Characteristic cembrane-type diterpenoids with nitric oxide inhibitory activity from the gum resin of Boswellia carterii Birdw.

Five new characteristic cembrane-type diterpenoids (olibacartiols A-E, 1-5) were acquired from the gum resin of Boswellia carterii. The structures of these diterpenoids were characterized by detailed spectroscopic analysis, and compounds 1-3 were unambiguously confirmed by single-crystal X-ray diffraction experiments. The anti-inflammatory activities of the isolated compounds were evaluated using LPS-induced BV2 cell model and compounds 2-5 showed moderate NO inhibitory effects with IC50 values of 8.84 ± 1.02, 9.82 ± 1.95, 9.75 ± 2.24, and 7.39 ± 1.24 µM, respectively.

[Chemical constituents of Lindera aggregata and their bioactivities: a review].

The medicinal Lindera aggregata(Lindera, Lauraceae) boasts abundant resources, which is widely used in clinical settings. It has been found that the main chemical constituents of this medicinal species are sesquiterpenoids, alkaloids, sesquiterpenoid dimers, flavonoids, and phenolic acids. Some unreported novel structures, including lindenane-type sesquiterpene dimers and trimers, have been discovered from L. aggregata in recent years. The extracts and active components of L. aggregata have anti-tumor, anti-inflammatory, antalgic, liver-protecting, antioxidant, lipid-lowering, and glucose-lowering activities, and their mechanisms of action have been comprehensively investigated. This study summarizes the research on the chemical constituents and bioactivities of L. aggregata over the past decade, which is expected to serve as a reference for the future research and utilization of L. aggregata.

Correlations between flavor and fermentation days and changes in quality-related physiochemical characteristics of fermented Aurantii Fructus.

The effects of different fermentation times (0, 1, 2, 3, 4, and 5 days) on the physicochemical properties and flavor components of fermented Aurantii Fructus (FAF) were evaluated. Component analysis identified 66 compounds in positive ion mode and 32 compounds in negative ion mode. Flash GC e-nose results showed that propanal, (+)-limonene and n-nonanal may be the flavor characteristic components that distinguish FAF with different fermentation days. Furthermore, we found that the change of total flavonoid content was closely related to colony growth vitality. The total flavonoid content of FAF gradually decreased from 3rd day and then increased from 5th day (3rd day: 0.766 ± 0.123 mg/100 g; 4th day: 0.464 ± 0.001 mg/100 g; 5th day: 0.850 ± 0.192 mg/100 g). Finally, according to antioxidant activity correlation analysis, meranzin, (+)-limonene and total flavonoids were found to be the key substances affecting the fermentation days of FAF. Overall, the optimal fermentation time for FAF was 4 days.

[Research progress on chemical constituents and biological activities of Sarcandra glabra].

Sarcandra glabra, a medicinal plant in family Chloranthaceae, has been taken as an important raw material for multiple Chinese patent drugs due to its diverse indications. Considering the diversified chemical constituents and rich biological activities of S. glabra, numerous phytochemical and pharmacodynamic investigations were conducted to explore the material basis for its medicinal use. It has been found that its main chemical constituents were sesquiterpenoids, sesquiterpenoid polymers, phenolic acids, coumarins, and flavonoids. As revealed by pharmacological research, it possesses multiple biological activities like anti-inflammation, anti-bacteria, anti-tumor, anti-oxidation, and neuroprotection. Some unreported novel structures, including polymers of lindenane sesquiterpenes and monoterpenes, sesquiterpene trimers, and adducts of flavonoids and monoterpenes, have been identified from S. glabra in recent years. Moreover, biological studies relating to its anti-tumor, anti-inflammatory, and anti-oxidant activities have been deepened. This paper reviewed the chemical constituents and bioactivities of S. glabra explored over the past ten years, so as to provide a scientific basis for further development and utilization of this plant.

Three pairs of sesquiterpene enantiomers from Chloranthus multistachys pei.

Phytochemical investigation on the whole plant of Chloranthus multistachys pei (Chloranthaceae) afforded three pairs of new sesquiterpene enantiomers (+)/(-)-chlorantene M [(+)/(-)-1], (+)/(-)-chlorantene M1 [(+)/(-)-2] and (+)/(-)-chlorantene N [(+)/(-)-3]. The structures of new compounds were determined through spectroscopic techniques (HR-ESI-MS, 1 D and 2 D NMR), besides, their absolute and relative configurations were established by using Single-crystal X-ray diffraction analysis and CD spectrum. The anti-inflammatory potential of all compounds was evaluated by applying LPS induced RAW 264.7 macrophage inflammatory model, and the results were that none of these compounds showed activity (IC50 > 100 µM).[Formula: see text].

Chlomultiols A-L, sesquiterpenoids from Chloranthus multistachys and their anti-inflammatory activities.

Twelve undescribed sesquiterpenoids, named chlomultiols A-L, involving three lindenane sesquiterpenoid dimers, three eudesmane sesquiterpenoids, three guaiane sesquiterpenoids, and three cadinane sesquiterpenoids, along with four known compounds, were obtained from the whole plant of Chloranthus multistachys. Their structures were determined through spectroscopic techniques (HRESIMS, 1D and 2D NMR). In addition, the absolute and relative configurations of the undescribed compounds were established by using single crystal X-ray crystallography, NOESY and CD spectroscopy. The inhibitory effects of chlomultiols A-M on the production of nitric oxide in RAW 264.7 cells induced by lipopolysaccharide were evaluated. Chlomultiols A-C, and chlomultiols K-L showed moderate anti-inflammatory activities with IC50 values of 3.34 ± 0.73, 15.06 ± 1.08, 13.13 ± 3.99, 6.63 ± 1.11, and 16.16 ± 1.88 µM, respectively.

[Chemical constituents of sesquiterpenes from Chloranthus multistachys].

With repeated silica gel, octadecyl silica(ODS), and Sephadex LH-20 column chromatography, normal-phase and reverse-phase high performance liquid chromatography(HPLC), etc., a pair of new enantiomers and 5 known compounds were separated from the 95% ethanol extract of Chloranthus multistachys. These compounds were identified by the nuclear magnetic resonance spectroscopy(including 1 D-NMR and 2 D-NMR), single-crystal X-ray diffraction, circular dichroism(CD) spectroscopy, mass spectrometry(MS), and some other methods as(1R,4R,5R,8S,10R)-chloraeudolide H(1 a),(1S,4S,5S,8R,10S)-chloraeudolide H(1 b), hydroxyisogermafurenolide(2), 4α-hydroxy-5α,8ß(H)-eudesm-7(11)-en-8,12-olide(3), chloraniolide A(4), chlorantene D(5), 4α,8ß-dihydroxy-5α(H)-eudesm-7(11)-en-8,12-olide(6). Compounds 1 a and 1 b are a pair of new eudesmane-type sesquiterpene enantiomers, and compounds 2-4 were isolated from C. multistachys for the first time.

[Research progress on chemical constituents from Chloranthus plants and their biological activities].

The genus Chloranthus has 13 species and 5 varieties in China, which can be found in the southwest and northeast regions. Phytochemical studies on Chloranthus plants have reported a large amount of terpenoids, such as diterpenoids, sesquiterpenoids, and sesquiterpenoid dimers. Their anti-inflammation, anti-tumor, antifungal, antivirus, and neuroprotection activities have been confirmed by previous pharmacological research. Herein, research on the chemical constituents from Chloranthus plants and their biological activities over the five years was summarized to provide scientific basis for the further development and utilization of Chloranthus plants.

Discovery of eudesmane-type sesquiterpenoids with neuroprotective effects from the roots of Chloranthus serratus.

Seven eudesmane-type sesquiterpenoids, including three pairs of racemic compounds (1a-3a and 1b-3b) and a sesquiterpenoid lactone (4), were obtained from the roots of Chloranthus serratus. The structures of these sesquiterpenoids were characterized based on spectroscopic analyses, ECD calculations, and X-ray diffraction experiment. Neuroprotection assays of the isolated eudesmane-type sesquiterpenoids were conducted on H2O2 damaged PC12 cells. At the concentration of 10 µM, compounds 1b and 4 increased cell viability from 54.8 ± 3.3% to 76.8 ± 2.3 and 72.7 ± 8.2%, respectively.

[A new sesquiterpene from Chloranthus henryi].

Eight sesquiterpenes were isolated and purified from the ethanol extract of Chloranthus henryi by column chromatographies over silica gel, ODS and Sephadex LH-20,and preparative HPLC. Their chemical structures were established by spectral data and physiochemical properties as(1S,6S,8S,10R)-8-ethoxy-10-methoxychlomultin C(1),tianmushanol(2),multistalide A(3),myrrhterpenoid N(4),1α,9α-dihydroxy-8,12-expoxy-eudesma-4,7,11-trien-6-one(5),4ß,10α-aromadendranediol(6),oplopanone(7),10α-hydroxycadinan-4-en-3-one(8). Among them, compound(1) was a new compound, and compounds 2-8 were isolated from Chloranthus henryi for the first time.

Sesquiterpenoids with neuroprotective activities from the Chloranthaceae plant Chloranthus henryi.

A rare sesquiterpenoid possessing a 6/6 bicyclic system fused with two clustered furan units and a pair of guaiane-type sesquiterpenoids were acquired from the roots of Chloranthus henryi. Their structures with absolute configurations were characterized with spectroscopic data, ECD, and X-ray diffraction analysis. All three sesquiterpenoids showed moderate neuroprotective activities on PC12 cells damaged with hydrogen peroxide.

[A new cembranoid diterpene from Olibanum].

Five compounds were isolated from the alcohol extract of Olibanum by MCI, silica gel, ODS, and Sephadex LH-20 column chromatographies and preparative high-performance liquid chromatography(HPLC). On the basis of spectral data and literature data, the compounds were identified as:(1S,3R,4S,7R,11S,12R)-1:12,4:7-diepoxisonane-8(19)-ene-3,11-diol(1), boscartin A(2),(+)-resinolin(3),(+)-5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one(4), and acerogenin A(5). Compound 1 is a new compound, and compounds 3-5 were isolated from Olibanum for the first time. The structure of compound 1 was determined by spectroscopic analysis and single-crystal X-ray diffraction. Compounds 1 and 2 were tested for PC12 neurotoxicity, and the results showed that they were both safe compounds.

Neuroprotective racemic germacranolides from the roots of Chloranthus henryi.

Three pairs of new germacranolides, (+)/(-)-chlogermacrones A-C, along with two known analogues were obtained from the roots of Chloranthus henryi. Spectroscopic techniques and single-crystal X-ray crystallographic analyses were used for the structure elucidation of the compounds. All of the isolated compounds were tested for their neuroprotective effects on H2O2 damaged PC12 cells, compounds 3 and 5 increased cell viability from 43.4 ± 1.3% to 99.6 ± 8.7 and 68.1 ± 4.8% at 10 µM, respectively.

Dihydroagarofuran sesquiterpenoids esterified with organic acids from the leaves of Tripterygium wilfordii.

Six new and one known dihydroagarofuran sesquiterpenoids esterified with organic acids were obtained from the leaves of Tripterygium wilfordii. Spectroscopic techniques (UV, IR, MS, NMR, ORD and CD) were used for the structure elucidation of the compounds. The structures of compounds 1 and 2 were confirmed by X-ray single crystallographic analyses. The inhibitory effects on NO production in LPS-induced macrophages of 1-7 were conducted. At 10 µmol/L, compounds 1, 2 and 7 showed moderate inhibitory effects on NO production in LPS-induced macrophages with inhibitory rate at 31.2 ±â€¯3.6, 40.9 ±â€¯4.3, and 66.79 ±â€¯3.1%, respectively.

Cytotoxic 9,19-cycloartane type triterpenoid glycosides from the roots of Actaea dahurica.

Ten undescribed 9,19-cycloartane type triterpenoid glycosides (cimdahxynoside A-J) and five known analogues were obtained from the phytochemical research on the roots of Actaea dahurica (syn. Cimicifuga dahurica). All compounds were characterised by spectroscopic experiments, chemical method and X-ray Single-crystal diffraction analysis. Cimdahxynoside A represented the first X-ray crystallography of 9,19-cycloartane type triterpenoid diglycoside. The cytotoxicity of all compounds were tested against five human cancer cell lines. Cimdahxynoside F showed significant cytotoxicity, with IC50 values between 6.6 and 9.9 µM.

Nototronesides A-C, Three Triterpene Saponins with a 6/6/9 Fused Tricyclic Tetranordammarane Carbon Skeleton from the Leaves of Panax notoginseng.

Three triterpene saponins, nototronesides A-C (1-3), possessing an unprecedented 6/6/9 fused tricyclic tetranordammarane core, were isolated from the leaves of Panax notoginseng. Their structures were elucidated on the basis of spectroscopic data, and the structure of sapogenin (1a) was further confirmed by X-ray crystallography. The existence of 1-3 adds a new dimension to the diversity of the triterpene family. Moreover, compound 2 showed a moderate neuroprotective effect on serum deficiency-induced cellular damage in PC12 cells.

Hepatoprotective glycosides from the rhizomes of Imperata cylindrical.

Three new C-methylated phenylpropanoid glycosides (1, 2), a new 8-4'-oxyneolignan (3), together with two known analogs (4, 5), were isolated from the rhizomes of Imperata cylindrical Beauv. var. major (Nees) C. E. Hubb. Their structures were determined by spectroscopic and chemical methods. Compounds 1, 2, and 5 (10 µM) exhibited pronounced hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in vitro assays. Furthermore, their antioxidant activities against Fe2+-cysteine-induced rat liver microsomal lipid peroxidation and the effects on the secretion of TNF-α in murine peritoneal macrophages (RAW264.7) induced by lipopolysaccharides were evaluated.

Magterpenoids A-C, Three Polycyclic Meroterpenoids with PTP1B Inhibitory Activity from the Bark of Magnolia officinalis var. biloba.

Magterpenoid A (1), possessing a rare 4,6,11-trioxatricyclo[5.3.1.01,5]undecane framework with an irregular monoterpenoid moiety, magterpenoid B (2), with an unprecedented 6/6/6/6 polycyclic skeleton, and magterpenoid C (3), a novel terpenoid quinone with a C6-C3 unit, were isolated from the bark of Magnolia officinalis var. biloba. Plausible biogenetic pathways of 1-3 are presented. Compounds 1 and 3 exhibited significant PTP1B inhibitory activities with IC50 values of 1.44 and 0.81 µM, respectively.

Triptergosidols A-D, nerolidol-type sesquiterpene glucosides from the leaves of Tripterygium wilfordii.

Four new nerolidol-type sesquiterpene glucosides, triptergosidols A-D (1-4) were isolated from the leaves of Tripterygium wilfordii. Three aglycones, named triptergerols A (1a), B (2a), and C (3a), were acquired by enzymatic hydrolysis of 1-3. The structures of nerolidol-type sesquiterpenes were elucidated on base of kinds of spectroscopic analysis, and their absolute configurations were determined by CD method. In addition, compounds 1-4 were tested for cytotoxicity against two cell lines and inhibitory effects against NO production in RAW264.7 macrophage.

Neuroprotective Dihydroagarofuran Sesquiterpene Derivatives from the Leaves of Tripterygium wilfordii.

Thirteen dihydroagarofuran derivatives, including 12 new sesquiterpenoid esters and one known sesquiterpenoid alkaloid, were obtained from the leaves of Tripterygium wilfordii. Spectroscopic techniques and the ECD method were used for the structure elucidation of the compounds. The structures of compounds 1 and 8 were confirmed by single-crystal X-ray crystallographic analyses. Compounds 8, 9, 11, 12, and 13 increased cell viability of the okadaic acid treated PC12 cells from 60.4 ± 23.0% to 72.4 ± 14.1, 71.5 ± 11.5, 75.7 ± 15.6, 81.2 ± 13.1, and 86.2 ± 25.5% at 10 µM, respectively.