In a continuing search for biological natural products with structure diversity from traditional Chinese herbs, five new sesquineolignans (1-5) were isolated from an ethyl acetate extract of the twigs of Litsea cubeba. Their structures were elucidated based on MS, 1D and 2D NMR spectroscopic data, as well as experimental electronic circular dichroism (ECD) spectra. Compounds 1-5 showed moderate inhibitory effects against LPS-induced NO production in RAW264.7 macrophages, with IC
Litsea ; Macrophages ; Molecular Structure

Cycloaddition Reaction ; Molecular Structure ; Alkadienes

To study chemical constituents of Polygonatum odoratum (Mill.) Druce, the compounds were separated with column chromatography and HPLC. On the basis of physicochemical properties and spectral data, their structures were confirmed. Nine compounds were isolated and identified as 5,7-dihydroxy-6-methoxyl-8-methyl-3-(2',4'-dihydroxybenzyl)chroman-4-one (1), 5,7-dihydroxy-6-methyl-3-(2',4'-dihydroxybenzyl)chroman-4-one (2), 5,7-dihydroxy-6-methoxyl-8-methyl-3-(4'-methoxybenzyl)chroman-4-one (3), disporopsin (4), chrysoeriol (5), 5,4'-dihydroxy-7-methoxy-6-methylflavone (6), N-trans-feruloyltyramine (7), N-trans-feruloyloctopamine (8), and (+)-syringaresinol (9). Compounds 1-3 are new homoisoflavanones. Compounds 4-9 are isolated from this plant for the first time.
Isoflavones ; isolation & purification ; Molecular Structure ; Polygonatum ; chemistry

Eight C_(19)-diterpenoid alkaloids( 1-8) were isolated from the ethyl acetate soluble fraction of 95% ethanol extract of the ground roots of Aconitum austroyunnanense through various column chromatographies on silica gel,ODS,Sephadex LH-20 and MCI gel.Their structures were elucidated as 14α-benzoyloxy-13β,15α-dihydroxy-1α,6α,8β,16β,18-pentamethoxy-19-oxoaconitan( 1),N-deethylaconitine( 2),spicatine B( 3),leucanthumsine A( 4),acofamine B( 5),macrorhynine B( 6),aconitilearine( 7),and ambiguine( 8) based on their chemical and physicochemical properties and spectroscopic data. Compound 1 was a new compound and alkaloids 2-8 were isolated from this plant for the first time. Some isolated alkaloids were tested in vitro for cytotoxic potential by employing the MTT method. As a result,alkaloid 1 exhibited weak cytotoxic activity against three tested tumor cell lines( A-549,He La,and Hep G2) with IC_(50) values less than 20 μmol·L~(-1).
Aconitum ; Alkaloids ; Diterpenes ; Molecular Structure ; Plant Roots

The tirucallane-type triterpenoids, composed of six isoprene units, belong to a group of tetracyclic triterpenoids. Although the naturally-derived tirucallane-type triterpenoids were found in a small amount, the kind of compounds showed various structures, which consist of apo-type, linear said-chain-type and cyclolike said-chain-type and broad bioactivities, such as cytotoxicity, anti-inflammation, antioxidation and anti-plasmin, etc. This paper summarized origins, structures and bioactivities of tirucallane-type triterpenoids in recent ten years. The future research and exploration of tirucallane-type triterpenoids were discussed and prospected.
Antineoplastic Agents, Phytogenic ; Molecular Structure ; Triterpenes

Hypericum species are distributed widely in China, especially in the southwest. This genus is rich in species types in China, including 55 species and 8 subspecies. The main chemical constituents of Hypericum species are flavonoids, xanthones and polycyclic polyprenylated acylphloroglucinols(PPAPs). PPAPs are characterized by polycyclic and branched-chain substitutions in their structures, which make their structure types diverse. Moreover, they have been found to have antitumor, antiviral, antibacterial, anti-inflammatory and other biological activities. This research classified and summarized 344 polycyclic polyprenylated acylphloroglucinols from Hypericum plants in order to provide a scientific basis for further development and utilization of PPAPs from the genus.
Flavonoids ; Hypericum ; Molecular Structure ; Phloroglucinol/pharmacology* ; Xanthones

Dicarabrols B and C (1 and 2), two new carabrane sesquiterpenoid dimers, along with one new carabrane sesquiterpenoid (3) were isolated from the whole plant of Carpesium abrotanoides L. Their full structures were established by extensive analysis of HR-ESI-MS and NMR spectroscopic data, and time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculations. Dicarabrol B possesses a novel C
Asteraceae ; Circular Dichroism ; Humans ; Molecular Structure ; Sesquiterpenes

OBJECTIVE: To create a protocol that could be used to construct chemical information database from scientific literature quickly and automatically. METHODS: Scientific literature, patents and technical reports from different chemical disciplines were collected and stored in PDF format as fundamental datasets. Chemical structures were transformed from published documents and images to machine-readable data by using the name conversion technology and optical structure recognition tool CLiDE. In the process of molecular structure information extraction, Markush structures were enumerated into well-defined monomer molecules by means of QueryTools in molecule editor ChemDraw. Document management software EndNote X8 was applied to acquire bibliographical references involving title, author, journal and year of publication. Text mining toolkit ChemDataExtractor was adopted to retrieve information that could be used to populate structured chemical database from figures, tables, and textual paragraphs. After this step, detailed manual revision and annotation were conducted in order to ensure the accuracy and completeness of the data. In addition to the literature data, computing simulation platform Pipeline Pilot 7.5 was utilized to calculate the physical and chemical properties and predict molecular attributes. Furthermore, open database ChEMBL was linked to fetch known bioactivities, such as indications and targets. After information extraction and data expansion, five separate metadata files were generated, including molecular structure data file, molecular information, bibliographical references, predictable attributes and known bioactivities. Canonical simplified molecular input line entry specification as primary key, metadata files were associated through common key nodes including molecular number and PDF number to construct an integrated chemical information database. RESULTS: A reasonable construction protocol of chemical information database was created successfully. A total of 174 research articles and 25 reviews published in Marine Drugs from January 2015 to June 2016 collected as essential data source, and an elementary marine natural product database named PKU-MNPD was built in accordance with this protocol, which contained 3 262 molecules and 19 821 records. CONCLUSION This data aggregation protocol is of great help for the chemical information database construction in accuracy, comprehensiveness and efficiency based on original documents. The structured chemical information database can facilitate the access to medical intelligence and accelerate the transformation of scientific research achievements.
Data Mining ; Databases, Chemical ; Molecular Structure ; Software

Due to their fascinating chemical structures and extensive pharmacological activities, polycyclic polyprenylated acylphloroglucinols(PPAPs) have become one of the current research hotspots of natural products. In particular, some of the PPAPs not only have novel non-traditional skeleton types, but also contain more unknown possible activities, which are of great significance for the development of lead compounds. The structure, source, biosynthetic pathway and pharmacological activities of PPAPs with non-traditio-nal skeleton types isolated and identified in recent years are reviewed, in order to provide references for further research on such compounds.
Biological Products ; Hypericum ; Molecular Structure ; Phloroglucinol

The combination of normal-phase silica gel column chromatography, octadecyl silica(ODS) column chromatography, semi-preparative high performance liquid chromatography(HPLC), etc. was employed to isolate and purify the chemical components from Euphorbia resinifera, and 7 triterpenoids were separated from the ethanol extract of the medicinal materials. Their structures were identified by various spectroscopy methods as cycloartan-1,24-diene-3-one(1), cycloartan-1,24-diene-3-ol(2), 3β-hydroxy-lanosta-8,24-diene-11-one(3), lnonotusane C(4), eupha-8,24-diene-3β-ol-7,11-dione(5), eupha-24-methylene-8-ene-3β-ol-7,11-dione(6), and eupha-8,24-diene-3β,11β-diol-7-one(7). Compounds 1 and 2 are new compounds, and compound 3 is obtained from nature for the first time.
Drugs, Chinese Herbal ; Euphorbia ; Molecular Structure ; Triterpenes