ABSTRACT
A fungus strain, Neopestalotiopsis clavispora AL01, was isolated from the leaf spot of the plant Phoenix dactylifera. Further chemical investigation of the fermentation extract of this strain afforded six new secondary metabolites (1-6), along with 11 known compounds (7-17) which included a new natural compound (7). Their structures were determined by extensive spectroscopic analysis including one-and two-dimensional (1D and 2D) NMR spectroscopy, high-resolution electrospray ionization mass spectrometry (HRESIMS), and ECD and NMR calculations. All compounds were evaluated for their phytotoxic activities. Among them, compounds 10, 12 and 13 exhibited phytotoxic activities against Nicotiana tabacum. Compound 3 exhibited weak antibacterial activity against methicillin-resistant Staphylococcus aureus, Micrococcus luteus and Vibrio harveyi. Taken collectively, these findings establish a solid research foundation for future investigations on bioactive natural products derived from phytopathogenic fungi.
Subject(s)
Anti-Bacterial Agents , Polyketides , Terpenes , Molecular Structure , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/chemistry , Polyketides/pharmacology , Polyketides/isolation & purification , Polyketides/chemistry , Terpenes/pharmacology , Terpenes/isolation & purification , Plant Leaves/chemistry , Nicotiana , Microbial Sensitivity Tests , China , Biological Products/pharmacology , Biological Products/isolation & purification , Biological Products/chemistry , Methicillin-Resistant Staphylococcus aureus/drug effectsABSTRACT
Twelve undescribed 2-(2-phenethyl)chromone dimers (1-12) were isolated from EtOAc extract of agarwood originating from Aquilaria filaria in the Philippines, guided by a UHPLC-MS analysis. Their structures were elucidated by 1D NMR, 2D NMR, and HR-ESI-MS spectra. The absolute configuration of 2-(2-phenylethyl)chromone dimers was determined by single-crystal X-ray diffraction analysis and comparison of the experimental and calculated ECD spectra. Compounds 1, 2, 5 and 9-12 exhibited potent to moderate anti-inflammatory activity with IC50 values in the range of 22.43 ± 0.86 to 53.88 ± 4.06 µM.
Subject(s)
Chromones , Thymelaeaceae , Wood , Thymelaeaceae/chemistry , Philippines , Chromones/chemistry , Chromones/isolation & purification , Chromones/pharmacology , Molecular Structure , Wood/chemistry , Animals , Structure-Activity Relationship , Mice , Dose-Response Relationship, Drug , Crystallography, X-Ray , FlavonoidsABSTRACT
Two new compounds named 3(S)-hydroxy-1-(2,4,5-trihydroxy-3,6- dimethylphenyl)-hex-4E-en-1-one (1) and acremonilactone (2), together with nine known compounds (3-11), were isolated from the fermentation broth of Acremonium sp. associated with marine sediments collected from South China Sea. NMR and HRESIMS spectroscopic analysis elucidated the structure of two new compounds. Compound 2 had characteristic rotary gate shape skeleton with a six-membered lactone. Compounds 1 and 9 showed DPPH radical scavenging activity with inhibition rates of 96.50 and 85.95% at the concentration of 0.5 mg/ml, respectively. Moreover, compounds 4, 6 and 11 showed definite antibacterial activity against Staphylococcus aureus ATCC 6538.
Subject(s)
Acremonium , Acremonium/chemistry , Molecular Structure , Fungi , Staphylococcus aureus , Magnetic Resonance Spectroscopy , Anti-Bacterial Agents/chemistryABSTRACT
Three new sesquiterpenoids, dendrohercoglin A - C (1-3), and one new bibenzyl derivative, dendronbiline D (4), together with nine known sesquiterpenoids (5-13) were isolated from Dendrobium hercoglossum. The structures of the new compounds were elucidated by extensive spectroscopic analysis as well as NMR and ECD calculations. All the compounds were evaluated for their neuroprotective and anti-inflammatory activities. Compounds 2 and 3 increased the H2O2-damaged SH-SY5Y cell viabilities from 43.3% to 58.6% and 68.4%, respectively. Compound 4 exhibited pronounced anti-inflammatory activity with IC50 value of 9.5 ± 0.45 µM which was superior to the reference compound quercetin (IC50: 15.7 ± 0.89 µM).
Subject(s)
Bibenzyls , Dendrobium , Neuroblastoma , Sesquiterpenes , Humans , Dendrobium/chemistry , Molecular Structure , Hydrogen Peroxide , Magnetic Resonance Spectroscopy , Sesquiterpenes/pharmacology , Bibenzyls/pharmacology , Bibenzyls/chemistry , Anti-Inflammatory Agents/pharmacologyABSTRACT
Four new 2-(2-phenethyl)chromone dimers (1-4) were isolated from EtOAc extract of agarwood originating from Aquilaria filaria from Philippines. Their structures were elucidated by spectroscopic analysis (1D and 2D NMR, and HRESIMS) and comparison of the experimental and computed ECD curves. Compounds 1-4 exhibited inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells with IC50 values in the range from 33.94 to 57.53 µM.
Subject(s)
Chromones , Thymelaeaceae , Chromones/pharmacology , Molecular Structure , Thymelaeaceae/chemistry , Magnetic Resonance Spectroscopy , Lipopolysaccharides , Flavonoids/chemistryABSTRACT
Six new 2-(2-phenylethyl)chromone dimers (1-6) were isolated from ethyl ether extract of red soil agarwood of Aquilaria crassna from Vietnam by LC-MS-guided fractionation procedure. Their structures were unambiguously elucidated based on HRESIMS, 1D and 2D NMR spectra. The absolute configuration of 2-(2-phenylethyl)chromone dimers was determined by comparison of the experimental and computed ECD spectra. Compound 6 displayed cytotoxicity against the human myeloid leukemia cell line (K562) with an IC50 value of 39.49 µM.
Subject(s)
Chromones , Thymelaeaceae , Chromatography, Liquid , Chromones/chemistry , Flavonoids/chemistry , Humans , Molecular Structure , Soil , Tandem Mass Spectrometry , Thymelaeaceae/chemistry , Wood/chemistryABSTRACT
A picrotoxane-type sesquiterpene, dendroterpene E (1), together with five benzene derivatives (2-6), were isolated from the stems of Dendrobium nobile Lindl. Their structures were elucidated by spectroscopic analysis and X-ray diffraction analysis. Compound 1 was a new picrotoxane-type sesquiterpene with a C-9/C-1/O/C-11 oxetane ring, which was first encountered in this type of compounds. Compounds 1-3 exhibited inhibitory activities against α-glycosidase.
Subject(s)
Dendrobium , Sesquiterpenes , Dendrobium/chemistry , Molecular Structure , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Spectrum AnalysisABSTRACT
Chemical investigation of an alcoholic extract from the stem of Daphne papyracea ("Xuehuagou") led to the isolation of the tetracyclic sesquiterpenoid daphnepapytone A (1), containing a unique caged skeleton with a cyclobutane ring having three tetrasubstituted chirality centers. Also isolated were new guaiane sesquiterpenoids, namely, daphnepapytones B-H (2-8), and one 1,5-diphenylpentanone 2-hydroxy-5-oxo-daphneone (9), together with 26 known compounds. The cyclic metabolites share a 5-isoprenyl-hexahydroazulene-2(1H)-one skeleton with different substitution patterns and a bridged cyclobutane, oxetane, or tetrahydrofuran ring. The planar structures and relative configuration of the new compounds were elucidated on the basis of spectroscopic analysis aided by DFT 13C NMR calculations. The absolute configurations of 1-7 were determined by X-ray single-crystal diffraction or TDDFT-ECD calculations. Daphnepapytones A and C (1 and 3), 2-hydroxy-5-oxodaphneone (9), daphnenone (10), daphneone (11), and 3-methyldaphneolone (12) showed α-glycosidase inhibitory activity, with IC50 values of 159.0, 102.3, 139.3, 43.3, 145.0, and 126.1 µM, respectively.
Subject(s)
Cyclobutanes/chemistry , Daphne/chemistry , Ethers, Cyclic/chemistry , Furans/chemistry , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/pharmacology , Plant Stems/chemistry , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Carbon-13 Magnetic Resonance Spectroscopy , Crystallography, X-Ray , Glycoside Hydrolase Inhibitors/isolation & purification , Molecular Structure , Sesquiterpenes/isolation & purification , StereoisomerismABSTRACT
Recently, cultivated "Qi-Nan" (CQN) agarwood has emerged as a new high-quality agarwood in the agarwood market owing to its similar characteristics, such as high content of resin and richness in two 2-(2-phenylethyl)chromone derivatives, 2-(2-phenylethyl)chromone (59) and 2-[2-(4-methoxyphenyl)ethyl]chromone (60), to the wild harvested "Qi-Nan" (WQN) agarwood. In this study, we compared the chemical constituents and fragrant components of two types of WQN agarwood from A. agallocha Roxb. and A. sinensis, respectively, with CQN agarwood and ordinary agarwood varieties. Additionally, we analyzed different samples of WQN agarwood and CQN agarwood by GC-MS, which revealed several noteworthy differences between WQN and CQN agarwood. The chemical diversity of WQN was greater than that of CQN agarwood. The content of (59) and (60) was higher in CQN agarwood than in WQN agarwood. For the sesquiterpenes, the richness and diversity of sesquiterpenes in WQN agarwood, particularly guaiane and agarofuran sesquiterpenes, were higher than those in CQN. Moreover, guaiane-furans sesquiterpenes were only detected by GC-MS in WQN agarwood of A. sinensis and could be a chemical marker for the WQN agarwood of A. sinensis. In addition, we summarized the odor descriptions of the constituents and established the correlation of scents and chemical constituents in the agarwood.
Subject(s)
Flavonoids/chemistry , Sesquiterpenes/chemistry , Thymelaeaceae/chemistry , Wood/chemistry , Flavonoids/analysis , Molecular Structure , Odorants/analysis , Perfume/analysis , Perfume/chemistry , Sesquiterpenes/analysisABSTRACT
Nine new sesquiterpenoids (1-9) were isolated from ethyl ether extract of agarwood originated from Aquilaria sp., including three novel sesquiterpenoids (1-3) derived from zizaane, together with six zizaane-type sesquiterpenoids (4-9). All structures were unambiguously elucidated based on 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of sesquiterpenoids was determined by comparison of the experimental and computed ECD spectra. In vitro anti-inflammatory assessment showed that compound 9 exhibited inhibition of NO production in LPS-stimulated RAW264.7 cells with an IC50 value of 62.22 ± 1.27 µM.
Subject(s)
Sesquiterpenes/chemistry , Thymelaeaceae/chemistry , Wood/chemistry , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/pharmacology , Cell Survival/drug effects , Chemical Phenomena , Magnetic Resonance Spectroscopy , Mice , Molecular Structure , RAW 264.7 Cells , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacologyABSTRACT
Two new compounds named asperpenes D (1) and E (2) were isolated from the marine-derived fungus Aspergillus sp. SCS-KFD66. Their structures were determined on the basis of spectroscopic methods. Compound 2 represents the first natural product bearing a 2-substituted-5-oxo-4-phenyl-2,5-dihydrofuran-3-carboxylic acid skeleton. All the compounds were tested for enzyme inhibitory activity against AChE and α-glucosidase and DPPH radical scavenging activity, respectively. [Formula: see text].
Subject(s)
Biological Products , Bivalvia , Animals , Aspergillus , Molecular Structure , alpha-GlucosidasesABSTRACT
Twelve undescribed 2-(2-phenylethyl)chromone derivatives, including one pair of enantiomers, together with eleven known ones, were isolated from the EtOAc extract of agarwood originating from Aquilaria filaria. All structures were elucidated by spectroscopic (NMR, UV, IR, MS) methods and compared with reported data in literatures. Twenty-one compounds were assessed for α-glucosidase inhibitory activity, which showed inhibition of α-glucosidase with IC50 values ranging between 7.8 ± 0.3 to 137.7 ± 3.0 µM (Acarbose, 743.4 ± 3.3 µM; Genistein, 8.3 ± 0.1 µM). Our results expanded the structural diversity of 2-(2-phenylethyl)chromones from agarwood, and revealed the potential of 2-(2-phenylethyl)chromones as α-glucosidase inhibitors.
Subject(s)
Glycoside Hydrolase Inhibitors , Thymelaeaceae , Chromones/pharmacology , Flavonoids , Glycoside Hydrolase Inhibitors/pharmacology , Molecular StructureABSTRACT
Two new compounds named epipaxilline (1) and penerpene J (2) were isolated from the marine-derived fungus Penicillium sp. KFD28. Their structures including absolute configurations were determined on the basis of spectroscopic methods and ECD analysis. Compounds 1 and 2 showed inhibitory activities against PTP1B with IC50 values of 31.5 and 9.5 µM, respectively, and compound 2 also showed inhibitory activities against TCPTP with IC50 value of 14.7 µM.
Subject(s)
Diterpenes , Penicillium , Fungi , Indoles , Molecular StructureABSTRACT
Five new sesquiterpenoids (1-5), together with a known compound 6 was isolated from ethyl ether extract of agarwood. Their structures were elucidated on the basis of spectroscopic techniques (UV, IR, MS, 1D and 2D NMR), as well as by comparison with literature data. Compound 5 exhibited inhibitory activity against acetylcholinesterase with inhibition ratio of 48.33 ± 0.17% at the concentration of 50 µg/mL.
Subject(s)
Sesquiterpenes/chemistry , Thymelaeaceae/chemistry , Wood/chemistry , Cholinesterase Inhibitors/chemistry , Cholinesterase Inhibitors/isolation & purification , Esters/chemistry , Molecular Structure , Phytochemicals/chemistry , Phytochemicals/isolation & purification , Plant Extracts/chemistry , Sesquiterpenes/isolation & purification , ThailandABSTRACT
Seven new quinazoline-containing indole alkaloids (1-7) named aspertoryadins A-G, along with nine known ones (8-16), were isolated from the marine-derived fungus Aspergillus sp. HNMF114 from the bivalve mollusk Sanguinolaria chinensis. The structures of the new compounds were elucidated from spectroscopic data, X-ray diffraction analysis, ECD spectra analysis, and ECD calculations. Compound 1 bears an aminosulfonyl group in the structure, which is rarely encountered in natural products. Compounds 6, 7, and 13 exhibited quorum sensing inhibitory activity against Chromobacterium violaceum CV026 with MIC values of 32, 32, and 16 µg/well, respectively.
Subject(s)
Aspergillus/chemistry , Indole Alkaloids/pharmacology , Quinazolines/pharmacology , Seawater/microbiology , Indole Alkaloids/chemistry , Indole Alkaloids/isolation & purification , Microbial Sensitivity Tests , Molecular Structure , Quinazolines/chemistry , Quinazolines/isolation & purification , Quorum Sensing/drug effectsABSTRACT
Five new indole-terpenoids named penerpenes E-I (1-5), along with seven known ones (6-12), were isolated from the marine-derived fungus Penicillium sp. KFD28 from a bivalve mollusk, Meretrix lusoria. The structures of the new compounds were elucidated from spectroscopic data and ECD spectroscopic analyses. Compound 1 was assigned as an indole-diterpenoid with a unique 6/5/5/6/6/5/5 heptacyclic ring system. Compound 2 represents an indole-diterpenoid with a new carbon skeleton derived from paxilline by the loss of three carbons (C-23/24/25). Compound 3 contains an additional oxygen atom between C-21 and C-22 compared to paxilline to form an unusual 6/5/5/6/6/7 hexacyclic ring system bearing a 1,3-dioxepane ring, which is rarely encountered in natural products. Compounds 1, 2, 4, and 6 showed inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) with IC50 values of 14, 27, 23, and 13 µM, respectively.
Subject(s)
Diterpenes/pharmacology , Indoles/pharmacology , Marine Biology , Penicillium/chemistry , Protein Tyrosine Phosphatases/antagonists & inhibitors , Diterpenes/chemistry , Indoles/chemistryABSTRACT
Ten new tricyclic prezizaane types sesquiterpenoids (1-10) were isolated from ethyl ether extract of agarwood originated from Aquilaria sp. Their structures were unambiguously elucidated on the basis of 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of the new prezizaenes 1, 2 and 4 was determined by single-crystal X-ray diffraction, while TDDFT-ECD method was applied for 6. Compounds 4 and 5 displayed significant inhibitory activities toward α-glucosidase with IC50 values of 0.22 and 1.99â¯mM, respectively.
Subject(s)
Glycoside Hydrolase Inhibitors/pharmacology , Sesquiterpenes/pharmacology , Thymelaeaceae/chemistry , Wood/chemistry , Glycoside Hydrolase Inhibitors/isolation & purification , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Sesquiterpenes/isolation & purification , Thailand , alpha-GlucosidasesABSTRACT
Four unusual indole-terpenoids, penerpenes A-D (1-4), along with two known ones paxilline (5) and emindole SB (6), were isolated from the marine-derived fungus Penicillium sp. KFD28. The absolute structures of 1-4 were elucidated on the basis of spectroscopic data and ECD spectra analysis along with quantum ECD calculations. Compounds 1 and 2 showed potent inhibitory activity toward protein tyrosine phosphatases (PTP1B and TCPTP). Plausible biosynthetic pathways of compounds 1-4 are proposed.
Subject(s)
Enzyme Inhibitors/pharmacology , Indoles/pharmacology , Penicillium/chemistry , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Protein Tyrosine Phosphatase, Non-Receptor Type 2/antagonists & inhibitors , Terpenes/pharmacology , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Humans , Indoles/chemistry , Indoles/isolation & purification , Models, Molecular , Molecular Conformation , Protein Tyrosine Phosphatase, Non-Receptor Type 1/metabolism , Protein Tyrosine Phosphatase, Non-Receptor Type 2/metabolism , Quantum Theory , Terpenes/chemistry , Terpenes/isolation & purificationABSTRACT
Six 8,12-epoxyguaiane sesquiterpenes (1-6), together with two known 2-(2-phenylethyl)chromone derivatives (7-8) were isolated from agarwood originating from Aquilaria filaria. Their structures were established by spectroscopic methods including IR, HRESIMS, 1D, and 2D NMR, and comparison with the published data. The absolute configuration of compound 1 was unambiguously determined by quantum chemical calculation of the electronic circular dichroism (ECD) spectrum. All compounds were tested for their α-glucosidase inhibitory activity and cytotoxicity. Compound 5 showed significant α-glucosidase inhibitory activity with IC50 value of 253.2⯱â¯9.7⯵M (Acarbose, 743. 4⯱â¯3.3⯵M). Compounds 2-4 displayed weak cytotoxicity against K562 tumor cell lines.
Subject(s)
Glycoside Hydrolase Inhibitors/pharmacology , Sesquiterpenes, Guaiane/pharmacology , Sesquiterpenes/pharmacology , Thymelaeaceae/chemistry , Cell Survival/drug effects , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/isolation & purification , Humans , K562 Cells , Molecular Structure , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes, Guaiane/chemistry , Sesquiterpenes, Guaiane/isolation & purification , Wood/chemistryABSTRACT
The ethyl ether extract of agarwood from an Aquilaria plant afforded six new sesquiterpenoids, Agarozizanol A - F (1-6), together with four known sesquiterpenoids and six known 2-(2-phenylethyl)chromones. Their structures were elucidated via detailed spectroscopic analysis, X-ray diffraction, and comparisons with the published data. All the isolates were evaluated for the α-glucosidase and tyrosinase inhibitory activities in vitro. Compounds 5, 7, 8, and 10 showed significant inhibition of α-glucosidase with IC50 values ranging between 112.3 ± 4.5 and 524.5 ± 2.7 µM (acarbose, 743. 4 ± 3.3 µM). Compounds 13 and 14 exhibited tyrosinase inhibitory effect with IC50 values of 89.0 ± 1.7 and 51.5 ± 0.6 µM, respectively (kojic acid, 46.1 ± 1.3). In the kinetic studies, compounds 5 and 14 were found to be uncompetitive inhibitors for α-glucosidase and mixed type inhibitors for tyrosinase, respectively. Furthermore, molecular docking simulations revealed the binding sites and interactions of the most active compounds with α-glucosidase and tyrosinase.