Sesquiterpene-neolignans from Manglietia hookeri

The comet assay-guided fractionation of the twigs of Manglietia hookeri resulted in the isolation of three sesquiterpene-neolignans, including a new one 5-allyl-2-(4-allyl-phenoxy)-3-[7-(1-hydroxy-1-methyl-ethyl)-1, 4a-dimethyl-decahydro-naphthalen-1-yloxy]-phenol (1), and eudesobovatol A (2) and eudesobovatol B (3), together with three lignans, obovatol (4), honokiol (5) and magnolol (6). Their structures were elucidated on the basis of spectral analysis and by comparison with related literature data. Compounds 1, 4–6 showed a protective effect on UV inductive DNA damage in mice lymphocyte cells, while compound 1 indicated the smallest Olive Tail Moment 7.34 ± 2.09 at 6 × 10^?6 μM.     

A new sesquiterpene from Kalimeris integrifolia

A new sesquiterpene kalinturoside A (1), and 17 known compounds friedelan-3-ol (2), 24-ethyl-5a-cholesta-7, 22(E)-dien-3-one (3), friedelin (4), syringaresinol (5), α-spinasterol (6), ciwujiatone (7), syringic acid (8), scopoletin (9), apocynin (10), 1-(3-hydroxy-4, 5-dimethoxyphenyl)ethan-1-one (11), apigenin (12), 5-hydroxymethylfurfural (13), stigmasterol-3-O-β-d-glucopy-ranoside (14), bidenoside C (15), citrusin (16), irioresinol A (17) and syringaresinol-4-O-β-d-glucopyranoside (18) were isolated from the herbs of Kalimeris integrifolia. The structures of these compounds were elucidated using spectroscopic techniques such as NMR and MS. All of the compounds were isolated from this genus for the first time.     

One new sterpurane sesquiterpene from cultures of the basidiomycete Pholiota nameko

Abstract

One new sterpurane sesquiterpene (1), named (3R,6S,7S,8R,10S)-3,7,14-trihydroxy-1-sterpurene was isolated from cultures of the basidiomycete Pholiota nameko. The structure of new compound was elucidated by extensive spectroscopic. Additionally, a single crystal X-ray diffraction not only confirmed the structure, but also determined the absolute configuration of the new compound. The compound was evaluated for cytotoxicity against five human cancer cell lines, but no significant cytotoxicity were found (IC₅₀ values > 40?μM).     

A new eudesmane sesquiterpene glycoside from Parepigynum funingense

A new eudesmane sesquiterpene glycoside,1α,6β-dihydroxy-5,10-bis-epi-eudesm-4(15)-ene-6-O-β-D-glucopyranoside(2), together with a known analogue compound,1α,6β-dihydroxy-5,10-bis-epi-eudesm-3-ene-6-O-β-D-glucopyranoside(1),were isolated from the roots of Parepigynumfuningense.The structure of 2 was determined by 1D and 2D NMR spectroscopy.Compound 1 was isolated from this plant for the first time.     

A new guaiane sesquiterpene from cultures of the fungus Fulvifomes kanehirae

A new guaiane sesquiterpene (1) was isolated from cultures of the fungus Fulvifomes kanehirae. Its structure was elucidated by spectroscopic methods including extensive 2D-NMR techniques. Meanwhile, the compound was tested for its inhibitory activity against isozymes of 11β-hydroxysteroid dehydrogenases (11β-HSD).     

A new sesquiterpene from the gorgonian coral Menella sp.

A new sesquiterpene named menecubebane B (1) and a known analogue (2) were isolated from the gorgonian coral Menella sp. Their structures were elucidated by the extensive analyses of spectroscopic data and by the comparison with related literature. Cytotoxic effect against both Eca9706 and HeLa cell lines was evaluated, revealing 1 exhibited moderate cytotoxicity against the two cell lines involved with IC₅₀ values being 20.8 and 30.6 μM, respectively.     

Three new eudesmane sesquiterpenes from Artemisia vestita

Three eudesmane sesquiterpene lactones,namely artemivestinolides A–C(1–3),along with three known 11-epimeric lactones(4–6),were isolated from the aerial parts of Artemisia vestita.Their structures were elucidated on the basis of extensive spectroscopic analyses(IR,HR-ESIMS,1D NMR and 2D NMR),and the absolute confgurations were determined by single-crystal X-ray diffraction(with copper radiation).Furthermore,in an in vitro assay,the three new compounds exhibited a moderate inhibition of the lipopolysaccharide(LPS)-induced nitric oxide(NO)production in BV-2 microglial cells.     

A new sesquiterpene from the South China Sea gorgonian coral Subergorgia suberosa

A new sesquiterpene, namely suberosoid (1), was isolated from the South China Sea gorgonian coral Subergorgia suberosa. The chemical structure of 1 was established as an unusual sesquiterpene containing 4-methylenecyclohex-2-enone system, by extensive analyses of NMR spectroscopy and high-resolution mass spectrometry. Suberosoid (1) exhibited cytotoxic effect against HeLa cell lines with IC₅₀ value being 10.6 μM.     

Two new sesquiterpene lactones from the fruits of Illicium jiadifengpi

Two new seco-prezizaane-type sesquiterpenes, 3,4-dehydroneomajucin (1) and 1,2,3,4-tetradehydroneomajucin (2), were isolated from the fruits of Illicium jiadifengpi. The structure of these compounds was determined using 1D and 2D NMR and ESI-MS. The isolates were evaluated for their anti-hepatitis B virus activities on the Hep G2.2.15 cell line. The inhibitory rates of compounds 1 and 2 on the HBeAg and HBsAg expression were 30.08 ± 3.09% and 11.43 ± 1.92% at a concentrations of 68.00 μM and 7.88 ± 1.21% and 16.96 ± 4.24% at a concentration of 68.50 μM, respectively.     

A new nor-sesquiterpene lactone from Ainsliaea fulvioides

A new nor-sesquiterpene lactone ainsliatone A (1) was isolated from the aerial parts of A insliaea fulvioides.Its structure was established by the basis of spectroscopic methods and single-crystal X-ray diffraction analysis.     

Dendocarbin A: a sesquiterpene lactone from Drimys winteri

The natural compound dendocarbin A, C₁₅H₂₂O₃, is a sesquiterpene lactone isolated for the first time from Drimys winteri for var chilensis. The compound crystallizes in the orthorhombic space group P2₁2₁2₁ and its X‐ray crystal structure confirmed the S/R character of the chiral centres at C‐5/C‐10 and C‐9/C‐11, respectively. The α‐OH group at C‐11 was found to be involved in intermolecular hydrogen bonding, defining chains along the <100> 2₁ screw axis.     

A new picrotoxane sesquiterpene from the berries of Baccaurea ramiflora with antifungal activity against Colletotrichum gloeosporioides

Three picrotoxane sesquiterpenes including one new glycoside and two known constituents, sapidolide A (2) and picrotoximaesin (3), were isolated from the berries of Baccaurea ramiflora. The structure of the new sesquiterpene glycoside, ramifloside (1), was elucidated as 2-one-6α-hydroxy-13-nor-11-picrotoxen-3(15β)-olide 10-O-β-d-glucopyranoside on the basis of extensive spectroscopic analysis. Compounds 1–3 exhibited antifungal activity against Colletotrichum gloeosporioides with MICs of 12.5, 12.5 and 50 μg/mL.     

Structural determination of three new germacrane-type sesquiterpene alcohols from curdione by microbial transformation

Five germacrane-type sesquiterpene alcohols obtained from curdione (1) by microbial biotransformation were isolated. Their structures were characterized as (2R)-2beta-hydroxycurdione (2), 1alpha, 10beta-epoxy-11-hydroxycurdione (3), (2S)-2alpha, 11-dihydroxycurdione (4), 11,15-dihydroxycurdione (5) and (3R)-3alpha-hydroxycurdione (6) based on the extensive NMR studies. Among them, 4, 5 and 6 are new compounds.     

Noralashinol A,a new norlignan from stem barks of Syringa pinnatifolia

One new norlignan, namely noralashinol A (1), one known analogue (2), together with seven known lignans (3–9) were isolated from the stem barks of Syringa pinnatifolia. Their structures were elucidated extensively by spectroscopic methods, including mass spectrometry and 1D and 2D NMR spectroscopies. Compound 8 significantly inhibited NO production in LPS-induced BV-2 murine microglia cells with its IC₅₀ value of 20.7 μM, compared to a positive control quercetin with its IC₅₀ value of 15.3 μM.     

Three New Polyketide Metabolites from the Endophytic Fungal Strain Cladosporium tenuissimum LR463 of Maytenus hookeri

Three new polyketide metabolites, the twelve‐membered macrolides (6R,12S)‐6‐hydroxy‐12‐methyloxacyclodoecane‐2,5‐dione ( 1 ), (10S,12S)‐10‐hydroxy‐12‐methyloxacyclododecane‐2,5‐dione ( 2 ), and 4,5‐dihydroxy‐12‐methyloxacyclododecan‐2‐one ( 3 ), were isolated from the endophytic fungal strain Cladosporium tenuissimum LR463 of Maytenus hookeri, together with three known compounds, cladospolide A, cladospolide B, and isocladospolide B. Their structures were elucidated by spectroscopic analysis including 1D‐ and 2D‐NMR experiments, and the absolute configurations of 1 and 2 were determined by the Mosher ester method.     

大叶橐吾中三个新的艾里莫芬型倍半萜

从大叶橐吾的根部分离得到三个新的艾里莫芬型倍半萜(1, 2和3), 经多种波谱方法和单晶X射线衍射确定它们的结构分别为: 6α,15β-环氧-8β-羟基-艾里莫芬-7(11)-烯-8α,12-内酯(1), 7-乙酰基-13β-羧酸-6(7)-烯-降-艾里莫芬烷(2), 艾里莫芬-7(11)-烯-6α,15β-内酯(3). 此外, 对化合物1进行了抗菌和抗癌活性测试.     

Halichonic acid,a new rearranged bisabolene-type sesquiterpene from a marine sponge Halichondria sp.

A new compound, halichonic acid (1), was isolated from a marine sponge Halichondria sp., together with (6R,7S)-7-amino-7,8-dihydro-α-bisabolene (2). The structure of 1 was elucidated by spectroscopic analysis and ECD spectrum calculation to be a rearranged bisabolene-type sesquiterpene having a 3-azabicyclo[3.3.1]nonene moiety. Compound 2 was cytotoxic against HeLa cells with an IC₅₀ value of 50?μM, whereas 1 did not show cytotoxicity even at 50?μM. It is possible that 1 is biosynthesized from farnesyl pyrophosphate and glycine, with rearrangement.     

A new sesquiterpene from Caragana intermediia

A new alloaromadendrane-type sesquiterpene,(-)-alloaromadendrane-3β,9β-diol(1),has been isolated from the aerial part of Caragana intermediia.The structure of (-)-alloaromadendrane-3β,9β-diol(1)was established by spectroscopic methods, including X-ray analysis that provided its relative stereochemistry.Bioassay showed that (-)-alloaromadendrane-3β,9β-diol (1)possesses anti-pyricularia oryzae P-2b activity with MIC value of 10μg/mL.     

Targeted Separation of COX-2 Inhibitor from Pterocephalus hookeri Using Preparative High-Performance Liquid Chromatography Directed by the Affinity Solid-Phase Extraction HPLC System

Pterocephalus hookeri, as a kind of popular traditional Tibetan medicine, is reputed to treat inflammatory related diseases. In the present work, a cyclooxygenase-2 functionalized affinity solid-phase extraction HPLC system was developed and combined with preparative-HPLC for rapidly screening and separating cyclooxygenase-2 ligand from P. hookeri extracts. Firstly, ligands of cyclooxygenase-2 were screened from extracts by affinity solid-phase extraction HPLC system. Then directed by the screening results, the recognized potential active compounds were targeted separated. As a result, the major cyclooxygenase-2 inhibitor of P. hookeri was obtained with a purity of >95%, which was identified as sylvestroside I. To test the accuracy of this method, the anti-inflammatory activity of sylvestroside I was inspected in lipopolysaccharide-induced RAW 264.7 cells. The results show that sylvestroside I significantly suppressed the release of prostaglandin E₂ with dose-dependent, which was in good agreement with the screening result of the affinity solid-phase method. This method of integration of screening and targeted separation proved to be very efficient for the recognition and isolation of cyclooxygenase-2 inhibitors from natural products.     

A new sesquiterpene from the roots of Vladimiria souliei

A new sesquiterpene, named vladimenal (1), was isolated from the roots of Vladimiria souliei. The structure was elucidated on the basis of spectroscopic analysis.