract
Four new labdane-type diterpenoids: hedychicoronarin (1), peroxycoronarin D (2), 7β-hydroxycalcaratarin A (3), and (E)-7β-hydroxy-6-oxo-labda-8(17),12-diene-15,16-dial (4), have been isolated from the rhizomes of Hedychium coronarium, together with 13 known compounds (5
[...] Read more.
Four new labdane-type diterpenoids: hedychicoronarin (1), peroxycoronarin D (2), 7β-hydroxycalcaratarin A (3), and (E)-7β-hydroxy-6-oxo-labda-8(17),12-diene-15,16-dial (4), have been isolated from the rhizomes of Hedychium coronarium, together with 13 known compounds (517). The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 3, 5, 6, and 10 exhibited inhibition (IC50 values ≤4.52 μg/mL) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 36, 10, and 11 inhibited fMLP/CB-induced elastase release with IC50 values ≤6.17 μg/mL. Full article
(This article belongs to the Section Biochemistry, Molecular and Cellular Biology)
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Open AccessArticle Four New Briarane Diterpenoids from Taiwanese Gorgonian Junceella fragilis
Mar. Drugs 2013, 11(6), 2042-2053; doi:10.3390/md11062042
Received: 15 April 2013 / Revised: 22 May 2013 / Accepted: 27 May 2013 / Published: 10 June 2013
Cited by 10 | Viewed by 1634 | PDF Full-text (848 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Four new 8-hydroxybriarane diterpenoids, frajunolides P–S (14), together with umbraculolide A, juncenolide C, junceellonoid A and juncin R, were isolated from the acetone extract of the gorgonian Junceella fragilis, collected from the southeast coast of Taiwan. Compound 1
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Four new 8-hydroxybriarane diterpenoids, frajunolides P–S (14), together with umbraculolide A, juncenolide C, junceellonoid A and juncin R, were isolated from the acetone extract of the gorgonian Junceella fragilis, collected from the southeast coast of Taiwan. Compound 1 contains an unusual pivaloyloxy group at C-2, while 3 is a rare compound having a chlorine atom on the olefinic carbon (C-6). The structures of the isolated compounds were established by extensive spectroscopic analysis, including 1D- and 2D-NMR, as well as HRMS data. Compound 1 was further confirmed by X-ray crystallographic analysis. In the anti-inflammatory test, compounds 1 and 2 exhibited moderate inhibition on superoxide anion generation and elastase release by human neutrophils in response to formylmethionylleucyl-phenylalanine/dihydrocytochalasin B (fMLP/CB). Full article
Open AccessArticle A New Hydroxychavicol Dimer from the Roots of Piper betle
Molecules 2013, 18(3), 2563-2570; doi:10.3390/molecules18032563
Received: 28 November 2012 / Revised: 8 February 2013 / Accepted: 21 February 2013 / Published: 26 February 2013
Cited by 5 | Viewed by 1879 | PDF Full-text (262 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A new hydroxychavicol dimer, 2-(g'-hydroxychavicol)-hydroxychavicol (1), was isolated from the roots of Piper betle Linn. along with five known compounds, hydroxychavicol (2), aristololactam A II (3), aristololactam B II (4), piperolactam A (5)
[...] Read more.
A new hydroxychavicol dimer, 2-(g'-hydroxychavicol)-hydroxychavicol (1), was isolated from the roots of Piper betle Linn. along with five known compounds, hydroxychavicol (2), aristololactam A II (3), aristololactam B II (4), piperolactam A (5) and cepharadione A (6). The structures of these isolated compounds were elucidated by spectroscopic methods. Compounds 1 and 2 exhibited inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Echinohalimane A, a Bioactive Halimane-Type Diterpenoid from a Formosan Gorgonian Echinomuricea sp. (Plexauridae)
Mar. Drugs 2012, 10(10), 2246-2253; doi:10.3390/md10102246
Received: 5 September 2012 / Revised: 24 September 2012 / Accepted: 8 October 2012 / Published: 17 October 2012
Cited by 10 | Viewed by 1989 | PDF Full-text (395 KB) | HTML Full-text | XML Full-text
Abstract
A new halimane-type diterpenoid, echinohalimane A (1), was isolated from a gorgonian, identified as Echinomuricea sp. The structure of 1 was determined by spectroscopic methods and this compound was found to exhibit cytotoxicity toward various tumor cells and display an inhibitory
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A new halimane-type diterpenoid, echinohalimane A (1), was isolated from a gorgonian, identified as Echinomuricea sp. The structure of 1 was determined by spectroscopic methods and this compound was found to exhibit cytotoxicity toward various tumor cells and display an inhibitory effect on the release of elastase by human neutrophils. Echinohalimane A (1) is the first halimane analogue from the marine organisms belonging to phylum Cnidaria. Full article
Open AccessArticle Echinoclerodane A: A New Bioactive Clerodane-Type Diterpenoid from a Gorgonian Coral Echinomuricea sp.
Molecules 2012, 17(8), 9443-9450; doi:10.3390/molecules17089443
Received: 9 July 2012 / Revised: 1 August 2012 / Accepted: 2 August 2012 / Published: 7 August 2012
Cited by 10 | Viewed by 1936 | PDF Full-text (229 KB) | HTML Full-text | XML Full-text
Abstract
A new clerodane-type diterpenoid, echinoclerodane A (1), was isolated from a Formosan gorgonian coral Echinomuricea sp. The structure of 1 was elucidated by spectroscopic methods. Echinoclerodane A (1) is the first clerodane-type compound obtained from the marine organisms belonging
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A new clerodane-type diterpenoid, echinoclerodane A (1), was isolated from a Formosan gorgonian coral Echinomuricea sp. The structure of 1 was elucidated by spectroscopic methods. Echinoclerodane A (1) is the first clerodane-type compound obtained from the marine organisms belonging to the phylum Cnidaria. Echinoclerodane A (1) exhibited moderate cytotoxicity toward MOLT-4, HL-60, DLD-1 and LoVo tumor cells and inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Constituents from Vigna vexillata and Their Anti-Inflammatory Activity
Int. J. Mol. Sci. 2012, 13(8), 9754-9768; doi:10.3390/ijms13089754
Received: 16 July 2012 / Revised: 29 July 2012 / Accepted: 31 July 2012 / Published: 6 August 2012
Cited by 4 | Viewed by 1828 | PDF Full-text (171 KB) | HTML Full-text | XML Full-text
Abstract
The seeds of Vigna genus are important food resources and there have already been many reports regarding their bioactivities. In our preliminary bioassay, the chloroform layer of methanol extracts of V. vexillata demonstrated significant anti-inflammatory bioactivity. Therefore, the present research is aimed to
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The seeds of Vigna genus are important food resources and there have already been many reports regarding their bioactivities. In our preliminary bioassay, the chloroform layer of methanol extracts of V. vexillata demonstrated significant anti-inflammatory bioactivity. Therefore, the present research is aimed to purify and identify the anti-inflammatory principles of V. vexillata. One new sterol (1) and two new isoflavones (2,3) were reported from the natural sources for the first time and their chemical structures were determined by the spectroscopic and mass spectrometric analyses. In addition, 37 known compounds were identified by comparison of their physical and spectroscopic data with those reported in the literature. Among the isolates, daidzein (23), abscisic acid (25), and quercetin (40) displayed the most significant inhibition of superoxide anion generation and elastase release. Full article
(This article belongs to the Section Biochemistry, Molecular and Cellular Biology)
Open AccessArticle Pseudoalteromone B: A Novel 15C Compound from a Marine Bacterium Pseudoalteromonas sp. CGH2XX
Mar. Drugs 2012, 10(7), 1566-1571; doi:10.3390/md10071566
Received: 12 June 2012 / Revised: 12 July 2012 / Accepted: 12 July 2012 / Published: 20 July 2012
Cited by 7 | Viewed by 2144 | PDF Full-text (181 KB) | HTML Full-text | XML Full-text
Abstract
A novel 15C compound, pseudoalteromone B (1), possessing a novel carbon skeleton, was obtained from a marine bacterium Pseudoalteromonas sp. CGH2XX. This bacterium was originally isolated from a cultured-type octocoral Lobophytum crassum, that was growing in cultivating tanks equipped with
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A novel 15C compound, pseudoalteromone B (1), possessing a novel carbon skeleton, was obtained from a marine bacterium Pseudoalteromonas sp. CGH2XX. This bacterium was originally isolated from a cultured-type octocoral Lobophytum crassum, that was growing in cultivating tanks equipped with a flow-through sea water system. The structure of 1 was established by spectroscopic methods. Pseudoalteromone B (1) displayed a modestly inhibitory effect on the release of elastase by human neutrophils. Full article
Open AccessArticle New Briarane Diterpenoids from the Gorgonian Coral Junceella juncea
Mar. Drugs 2012, 10(6), 1321-1330; doi:10.3390/md10061321
Received: 29 March 2012 / Revised: 18 May 2012 / Accepted: 29 May 2012 / Published: 7 June 2012
Cited by 12 | Viewed by 2403 | PDF Full-text (688 KB) | HTML Full-text | XML Full-text
Abstract
Chemical investigation of Junceella juncea has resulted in the isolation of three new briaranes designated juncenolides M–O (13). The structures of these compounds were determined by spectroscopic analysis including 2D-NMR (COSY, HMBC and NOESY) and HRMS. Compound 1 is
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Chemical investigation of Junceella juncea has resulted in the isolation of three new briaranes designated juncenolides M–O (13). The structures of these compounds were determined by spectroscopic analysis including 2D-NMR (COSY, HMBC and NOESY) and HRMS. Compound 1 is a new chlorinated briarane while compound 3 contains a rare methyl ester at C-16. The anti-inflammatory activities tested on superoxide anion generation and elastase release by human neutrophils in response to FMLP/CB were evaluated. Full article
Open AccessShort Note Menelloides C and D, New Sesquiterpenoids from the Gorgonian Coral Menella sp.
Mar. Drugs 2011, 9(9), 1534-1542; doi:10.3390/md9091534
Received: 20 July 2011 / Revised: 22 August 2011 / Accepted: 5 September 2011 / Published: 14 September 2011
Cited by 16 | Viewed by 2800 | PDF Full-text (236 KB) | HTML Full-text | XML Full-text
Abstract
Two new metabolites, including a lindenane-type sesquiterpenoid, menelloide C (1), and a germacrane-type sesquiterpenoid, menelloide D (2), were isolated from a Formosan gorgonian coral identified as Menella sp. The structures of 1 and 2 were established by spectroscopic methods
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Two new metabolites, including a lindenane-type sesquiterpenoid, menelloide C (1), and a germacrane-type sesquiterpenoid, menelloide D (2), were isolated from a Formosan gorgonian coral identified as Menella sp. The structures of 1 and 2 were established by spectroscopic methods and 2 displayed a weak inhibitory effect on the release of elastase by human neutrophils. Full article
Open AccessArticle Frajunolides L–O, Four New 8-Hydroxybriarane Diterpenoids from the Gorgonian Junceella fragilis
Mar. Drugs 2011, 9(9), 1477-1486; doi:10.3390/md9091477
Received: 8 July 2011 / Revised: 23 August 2011 / Accepted: 25 August 2011 / Published: 2 September 2011
Cited by 11 | Viewed by 2841 | PDF Full-text (1085 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Four new 8-hydroxybriarane diterpenoids, frajunolides L–O (14), were isolated from the Taiwanese gorgonian Junceella fragilis. The structures of compounds 14 were elucidated based on spectroscopic analysis, especially 2D NMR (1H-1H COSY, HSQC,
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Four new 8-hydroxybriarane diterpenoids, frajunolides L–O (14), were isolated from the Taiwanese gorgonian Junceella fragilis. The structures of compounds 14 were elucidated based on spectroscopic analysis, especially 2D NMR (1H-1H COSY, HSQC, HMBC and NOESY) and HRMS. Compounds 1 and 4 showed weak anti-inflammatory activity as tested by superoxide anion generation and elastase release by human neutrophil in response to fMLP/CB. Compound 3 showed selective inhibition on elastase release in vitro. Full article
Open AccessArticle Anti-Inflammatory and Antioxidant Components from Hygroryza aristata
Molecules 2011, 16(3), 1917-1927; doi:10.3390/molecules16031917
Received: 4 January 2011 / Revised: 21 February 2011 / Accepted: 23 February 2011 / Published: 25 February 2011
Cited by 10 | Viewed by 5704 | PDF Full-text (356 KB)
Abstract
Twenty-six known compounds and two new compounds, including a new lignan, (7S*,8R*,7’R*,8’S*)-icariol A2-9-O-b-xylopyranoside (1), and a new indole alkaloid, hygarine (2), were isolated from the extracts of
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Twenty-six known compounds and two new compounds, including a new lignan, (7S*,8R*,7’R*,8’S*)-icariol A2-9-O-b-xylopyranoside (1), and a new indole alkaloid, hygarine (2), were isolated from the extracts of Hygroryza aristata (Gramineae). The structures of all compounds were elucidated on the basis of NMR spectral analysis. The compounds (-)-epigallocatechin-3-O-gallate (4) and (-)-epicatechin-3-O-gallate (5) possess free radical scavenging activities and compound 1 could inhibit superoxide anion generation and elastase release by fMLP/CB-induced human neutrophils with IC50 values of 19.33 ± 0.86 and 24.14 ± 1.59 mM, respectively. Full article
(This article belongs to the Section Natural Products)
Open AccessArticle Cladielloides A and B: New Eunicellin-Type Diterpenoids from an Indonesian Octocoral Cladiella sp.
Mar. Drugs 2010, 8(12), 2936-2945; doi:10.3390/md8122936
Received: 29 October 2010 / Revised: 25 November 2010 / Accepted: 1 December 2010 / Published: 6 December 2010
Cited by 29 | Viewed by 5453 | PDF Full-text (233 KB) | HTML Full-text | XML Full-text
Abstract
Two new eunicellin-type diterpenoids, cladielloides A (1) and B (2), which were found to possess a 2-hydroxybutyroxy group in their structures, were isolated from an Indonesian octocoral identified as Cladiella sp. The structures of eunicellins 1 and 2 were
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Two new eunicellin-type diterpenoids, cladielloides A (1) and B (2), which were found to possess a 2-hydroxybutyroxy group in their structures, were isolated from an Indonesian octocoral identified as Cladiella sp. The structures of eunicellins 1 and 2 were elucidated by spectroscopic methods. Cladielloide B (2) exhibited moderate cytotoxicity toward CCRF-CEM tumor cells and this compound displayed significant inhibitory effects on superoxide anion generation and elastase release by human neutrophils. Full article
Open AccessArticle Carijoside A, a Bioactive Sterol Glycoside from an Octocoral Carijoa sp. (Clavulariidae)
Mar. Drugs 2010, 8(7), 2014-2020; doi:10.3390/md8072014
Received: 12 May 2010 / Revised: 8 June 2010 / Accepted: 28 June 2010 / Published: 29 June 2010
Cited by 13 | Viewed by 7723 | PDF Full-text (140 KB) | HTML Full-text | XML Full-text
Abstract
A new bioactive sterol glycoside, 3β-O-(3',4'-di-O-acetyl-β-D-arabinopyranosyl)-25ξ-cholestane-3β,5α,6β,26-tetrol-26-acetate) (carijoside A, 1), was isolated from an octocoral identified as Carijoa sp. The structure of glycoside
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A new bioactive sterol glycoside, 3β-O-(3',4'-di-O-acetyl-β-D-arabinopyranosyl)-25ξ-cholestane-3β,5α,6β,26-tetrol-26-acetate) (carijoside A, 1), was isolated from an octocoral identified as Carijoa sp. The structure of glycoside 1 was established by spectroscopic methods and by comparison with spectral data for the other known glycosides. Carijoside A (1) displayed significant inhibitory effects on superoxide anion generation and elastase release by human neutrophils and this compound exhibited moderate cytotoxicity toward DLD-1, P388D1, HL-60, and CCRF-CEM tumor cells. Full article
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Open AccessArticle Excavatoids E and F: Discovery of Two New Briaranes from the Cultured Octocoral Briareum excavatum
Mar. Drugs 2009, 7(3), 472-482; doi:10.3390/md7030472
Received: 26 August 2009 / Revised: 19 September 2009 / Accepted: 23 September 2009 / Published: 23 September 2009
Cited by 15 | Viewed by 7068 | PDF Full-text (141 KB) | HTML Full-text | XML Full-text
Abstract
Two new briarane-related diterpenoids, designated as excavatoids E (1) andF (2), were isolated from the cultured octocoral Briareum excavatum. The structures ofcompounds 1 and 2 were established on the basis of extensive spectral data analysis. Briaranes 1 and 2 were found to exhibit
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Two new briarane-related diterpenoids, designated as excavatoids E (1) andF (2), were isolated from the cultured octocoral Briareum excavatum. The structures ofcompounds 1 and 2 were established on the basis of extensive spectral data analysis. Briaranes 1 and 2 were found to exhibit moderate inhibitory effects on elastase release by human neutrophils. Full article
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