Journal of Asian Natural Products Research

Guiding by LC-MS/MS analysis and the Global Natural Products Social (GNPS) Molecular Networking, three undescribed sesquiterpenoids, stedapgens A-C, and two known analogues were discovered in the barks of Daphne genkwa Sieb. et Zucc. The structures were determined by analysis of their spectroscopic data and quantum-chemical calculations. All the isolated novel compounds were tested for their acetylcholinesterase inhibitory activities with IC50 = 0.754 ± 0.059, 0.696 ± 0...

Two new sesquiterpenoid glycosides, 8 α ( H )-eudesmane-1,3,11 (13)-triene-2-one -12- O - β -D-glucopyranoside ( 1 ) and dmetelisproside B ( 2 ), together with ten known compounds ( 3 - 12 ) were isolated from calyces of Physalis alkekengi L. var. franchetii (Mast.) Makino (PAF). Their structures were unambiguously elucidated through HR-ESI-MS, UV, IR, and NMR spectral data. Compounds 1 , 10 , and 12 exhibited DPPH scavenging ability with IC50 values of 33.69 ± 6.65, 6.29 ± 0...

A new seco -A tirucallane triterpenoid named excelxylin A ( 1 ), along with two known seco -A triterpenoids ( 2-3 ), were isolated from the n -hexane extract of Dysoxylum excelsum (Spreng.) Blume ex G.Don stem bark. The structure and stereochemistry configuration of compounds 1-3 was established by NMR, IR, and HR-ESI-MS spectroscopic data analyses and comparison of their NMR data with literatures. The compounds exhibited the carbon framework for seco -A ring tirucallane triterpenoid, first reported in the Dysoxylum genus...

Thrombosis plays an important role in the occurrence and development of cardiovascular and cerebrovascular diseases that contribute to high mortality and morbidity in patients. L-(-)-Quebrachitol (QCT), a natural product, was first isolated from quebracho bark. It can inhibit PAF receptor and decrease gastric damage induced by indomethacin, as a drug against platelet aggregation. Here, five QCT derivatives were synthesized and investigated for their inhibitory effects on platelet aggregation. Among them, compound 3a showed anticoagulant effects comparable to aspirin, while compound 4b showed dose-independent inhibitory activities in rats that were stronger than aspirin...

Three new monoterpene phenol dimers, bisbakuchiols V-X ( 1-3 ), and two bakuchiol ethers ( 4 and 5 ), along with four known compounds ( 6 - 9 ) were isolated from the fruits of Psoralea corylifolia . Their structures were elucidated based on extensive spectral analysis. The absolute configurations of 1 , 2 , 4 , and 5 were specified by quantum chemical calculations of ECD spectra.

Nineteen isosteviol derivatives were designed and synthesized by C-16, C-19 and D-ring modifications of isosteviol. These compounds were screened for their cytotoxic activities against Hela and A549 cells in vitro . Among them, the inhibitory effect of compounds 3b and 16 on Hela cells was comparable to that of the positive control gefitinib, and the compounds 3b (IC50 =7.84 ± 0.84 μM) and 7a (IC50 =6.89 ± 0.33 μM) exhibited significant cytotoxicity superior to gefitinib (IC50 =11...

Phytochemical study on 90% ethanol extract from the green walnut husks of Juglans mandshurica Maxim. resulted into the isolation of three undescribed triterpenoids, juglansmanoids A-C ( 1 - 3 ). Structural elucidation of all the compounds were performed by spectral methods such as 1D and 2D (1 H-1 H COSY, HMQC, and HMBC) NMR spectroscopy, in addition to high resolution mass spectrometry. The isolated components were evaluated in vitro for anti-hyaluronidase activities. As a result, triterpenoid 1 exhibited potent anti-hyaluronidase activity (IC50 = 9...

Two previously undescribed iridoid glycosides, 6'- O -trans-feruloyl-(4 S ,6 R )-3,4-dihydro-3 β -ethoxypaederoside ( 1 ) and 6'- O -trans-caffeoyl-(4 S ,6 R )-3,4-dihydro-2'- O -3 α -paederoside ( 2 ), were isolated from the 90% EtOH extract of the air dried aerial parts of Paederia Foetida . Structural elucidation of all the compounds was performed by spectral methods such as 1D and 2D (1 H - 1 H COSY, HMQC, and HMBC) NMR spectroscopy. The two isolated iridoid glycosides were tested in vivo for their antinociceptive properties...

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Two new cassane diterpenoids, sucupiranin MN ( 1 ) and sucupiranin ML ( 2 ), together with two known compounds sucutinirane C ( 3 ) and deacetylsucutinirane C ( 4 ) were isolated from the seed kernels of Caesalpinia sinensis . Their structures were elucidated by means of analysis of comprehensive spectroscopic data, especially HRESIMS and 1D/2D NMR spectroscopy. Compounds 1-4 are typical furan-type cassane derivatives with an aromatized C ring. Biological evaluation revealed that compounds 1-4 at the concentration of 10 μM could inhibit the overproduction of NO in LPS-stimulated RAW 264...

White matter lesions (WMLs), characterized by focal demyelination or myelination disorders, are commonly present in cerebral small vessel disease and various neurological diseases. Multiple etiologies lead to WMLs. However, there is no specific therapy or effective drugs for relieving WMLs. Natural products and their derivatives originate from bacterial, fungal, plant, and marine animal sources, many of which have multiple therapeutic targets. Compared to single target compounds, natural products and their derivatives are promising to be developed as better drugs to attenuate WMLs...

Two new aporphine alkaloids, 6a R -2'-(3-oxobutenyl)-thaliadin ( 1 ) and N -methylthalisopynine ( 2 ), along with ten known analogs ( 3 - 12 ), were isolated from the roots of Thalictrum omeiense W. T. Wang et S. H. Wang. Their structures were determined by extensive spectroscopic and X-ray crystallographic analyses. Compounds 1 - 7 and 9 - 12 were tested for their antiproliferative effects in vitro against two human cancer cell lines (A549 and MCF-7). Among them, compounds 1 , 3, and 7 exhibited moderate inhibitory activity against the tested cell lines with IC50 values ranging from 23...

An unprescribed nortriterpenoid with an aromatic E ring, uncanortriterpenoid A ( 1 ), together with fourteen known triterpenoids ( 2 - 15 ), were isolated from the hook-bearing stems of Uncaria rhynchophylla Miq. Based on extensive spectroscopic analyses, the NMR data of 2 , 5, and 10 in CD3 OD were assigned for the first time, and the wrongly assigned δ C of C-27 and C-29 of 2 were revised. Among the known compounds, 7 , 13, and 15 were isolated from this species for the first time, and 15 represents the first lanostane triterpenoid bearing an extra methylidene at C-24 for the Rubiaceae family...

Three Diels-Alder type adducts ( 1 - 3 ) along with their precursors, including one 2-arylbenzofuran ( 4 ) and one stilbene ( 5 ), were isolated from the MeOH extract of M. alba var. shalun root cultures. Among them, 1 is a new Diels-Alder type adduct named morushalunin D. The molecular structures of 1 - 5 were elucidated based on spectroscopic data and comparison with the literatures. Cytotoxic properties of compounds 1 - 5 were evaluated against murine leukemia P-388 cells. Morushalunin D ( 1 ), mulberrofuran T ( 2 ), sorocein A ( 3 ), moracin M ( 4 ), and oxyresveratrol ( 5 ) were active, significantly inhibiting the growth of P-388 cells with IC50 values of 0...

To clarify the chemical basis of the total alkaloids of Uncaria rhynchophylla , HPLC-VWD chromatogram of total alkaloids was established. Under its guidance, modern chromatographic and spectroscopic techniques were used to track, isolate and identify the representative principal components. As a result, one new monoterpenoid indole alkaloid, 3 S ,15 S - N 4-methoxymethyl-geissoschizine methyl ether (1), together with 20 known alkaloids ( 2-21 ), and 5 other known compounds ( 22-26 ) were obtained. Meanwhile, sixteen characteristic peaks were identified from the total alkaloids using HPLC analysis...

In this study, two new ( 1, 13 ) and fourteen known ( 2 - 12, 14 - 16 ) compounds were isolated from the branches and leaves of Daphne retusa. On the basis of chemical evidence and spectral data analysis (UV, ECD NMR, and HR-ESI-MS), the structures of new compounds were elucidated. Furthermore, all compounds have been tested for their inhibitory effects on NO production in LPS-induced RAW 264.7 cells, and compound 3 showed obvious inhibitory effect. Through target screening and molecular docking technology, potential binding targets for compound 3 to exert anti-inflammatory effects have been predicted...

Kinase is an enzyme that helps in the phosphorylation of the targeted molecules and can affect their ability to react with other molecules. So, kinase influences metabolic reactions like cell signaling, secretory processes, transport of molecules, etc. The increased activity of certain kinases may cause various types of cancer, i.e. leukemia, glioblastoma, and neuroblastomas. So, the growth of particular cancer cells can be prevented by the inhibition of the kinase responsible for those cancers. Natural products are the key resources for the development of new drugs where approximately 60% of anti-tumor drugs are being developed with the same including specific kinase dwellers...

Five new sesquiterpenoids, including a campherenane-type ( 1 ), a bergamotane-type ( 2 ), a drimane-type ( 3 ), and two bisabolane-type ( 5-6 ) sesquiterpenoids have been isolated from Biscogniauxia sp. 71-10-1-1. Their structures were determined by spectroscopic analyses, quantum chemical ECD calculations,13 C chemical shifts calculations, and X-ray crystallography. This is the first report of campherenane-type and drimane-type sesquiterpenoids from Biscogniauxia . Furthermore, the anti-inflammatory assays of all compounds are evaluated, and the results showed that compounds 3 and 7 exhibited the effects against the production of the pro-inflammatory cytokine TNF- α ...

A series of novel substituted uracil-1'( N )-acetic acid esters ( 5 - 9 ) and 4-pyridone-1'( N )-acetic acid esters ( 10 - 11 ) of 20(S)-camptothecins (CPTs) have been synthesized by the acylation method. All of these new esters were assayed for in vitro cytotoxicity against five human cancer cell lines A549, Bel7402, BGC-823, HCT-8 and A2780. The in vitro bioassay results showed that all the synthesized compounds 5 - 11 had cytotoxities that were higher than TPT and comparable to CPT on these five tumor cell lines, some of them even showed comparable or superior cytotoxic activity to CPT...

Gastric cancer is one of the common malignant tumors. It is reported that daphne-type diterpenes have inhibitory effects on gastric cancer cells, but the mechanism is still unknown. To explore the detailed mechanism of the anticancer effect of daphne-type diterpenes, we carried out an integrated network pharmacology prediction study and selected an effective component (yuanhuacine, YHC) for the following validation in silico and in vitro . The result showed that daphne-type diterpenes exerted an anti-tumor effect by targeting proto-oncogene tyrosine-protein kinase SRC as well as regulating the Ras/MAPK signaling pathway, which caused the apoptosis and mitochondrial damage in gastric cancer cells...