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1.
J Asian Nat Prod Res ; 19(3): 241-246, 2017 Mar.
Article in English | MEDLINE | ID: mdl-27400392

ABSTRACT

Two rare types of 4,6-dimethyl-3,4-dihydrochromen-2-one derivatives, named cralactones A and B (1 and 2), were isolated from the culture broth of Craterellus odoratus. The structures of the new ones were established on the basis of extensive spectroscopic analysis, and it was found that the new compounds did not show pancreatic lipase inhibitory activity. Compounds 1 and 2 are the first examples of 4,6-dimethyl-3,4-dihydrochromen-2-one.


Subject(s)
Basidiomycota/chemistry , Chromones/isolation & purification , Lipase/antagonists & inhibitors , Chromones/chemistry , Chromones/pharmacology , Molecular Structure , Pancreas/enzymology
2.
ChemistryOpen ; 5(2): 142-9, 2016 04.
Article in English | MEDLINE | ID: mdl-27308232

ABSTRACT

A variety of novel natural products with significant bioactivities are produced by the basidiomycete Boreostereum vibrans. In the present study, we describe 16 novel natural oximes and oxime esters with a vibralactone backbone, vibralactoximes, which were isolated from the scale-up fermentation broth of B. vibrans. Their structures were determined through extensive spectroscopic analyses. These compounds represent the first oxime esters from nature. The hypothetical biosynthetic pathway of these compounds was also proposed. Seven compounds exhibited significant pancreatic lipase inhibitory activity, while ten compounds exhibited cytotoxicities against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480), with IC50 values comparable with those of cisplatin.

3.
Fitoterapia ; 109: 91-8, 2016 Mar.
Article in English | MEDLINE | ID: mdl-26687559

ABSTRACT

Eighteen new lanostane-type triterpenoids, namely leucocontextins A-R (1-18) were isolated from the fruiting bodies of Ganoderma leucocontextum. Their structures were established by 1D and 2D NMR data in conjunction with HRESIMS/HREIMS, X-ray single crystal diffraction analysis. Compound 18 exhibited weak cytotoxicity against K562 and MCF-7 cell lines with IC50 of 20-30 µM.


Subject(s)
Ganoderma/chemistry , Triterpenes/chemistry , Fruiting Bodies, Fungal/chemistry , Humans , K562 Cells , MCF-7 Cells , Molecular Structure , Triterpenes/isolation & purification
4.
J Asian Nat Prod Res ; 18(4): 354-9, 2016.
Article in English | MEDLINE | ID: mdl-26629595

ABSTRACT

One new lignan, fructusol A (1), and one new thiazine derivative, 2-hydroxy-xanthiazone (2), along with eight known ones, were isolated from the seeds of Xanthium strumarium. The structures of new compounds were elucidated on the basis of extensive spectroscopic methods. Meanwhile, compounds 1-3 were tested for their antifungal activities against Candida albicans (ATCC 10231) in vitro. No one showed obvious inhibitions (MIC90 > 128 µg/ml).


Subject(s)
Antifungal Agents/isolation & purification , Lignans/isolation & purification , Thiazines/isolation & purification , Xanthium/chemistry , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Candida albicans/drug effects , Lignans/chemistry , Lignans/pharmacology , Molecular Structure , Seeds/chemistry , Thiazines/chemistry , Thiazines/pharmacology
5.
J Asian Nat Prod Res ; 18(2): 184-8, 2016.
Article in English | MEDLINE | ID: mdl-26208091

ABSTRACT

Studies of the fermentation broth of fungus Antrodiella gypsea led to the isolation of a new bisabolane-type sesquiterpenoid that was named gypseatriol (1), together with the known compound 2,10-dodecadiene-1,6,7-triol (2). The structure of this new metabolite was assigned by analysis of 2D NMR and HR-EI-MS. Absolute configuration was assigned by single crystal X-ray diffraction analysis. Compound 1 was evaluated for its antifungal activity on Candida albicans.


Subject(s)
Basidiomycota/chemistry , Sesquiterpenes/isolation & purification , Coriolaceae , Crystallography, X-Ray , Fermentation , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology
6.
J Asian Nat Prod Res ; 18(1): 46-50, 2016.
Article in English | MEDLINE | ID: mdl-26095767

ABSTRACT

Two new sesquiterpenoids, trefoliol B (1) and trefoliol C (2), together with known echinocidin A (3), were isolated from cultures of the basidiomycetes Tremella foliacea. The new structures were elucidated on the basis of extensive spectroscopic methods. At the same time, trefoliol B (1) and echinocidin A (3) were tested for their cytotoxicities against five human cancer cell lines and for their inhibitory activities against isozymes of 11ß-hydroxysteroid dehydrogenases (11ß-HSD). No compound showed significant activity (IC50 > 40 µM). Compound 1 showed moderate inhibitory activities against 11ß-HSD1 (human IC50 = 13.1 µM; mouse IC50 = 91.8 µM).


Subject(s)
11-beta-Hydroxysteroid Dehydrogenase Type 1/antagonists & inhibitors , Antineoplastic Agents/isolation & purification , Basidiomycota/chemistry , Sesquiterpenes/isolation & purification , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Drug Screening Assays, Antitumor , Female , Humans , Isoenzymes , Mice , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Sesquiterpenes/chemistry , Tetrazolium Salts/pharmacology , Thiazoles/pharmacology
7.
J Asian Nat Prod Res ; 17(12): 1160-5, 2015.
Article in English | MEDLINE | ID: mdl-26666338

ABSTRACT

Four new polycylic alkaloids, lucidimine A-D, were isolated from the fruiting bodies of Ganoderma lucidum. Their chemical structures were established based on 1D and 2D NMR data as well as HREIMS/HRESIMS analyses.


Subject(s)
Alkaloids/isolation & purification , Reishi/chemistry , Alkaloids/chemistry , Fruiting Bodies, Fungal/chemistry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular
8.
Fitoterapia ; 105: 127-31, 2015 Sep.
Article in English | MEDLINE | ID: mdl-26136058

ABSTRACT

Four new spiroaxane sesquiterpenes, tramspiroins A-D (1-4), one new rosenonolactone 15,16-acetonide (5), and the known drimane sesquiterpenes isodrimenediol (6) and funatrol D (7) have been isolated from the cultures of Basidiomycete Trametes versicolor. The structures of new compounds were elucidated by means of spectroscopic methods. Compounds 1-7 were investigated for their cytotoxicities against five human cancer cell lines.


Subject(s)
Diterpenes/chemistry , Lactones/chemistry , Sesquiterpenes/chemistry , Trametes/chemistry , Cell Line, Tumor/drug effects , Diterpenes/isolation & purification , Humans , Lactones/isolation & purification , Molecular Structure , Sesquiterpenes/isolation & purification
9.
Nat Prod Bioprospect ; 5(3): 129-157, 2015 Jun.
Article in English | MEDLINE | ID: mdl-26085282

ABSTRACT

The unusual fused ß-lactone vibralactone was isolated from cultures of the basidiomycete Boreostereum vibrans and has been shown to significantly inhibit pancreatic lipase. In this study, a structure-based lead optimization of vibralactone resulted in three series of 104 analogs, among which compound C1 exhibited the most potent inhibition of pancreatic lipase, with an IC50 value of 14 nM. This activity is more than 3000-fold higher than that of vibralactone. The effect of compound C1 on obesity was investigated using high-fat diet (HFD)-induced C57BL/6 J obese mice. Treatment with compound C1 at a dose of 100 mg/kg significantly decreased HFD-induced obesity, primarily through the improvement of metabolic parameters, such as triglyceride levels.

10.
J Asian Nat Prod Res ; 17(11): 1054-8, 2015.
Article in English | MEDLINE | ID: mdl-26000880

ABSTRACT

Chemical investigation on the cultures of Phellinus tuberculosus and Laetiporus sulphureus lead to the isolation of two new illudin-type sesquiterpenoids (phellinuin J and sulphureuine A). Their structures were elucidated by 1D, 2D NMR and MS spectroscopic data. These compounds were purposely evaluated for their cytotoxicity against HL-60, SMMC-7721, A549, MCF-7, and SW480 cell lines.


Subject(s)
Agaricales/chemistry , Antineoplastic Agents/isolation & purification , Sesquiterpenes/isolation & purification , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Coriolaceae , Drug Screening Assays, Antitumor , HL-60 Cells , Humans , Molecular Structure , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology
11.
Fitoterapia ; 104: 50-4, 2015 Jul.
Article in English | MEDLINE | ID: mdl-25987321

ABSTRACT

Three new brasilane-type sesquiterpenoids, brasilanes A-C (1-3), together with two new alkane derivatives, colisiderin A (4) and 7(E),9(E)-undecandiene-2,4,5-triol (5), were isolated from cultures of the basidiomycete Coltricia sideroides. Their structures were elucidated by NMR and MS data analyses. The absolute configuration of 4 was determined by TDDFT ECD calculations while brasilane-type sesquiterpenoids were isolated from cultures of mushroom for the first time. Compounds 2 and 4 showed weak cytotoxicities against HL-60 and SW480, respectively.


Subject(s)
Basidiomycota/chemistry , Sesquiterpenes/chemistry , Agaricales/chemistry , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Cell Line, Tumor/drug effects , HL-60 Cells/drug effects , Humans , Molecular Structure , Sesquiterpenes/isolation & purification
12.
Nat Prod Bioprospect ; 2015 Apr 08.
Article in English | MEDLINE | ID: mdl-25850378

ABSTRACT

One new cleistanthane-type diterpene named engleromycenolic acid A (1), one new rosane-type diterpene named engleromycenolic acid B (2) and one new natural rosane-type diterpene, engleromycenol (3), along with three known rosane-type diterpenes, rosololactone (4), rosenonolactone (5) and 7-deoxyrosenonolactone (6) were isolated from cultures of the fungus Engleromyces goetzii, where it naturally grows on Alpine bamboo culms. The new compounds were elucidated based on their spectroscopic data. In addition, compounds 1-6 were evaluated for their cholesterol ester transfer protein (CETP) inhibition activity. This paper reports the isolation, structural elucidation, and CETP inhibition activity of these compounds.

13.
Nat Prod Bioprospect ; 2015 Mar 28.
Article in English | MEDLINE | ID: mdl-25821175

ABSTRACT

Investigation on the cultures of Hypsizygus marmoreus resulted in the isolation of a new viscidane diterpene, 8-oxoviscida-3,11(18)-diene-13,14,15,19-tetraol (1) and two new polyacetylenes, (E)-10-(1,1-dimethyl-2-propenyloxy)-2-decene-4,6,8-triyn-1-ol (2) and 10-(1,1-dimethyl-2-propenyloxy)deca-4,6,8-triyn-1-ol (3), together with two known polyacetylenes, (E)-2-decen-4,6,8-triyn-1-ol (4) and 4,6,8-decatriyn-1-ol (5). Their structures were elucidated on the basis of extensive spectroscopic studies. Compound 1 is the first finding of viscidane diterpene in mushrooms. Compounds 1, 3 and 5 were tested for cytotoxicity against human tumor cell lines HL-60, SMMC-7721, A-549, MCF-7 and SW-480. None of the compounds showed cytotoxic activity (IC50 > 40 µM).

14.
Fitoterapia ; 102: 1-6, 2015 Apr.
Article in English | MEDLINE | ID: mdl-25665943

ABSTRACT

Seven new drimane-type sesquiterpenoids, sulphureuines B-H (1-7), together with four known compounds (8-11), were obtained from cultures of mushroom Laetiporus sulphureus. All of these compounds were tested for their cytotoxicities against five human cancer cell lines (HL-60, SMMC-721, A-549, MCF-7, SW-480), compound 10 showed potent cytotoxic activity against HL-60, SMMC-721, A-549, SW-480, with IC50 values of 37.5, 14.8, 15.6, and 36.1µM, respectively.


Subject(s)
Antineoplastic Agents/chemistry , Polyporales/chemistry , Sesquiterpenes/chemistry , Agaricales/chemistry , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Drug Screening Assays, Antitumor , Humans , Molecular Structure , Polycyclic Sesquiterpenes , Sesquiterpenes/isolation & purification
15.
J Asian Nat Prod Res ; 17(7): 750-5, 2015.
Article in English | MEDLINE | ID: mdl-25631072

ABSTRACT

Two new triterpenoids, (24E)-9α,11α-epoxy-3ß-hydroxylanosta-7,24-dien-26-al (1) and (22Z,24Z)-13-hydroxy-3-oxo-14(13 â†’ 12)abeo-lanosta-8,22,24-trien-26,23-olide (2) were isolated from dried fruiting bodies of fungus Ganoderma lucidum. The structures of these two new compounds were elucidated on the basis of extensive spectroscopic analyses. Compound 1 possessed a lanostane skeleton, while compound 2 was based on a rare 14 (13 â†’ 12)abeo-lanostane skeleton with a 26,23-olide moiety. Both of them were evaluated for their antifungal and cytotoxic activities. Neither of them displayed obvious inhibition on Candida albicans and five human cancer cell lines.


Subject(s)
Ganoderma/chemistry , Triterpenes/isolation & purification , Candida albicans/drug effects , China , Drug Screening Assays, Antitumor , Fruiting Bodies, Fungal/chemistry , HL-60 Cells , Humans , Microbial Sensitivity Tests , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Triterpenes/chemistry , Triterpenes/pharmacology
16.
Nat Prod Bioprospect ; 2015 Jan 30.
Article in English | MEDLINE | ID: mdl-25633363

ABSTRACT

Engleromyces goetzii is a traditional medicinal mushroom that is widely used to treat infection, inflammation and cancer in Tibet, Sichuan and Yunnan provinces of China. Two new trichothecenes, engleromycones A and B (1 and 2), one new cuparane-type sesquiterpenoid named infuscol F (11), eight known trichothecene analogs, sambucinol (3), 3-deoxysambucinol (4), trichothecolone (5), trichodermol (6), 8-deoxytrichothecin (7), trichothecin (8), trichothecinol B (9) and trichothecinol A (10), and one known cyclopentanoid sesquiterpene cyclonerodiol (12) were isolated from the cultures of E. goetzii. The new compounds were elucidated through spectroscopic analyses. The anticancer effects of trichothecenes 1-10 were examined in the HL-60, SMMC-7721, A549, MCF-7, and SW-480 human cancer cell lines using an MTT assay. Trichothecinol A (10) significantly inhibited the growth of MCF-7 cells, with an IC50 value of 0.006 µM, which was comparable to the cytotoxic activity of the positive control, paclitaxel, indicating that trichothecinol A (10) represents a potential anticancer agent.

17.
J Asian Nat Prod Res ; 17(1): 1-6, 2015.
Article in English | MEDLINE | ID: mdl-25027260

ABSTRACT

Three new sesquiterpenoids (1-3), along with four known compounds (4-7), were isolated from cultures of the fungus Conocybe siliginea. The structures of new compounds were elucidated using spectroscopic methods. The known compounds were identified by comparing their spectroscopic data with those reported in the literature. All new compounds were evaluated for cytotoxicity against five human cancer cell lines, but none of them possesses significant activity (IC50>40µM).


Subject(s)
Basidiomycota/chemistry , Sesquiterpenes/isolation & purification , Drug Screening Assays, Antitumor , Humans , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology
18.
Nat Prod Bioprospect ; 2014 Dec 10.
Article in English | MEDLINE | ID: mdl-25491089

ABSTRACT

Four new sesquiterpenoids, namely 12-hydroxy-3-oxodrimenol (1), 11-hydroxyacetoxydrim-7-en-3ß-ol (2), 2,6-dimethyl-7,10-epoxy-10-hydroxymethyldodeca-2,11-dien-6-ol (3), and 7,10-epoxy-2,6,10-trimethyldodeca-2,11-diene-4,6-diol (4), along with fourteen known compounds, were isolated from the cultures of Phellinidium sulphurascens. The structures of compounds 1-4 were established on the basis of extensive spectroscopic analysis. All of them were evaluated for their cytotoxic activities.

19.
Nat Prod Bioprospect ; 2014 Nov 29.
Article in English | MEDLINE | ID: mdl-25432445

ABSTRACT

Two new steroids, 3α,17α,19,20-tetrahydroxy-4α-methylpregn-8-ene (1) and 3α,12α,17α,20-tetrahydroxy-4α-methylpregn-8-ene (2) and three new sesquiterpenoids, 12-hydroxy-α-cadinol (3), 3α,12-dihydroxy-δ-cadinol (4), and 3α,6α-dihydroxyspiroax-4-ene (5), have been isolated from cultures of the fungus Phellinus igniarius. Their structures were characterized based on extensive spectroscopic data. In preliminary in vitro assays, compounds 3 and 4 exhibited the vascular-activities against phenylephrine-induced vasoconstriction with the relaxing rates of 11.0 % and 7.0 % at 3 × 10-4 M, respectively.

20.
J Asian Nat Prod Res ; 16(6): 581-6, 2014.
Article in English | MEDLINE | ID: mdl-24974836

ABSTRACT

Three new bisabolane sesquiterpenoids, inonotic acid A (1), 3-O-formyl inonotic acid A (2), inonotic acid B (3), and one new drimane sesquiterpenoid 3α,6ß-dihydroxycinnamolide (4), were isolated from the fruiting bodies of mushroom Inonotus rickii. Their structures were elucidated by means of extensive spectroscopic methods. Compound 4 had moderate inhibitory activity on human colon cancer SW480 (IC50 = 20.4 µmol).


Subject(s)
Agaricales/chemistry , Antineoplastic Agents/isolation & purification , Sesquiterpenes/isolation & purification , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , China , Drug Screening Assays, Antitumor , Fruiting Bodies, Fungal/chemistry , Humans , Inhibitory Concentration 50 , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Polycyclic Sesquiterpenes , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology
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