Sesquiterpenoids and iridoid glycosides from Valeriana fauriei.

A new guaiane sesquiterpenoid glycoside together with known sesquiterpenoids and iridoid glycosides have been isolated from the rhizomes and roots of Valeriana fauriei. The 13C NMR assignments of the isolated compounds are presented.     

Anti-plasmodial sesquiterpenoids from the African Reneilmia cincinnata

A new isodaucane sesquiterpenoid, 6,7,10-trihydoxyisodaucane, was isolated from the fruits of Reneilmia cincinnata, together with the known sesquiterpenoids oplodiol, oplopanone, 5E,10(14)-germacradien-1 beta, 4 beta-diol, 1(10)E,5E-germacradien-4 alpha-ol and eudesman-1,4,7-triol. A large amount of 5-hydroxy-3,7,4'-trimethoxyflavone was also isolated. Their structures were established by NMR techniques using 1D and 2D experiments. Three of the known sesquirernenoids exhibited noteworthy anti-plasmodial activity against Plasmodium falciparum strains.     

Hirsutane sesquiterpenoids from the marine-derived fungus Chondrostereum sp

A new hirsutane sesquiterpenoid, hirsutanol E (1), together with the known compounds hirsutanol A (2) and hirsutanol F (3; gloeosteretriol) were obtained from AcOEt extract of the marine fungus Chondrostereum sp., which was isolated from the soft coral Sarcophyton tortuosum. The structures were elucidated mainly on the basis of the NMR, MS, and X-ray single-crystal diffraction data. Hirsutanol A (2) exhibited potent cytotoxic activities against various cancer cell lines.     

New Lactarane Sesquiterpenoid from the Fungus Russula emetica

A new lactarane sesquiterpenoid with a β,γ-epoxy-γ-lactone moiety was isolated from the neutral fraction of an extract of Russula emetica, together with three known sesquiterpenoids. The structures of these compounds were identified by chemical transformation of related compounds and by spectroscopic methods.     

Isolation,Characterization, and Possible Anti‐Alzheimer's Disease Activities of Bisabolane‐Type Sesquiterpenoid Derivatives and Phenolics from the Rhizomes of Curcuma longa

One new bisabolane‐type sesquiterpenoid, together with four known bisabolane‐type sesquiterpenoid derivatives and seven phenolics, was isolated from the rhizomes of Curcuma longa. Their structures were elucidated by extensive spectroscopic (IR, HR‐ESI‐MS, and NMR) data analysis. The possible anti‐Alzheimer's disease (AD) activities of the isolated compounds were also evaluated using Caenorhabditis elegans AD pathological model, and 1β‐hydroxybisabola‐2,10‐dien‐4‐one had the highest possible anti‐AD activity.     

Trinorguaian and germacradiene type sesquiterpenes along with flavonoids from the herbs of Pimpinella cappadocica Boiss. & Bal.

A trinorguaian-type sesquiterpenoid named kanalpin and two acylated flavonol glycosides named erzurumin and ilicanin have been isolated from Pimpinella cappadocica Boiss. & Bal., together with three known sesquiterpenoids and six known flavonoid glycosides. The structures of these compounds were determined by extensive spectroscopic (UV, IR, EI–MS, APCI–MS, HR-ESI-MS, 1D and 2D NMR) analyses. Antioxidant capacity of isolated secondary metabolites containing extracts of P. cappadocica was evaluated.     

Anti-inflammatory spiroaxane and drimane sesquiterpenoids from Talaromyces minioluteus (Penicillium minioluteum)

A new spiroaxane sesquiterpenoid talaminoid A (1) and two drimane sesquiterpenoid talaminoids B and C (2 and 3), together with four known compounds (4–7), were isolated from the solid culture broth of fungus Talaromyces minioluteum. The structures were determined by extensive 1D and 2D NMR and HRESIMS spectroscopic data analyses, and the absolute configuration of these new compounds were undoubtedly confirmed by X-ray crystal diffrations. Compound 1 is a rare spiroaxane sesquiterpenoid and the absolute configuration of spiroaxane sesquiterpenoid was determined for the first time. Compound 2 is the first drimane-type sesquiterpenoid containing both amino acid residue and butanediol group. Compounds 1, 4, and 5 showed significant suppressive effect on the production of NO on LPS induced BV-2 cells, with IC₅₀ values ranging from 4.97 to 7.81 μM. In addition, 1, 4, and 5 exhibited significant anti-inflammatory activities against the production of TNF-α and IL-6. Further immunofluorescence experiments revealed the mechanism of action to be inhibitory the NF- κB-activated pathway.     

Neolignans and Sesquiterpenoid from Piper yunnanense

Two biphenyl-type neolignans with a rare dibenzofuran skeleton, including a new one piyunneolignan A ( 1 ) and a known one piperneolignan D ( 2 ), together with a new sesquiterpenoid piyunin A ( 3 ), were isolated from the leaves and twigs of Piper yunnanense. Their structures were established on the basis of comprehensive spectroscopic data analysis and electronic circular dichroism (ECD) calculation. Piyunneolignan A ( 1 ) featured a rare C-2−C-2′/C-3−O−C-3′ linkage. Compounds 1 – 3 were evaluated for their antimicrobial and cytotoxic activities against a panel of bacteria, fungi, and human cancer cell lines, respectively.     

Charminarone,a seco-pseudoguaianolide from Parthenium hysterophorus

A novel sesquiterpenoid, charminarone, the first seco-pseudoguaianolide, has been isolated along with several known compounds from the whole plant of Parthenium hysterophorus. The structure of the new compound has been settled as 1,10-seco-dihydroisoparthenin 1,10-dione from its spectral data as well as from its conversion by reductive coupling reaction with Zn/TiCl(4) reagent to the known compound, anhydrodihydroisoparthenin. The reagent Zn/TiCl(4) has been used here for the first time to construct the seven membered ring of a pseudoguaianolide sesquiterpenoid.     

seco-Cuparane-type sesquiterpenoid from the Japanese liverwort Jungermannia infusca

A 2,3-seco-cuparane-type sesquiterpenoid and the previously known barbatane-type sesqui- and ent-kaurane-type diterpenoids were isolated from the Japanese liverwort Jungermannia infusca (Mitt.) Steph. The structure of the 2,3-seco-cuparane-type sesquiterpenoid was determined by NMR spectroscopic analyses.     

4-Hydroxydehydromyoporone from infected Ipomoea batatas root tissue

A new sesquiterpenoid, 4-hydroxydehydromyoporone, was isolated from Ceratocystis fimbriata— infected root tissue of Ipomoea batatas. We showed that it was a derivative of myoporane with one hydroxyl group at C-8 and one double bond at C-12 by spectroscopic comparison with known compounds.     

Three Sesquiterpenoid Dimers from Chloranthus japonicus: Absolute Configuration of Chlorahololide A and Related Compounds

A novel sesquiterpenoid dimer, named multistalide C ( 1 ), together with two known congeners, shizukaols C ( 2 ) and D ( 3 ), was isolated from the whole plant of Chloranthus japonicus Sieb. The structures of compounds 1 , 2 , 3 were elucidated by extensive HR‐ESI‐MS, 1D, and 2D NMR spectroscopic analysis. Compounds 1 , 2 , 3 exhibited significant toxic effects on brine shrimp larvae (Artemia salina). The absolute configuration of 1 was established by CD/TDDFT calculations. The related compound chlorahololide A was also reinvestigated. The previous assignment of the absolute configuration of chlorahololide A and several related sesquiterpenoid dimers, based on an incorrect application of the exciton chirality method, is criticized. Chirality 28:158–163, 2015. © 2015 Wiley Periodicals, Inc.     

A new secoiridoid glycoside and a new sesquiterpenoid glycoside from Valeriana jatamansi with neuroprotective activity

A new secoiridoid glycoside, isopatrinioside (1) and a new sesquiterpenoid glycoside, valeriananoid F (2), together with nine known compounds, were isolated from the roots of Valeriana jatamansi. Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 was an unusual monocyclic iridoid glycoside ring-opened between C-1 and C-2 produced by the cleavage of the pyran ring. Of the eleven isolates, compounds 1 and 4 exhibited moderate neuroprotective effects against CoCl₂-induced neuronal cell death in PC12 cells.     

Sesquiterpenoids with Anti‐MDR Staphylococcus aureus Activities from Ferula ferulioides

Seven new sesquiterpenoids together with 21 known sesquiterpenoid derivatives were isolated from the medicinal plant Ferula ferulioides (Steud .) Korovin . Their structures were elucidated by comprehensive spectroscopic analyses and chemical transformations. The isolated compounds were evaluated for their antibacterial activities against a panel of bacteria including multidrug‐resistant (MDR) and methicillin‐resistant Staphylococcus aureus (MRSA), displaying minimum inhibitory concentration (MIC) values in the range of 0.5–128 mg/l.     

Drimane Sesquiterpenoids from the Aspergillus oryzae QXPC‐4

Three new drimane sesquiterpenoids, astellolides C–E ( 1 – 3 , resp.), four new drimane sesquiterpenoid p‐hydroxybenzoates, astellolides F–I ( 4 – 7 , resp.), together with two known compounds astellolides A and B ( 8 and 9 , resp.), have been isolated from the liquid culture of Aspergillus oryzae (strain No. QXPC‐4). Their structures were established by comprehensive analysis of spectroscopic data. The relative and absolute configurations were determined on the basis of NOESY and CD data, together with single‐crystal X‐ray diffraction analyses of compounds 1 – 3 . The metabolites were evaluated for their cytotoxic activities, however, no compounds showed a significant cytotoxicity against the tested cell lines at a concentration of 20 μM .     

金针菇固体发酵菌丝体次级代谢产物分离鉴定

采用硅胶柱色谱、ODS柱色谱、Sephadex LH-20柱色谱、HPLC等分离方法对金针菇大米发酵乙酸乙酯提取物进行分离,根据理化性质和波谱数据鉴定化合物结构：鉴定了4个倍半萜,包括1个新的桉叶烷型倍半萜,3个侧柏烷型倍半萜,分别是flamvelutpenol A(1),aquaticol(2),enokipodin C(3),limacellone(4)。并通过与Rh2(OCOCF3)4络合的方法确定了新化合物flamvelutpenol A(1)和limacellone(4)的绝对构型。其中化合物3具有较好的抗菌活性,对耐甲氧西林金黄色葡萄球菌和枯草芽孢杆菌的MIC值分别为12.5mg/L,25mg/L。且化合物1－4均是首次从该种真菌中分离得到。     

Natural anti-HIV agents-part I: (+)-demethoxyepiexcelsin and verticillatol from Litsea verticillata

The eudesmane sesquiterpenoid, verticillatol (1), as well as the lignan, (+)-5'-demethoxyepiexcelsin (2), and a known lignan, (+)-epiexcelsin (3), were isolated from Litsea verticillata Hance. Lignan 2 showed moderate anti-HIV activity with an IC(50) value of 16.4 microg/ml (42.7 microM), while the known lignan 3 was inactive up to a concentration of 20 microg/ml (48.3 microM). Compound 1 demonstrated weak activity with an IC(50) value of 34.5 microg/ml (144.7 microM) while being devoid of cytotoxicity at 20 microg/ml. The structures were elucidated by 1D and 2D NMR spectroscopy, and the absolute configuration of the new sesquiterpenoid was determined by the generation of Mosher esters.     

New Polyketide and Sesquiterpenoid Derivatives from the Magellan Seamount-Derived Fungus Penicillium rubens AS-130

Rubenpolyketone A ( 1 ), a polyketide featuring a new carbon skeleton having cyclohexenone condensed with a methyl octenone chain and a new linear sesquiterpenoid, chermesiterpenoid D ( 2 ), together with seven known secondary metabolites ( 3 – 9 ) were isolated and identified from the Magellan Seamount-derived fungus Penicillium rubens AS-130. Their structures were determined based on detailed analysis of NMR and mass spectroscopic data and the absolute configurations of these two new compounds were elucidated by the combination of quantum mechanical (QM)-NMR and time-dependent density functional (TDDFT) ECD calculation approaches. Chermesiterpenoids B ( 3 ) and C ( 4 ) showed potent inhibitory activities against the aquatic pathogen Vibrio anguillarum with MIC values of 0.5 and 1 μg/mL, respectively, while chermesin F ( 6 ) exhibited activity against Escherichia coli with MIC value of 1 μg/mL.     

Rearranged abietane diterpenoid hydroquinones from aerial parts of Ajuga decumbens Thunb

Four new rearranged abietane diterpenoid hydroquinones, ajudecumins A–D (1–4), together with two known rearranged abietane diterpenoids, three neo-clerodane diterpenoids, four megastigmane derivatives, two flavonoids as well as a bisabolene sesquiterpenoid were isolated from the aerial parts of Ajuga decumbens. Their structures were established on the basis of extensive spectroscopic analysis and the stereochemistry of 1 was confirmed by single-crystal X-ray diffraction analysis. Among the diterpenoids, compounds 1 and 3 exhibited moderate inhibitory activity on the proliferation of human breast cancer MCF-7 cells.     

A new sesquiterpenoid from Sclerorhachis platyrachis (Boiss.) Podlech ex Rech.f

A new eudesmane-type sesquiterpenoid together with two known flavonoids were isolated from the chloroform extract of the aerial part of Sclerorhachis platyrachis. The structure of the new compound was deduced from its comprehensive spectroscopic analysis including IR, EI-MS, ¹H NMR, ¹³C NMR, DEPT, COSY, HMBC and HMQC and was shown to be 4R^*-hydroxy-6S^*-tigloyloxyeudesma-7S^*-11 (13)-en-12-oic acid (1). Finally, the structure of the new compound was unambiguously confirmed by single-crystal X-ray analysis. The structure of known compounds 2 and 3 were identified by comparison of their spectral data with those reported in the literature.