Three New Polyyne (=Polyacetylene) Glucosides from the Edible Roots of Codonopsis cordifolioidea

Three new linear C₁₄ polyyne (=polyacetylene) glucosides, cordifolioidynes A–C ( 1 – 3 ), together with two known polyynes, lobetyol ( 4 ) and lobetyolin ( 5 ), and five known phenylpropanoids, i.e., sinapinaldehyde ( 6 ), coniferaldehyde ( 7 ), coniferoside ( 8 ), sachaliside ( 9 ), and isoconiferin ( 10 ), were isolated from the roots of Codonopsis cordifolioidea. The structures of 1 – 3 were established from spectral evidences and by characterization of their hydrolysis products. Acid hydrolysis of 1 afforded the aglycone 1a , while hydrolysis of 2 and 3 gave the cyclization products 2a and 3a , respectively. Compounds 4 – 10 were isolated from this plant for the first time. The antibacterial activity of compounds 1 – 5 were assessed against eight microbial strains by the agar dilution method, none of them exhibited antibacterial effects at concentrations up to 100 μg/ml.     

Four New Nortriterpenoids from Schisandra lancifolia

Four new highly oxygenated nortriterpenoids, lancifodilactones O–R ( 1 – 4 ), together with six known ones, i.e., 5 – 10 , were isolated from the leaves and stems of Schisandra lancifolia. Their structures were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR experiments and mass spectrometry. Compounds 1 – 3 were evaluated for their cytotoxicity against NB4, A549, SHSY5Y, PC‐3, and MCF‐7 cell lines. No compounds exhibited significant cytotoxicity, the IC₅₀ values being above 50 μM .     

Five New Aromatic Glycosides from Carthamus tinctorius

Five new aromatic glycosides, 1 – 5 , named as carthamosides B₄–B₈, together with three known compounds, 4′‐(hydroxyphenacyl)‐β‐D ‐glucopyranoside ( 6 ), benzyl‐O‐α‐L ‐rhamnopyranosyl‐(1→6)‐β‐D ‐glucopyranoside ( 7 ), and 4‐(methoxybenzyl)‐O‐β‐D ‐glucopyranoside ( 8 ), have been isolated from the air‐dried flower of Carthamus tinctorius. Their structures were identified on the basis of chemical and spectroscopic methods.     

Limonoids from the Twigs and Leaves of Chukrasia tabularis

Seven new limonoids, tabularisins J–P ( 1 – 7 , resp.), together with eight known compounds, were isolated from the twigs and leaves of Chukrasia tabularis. Their structures were determined primarily by spectroscopic methods. The potassium channel blocking activities of some of these isolates were evaluated, and a few of them exerted significant activities on the delayed rectifier (I_K) K⁺ current.     

Five New Cycloartane‐Type Triterpenoid Saponins from Nervilia fordii

Five new cycloartane glycosides, nervisides D–H ( 1 – 5 ), were isolated from the AcOEt‐ and H₂O‐soluble portions of the 90% EtOH extract of the aerial part of the plant Nervilia fordii. The structures of the isolated glycosides were elucidated by extensive spectroscopic analysis including HR‐ESI‐MS and NMR data. The isolated nervisides D–H were evaluated for the cytotoxic activity in vitro against human‐tumor cell lines (CNE, Hep‐2 and HepG2) with the MTT method.     

Nortriterpenoids from Schisandra wilsoniana

Three new highly oxygenated nortriterpenoids, wilsonianadilactones A–C ( 1 – 3 ), together with twelve known ones, i.e., 4 – 15 , were isolated from the leaves and stems of Schisandra wilsoniana. Their structures were established by means of extensive analysis of spectroscopic data, and compound 1 was further confirmed by X‐ray crystallographic diffraction. Compounds 1 – 3 showed weak anti‐HIV‐1 activity with EC₅₀ values of 23.5, 55.5, and 66.4 μg/ml, respectively.     

Irciformonins E – K,C22‐Trinorsesterterpenoids from the Sponge Ircinia formosana

Chemical investigation of the sponge Ircinia formosana resulted in the isolation of seven new linear C₂₂‐sesterterpenoids, irciformonins E–K ( 1 – 7 ) in addition to irciformonin A ( 8 ), a previously isolated furanosesterterpenoid (=a furan‐moiety‐containing sesterterpenoid) from the same species. The structures were determined by interpretation of HR‐ESI‐MS and 2D‐NMR spectra. The structure of irciformonin A ( 8 ) was revised. Compound 5 exhibited significant inhibition of peripheral blood mononuclear cell proliferation induced by phytohemaglutinin.     

Medicinal Flowers. Part 29. Acylated Oleanane‐Type Triterpene Bisdesmosides: Perennisaponins G,H, I,J, K,L, and M with Pancreatic Lipase Inhibitory Activity from the Flowers of Bellis perennis

The MeOH extract from the flowers of Bellis perennis was found to show pancreatic‐lipase inhibitory activity (IC₅₀ 455 μg/ml). From the extract, seven new triterpene saponins named perennisaponins G ( 1 ; IC₅₀ 163 μM ), H ( 2 ; 137 μM ), I ( 3 ; 147 μM ), J ( 4 ; 148 μM ), K ( 5 ; 223 μM ), L ( 6 ; 81.4 μM ), and M ( 7 ; 195 μM ) were isolated as pancreatic lipase inhibitors. The stereostructures of 1 – 7 were elucidated on the basis of chemical and spectroscopic evidence.     

Flavonoid Constituents from Spiraea brahuica

Sparins A–C ( 1 – 3 , resp.), three new flavonoids, were isolated from the CHCl₃ subfraction of the EtOH extract of the whole plant of Spiraea brahuica, along with 3′,7‐di‐O‐methylquercetin ( 4 ) and luteolin 7‐β‐D ‐glucopyranoside ( 5 ), reported for the first time from this species. The structures of the new compounds were elucidated by spectroscopic techniques including MS and 2D‐NMR spectroscopy.     

neo‐Clerodane Diterpenoids from the Aerial Part of Scutellaria barbata

Three new neo‐clerodane diterpenoids, barbatellarines C–E ( 1 – 3 ), were isolated from the CHCl₃‐soluble fraction of the aerial part of Scutellaria barbata. Their chemical structures were elucidated by detailed analysis of NMR and MS data. Compounds 1 and 2 were C(13) epimers, which was confirmed by an NOE difference experiment and the NOESY spectrum. The relative configuration was determined on the basis of the ¹H‐NMR J‐value and NOE data, while the absolute configuration of the previously isolated analogue, barbatellarine B ( 4 ), as a representative member of the group, was assigned by CD analysis.     

Seven New Lignan Esters from Kadsura philippinensis

Five new oxygenated lignans with a dibenzocyclooctadiene skeleton, kadsuphilols P–T ( 1 – 5 ), and two new C₁₉ homolignans, kadsuphilols U and V ( 6 and 7 ), were isolated by chromatographic fractionation of an AcOEt extract of the stems of Kadsura philippinensis. The structures of the isolated metabolites were elucidated through extensive spectroscopic analysis including HR‐ESI‐MS and 2D‐NMR (HMQC, COSY, and HMBC). The configuration at the chiral centers and at the biphenyl moiety were determined by interpretation of NOESY and CD data, respectively.     

Three New Phthalides from Gnaphalium adnatum

Three new phthalides, gnaphalides A–C ( 1 – 3 , resp.), together with three known phthalides, were isolated from the aerial part of Gnaphalium adnatum. The structures of the new compounds were elucidated as 6‐(1,1‐dimethylprop‐2‐en‐1‐yl)‐5,7‐dihydroxy‐2‐benzofuran‐1(3H)‐one ( 1 ), 5‐hydroxy‐7‐[(2‐hydroxy‐3‐methylbut‐3‐en‐1‐yl)oxy]‐2‐benzofuran‐1(3H)‐one ( 2 ), and 1,3‐dihydro‐7‐[(3‐methylbut‐2‐en‐1‐yl)oxy]‐1‐oxo‐2‐benzofuran‐5‐yl β‐D ‐glucopyranoside ( 3 ) on the basis of spectral analyses. The structure of 1 was also confirmed by X‐ray crystallographic analysis. The three known phthalides, identified as 5,7‐dihydroxyisobenzofuran‐1(3H)‐one ( 4 ), anaphatol ( 5 ), and 7‐O‐(β‐glucopyranosyl)‐5‐hydroxyisobenzofuran‐1(3H)‐one ( 6 ), were isolated from the genus Gnaphalium for the first time.     

Four New Cuparene‐Type Sesquiterpenes from Flammulina velutipes

Flamvelutpenoids A–D ( 1 – 4 ), four new cuparene‐type sesquiterpenes, were isolated from the solid culture of Flammulina velutipes. Their structures were elucidated by NMR experiments. The absolute configurations of 1 and 2 were assigned via the circular dichroism data of the [Rh₂(OCOCF₃)₄] complex, whereas that of C(3) of 3 was determined by applying the octant rule for the α,β‐unsaturated ketone moiety. Compounds 1 – 4 showed weak antibacterial activity against Escherichia coli, Bacillus subtilis, and methicillin‐resistant Staphylococcus aureus with MIC values larger than 100 μM .     

Bioactive Cytochalasins from Aspergillus flavipes,an Endophytic Fungus Associated with the Mangrove Plant Acanthus ilicifolius

Five new cytochalasins, Z₁₆–Z₂₀ ( 1 – 5 ), and three known ones, 6 – 8 , were isolated from Aspergillus flavipes, an endophytic fungus associated with Acanthus ilicifolius. Their structures were elucidated on the basis of comprehensive spectral analysis. Cytochalasin Z₁₇ ( 2 ) and rosellichalasin ( 8 ) showed cytotoxic activities against A‐549 cell lines with IC₅₀ values of 5.6 and 7.9 μM , respectively.     

Norlignans and Phenylpropanoids from Metasequoia glyptostroboides Hu et Cheng

Five new compounds, i.e., the three new norlignans metasequirins G–I ( 1 – 3 ) and the two new phenylpropanoids 7‐(3‐ethoxy‐5‐methoxyphenyl)propane‐7,8,9‐triol (=1‐(3‐ethoxy‐5‐methoxyphenyl)propane‐1,2,3‐triol; 4 ) and 7‐(3‐hydroxy‐5‐methoxyphenyl)propane‐7,8,9‐triol (=1‐(3‐hydroxy‐5‐methoxy‐phenyl)propane‐1,2,3‐triol; 5 ), were isolated from the branches and stems of Metasequoia glyptostroboides Hu et Cheng . Their structures were elucidated by physical, chemical, and spectroscopic methods, including 1D‐ and 2D‐NMR and HR‐ESI‐MS. The cytotoxicites of the five compounds were tested against A549 and Colo 205 cell lines by the MTT method.     

Xylocosides A – G,Phenolic Glucosides from the Stems of Xylosma controversum

Seven new phenolic glucosides, xylocosides A–G ( 1 – 7 ), together with 18 known compounds were isolated from the stems of Xylosma controversum Clos . In compounds 3 – 6 , the glucose residue is esterified at C(6) by 2‐hydroxycyclopentanecarboxylic acid. These new structures were established by spectroscopic‐data interpretation and chemical methods.     

Three New Bisabolane Sesquiterpenes from Ligularia songarica

Three new bisabolane sesquiterpenes, songaricalarins F–H ( 1 – 3 , resp.), and five known analogs, 4 – 8 , were isolated from roots and rhizomes of Ligularia songarica. The structures were elucidated by spectroscopic methods, including 2D‐NMR techniques. The isolated compounds were also evaluated for their cytotoxic activities, against human lung carcinoma (A‐549) and human breast adenocarcinoma (MCF‐7) cell lines, and three compounds were found to show moderate cytotoxicities.     

Three New Xanthones from the Fungus Penicillium sp. NH‐7‐1

Three new xanthones, drimiopsins G–I ( 1 – 3 , resp.), and two known congeners, griseoxanthone C ( 4 ) and norlichexanthone ( 5 ), were isolated from a fungal isolate, Penicillium sp. NH‐7‐1. The structures of all compounds were determined on the basis of extensive spectroscopic analyses, as well as by comparison with literature reports, and the structure of compound 1 was further confirmed by single‐crystal X‐ray diffraction.     

New Diterpenoid Alkaloids from Aconitum liangshanicum

One new C₁₉‐diterpenoid alkaloid, named liangshantine ( 1 ), and three new C₂₀‐diterpenoid alkaloids, liangshansines A–C ( 2 – 4 , resp.), as well as eight known compounds, were isolated from the roots of Aconitum liangshanicum. The structures of these new alkaloids were elucidated by spectroscopic methods.     

Three New Diterpenoids from Isodon nervosus

Three new ent‐kaurane diterpenoids, rabdonervosins D–F ( 1 – 3 ), were isolated from the leaves and stems of Isodon nervosus. Their structures were elucidated on the basis of spectroscopic methods including 1D‐ and 2D‐NMR analyses. Compounds 1 – 3 were evaluated for their cytotoxicity against HepG2, CNE2, PC‐9/ZD, HeLa, MCF‐7, and HCT116 cell lines. No compounds exhibited potent cytotoxicity.