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1.
Nat Prod Res ; 35(14): 2308-2314, 2021 Jul.
Article in English | MEDLINE | ID: mdl-31581856

ABSTRACT

As our ongoing chemical investigation, two new pregnane steroidal glycosides, cynataihosides G (1), with a new aglycone, and H (2) were isolated from the 95% ethanol extract of Cynanchum taihangense. Their structures were elucidated on the basis of 1 D and 2 D NMR spectral data, HR-ESI-MS analysis and qualitative chemical methods. The compounds were subjected to detect the cytotoxicity against three human tumor cell lines (HL-60, THP-1 and PC-3). The compounds displayed no significant cytotoxicity.Supplemental data for this article can be accessed at https://doi.org/10.1080/14786419.2019.1672682.


Subject(s)
Cynanchum/chemistry , Glycosides/isolation & purification , Pregnanes/isolation & purification , Steroids/isolation & purification , Carbon-13 Magnetic Resonance Spectroscopy , Cell Death/drug effects , Cell Line, Tumor , Glycosides/pharmacology , Humans , Inhibitory Concentration 50 , Plant Roots/chemistry , Pregnanes/pharmacology , Proton Magnetic Resonance Spectroscopy , Steroids/chemistry , Steroids/pharmacology
2.
J Asian Nat Prod Res ; 22(3): 287-294, 2020 Mar.
Article in English | MEDLINE | ID: mdl-30621449

ABSTRACT

A new xanthyletin-type coumarin, neopeucedalactone (1), was isolated from the roots of Peucedanum praeruptorum Dunn. Its chemical structure was elucidated based on extensive spectroscopic interpretation. The absolute configurations of xanthyletin-type coumarin were determined by comparing experimental and calculated ECD spectra for the first time. Compound 1 exhibited moderate cell growth inhibitory activities in vitro against human leukemic HL-60, THP-1 cell lines, and human prostate cancer PC-3 cell lines, with IC50 values of 9.97, 27.80, and 48.68 µM, respectively. [Formula: see text].


Subject(s)
Apiaceae , Coumarins , Male , Molecular Structure , Plant Roots
3.
J Asian Nat Prod Res ; 21(1): 33-42, 2019 Jan.
Article in English | MEDLINE | ID: mdl-29502438

ABSTRACT

Three new tetralol analogs, myrochromanols A-C (1-3), together with 11 known trichothecenes (4-14), were isolated from a soil fungus Myrothecium verrucaria HL-P-1. The structures of the three new compounds were elucidated by extensive spectroscopic analysis including HRESIMS, NMR, and ECD calculation. All of the new compounds were tested for their anti-inflammatory activity and cytotoxicity. Compounds 1 and 3 inhibited lipopolysaccharide (LPS)-induced NO production in BV2 cells with IC50 values of 26.04 and 25.80 µM, respectively.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Hypocreales/metabolism , Soil Microbiology , Tetralones/isolation & purification , HL-60 Cells , Humans , Tetralones/chemistry , Tetralones/pharmacology
4.
J Asian Nat Prod Res ; 21(6): 528-534, 2019 Jun.
Article in English | MEDLINE | ID: mdl-29693414

ABSTRACT

A new fumiquinazoline-type alkaloid 2-methyl-versiquinazoline C (1), together with six known compounds (2-7), was isolated from Aspergillus flavipes PJ03-11 using OSMAC method. Their structures were elucidated on the basis of extensive spectroscopic analysis, and the absolute configuration of compound 1 was determined by the experimental and calculated ECD data. In addition, the cytotoxic activities against three human cancer cell lines (HL-60, THP-1, and PC-3) were evaluated.


Subject(s)
Alkaloids/chemistry , Alkaloids/pharmacology , Antibiotics, Antineoplastic/chemistry , Antibiotics, Antineoplastic/pharmacology , Aspergillus/chemistry , Quinazolines/chemistry , Quinazolines/pharmacology , Cell Line, Tumor , Fermentation , HL-60 Cells , Humans , Molecular Structure
5.
Fitoterapia ; 125: 249-257, 2018 Mar.
Article in English | MEDLINE | ID: mdl-29395667

ABSTRACT

A search for cytotoxic agents from cultures of the Penicillium sp., isolated from the rhizosphere soil of Pulsatilla chinensis, led to the isolation of four new hybrid polyketide-terpenoid metabolites (1-4), together with fourteen known compounds (5-18). Using a bioassay-guided fractionation approach, eighteen compounds were obtained from the ethyl acetate extract of this fungus. Structure elucidation was achieved by extensive analysis of spectroscopic data (1D/2D NMR, HRESIMS and IR). The absolute configurations of compounds 1-4 were determined by means of electronic circular dichroism (ECD) calculation. Compounds 1-4, 7-9, 11, 12, 14 and 17 were tested for their cytotoxicity against HL-60, THP-1 and Caco2 cell lines. Compound 1 showed potent cytotoxic capability against HL-60, THP-1 and Caco2 cell with IC50 values of 3.4µM, 4.3µM, 10.5µM, and compound 2 showed significant inhibiting activities against HL-60 cell line and THP-1 cell line (IC50=7.9µM, 11.3µM, respectively), using 5-fluorouracil as the positive drug with IC50 values of 6.4µM, 4.4µM, 56.6µM for HL-60, THP-1 and Caco2 cells, respectively. And compound 1 showed antibacterial activity toward Bacillus cereus (IC50=49µg/mL, IC90=111µg/mL) and Bacillus subtilis (IC50=10µg/mL, IC90=85µg/mL).


Subject(s)
Penicillium/chemistry , Polyketides/chemistry , Pulsatilla/microbiology , Terpenes/chemistry , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Bacillus/drug effects , Cell Line, Tumor , Humans , Molecular Structure , Polyketides/isolation & purification , Rhizosphere , Soil Microbiology , Terpenes/isolation & purification
6.
J Asian Nat Prod Res ; 20(9): 875-882, 2018 Sep.
Article in English | MEDLINE | ID: mdl-29171292

ABSTRACT

As a part of our continuing research for bioactive constituents from Cynanchum limprichtii Schltr., two new C21 steroidal glycosides limproside A (1) and limproside B (2) were isolated from the roots of Cynanchum limprichtii. Their structures were elucidated on the basis of 1D- and 2D-NMR spectroscopic data as well as HR-ESI-MS analysis. The cytotoxicity of two compounds against two selected human cancer cell lines was assayed.


Subject(s)
Cynanchum/chemistry , Phytosterols/isolation & purification , Saponins/isolation & purification , Cell Line, Tumor , Humans , Magnetic Resonance Spectroscopy , Phytosterols/chemistry , Phytosterols/pharmacology , Plant Roots/chemistry , Saponins/chemistry , Saponins/pharmacology
7.
J Asian Nat Prod Res ; 20(9): 852-859, 2018 Sep.
Article in English | MEDLINE | ID: mdl-29099237

ABSTRACT

Two new 13,14:14,15-disecopregnane-type C21 steroidal glycosides, namely komarosides R (1) and S (2), along with four known compounds (3-6), were obtained from the 95% ethanol extract of the whole herbs of Cynanchum komarovii Al.Iljinski (Asclepiadaceae). The structures of new compounds were elucidated on the basis of 1D, 2D NMR spectroscopic data and acid hydrolysis. Compounds 1 and 2 showed potent inhibitory activities against human leukemia cell line (HL-60) with IC50 values being 6.2 and 17.6 µM, respectively, compared to the positive control 5-fluorouracil (6.4 µM).


Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Cynanchum/chemistry , Glycosides/isolation & purification , Phytosterols/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Glycosides/chemistry , Glycosides/pharmacology , HL-60 Cells , Humans , Magnetic Resonance Spectroscopy , Phytosterols/chemistry , Phytosterols/pharmacology
8.
J Asian Nat Prod Res ; 20(3): 263-269, 2018 Mar.
Article in English | MEDLINE | ID: mdl-28537086

ABSTRACT

Two new C21 steroidal glycosides, cynataihosides E (1) and F (2), together with a known one, sublanceoside H2 (3), were isolated from Cynanchum taihangense. The aglycone of cynataihoside F (2) was also a new compound. Their structures were elucidated on the basis of NMR spectroscopic data, HR-ESI-MS analysis, and chemical evidence. Their cytotoxic activities against three human tumor cell lines (HL-60, THP1, and Caco2) were reported.


Subject(s)
Cynanchum/chemistry , Glycosides/isolation & purification , Steroids/isolation & purification , Caco-2 Cells , Glycosides/chemistry , Glycosides/pharmacology , HL-60 Cells , Humans , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Roots/chemistry , Steroids/chemistry , Steroids/pharmacology
9.
Bioorg Med Chem Lett ; 27(16): 3723-3725, 2017 08 15.
Article in English | MEDLINE | ID: mdl-28697923

ABSTRACT

Four new α-pyrone derivatives phomones C-F (1-4) together with four known compounds (5-8) were isolated from the endophytic fungus Phoma sp. YN02-P-3. Compound 1 is the first example of 6-α,ß-unsaturated ester-2-pyrone dimers via intermolecular symmetrical [2+2] cycloaddition. The chemical structures of these compounds were determined from spectroscopic data (1D/2D NMR, MS and IR). The acetylated product (9) of 1 along with compounds 1-8 were then tested for their cytotoxicity against HL-60, PC-3 and HCT-116 cell lines. Compounds 2, 3, 5 and 9 with acetyl groups showed significant inhibitory activities against the three cell lines with IC50 values in the range 0.52-9.85µM. while compounds 1, 4 and 6-8 that possess no acetyl group showed no inhibitory activity (IC50>50µM), indicating that the acetyl group at 10- or 12- are essential for their cytotoxic activities. The structure-activity relationships of these phomones were also reported.


Subject(s)
Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Pyrones/chemistry , Pyrones/pharmacology , Antineoplastic Agents/toxicity , Cell Line , Cell Survival/drug effects , Cycloaddition Reaction , Fungi/chemistry , HCT116 Cells , HL-60 Cells , Humans , Magnetic Resonance Spectroscopy , Molecular Conformation , Pyrones/toxicity , Structure-Activity Relationship
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