RESUMO
Six new dimeric 2-(2-phenylethyl)chromones (1-6) were successfully isolated from the ethanol extract of agarwood of Aquilaria filaria from Philippines under HPLC-MS guidance. Compounds 1-6 are all dimers formed by linking 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone and flindersia 2-(2-phenylethyl)chromone via a single ether bond, and the linkage site (C5-O-C8'') of compound 2 is extremely rare. A variety of spectroscopic methods were used to ascertain their structures, including extensive 1D and 2D NMR spectroscopic analysis, HRESIMS, and comparison with literature. The in vitro tyrosinase inhibitory and anti-inflammatory activities of each isolate were assessed. Among these compounds, compound 2 had a tyrosinase inhibition effect with an IC50 value of 27.71 ± 2.60 µM, and compound 4 exhibited moderate inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells with an IC50 value of 35.40 ± 1.04 µM.
Assuntos
Anti-Inflamatórios , Monofenol Mono-Oxigenase , Óxido Nítrico , Thymelaeaceae , Madeira , Células RAW 264.7 , Animais , Thymelaeaceae/química , Camundongos , Estrutura Molecular , Madeira/química , Óxido Nítrico/metabolismo , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/química , Monofenol Mono-Oxigenase/antagonistas & inibidores , Filipinas , Cromonas/isolamento & purificação , Cromonas/farmacologia , Cromonas/química , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , FlavonoidesRESUMO
Two new rare trachylobane euphoratones A-B (1-2), together with five known diterpenoids (compounds 3-7), were isolated from the aerial parts of Euphorbia atoto. Their structures were unambiguously elucidated through HRESIMS, 1D and 2D NMR spectral analysis. Compounds 1, 3, 4 and 7 showed weak anti-inflammatory activities (IC50 77.49 ± 6.34, 41.61 ± 14.49, 16.00 ± 1.71 and 33.41 ± 4.52 µM, respectively), compared to the positive control quercetin (IC50 15.23 ± 0.65 µM).
Assuntos
Diterpenos , Euphorbia , Estrutura Molecular , Euphorbia/química , Espectroscopia de Ressonância Magnética , Diterpenos/farmacologia , Diterpenos/química , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/químicaRESUMO
Phytochemical investigation on the stems of Strophanthus divaricatus led to the isolation of four undescribed cardiac glycosides and one undescribed C21 pregnane, together with eleven known steroids. Their structures were elucidated by a comprehensive analysis of HRESIMS, 1D and 2D NMR spectra. The absolute configuration of 16 was determined by comparison of the experimental and computed ECD spectra. Compounds 1-13 and 15 displayed potent to significant cytotoxicity against human cancer cell lines K562, SGC-7901, A549 and HeLa with IC50 values of 0.02-16.08, 0.04-23.13, 0.06-22.31 and 0.06-15.13 µM, respectively.
Assuntos
Antineoplásicos , Strophanthus , Humanos , Glicosídeos/química , Pregnanos/farmacologia , Pregnanos/química , Linhagem Celular Tumoral , Estrutura MolecularRESUMO
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.
Assuntos
Dendrobium , Sesquiterpenos , Dendrobium/química , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Análise EspectralRESUMO
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.
Assuntos
Ciclobutanos/química , Daphne/química , Éteres Cíclicos/química , Furanos/química , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Caules de Planta/química , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Cristalografia por Raios X , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Estrutura Molecular , Sesquiterpenos/isolamento & purificação , EstereoisomerismoRESUMO
Thirty-one Vincan- and two Eburnan-type alkaloids were isolated from the aerial parts of Tabernaemontana bovina, whereas 20 of them are described the first time. Within the purified alkaloids, the firstly described taberbovcamine A features a 6/5/6/6/5 ring system. All the chemical structures were elucidated by employing extensive spectroscopic, computational electronic circular dichroism and X-ray diffraction methods. The two Eburnan-type alkaloids, 10,11-dimethoxy-16-O-methyllisoeburnamenine and 10,11-dimethoxy-isoeburnamenine were simultaneously identified by using the mentioned spectroscopic methods. Within the identified alkaloids, 10-hydroxy-14,15-didehydrovincanmine, 14,15-didehydrovincanmine, 14,15-didehydroapovincanmine, and criocerine increased the glucose consumption in a L6 myotube model.
Assuntos
Alcaloides , Tabernaemontana , Alcaloides/farmacologia , Hipoglicemiantes/farmacologia , Alcaloides Indólicos , Estrutura MolecularRESUMO
A new genus and new species of terrestrial freshwater crab, Calcipotamon puglabrum gen. nov. et sp. nov., is described from the limestone forests of Changjiang, Hainan Island, China, based on morphology and mitochondrial 16S rDNA sequences. The new genus is closest to Neotiwaripotamon Dai Naiyanetr, 1994, and Tiwaripotamon Bott, 1970, but differs in a combination of carapace, third maxilliped, ambulatory leg and male gonopod characters. Molecular analysis shows that the new genus is closely related with but not clustered within other Hainan potamid genera. Notes on the general biology of this new species are also provided.
Assuntos
Braquiúros , Animais , Carbonato de Cálcio , China , Água Doce , Ilhas , MasculinoRESUMO
Two new triterpenoids, named kadsuricoccins A and B, together with three known ones, were isolated from the Li folk herb Heilaohu, the stems of Kadsura coccinea (Lem.) A. C. Smith, which was used for food and as a healthy supplement. Their structures were elucidated by comprehensive analyses of mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopic data. To search healthy components, an acetylcholinesterase (AChE) inhibitory activity test by Ellman's Method was conducted, kadsuricoccins A and B showed activity with the AChE inhibit index (AII) up to 68.96% ± 0.19% and 57.8% ± 0.11% at 94 nM (compared with positive control tacrine AII 79.80% ± 0.20%, 9.4 nM), respectively.
Assuntos
Inibidores da Colinesterase/isolamento & purificação , Inibidores da Colinesterase/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Kadsura/química , Caules de Planta/química , Inibidores da Colinesterase/química , Relação Dose-Resposta a Droga , Medicamentos de Ervas Chinesas/química , Ativação Enzimática/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
Twelve undescribed compounds including six phenanthrene derivatives (parviphenanthrines A-F), two stilbene derivatives (parvistilbines A-B), three esters (parviesters A-C), and one sesquiterpenoid (parvidiol A) were isolated from the roots of Stemona parviflora, together with twenty-two known ones. The structures of the undescribed compounds were elucidated based on the analyses of their spectroscopic data. The absolute configuration of parviphenanthrine A was determined by the quantum ECD calculations. Parviphenanthrines A and E, stemanthrene A, stilbostenin E, 4-hydroxy-benzenepropanol-α-benzoate, and (E)-4-hydroxycinnamic acid methyl ester showed nematocidal activity against Meloidogyne incognita with IC50 values of 14.02⯱â¯0.32, 2.51⯱â¯0.13, 17.10⯱â¯0.65, 2.05⯱â¯0.07, 4.22⯱â¯0.31, and 1.07⯱â¯0.05⯵M, respectively.
Assuntos
Antinematódeos/farmacologia , Compostos Fitoquímicos/química , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Stemonaceae/química , Concentração Inibidora 50 , Estrutura MolecularRESUMO
Daphnauranins Câ»E (compounds 1â»3), two sesquiterpenoids and one monoterpenoid were isolated from the roots of Daphne aurantiaca Diels. Daphnauranin C is a 9-O-13 etherified and hydroperoxy-substituted guaiane sesquiterpenoid, daphnauranin D is a guaiane sesquiterpenoid ketal, and daphnauranin E is a monoterpenoid lactone. Their structures were elucidated by comprehensive analyses of MS, 1D NMR, and 2D NMR spectroscopic data. In an anti-feeding activities test, daphnauranins Câ»E showed activity against male fruit fly with anti-feeding indexes (AI) up to 39.1, 39.2, and 27.8% respectively, at 1 mM.
Assuntos
Daphne/química , Drosophila melanogaster/efeitos dos fármacos , Repelentes de Insetos/química , Sesquiterpenos/química , Animais , Drosophila melanogaster/fisiologia , Repelentes de Insetos/farmacologia , Espectroscopia de Ressonância Magnética , Masculino , Estrutura Molecular , Raízes de Plantas/química , Sesquiterpenos/farmacologiaRESUMO
An unusual adenine-substituted germacrane sesquiterpene lactone, tomenphantadenine (1), has been isolated from the whole plant of Elephantopus tomentosus L. The structure of this compound was established by comprehensive spectroscopic analysis including high resolution (HR) ESI-MS, 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data. This compound features novel hybrid pattern of germacrane sesquiterpene with adenine through C-N linkage, and a possible biosynthetic pathway for it was proposed. Compound 1 showed potent antibacterial activity against the gram-positive Staphylococcus aureus and weak acetylcholinesterase (AChE) inhibitory activity.
Assuntos
Adenina/química , Asteraceae/química , Sesquiterpenos de Germacrano/química , Adenina/isolamento & purificação , Antibacterianos/isolamento & purificação , China , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Estrutura Molecular , Plantas Medicinais/química , Sesquiterpenos de Germacrano/isolamento & purificação , Staphylococcus aureus/efeitos dos fármacosRESUMO
Two new compounds, philippin (1) and 3ß,9α,14α-trihydroxy-(22E,24R)-ergost-22-en-7-one (2), were isolated from the fruiting bodies of Ganoderma philippii. Their structures were elucidated on the basis of the spectroscopic technologies, including 1D and 2D NMR as well as MS. The bioassay of inhibitory activity against acetylcholinesterase (AChE) showed compound 1 exhibited weak inhibitory activity against AChE.
Assuntos
Inibidores da Colinesterase/isolamento & purificação , Ergosterol/análogos & derivados , Ganoderma/química , Hidroquinonas/isolamento & purificação , Acetilcolinesterase/efeitos dos fármacos , Inibidores da Colinesterase/química , Inibidores da Colinesterase/farmacologia , Ergosterol/química , Ergosterol/isolamento & purificação , Carpóforos/química , Hidroquinonas/química , Estrutura Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
To search for active anti-cancer constituents in the fruiting body of Ganoderma calidophilum, we have successfully isolated four previously undescribed spiro-lactone lanostane triterpenoids (spiroganocalitones A-D), two previously undescribed lanostanoids (ganodecalones A and B) together with twenty-three known ones. The structures of the six previously undescribed compounds were elucidated based on 1D, 2D-NMR, and HRMS analyses. Ganoderone A showed moderate cytotoxic activity against K562, BEL7402, and SGC790 cell lines with IC50 values of 7.62, 6.28, and 3.55 µM, respectively.
Assuntos
Carpóforos/química , Ganoderma/química , Lanosterol/análogos & derivados , Triterpenos/isolamento & purificação , Humanos , Concentração Inibidora 50 , Lanosterol/química , Lanosterol/isolamento & purificação , Lanosterol/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Triterpenos/química , Triterpenos/farmacologiaRESUMO
Daphnauranins A (1) and B (2), two sesquiterpenoids were isolated from the roots of Daphne aurantiaca Diels. One is an unprecedented 5/7 oxacycloheptane ring system, the other is a sesquiterpene-lignan complex. Their structures were elucidated by comprehensive spectroscopic methods including MS and NMR. Their absolute configurations were further confirmed by the quantum ECD calculations. Daphnauranins A and B showed anti-insect activities against male fruit fly with anti-feeding rate up to 46.2±7.1 and 44.7±5.4% at 1mM, respectively.
Assuntos
Daphne/química , Inseticidas/química , Lignanas/química , Raízes de Plantas/química , Sesquiterpenos/química , Animais , Drosophila melanogaster , Inseticidas/isolamento & purificação , Lignanas/isolamento & purificação , Masculino , Estrutura Molecular , Sesquiterpenos/isolamento & purificaçãoRESUMO
Six new meroterpenoids, chrodrimanins K-N (1-4), including two uncommon chlorinated ones (1 and 2), and verruculides B2 (5) and B3 (6), as well as seven known ones (7-13), were isolated from the fermentation broth of Penicillium sp. SCS-KFD09 isolated from a marine worm, Sipunculus nudus, from Haikou Bay, China. The structures including the absolute configurations of the new compounds were unambiguously elucidated by spectroscopic data, X-ray diffraction analysis, and ECD spectra analysis along with quantum ECD calculations. In addition, the X-ray crystal structures and absolute configurations of two previously reported meroterpenoids, chrodrimanins F (9) and A (11), are described for the first time. Compounds 1, 4, and 7 displayed anti-H1N1 activity with IC50 values of 74, 58, and 34 µM, respectively, while compound 5 showed weak inhibitory activity against Staphylococcus aureus with an MIC of 32 µg/mL.
Assuntos
Nematoides/microbiologia , Penicillium/química , Policetídeos/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Terpenos/isolamento & purificação , Animais , China , Cristalografia por Raios X , Vírus da Influenza A Subtipo H1N1/efeitos dos fármacos , Biologia Marinha , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Policetídeos/química , Policetídeos/farmacologia , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Terpenos/químicaRESUMO
Chemical investigation on the cultures of the fungus Psilocybe merdaria resulted in the first isolation of 10 compounds including two new ones 11,14-dihydroxylneoechinulin E (1) and (S)-4-(4-methylpent-3-en-1-yl)-butyrolactone (2). Their structures were elucidated from the analysis of 1D and 2D NMR and MS data. Among them, compound 7 showed inhibitory activity against AChE with 20% percentage at a concentration of 50 µg/ml.
Assuntos
4-Butirolactona/análogos & derivados , Inibidores da Colinesterase/isolamento & purificação , Alcaloides Indólicos/química , Psilocybe/química , 4-Butirolactona/química , 4-Butirolactona/isolamento & purificação , 4-Butirolactona/farmacologia , Acetilcolinesterase/efeitos dos fármacos , China , Inibidores da Colinesterase/química , Inibidores da Colinesterase/farmacologia , Fungos/metabolismo , Alcaloides Indólicos/isolamento & purificação , Alcaloides Indólicos/farmacologia , Concentração Inibidora 50 , Estrutura MolecularRESUMO
Three new compounds named penicitor A, aculene E and penicitor B, as well as four known compounds, were isolated from the fermentation broth of Penicillium sp. SCS-KFD08 associated with a marine animal Sipunculus nudus from the Haikou bay of China. Their planar structures and absolute configurations were unambiguously elucidated by spectroscopic data, Mosher's method, CD spectrum analysis along with quantum ECD calculation. Among them, compounds 2-7 showed quorum sensing inhibitory activity against Chromobacterium violaceum CV026, and could significantly reduce violacein production in N-hexanoyl-l-homoserine lactone (C6-HSL) induced C. violaceum CV026 cultures at sub-inhibitory concentrations.
Assuntos
Organismos Aquáticos/metabolismo , Organismos Aquáticos/microbiologia , Bactérias Gram-Negativas/metabolismo , Penicillium/metabolismo , Percepção de Quorum/fisiologia , Animais , Bactérias Gram-Negativas/isolamento & purificação , Penicillium/isolamento & purificaçãoRESUMO
Eight new alkaloids, 3ß-n-butylstemonamine (1), 8-oxo-3ß-n-butylstemonamine (2), 3-n-butylneostemonine (3), 10-epi-3-n-butylneostemonine (4), 8-oxo-oxymaistemonine (5) protostemonine N4-oxide (6), (19S)-hydroxy-21-methoxystemofoline (7), and parvistemonine A (8), were isolated from the roots of Stemona parviflora, together with 17 known alkaloids. The structures of the new alkaloids were elucidated based on a comprehensive spectroscopic data analysis. The absolute configurations of 1-4 were determined by the ECD exciton chirality method and quantum ECD calculations. Protostemonine (10) and stemofoline (12) showed strong nematicidal activity against Panagrellus redivevus, with IC50 values of 0.10 and 0.46 µM, respectively.
Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antinematódeos/isolamento & purificação , Antinematódeos/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Stemonaceae/química , Alcaloides/química , Antinematódeos/química , Medicamentos de Ervas Chinesas/química , Compostos Heterocíclicos de 4 ou mais Anéis , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Raízes de Plantas/químicaRESUMO
Three new sesquiterpenoids (1-3), together with two known ones were isolated from the EtOAc extract of agarwood originating from Aquilaria crassna. The new compounds were elucidated on the basis of spectroscopic techniques (UV, IR, MS, 1D and 2D NMR). Compounds 1-5 were isolated from agarwood of A. crassna for the first time. In the acetylcholinesterase inhibition experiment of 2-5, compound 3 showed acetylcholinesterase inhibition activity (IR 42.9±0.6%). Compound 5 expressed antibacterial activities against Staphylococcus aureus and Ralstonia solanacearum with diameter of the inhibition zones of 12.35±0.11mm and 16.90±0.09mm, respectively.
Assuntos
Antibacterianos/química , Inibidores da Colinesterase/química , Sesquiterpenos/química , Thymelaeaceae/química , Antibacterianos/isolamento & purificação , Inibidores da Colinesterase/isolamento & purificação , Estrutura Molecular , Ralstonia solanacearum/efeitos dos fármacos , Sesquiterpenos/isolamento & purificação , Staphylococcus aureus/efeitos dos fármacos , Madeira/químicaRESUMO
Two new compounds, one flavanol dimer dapholosericol A (1) and one tigliane diterpene dapholosericin A (2), together with ten known ones, were isolated from the AcOEt extract of Daphne holosericea (Diels) Hamaya. Their structures were elucidated by their spectroscopic data analysis. Compounds 1 and 2 showed moderate activities against acetylcholinesterase with inhibition ratio of 36% and 29% at a concentration of 100 µmol/l, respectively.