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1.
Nat Prod Res ; 36(1): 186-192, 2022 Jan.
Article in English | MEDLINE | ID: mdl-32594764

ABSTRACT

Two new iridoid glycosides, 2'-O-cis-coumaroylgardoside (1), and 6'-O-caffeoylioxide (2), were isolated from the fruit of Gardenia jasminoides. The structures of these compounds were elucidated based on spectroscopic analysis (HR-ESI-MS, NMR) and chemical methods. The anti-inflammatory activities of the isolates were evaluated by measuring their inhibitory effects on PGE2 production in LPS stimulated RAW 264.7 macrophages, compounds 1 and 2 could reduce PGE2 levels in LPS-activated RAW 264.7 macrophages with IC50 values of 121.4 and 83.38 µM, respectively.


Subject(s)
Anti-Inflammatory Agents , Gardenia , Iridoid Glycosides , Animals , Anti-Inflammatory Agents/pharmacology , Fruit/chemistry , Gardenia/chemistry , Iridoid Glycosides/pharmacology , Mice , Plant Extracts/pharmacology , RAW 264.7 Cells
2.
Nat Prod Res ; 35(20): 3432-3438, 2021 Oct.
Article in English | MEDLINE | ID: mdl-32233654

ABSTRACT

A new nitrogen-containing iridoid glycoside, named (7 R,3'R)-lonijapospiroside A (1), together with thirteen known iridoid glycosides, were isolated from the flower buds of Lonicera macranthoides. The structures of these compounds were established on the basis of spectroscopic analyses. Among them, compounds 1-4 are four diastereoisomers, and their absolute configurations were accurately established by the NOE spectra as well as comparison of their experimental and calculated ECD spectra. The anti-inflammatory activities of all isolates were evaluated by measuring their inhibitory effects on NO, IL-6, and TNF-α production in LPS stimulated RAW 264.7 macrophages. Compound 14 exhibited anti-inflammatory activities by inhibiting IL-6 with an IC50 value of 54.70 µM, comparable to that of the positive control (hydrocortisone, IC50: 62.6 ± 1.7 µM).


Subject(s)
Anti-Inflammatory Agents/pharmacology , Cardiac Glycosides , Iridoid Glycosides/pharmacology , Lonicera , Anti-Inflammatory Agents/chemistry , Inhibitory Concentration 50 , Iridoid Glycosides/chemistry , Iridoid Glycosides/isolation & purification , Nitrogen/chemistry
3.
Nat Prod Res ; 35(21): 3634-3643, 2021 Nov.
Article in English | MEDLINE | ID: mdl-32009445

ABSTRACT

Ten cycloart-7-ene triterpenoid glycosides, including three new compounds (1-3), were isolated from the roots of Cimicifuga dahurica. Their structures were elucidated on the basis of extensive spectroscopic analyses, chemical methods and comparison with literatures. In addition, the isolates were evaluated for their inhibitory effects on the production of NO, as well as the expressions of iNOS and COX-2 in LPS-stimulated RAW 264.7 macrophages. The results showed that compounds 3, 5, 6, 7 and 8 can reduce the release of NO in a dose-dependent manner. Mechanistically, Western blot analysis indicated that the NO inhibitory effects relied on down-regulating the expression of iNOS, and partially associated with lowering the expression of COX-2.


Subject(s)
Actaea , Cimicifuga , Triterpenes , Anti-Inflammatory Agents/pharmacology , Glycosides/pharmacology , Triterpenes/pharmacology
4.
Chin J Nat Med ; 17(1): 27-32, 2019 Jan.
Article in English | MEDLINE | ID: mdl-30704620

ABSTRACT

The flower buds of Lonicera macranthoides (Shan Yin-Hua), represent an important traditional Chinese medicine and food ingredient. A phytochemical investigation of the 70% EtOH extract of the flower buds of L. macranthoides resulted in the isolation of 12 triterpenoids (1-12), including two new ursane-type nortriterpenes, 2α, 24-dihydroxy-23-nor-ursolic acid (1) and 2α, 4α-dihydroxy-23-nor-ursolic acid (2). Their structures were established by multiple spectroscopic methods and comparison with literature data. All isolated compounds were evaluated for their anti-inflammatory effects in LPS-activated RAW264.7 cells. Compounds 1 and 2 exhibited inhibitory effects on iNOS at the concentration of 30 µmol·L-1.


Subject(s)
Enzyme Inhibitors/chemistry , Enzyme Inhibitors/pharmacology , Lonicera/chemistry , Nitric Oxide Synthase Type II/antagonists & inhibitors , Triterpenes/chemistry , Triterpenes/pharmacology , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Drugs, Chinese Herbal/chemistry , Ethanol/chemistry , Flowers/chemistry , Macrophages/drug effects , Macrophages/metabolism , Mice , Molecular Structure , Nitric Oxide/metabolism , Plant Extracts/chemistry , Plants, Edible/chemistry , RAW 264.7 Cells , Ursolic Acid
5.
RSC Adv ; 9(38): 22011-22016, 2019 Jul 11.
Article in English | MEDLINE | ID: mdl-35518883

ABSTRACT

Lonimacranaldes A and B (1 and 2), along with one biogenetically related intermediate, lonimacranalde C (3), were isolated from the flower buds of Lonicera macranthoides. Characterized by an iridoid structure and an additional C-6 unit with an aldehyde group, compounds 1 and 2 are the first examples of hybrid iridoids possessing an unexpected 6/5/6 fused tricyclic ring system, while compound 3 serves as an important precursor for their generation. The structures of lonimacranaldes A-C (1-3) were revealed by extensive spectroscopic and X-ray diffraction analyses. A plausible biogenetic pathway for them was proposed. Compound 3 showed anti-inflammatory activities by inhibiting the production of IL-6 on LPS-induced RAW 264.7 cells with an IC50 value of 6.33 µM.

6.
Nat Prod Res ; 31(2): 143-148, 2017 Jan.
Article in English | MEDLINE | ID: mdl-27573377

ABSTRACT

A rare hetero dimeric terpenoid derivative, named japonicaside C, together with five known secoiridoid gloucosides were isolated from the flower buds of Lonicera japonica. The structures of these compounds were established on the basis of spectroscopic analyses. Japonicaside C is the first representative of a novel type of hetero dimeric terpenoid, biogenetically originated from a guaiane-type sesquiterpenoid and a secoiridoid glucoside. Anti-virus activity of the isolated compounds was evaluated in vitro.


Subject(s)
Flowers/chemistry , Lonicera/chemistry , Terpenes/chemistry , Antiviral Agents/pharmacology , Chromatography, High Pressure Liquid , Cytopathogenic Effect, Viral/drug effects , Magnetic Resonance Spectroscopy , Plant Extracts/chemistry , Respiratory Syncytial Virus, Human/drug effects , Spectrometry, Mass, Electrospray Ionization , Terpenes/pharmacology
7.
Drug Des Devel Ther ; 9: 1743-59, 2015.
Article in English | MEDLINE | ID: mdl-25848211

ABSTRACT

Factor IXa (FIXa), a blood coagulation factor, is specifically inhibited at the initiation stage of the coagulation cascade, promising an excellent approach for developing selective and safe anticoagulants. Eighty-four amidinobenzothiophene antithrombotic derivatives targeting FIXa were selected to establish three-dimensional quantitative structure-activity relationship (3D-QSAR) and three-dimensional quantitative structure-selectivity relationship (3D-QSSR) models using comparative molecular field analysis and comparative similarity indices analysis methods. Internal and external cross-validation techniques were investigated as well as region focusing and bootstrapping. The satisfactory q (2) values of 0.753 and 0.770, and r (2) values of 0.940 and 0.965 for 3D-QSAR and 3D-QSSR, respectively, indicated that the models are available to predict both the inhibitory activity and selectivity on FIXa against Factor Xa, the activated status of Factor X. This work revealed that the steric, hydrophobic, and H-bond factors should appropriately be taken into account in future rational design, especially the modifications at the 2'-position of the benzene and the 6-position of the benzothiophene in the R group, providing helpful clues to design more active and selective FIXa inhibitors for the treatment of thrombosis. On the basis of the three-dimensional quantitative structure-property relationships, 16 new potent molecules have been designed and are predicted to be more active and selective than Compound 33, which has the best activity as reported in the literature.


Subject(s)
Amidines/pharmacology , Anticoagulants/pharmacology , Drug Design , Factor Xa Inhibitors/pharmacology , Factor Xa/metabolism , Thiophenes/pharmacology , Amidines/chemistry , Anticoagulants/chemistry , Factor Xa Inhibitors/chemistry , Humans , Models, Molecular , Molecular Structure , Structure-Activity Relationship , Thiophenes/chemistry
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