[Lignans from Agrimonia pilosa].

Thirteen lignans were isolated from 60% ethanol extract of Agrimonia pilosa by column chromatography over silica gel, ODS, and MCI and preparative high performance liquid chromatography(HPLC). Their chemical structures were identified by physiochemical properties and spectral data as(7S,8S)-threo-4,7,9,9'-tetrahydroxy-3,3',5'-trimethoxy-8-O-4'-neolignan(1),(+)-4,9,9'-trihydroxy-3-methoxy-3',7-epoxy-8,4'-oxyneolignan(2), dihydrodehydro-diconiferyl alcohol(3), 4,9,9'-trihydroxy-3,3',5-trimethoxy-4',7-epoxy-8,5'-neolignan(4),(-)-secoisolariciresinol(5), 4,7,9,9'-tetrahydroxy-3,3',5'-trimethoxy-8-O-4'-neolignan(6),(+)-isolariciresinol(7), 4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan(8), burselignan(9),(-)-evofolin B(10), icariol A2(11), ciwujiatone(12), and(+)-4″,4-dihydroxy-3,3',3″,3,5,5'-hexamethoxy-7,9';7',9-diepoxy-4,8″;4',8-bisoxy-8,8'-dineolignan-7″,7,9″,9-tetraol(13). Compound 1 was a new compound, and compounds 1-13 were isolated from Agrimonia plant for the first time. This study can enrich the chemical components in A. pilosa and provide material conditions for the follow-up study of its biological activity and the elucidation of its pharmacodynamic substances.

[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.

[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.

[A new labdane-type diterpenoids from Callicarpa nudiflora].

The purpose of the research is to study the bioactive constituents of Callicarpa nudiflora. From the 65% ethanol extract of C. nudiflora leaves, ten compounds were isolated by macroporous adsorption resin, Sephadex LH-20, ODS, silica gel, and preparative HPLC. These compounds were identified as callicapene M6(1), sterebin A(2), isomartynoside(3), crenatoside(4), luteolin-7-O-neohesperidoside(5), apigenin-7-O-ß-D-neohesperidoside(6), isoacteoside(7), acteoside(8),(7R)-campneoside I(9), and(7S)-campneoside I(10) on the basis of NMR, HR-ESI-MS, and optical rotation data. Compound 1 was obtained as a new compound. Compounds 2 and 4 were isolated from the genus Callicarpa for the first time. Compounds 9 and 10 were isolated from C. nudiflora for the first time.

[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.

[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.

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.

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.

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.