Dichapetalin-type triterpenoids from Dichapetalum longipetalum and their anti-inflammatory activity.

A phytochemical research on the twigs of Dichapetalum longipetalum (Turcz.) Engl. Resulted in five undescribed dichapetalin-type triterpenoids 1-5.

Calix[4]arene Bridge Mononitration with -Butyl Nitrite: Synthesis of Bridging Chiral --Butylcalix[4]arene with a Mononitro Bridge Substituent.

To explore the reaction universality of bridge nitration, the mononitration of different butylcalix[4]arene derivatives was executed with -butyl nitrite as a nitration reagent. The effects of calix[4]arene conformations, substituents on the lower rim, and reaction conditions on bridge mononitration are systematically studied. The bridge nitration of butylcalix[4]arene derivatives in 1,3-alternate, 1,2-alternate, and partial cone conformations can be smoothly executed while that of butylcalix[4]arene derivatives strictly regulated in a cone conformation cannot.

Antifouling activity of terpenoids from the corals and sp. against the bryozoan .

Marine natural products are promising sources of green antifoulants. Here, a new compound () was isolated from the soft coral . This compound, another nine cembranoids (-) from , and three eunicellin-type diterpenoids (-) from the gorgonian sp.

Longipetalol A: A Highly Modified Triterpenoid from .

Longipetalol A () is an unprecedented highly modified triterpenoid with a unique 1,2--3-(2-oxo-phenylethyl)-17α-13,30-cyclodammarane skeleton, featuring an acetal-lactone fragment. It was isolated from along with two additional derivatives, namely, longipetalols B () and C (). Their structures were elucidated using spectroscopic analyses combined with single-crystal X-ray diffraction.

Nine new dichapetalin-type triterpenoids from the twigs of Dichapetalum gelonioides (Roxb.) Engl.

Nine previously undescribed dichapetalin-type triterpenoids (1-9), along with 12 reported compounds (10-21), were isolated from the twigs of Dichapetalum gelonioides. Their chemical structures were mainly elucidated by comprehensive analysis of HRMS, 1D and 2D NMR spectroscopic data. The absolute configuration of compound 1 was further determined based on single-crystal X-ray diffraction.

Mononitration of a Calix[4]arene Methylene Bridge: Synthesis and Preliminary Catalysis Performances of Bridging Chiral --Butylcalix[4]arenes with a Monoamino Bridge Substituent in a 1,3-Alternate Conformation.

In order to prepare bridging chiral --butylcalix[4]crown-5 with a mononitro bridge substituent in a 1,3-alternate conformation, a mononitration method of calix[4]arene bridging methylene has been first developed with -butyl nitrite as a nitration reagent. The effects of solvent, reaction temperature, reaction time, and nitration reagent dosage on bridge mononitration have been deeply explored to obtain an optimal nitration condition. The facile nitration presents a new key for calix[4]arene bridge derivatization.

Steroidal saponins from the rhizome of Polygonatum sibiricum.

Four new steroidal saponins, 3-O-β-D-glucopyranosyl(1→4)-β-D-fucopyranosyl -(25R)-spirost-5-en-3β,17α-diol (1), 3-O-β-D-glucopyranosyl(1→4)-β-D- fucopyranosyl-(25S)-spirost-5-en-3β,17α-diol (2), 3-O-β-D-glucopyranosyl(1→2) -β-D-glucopyranosyl(1→4)-β-D-fucopyranosyl-(25R)-spirost-5-en-3β,17α-diol (3), 3-O-β-D-glucopyranosyl(1→4)-β-D-fucopyranosyl-(25R/S)-spirost-5-en-3β,12β-diol (4), together with five known steroidal saponins were isolated from the ethanolic extract of the rhizome of Polygonatum sibiricum. Chemical structures of these compounds were elucidated by spectroscopic techniques. Anti-inflammatory activities of these new compounds were evaluated.

1,6-O,O-Diacetylbritannilactone Inhibits Eotaxin-1 and ALOX15 Expression Through Inactivation of STAT6 in A549 Cells.

1,6-O,O-Diacetylbritannilactone (OODBL), a plant sesquiterpene lactone, was previously reported to show multiple pharmacological effects such as anti-cancer and anti-inflammatory activities. In this study, we investigated the anti-inflammatory effect of OODBL on interleukin (IL)-4-induced signal transducer and activator of transcription 6 (STAT6) signaling pathway in human lung A549 cells. We found that OODBL dramatically inhibited IL-4-induced messenger RNA (mRNA) expression of eotaxin-1 and arachidonate 15-lipoxygenase-1 (ALOX15) in a dose-dependent manner.

1,6-O,O-Diacetylbritannilactone suppresses activation of mast cell and airway hyper-responsiveness.

Mast cells play critical roles in allergic disorders such as atopic dermatitis and allergic asthma. The aim of this study was to investigate the anti-inflammatory and anti-asthmatic activities of 1,6-O,O-diacetylbritannilactone (OODBL) isolated from Inula japonica Thunb. (I.

Jaspiferin G, a new isomalabaricane-type triterpenoid from the sponge Jaspis stellifera.

A new isomalabaricane-type triterpenoid, jaspiferin G (1), together with four known isomalabaricane-type triterpenoids, isogeoditin A (2), 13-(E)-isogeoditin A (3), jaspolide E (4), and 22,23-dihydrostellettin D (5), was isolated from the marine sponge Jaspis stellifera. The structures were elucidated on the basis of spectroscopic data ((1)H and (13)C NMR, (1)H(-1)H COSY, HSQC, HMBC, and ROESY) and mass spectrometry.

Two new eunicellin diterpenoids from the East China Sea gorgonian Muricella sp.

A phytochemical investigation on gorgonian Muricella sp. from East China Sea resulted in the isolation of eight eunicellin diterpenoids including two new ones, muricellins A-B (1, 2). Chemical structures of these compounds were elucidated by spectroscopic techniques (1D and 2D NMR and MS) and by comparison with data reported in the literature.

[Anti-tumor metastatic constituents from Rhodiola wallichiana].

To study the anti-tumor metastatic constituents in Rhodiola wallichiana (HK) S H Fu var Cholaensis (Praeg) S H Fu, chemical constituents were isolated and purified by repeated column chromatography (silica gel, Toyopearl HW-40C and preparative HPLC). Their structures were elucidated on the basis of spectral data analysis. The anti-tumor metastasis assay was applied to evaluate the activities of the isolated compounds.

IVSE, isolated from Inula japonica,suppresses LPS-induced NO production via NF-κB and MAPK inactivation in RAW264.7 cells.

Aims: Our previous study showed that the extract of Inula japonica Thunb. (I. japonica) has anti-inflammatory and anti-asthmatic activities.

Three new polyunsaturated lipids from a Guangxi marine sponge Haliclona sp.

Three new polyunsaturated lipids, (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraen-3-one (1), (6Z,9Z,12Z,15Z)-1-bromooctadeca-6,9,12,15-tetraen-3-one (2), and (Z)-ethyl docos-5-enoate (3), together with two known polyunsaturated lipids, 4(Z),7(Z),10(Z)-tridecatrienoic acid (4) and (6Z,9Z,12Z,15Z)-octadeca-1,6,9,12,15-pentaen-3-one (5), were isolated from the marine sponge Haliclona sp., which was collected from Guangxi, using HSCCC and HPLC methods. Chemical structures of the five compounds were elucidated by spectroscopic techniques.

Inhibitory Effects of JEUD-38, a New Sesquiterpene Lactone from Inula japonica Thunb, on LPS-Induced iNOS Expression in RAW264.7 Cells.

We isolated JEUD-38, a new sesquiterpene lactone from Inula japonica Thunb. JEUD-38 dramatically attenuated lipopolysaccharide (LPS)-induced nitric oxide (NO) production. Consistent with this finding, the protein expression of inducible nitric oxide synthase (iNOS) was blocked by JEUD-38 in a concentration-dependent manner.

In vitro antitumor activity of stellettin B, a triterpene from marine sponge Jaspis stellifera, on human glioblastoma cancer SF295 cells.

Stellettin B was isolated from marine sponge Jaspis stellifera. In vitro antitumor activities were investigated on 39 human cancer cell lines. Stellettin B exhibited highly potent inhibition against the growth of a human glioblastoma cell line SF295, with a GI50 of 0.

Jaspiferins C-F, four new isomalabaricane-type triterpenoids from the South China Sea sponge Jaspisstellifera.

A chemical investigation of marine sponge Jaspis stellifera, collected from the South China Sea, led to the isolation of four new isomalabaricane-type triterpenoids, jaspiferins C-F (1-4). The structures of those compounds were elucidated by extensive spectroscopic methods. Jaspiferin C (1), which has the six-membered carbon ring at the side chain, was discovered for the first time from the isomalabaricane-type triterpenoids.

[Anti-inflammatory constituents from Inula japonica].

Chemical constituents of Inula japonica were isolated and purified by repeated column chromatographies, over silica gel, and Toyopearl HW-40, and preparative HPLC. On the basis of spectral data analysis, including NMR and MS data, the structures of the isolates were elucidated and their anti-inflammatory activities were assayed. Fifteen compounds were isolated from the ethyl acetate extract of I.

Anti-inflammatory terpenes from flowers of Inula japonica.

Five new terpenes (1-5) and ten known compounds (6-15) were isolated from Inula japonica, and their structures were identified by spectroscopic analysis. Compounds 3 and 14 showed positive inhibitory effects on nitric oxide production. Furthermore, compound 14 suppressed both leukotriene C4 synthesis and degranulation in c-kit ligand-induced bone marrow-derived mast cells.

Antitumor metastasis pregnane alkaloids from Pachysandra terminalis.

Three new pregnane alkaloids, named terminamines H-J (1-3), together with two known alkaloids (4 and 5), were isolated from the ethanol extract of Pachysandra terminalis. The structures of isolated compounds were elucidated by spectroscopic methods, including (1)H and (13)C NMR, 2D NMR, and HR-ESI-MS. Compounds 1, 4, and 5 revealed significant anti-metastasis activities.

Novel polyhydroxylated steroids from the East China Sea gorgonian Echinogorgia sassapo reticulata with suppressive activity of leukotriene C4 generation and degranulation in bone marrow-derived mast cells.

The gorgonian Echinogorgia sassapo reticulata contains two new bioactive polyhydroxylated steroids, sassapols A (1), B (2), and five related known compounds (3-7). Compound 6 has been encountered for the first time in natural sources. The structures of these new compounds were defined by spectroscopic analysis.

Flavonoids from Tetrastigma obtectum enhancing glucose consumption in insulin-resistance HepG2 cells via activating AMPK.

Four new flavonoids including three C-glycosidic flavonoids, named tetrastigma A-D (1-4) and five known flavones (5-9) were isolated from the herbs of Tetrastigma obtectum (Wall.) Planch. The structures of 1-4 were elucidated by 1D- and 2D-NMR and HR mass spectrometric methods.

[Chemical constituents from Pachysandra terminalis].

To study chemical constituents from Pachysandra terminalis. By repeated column chromatography, including silica gel, Toyopearl HW-40, and preparative HPLC, four new (14) and one known (5) compounds were isolated and purified. On the basis of spectral data analysis, the structure of isolated compounds were elucidated as follow: 2-methyl-3-methylenepentane-1, 2, 5-triol (1), 4-methyl-3-methylenepentane-1, 2, 5-triol (2), 4-methyl-3-methylenepentane-1, 2, 5-triol-5-O-beta-D-glucopyranoside (3), 4-methyl-3-methylenep- entane-1, 2, 5-triol-1-O-beta-D-glucopyranoside (4), (7S, 8R, 8' R)-(+)-lariciresinol-9-O-beta-D-glucopyrano-side (5).

[Chemical constituents contained in Tetraena mongolica].

To study chemical constituents contained in Tetraena mongolica. Chemical constituents were separated and purified by using such methods as silica gel, Toyopearl HW-40C and HPLC preparative chromatography. Their structures were identified by organic spectral method.

Four new triterpenes from the endemic relict shrub Tetraena mongolica.

A chemical investigation of the endemic relict shrub Tetraena mongolica led to the isolation of four new triterpenes: 11α,12α:13β,28-diepoxyoleanane-3β-yl trans-caffeate (1), 3β-hydroxy-11α,12α-epoxyoleanane-28-al (2), olean-11-en-28-al-3β-yl trans-caffeate (3), and 28-acetoxy-olean-12-en-3β-yl trans-caffeate (4). Their structures were elucidated by extensive spectroscopic methods.