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1.
Fitoterapia ; 165: 105431, 2023 Mar.
Article in English | MEDLINE | ID: mdl-36638848

ABSTRACT

Twelve undescribed compounds including five sesquiterpenes (1-5), one monoterpene (6), and four lignans (7a/7b and 8a/8b), along with two other types (9 and 10) were isolated from the rhizomes of Atractylodes macrocephala. Among them, two pairs of enantiomers (7a/7b and 8a/8b) were successfully separated by chiral-phase HPLC, while racemate 9 could not be resolved. Their structures and absolute configurations were unambiguously elucidated by spectroscopic data analysis and electronic circular dichroism (ECD) calculations. Notably, compounds 1 and 2 are rare sesquiterpene hybrids featuring an eudesmanolactam linked to a resorcinol or methyl 2-methylpentanoat through a CN bond. Compound 3 represents the first example of eudesmanolide sesquiterpene with an oxygen-bridge between C-8 and C-14. Compounds 7a and 7b are a pair of rare enantiomeric benzodioxane norneolignans. Additionally, compound 2 exhibited weak cytotoxicity against SGC-7901 cells. Compound 4 significantly promoted the proliferation of LPS-induced IEC-6 cells with the rate of 117.2%.


Subject(s)
Atractylodes , Lignans , Sesquiterpenes , Molecular Structure , Atractylodes/chemistry , Rhizome/chemistry , Lignans/pharmacology , Lignans/chemistry , Sesquiterpenes/chemistry
2.
Phytochemistry ; 206: 113545, 2023 Feb.
Article in English | MEDLINE | ID: mdl-36481315

ABSTRACT

Fifteen undescribed eudesmane-type sesquiterpenes, named atramacronoids D-R, along with fourteen known analogues were isolated from the rhizomes of Atractylodes macrocephala. The structures of atramacronoids D-R were elucidated based on extensive spectroscopic data analysis, Snatzke's rule, electronic circular dichroism (ECD) calculations, and X-ray crystallographic analysis. Notably, of the undescribed isolates, atramacronoids D and E are the first example of eudesmanolactam-phenol and eudesmanolactam-ethyl hybrids obtained from plants, respectively. A pair of enantiomers, (+)- and (-)-atramacronoids F, were successfully resolved by chiral-phase HPLC. Atramacronoid D exhibited weak cytotoxicity against SGC-7901 cells. Atramacronoid E significantly promoted the proliferation of LPS-induced IEC-6 cells.


Subject(s)
Atractylodes , Sesquiterpenes, Eudesmane , Sesquiterpenes , Sesquiterpenes, Eudesmane/pharmacology , Sesquiterpenes, Eudesmane/analysis , Sesquiterpenes, Eudesmane/chemistry , Atractylodes/chemistry , Sesquiterpenes/chemistry , Rhizome/chemistry , Molecular Structure
3.
Nat Prod Res ; 35(21): 3667-3674, 2021 Nov.
Article in English | MEDLINE | ID: mdl-32019347

ABSTRACT

Two new phenolic acids, ethyl 3,3',4,4'-tetrahydroxy-δ-truxinate (1), 3-O-p-coumaroyl-4-O-caffeoyl quinic acid methyl ester (2), together with three known compounds (3-5) were isolated from the whole plant of Elephantopus scaber Linn. The structures of the new compounds were elucidated using detailed spectroscopic analysis. Compound 3 was obtained and given its NMR data for the first time. All isolates were evaluated for their anti-inflammatory activity via inhibiting the production of nitric oxide (NO) in lipopolysaccharide (LPS)-stimulated murine macrophage RAW 264.7 cells, and 1, 4 and 5 showed a moderate inhibition with IC50 values ranging from 11.85 to 20.62 µM.


Subject(s)
Asteraceae , Animals , Anti-Inflammatory Agents/pharmacology , Lipopolysaccharides , Macrophages , Mice , Nitric Oxide , RAW 264.7 Cells
4.
Fitoterapia ; 140: 104413, 2020 Jan.
Article in English | MEDLINE | ID: mdl-31705953

ABSTRACT

Five new 5,6-ß-epoxywithanolides (1-5) were isolated from the whole plants of Physalis minima L. Their structural elucidations were achieved by the extensive spectroscopic analysis (IR, UV, HR-ESI-MS, 1D-NMR, and 2D-NMR). The isolates were evaluated for their anti-inflammatory activities on lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells and cytotoxic activities against three cancer cell lines, viz. A549 lung adenocarcinoma cells, SMMC-7721 hepatic carcinoma cells and MCF-7 breast cancer cells by using the MTT-based assay. All of them possessed moderate inhibition to the production of nitric oxide with IC50 values from 42.18 to 73.26 µM, and the IC50 values of the cytotoxic activities were in the range of 31.25 to 80.14 µM.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Antineoplastic Agents, Phytogenic/pharmacology , Physalis/chemistry , Withanolides/pharmacology , A549 Cells , Animals , Anti-Inflammatory Agents/isolation & purification , Antineoplastic Agents, Phytogenic/isolation & purification , China , Humans , MCF-7 Cells , Mice , Molecular Structure , Nitric Oxide/metabolism , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , RAW 264.7 Cells , Withanolides/isolation & purification
5.
RSC Adv ; 9(20): 11493-11502, 2019 Apr 09.
Article in English | MEDLINE | ID: mdl-35520265

ABSTRACT

Six new highly oxygenated (2-7) and one known (1) germacranolides were isolated from the whole plant of Carpesium divaricatum. The planar structures and relative configurations of the new compounds were determined by detailed spectroscopic analysis. The absolute configurations of 1 and 3 were established by circular dichroism (CD) and X-ray crystallographic analyses, and the stereochemistry of the new compounds 2 and 4-6 were determined by similar CD data to 1 and 3, respectively. All isolates were evaluated for their antiproliferative activities against three human tumor cell lines, and compounds 3 and 6 show antiproliferative activities against HeLa and Hep G2 cells with IC50 values of 4.13-8.37 µM. Intensive mechanism study showed that 3 caused cell-cycle arrest at the S/G2 phase and induced apoptosis in Hep G2 cells through a mitochondria-related pathway.

6.
Sci Rep ; 8(1): 12418, 2018 08 20.
Article in English | MEDLINE | ID: mdl-30127485

ABSTRACT

Five sets of germacrane isomers (1/8/17, 2/7/10/11/13/16/18, 3/4/5/14/20, 6/12/15, and 9/19) with different skeletal types, including seven new ones (1-3, 8-9, and 15-16) were isolated from the whole plant of Carpesium divaricatum. Among them, there are six pairs of stereoisomers (1/8, 2/13, 4/14, 6/12, 7/11 and 10/11). The planar structures and relative configurations of the new compounds were elucidated by detailed spectroscopic analysis. The absolute configurations of 4, 10, 11, and 17 were established by circular dichroism (CD) spectra and X-ray crystallographic analyses, and the stereochemistry of the new compounds 1-3, 8-9, and 15-16 were determined by similar CD spectra with 4, 10, 11, and 17, respectively. The confusion in the literature about subtypes I and II of germacranolides was clarified in this paper. The NMR data of 10-11, and the absolute configurations of the known compounds 4-6, 13-14, and 17-20 were reported for the first time. Compounds 13, 17, and 18 showed cytotoxicity against human cervical (HeLa), colon (LoVo) and stomach cancer (BGC-823) cell lines with IC50 values in the range 4.72-13.68 µM compared with the control cis-platin (7.90-15.34 µM).

7.
Molecules ; 23(5)2018 May 03.
Article in English | MEDLINE | ID: mdl-29751555

ABSTRACT

Three new highly oxygenated (2⁻4), and two known (1 and 5) germacranolides, were isolated from the whole plant of Carpesium divaricatum. The planar structures and relative configurations of the new compounds were determined by detailed spectroscopic analysis. The absolute configuration of 1 was established using the circular dichroism (CD) method and X-ray diffraction, and the stereochemistry of the new compounds 2⁻4 were determined using similar CD spectra with 1. The new compound 2 and the known compound 5 exhibited potent cytotoxicity against hepatocellular cancer (Hep G2) and human cervical cancer (HeLa) cells, superior to those of the positive control cis-platin.


Subject(s)
Asteraceae/chemistry , Sesquiterpenes, Germacrane/chemistry , Sesquiterpenes, Germacrane/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Cell Survival/drug effects , Circular Dichroism , Humans , Magnetic Resonance Spectroscopy , Models, Molecular , Molecular Conformation , Molecular Structure , Sesquiterpenes, Germacrane/isolation & purification , Structure-Activity Relationship , X-Ray Diffraction
8.
J Agric Food Chem ; 66(13): 3408-3416, 2018 Apr 04.
Article in English | MEDLINE | ID: mdl-29534566

ABSTRACT

The pericarp of Zanthoxylum bungeanum Maxim., commonly known as Sichuan pepper, is a widely used spice to remove fishy odor and add palatable taste. A phytochemical investigation of the 95% ethanol extract of Sichuan pepper resulted in the isolation of 21 isobutylhydroxyamides, including 8 new ones named ZP-amides G-N, among which the chiral resolution of racemic ZP-amide A and ZP-amide B was successfully accomplished. The protective activity on corticosterone-treated PC12 cells of the isolated isobutylhydroxyamides was also evaluated. The new compounds 3-5 and the known compounds 1, 1a, 2, 2a, 11, and 15 improved the survival rate of PC12 cells. The bioactivity studies disclosed the potential of Sichuan pepper to be developed as new neuroprotective functional food.


Subject(s)
Amides/pharmacology , Butanes/pharmacology , Corticosterone/toxicity , Neuroprotective Agents/pharmacology , Plant Extracts/pharmacology , Zanthoxylum/chemistry , Amides/chemistry , Animals , Butanes/chemistry , Cell Survival/drug effects , Neurons/cytology , Neurons/drug effects , Neuroprotective Agents/chemistry , PC12 Cells , Plant Extracts/chemistry , Rats
9.
Chin J Nat Med ; 15(4): 288-291, 2017 Apr.
Article in English | MEDLINE | ID: mdl-28527514

ABSTRACT

The present study was designed to investigate the chemical constituents of the whole herb of Dichrocephala benthamii. A new megastigmane glucoside (compound 1), together with its four known analogues (compounds 2-5), was obtained. Their structures were elucidated on the basis of spectroscopic analyses (UV, IR, MS, and 1D and 2D NMR). The absolute configuration of compound 1 was assigned on the basis of CD method and chemical evidence. In addition, their cytotoxicity against human hepatoma cells (HepG-2) was evaluated by the MTT method. Compound 5 showed weak activity against HepG-2, while the other compounds did not show remarkable inhibitory effects.


Subject(s)
Asteraceae/chemistry , Cyclohexanones/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Glucosides/isolation & purification , Norisoprenoids/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , China , Cyclohexanones/chemistry , Cyclohexanones/pharmacology , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/chemistry , Glucosides/chemistry , Glucosides/pharmacology , Hep G2 Cells , Humans , Molecular Structure , Norisoprenoids/chemistry , Norisoprenoids/pharmacology , Plants, Medicinal
10.
J Asian Nat Prod Res ; 19(11): 1102-1107, 2017 Nov.
Article in English | MEDLINE | ID: mdl-28361583

ABSTRACT

Two new unsaturated fatty acids, (Z)-octadec-13-en-11-ynoic acid (1) and (Z)-octadec-16-en-12,14-diynoic acid (2), along with six known compounds were isolated from the whole plant of Pothos chinensis. The structures of these compounds were elucidated by detailed spectroscopic analysis, including 1D and 2D NMR data. Compound 2 showed moderate antibacterial activity against Staphylococcus aureus.


Subject(s)
Anti-Bacterial Agents/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Fatty Acids, Unsaturated/isolation & purification , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Fatty Acids, Unsaturated/chemistry , Fatty Acids, Unsaturated/pharmacology , Hep G2 Cells , Humans , Microbial Sensitivity Tests , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Staphylococcus aureus/drug effects , Stereoisomerism
11.
J Nat Prod ; 79(10): 2487-2494, 2016 10 28.
Article in English | MEDLINE | ID: mdl-27759375

ABSTRACT

Overexpression of laeA in Chaetomium globosum CBS148.51 up-regulated expression of the chaetoglobosin gene cluster and resulted in the isolation of a new cytochalasan, chaetoglobosin Z (1), together with six known analogues, chaetoglobosins A (2), B (3), D (4), E (5), O (6), and V (7). RT-PCR analysis confirmed that the key genes in the chaetoglobosin gene cluster were significantly up-regulated. The structure of the new compound chaetoglobosin Z (1) was elucidated using NMR data. The relative and absolute configurations were determined by NOESY and electronic circular dichroism combined with quantum-chemical calculations adopting time-dependent density functional theory methods, respectively. These compounds displayed strong biological effects against the HepG 2 cell line compared with the positive control. The results further supported that LaeA is a global regulator that could up-regulate and/or activate cryptic gene clusters to produce new secondary metabolites.


Subject(s)
Chaetomium/chemistry , Indole Alkaloids/chemistry , Chaetomium/genetics , China , Hep G2 Cells , Humans , Indole Alkaloids/metabolism , Inhibitory Concentration 50 , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Polymerase Chain Reaction
12.
Sci Rep ; 6: 27237, 2016 06 06.
Article in English | MEDLINE | ID: mdl-27265755

ABSTRACT

Eight highly oxygenated germacranolides (1-8) including four new ones (2-5) were isolated from the whole plant of Carpesium divaricatum. The planar structures and relative configurations of the new compounds were determined by NMR experiment and HRESIMS data. The absolute configuration of 1 was established by circular dichroism (CD) method and X-ray diffraction, and the stereochemistry of the new compounds 2-5 were determined by similar CD spectra with 1. Compound 2 is the first hydroperoxyl germacrane from the genus Carpesium. The (13)C NMR data of 1, NMR data of 6-7, and their absolute configurations were reported for the first time. Two new compounds (2 and 4) and two known compounds (6 and 8) exhibited potent cytotoxicity against human cervical cancer (HeLa) cells, superior to that of the positive control doxorubicin.


Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Asteraceae/chemistry , Sesquiterpenes, Germacrane/chemistry , Sesquiterpenes, Germacrane/pharmacology , Cell Proliferation/drug effects , Cell Survival/drug effects , Circular Dichroism , HeLa Cells , Humans , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/pharmacology , Stereoisomerism , X-Ray Diffraction
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