Four New Compounds from Sinacalia tangutica

Four new compounds, 9α‐hydroxy‐1β‐methoxycaryolanol ( 1 ), stigmast‐5‐ene‐7α,22α‐diol‐3β‐tetradecanoate ( 2 ), 7‐O‐(6′‐acetoxy‐β‐D ‐glucopyranosyl)coumarin ( 3 ), and 8‐O‐(6′‐acetoxy‐β‐D ‐glucopyranosyl)‐7‐hydroxycoumarin ( 4 ), together with ten known compounds, were isolated from the aerial parts of Sinacalia tangutica. The structures of the new compounds were established by means of extensive spectroscopic analyses (1D‐ and 2D‐NMR, EI‐MS, HR‐ESI‐MS, as well as IR and UV) and by comparison of their spectroscopic data with those of structurally related compounds reported in the literature.     

A New Ent‐Trachylobane Diterpenoid from the Roots of Sapium Sebiferum

A new ent‐trachylobane diterpenoid, saposebifeic acid, together with thirteen known compounds, were isolated from the roots of Sapium sebiferum. Compounds, 5,7,8‐trimethoxycoumarin, baccatin, n‐alkyl trans‐ferulate and 2,6‐dimethoxyquinone, were reported for the first time from this plant. The structures of the new and known compounds were established on the basis of extensive 1D and 2D NMR spectral data.     

Structure elucidation of new fusarielins from Fusarium sp. and their antimicrobial activity

Three new fusarielins, 3‐epi‐fusarielin H ( 1 ), 3‐O‐methyl‐fusarielin H ( 2 ), and 3‐O‐methyl‐epi‐fusarielin H ( 3 ), were isolated from the fungus Fusarium sp. together with the known analogues, fusarielins F ( 4 ) and G ( 5 ). The structures of these compounds were elucidated by analysis of their ESI‐HRTOFMS, 1D and 2D NMR spectroscopic data. The new compounds exhibited weak antibacterial effect against Staphylococcus aureus.     

New Glycosides from Salvia moorcroftiana (Lamiaceae)

From the MeOH extract of Salvia moorcroftiana Wall. (Lamiaceae), four new compounds, the two flavonoid glycosides genkwanin 4′‐[O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐galactopyranoside] ( 1 ) and genkwanin 4′‐[O‐α‐L ‐arabinopyranosyl‐(1→3)‐α‐L ‐rhamnopyranoside] ( 2 ), and the two benzene derivatives 4‐hydroxy‐2‐isopropyl‐5‐methylphenyl O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucopyranoside ( 3 ) and nonyl 4‐hydroxybenzoate ( 4 ), were isolated in addition to two known compounds. The structures of all new compounds were determined by 1D and 2D homonuclear and heteronuclear NMR spectroscopy and by comparison with published data.     

New Polyketides Isolated from Botryosphaeria australis Strain ZJ12‐1A

Four new polyketides, botryosphaerones A–D ( 1 – 4 , resp.), were obtained from the fermentation culture of Botryosphaeria australis strain ZJ12‐1A, together with four known compounds, O‐methylasparvenone ( 5 ), 6‐ethyl‐2,7‐dimethoxyjuglon ( 6 ) and its monoacetyl derivative 7 , and O‐methylaspmenone ( 8 ). Their structures were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR experiments, and HR‐Q‐TOF mass spectrometry, and by comparison with reported data. All compounds were evaluated for their cytotoxic and antimicrobial activities in vitro. Only compounds 6 and 7 showed cytotoxic and antimicrobial activities, as already reported.     

Sesquiterpenoids and Lignans from Ligularia virgaurea spp. oligocephala

From the BuOH extract of the whole plant of Ligularia virgaurea spp. oligocephala, a series of sesquiterpenes, sesquiterpene glycosides, and lignan glycosides were isolated, including the three new compounds (1α)‐1‐hydroxy‐8‐oxo‐eremophila‐6,9‐dien‐12‐oic acid ( 1 ), 8‐[(β‐D ‐glucopyranosyl)oxy]eremophila‐1(10),8,11‐trien‐2‐one ( 2 ), and 4‐[(β‐D ‐glucopyranosyl)oxy]pinoresinol ( 4 ). Their structures were elucidated by 1D‐ and 2D‐NMR as well as HR‐ESI‐MS analyses, and by comparison of the spectroscopic data with those reported for structurally related compounds.     

New Lignans from the Aerial Parts of Rudbeckia laciniata

Three new furofuran lignans, (+)‐4,4′‐O‐diangeloylpinoresinol ( 1 ), (+)‐4,4′‐O‐diangeloylmedioresinol ( 2 ), and (+)‐4,4′‐O‐diangeloylsyringaresinol ( 3 ), together with the known compound (+)‐syringaresinol, were isolated from the MeOH extract of Rudbeckia laciniata. The structure elucidation of these compounds were based on 1D‐ and 2D‐NMR, and HR‐ESI‐MS data. The additional structural evidence was obtained from alkaline hydrolysis of the compounds.     

Constituents of the Endophytic Fungus Annulohypoxylon boveri var. microspora BCRC 34012

A new azaphilone metabolite with a new substitution pattern, named annulohypoxylin ( 1 ), together with twelve known compounds, were isolated from the BuOH‐soluble fraction of the 95% EtOH extract of long‐grain rice (Oryza sativa) fermented with the endophytic fungus Annulohypoxylon boveri var. microspora (BCRC 34012). Annulohypoxylin ( 1 ) contains a dihydrobenzofuran‐2,4‐dione backbone, 1‐hydroxyoctyl side chain, and one γ‐lactone ring. Its structure was determined on the basis of extensive 1D‐ and 2D‐NMR analyses in combination with HR‐ESI‐MS. The relative configuration of 1 was confirmed by NOESY experiment. Other known compounds were identified by comparing their spectral data with those in the literature. All known compounds were isolated from this species for the first time.     

New Cytochalasins from the Marine‐Derived Fungus Xylaria sp. SCSIO 156

Two new cytochalasins, 18‐deoxycytochalasin Q ( 1 ) and 21‐O‐deacetylcytochalasin Q ( 2 ), together with four known analogues, cytochalasin Q ( 3 ), 19,20‐epoxycytochalasin Q ( 4 ), 21‐O‐deacetyl‐19,20‐epoxycytochalasin Q ( 5 ), and cytochalasin D ( 6 ), were isolated from the fungus Xylaria sp. SCSIO156 originated from the South China Sea marine sediment. The structures of 1 and 2 were elucidated by MS and 1D‐ and 2D‐NMR data analyses, and comparison with known compounds. The known compounds 3 – 6 were identified by comparison of their MS and NMR data with those reported in the literature. In the in vitro antitumor assay, compounds 2 – 6 showed mild cytotoxicity against three tumor cell lines (MCF‐7, SF‐268, and NCI‐H460).     

Two New Cytotoxic Spirostane‐Steroidal Saponins from the Roots of Bletilla striata

Two new spirostane‐steroidal saponins, bletilnoside A ( 1 ) and bletilnoside B ( 2 ), together with five known compounds, 3 – 7 , were isolated from the roots of Bletilla striata (Thunb .) Reichb . F. The structures of the new compounds were determined based on their 1D‐ and 2D‐NMR spectral data. The isolated compounds 1 – 7 were tested for cytotoxicity against four human tumor cells (A549, SK‐OV‐3, SK‐MEL‐2, and HCT15) in vitro using a sulforhodamin B bioassay, and compounds 1, 2 , and 5 showed significant cytotoxicities against all tested tumor cell lines with IC₅₀ values ranging from 3.98±0.16 to 12.10±0.40 μM .     

A New Steroid Glycoside Derivative from Acorus Calamus L.

A new steroid glycoside derivative, 4′‐O‐docosanoyl‐3‐O‐β‐D‐glucosyl‐sitosterol, along with six known steroids has been isolated from the ethanol extract of the rhizoma of Acorus calamus L. The structures of the new and known compounds were established on the basis of extensive 1D and 2D NMR spectral data.     

Triterpenoids and other Constituents from Euphorbia Humifusa

A novel lupane‐type triterpenoid, 3,4‐seco‐lupa‐4(23), 20(29)‐dien‐24‐hydroxy‐3‐oic acid (1) and a new cycloartane‐type triterpenoid, 23(E)‐cycloart‐23‐en‐25‐ethoxy‐3β‐ol (7), as well as eighteen known compounds, were isolated from the hot ethanol extract of the whole plant of Euphorbia humifusa Willd. The new structures were characterized by means of spectroscopic methods including 1D, 2D NMR and HRESIMS, and the known ones were established on the basis of comparing their NMR data with those of the corresponding compounds in the literature. In addition, cytotoxicity against selected cancer cell human gastric carcinoma (SGC‐7901) of compounds 1,3,4,6 were measured in vitro.     

Hypenol,a New Lignan from Hypenia salzmannii

A new lignan, (?)‐secoisolariciresin‐9‐yl 6‐O‐p‐coumaroyl‐β‐D ‐glucopyranoside ( 1 ), named hypenol, along with eleven known compounds, i.e., hyperin, rosmarinic acid, methyl rosmarinate, a mixture of the triterpenes betulinic acid, ursolic acid, and oleanolic acid, glycosylated β‐sitosterol, a mixture of the flavanones sakuranetin and isosakuranetin, hinokinin, and β‐peltatin A dimethyl ether were isolated from the EtOH extract of the leaves of Hypenia salzmannii (Benth. ) Harley . The structures of the compounds were elucidated based on the analysis of spectral data, including MS, 1D‐ and 2D‐NMR, and comparison with data in the literature.     

A New Cyclopropyl‐Triterpenoid from Ochradenus arabicus

One new cyclopropyl‐triterpenoid ( 1 ), along with four known constituents including octacosan‐1‐ol ( 2 ), pentacosanoic acid ( 3 ), β‐sitosterol ( 4 ), and β‐sitosterol 3‐O‐β‐D ‐glucopyranoside ( 5 ) were isolated from the aerial parts of Ochradenus arabicus for the first time. These compounds were isolated by repeated column chromatography followed by further purification through recycling HPLC. The structure of the new secondary metabolite 1 was established on the basis of UV, IR, 1D‐ (¹H‐ and ¹³C‐) and 2D‐NMR (HMBC and HSQC), and MS spectral data. The molecular mass was determined by HR‐MS, and hence the molecular formula was deduced. The configurations of stereogenic centers in the molecule were assigned by NOESY experiments, along with biogenetic considerations. The structures of the known compounds were confirmed by comparison of their physical and spectroscopic data with those reported in literature.     

Polyprenylated Xanthones and Benzophenones from the Bark of Garcinia oblongifolia

A new polyprenylated xanthone (=9H‐xanthen‐9‐one) and a new polyprenylated benzophenone, namely oblongifolixanthone A ( 1 ) and garciniagifolone A ( 2 ), were isolated from the bark of Garcinia oblongifolia, together with five known compounds including the four xanthones 3 – 5 and 7 and a benzophenone 6 . The structures of 1 and 2 were established by detailed analysis of their spectroscopic data, especially 1D‐ and 2D‐NMR spectra and HR‐ESI‐MS data. All these compounds were assayed for their cytotoxic activities against three human tumor cell lines (HeLa, SGC7901, and HepG2). The 1,3,6,7‐tetrahydroxy‐9H‐xanthen‐9‐one ( 3 ) was inactive, and the other compounds showed weak to moderate activity.     

Chemical Constituents from Myrsine africana L.

Three new compounds, myrsinoside A (=2,4‐dihydroxy‐6‐methylphenyl β‐D ‐(6′‐galloyl)glucopyranoside; 1 ), myrsinoside B (2,4‐dihydroxy‐6‐methylphenyl β‐D ‐glucopyranoside; 2 ), and (3β,16α,20α)‐3,16,28‐trihydroxyolean‐12‐en‐29‐oic acid 3‐{O‐β‐D ‐glucopyranosyl‐(1→2)‐O‐[β‐D ‐glucopyranosyl‐(1→4)]‐α‐L ‐arabinopyranoside} ( 3 ), along with four known compounds, were isolated from the stems of Myrsine africana L. The structures of these new compounds were elucidated on the basis of spectroscopic analysis, including 1D‐ and 2D‐NMR and ESI‐MS techniques, and chemical methods.     

Phenolic Metabolites from the Stems and Leaves of Sophora flavescens

Two new compounds, (?)‐(6aR,11aR)‐4‐methoxy‐8,9‐(methylenedioxy)pterocarpan 3‐O‐β‐D ‐glucopyranoside ( 1 ) and 5‐hydroxy‐7‐methoxyisoflavone 4′‐O‐β‐D ‐xylopyranosyl‐(1→6)‐β‐D ‐glucopyranoside ( 2 ), were isolated, together with 30 known compounds from the stems and leaves of Sophora flavescens Aition . Their structures were elucidated by extensive spectroscopic analysis, including HR‐ESI‐MS data. A preliminary comparison of phenolic metabolite profiles, based on the qualitative HPLC analysis, indicated that the composition of the roots and the aerial parts were significantly different.     

Bioactive Trichothecenes Produced by the Myrothecium sp. QB‐1

Three new simple trichothecenes, 15‐acetyltrichoverrol B ( 3 ), 13′‐acetyltrichoverrin B ( 5 ), and 6′‐dehydroxytrichoverrin B ( 6 ), along with five known trichothecenes trichodermadienediol B ( 1 ), trichoverrol B ( 2 ), trichoverrin B ( 4 ), and roridins A ( 7 ) and D ( 8 ), have been isolated from the liquid culture of Myrothecium roridum (strain no. QB‐1). The structures of the new compounds were established by comprehensive analysis of 1D‐ and 2D‐NMR data. All the compounds were evaluated for antifungal activity, only compounds 7 and 8 showed significant antifungal activity against the tested fungi (MIC ranged from 10 to 5 μg/ml).     

Epunctanone,a New Benzophenone,and Further Secondary Metabolites from Garcinia epunctata Stapf (Guttiferae)

A new polyprenylated benzophenone, named epunctanone ( 1 ), was isolated from the stem bark of Garcinia epunctata Stapf , together with eight known compounds, 7‐epiisogarcinol ( 2 ), 2,6‐dimethoxy‐p‐benzoquinone ( 3 ), friedelin ( 4 ), lupeol ( 5 ), 16β‐hydroxylupeol ( 6 ), betulin ( 7 ), stigmasterol ( 8 ), and rheediaxanthone A ( 9 ). The structure of epunctanone ( 1 ) was established by detailed analysis of its spectroscopic data, especially 1D‐ and 2D‐NMR, and HR‐MS data. All these compounds were evaluated for their antimicrobial and anti‐protozoan activities. They were also assayed to determine if any of the compounds were nonpeptide agonist ligands for nematodal G‐protein‐coupled receptors, which would be an indication of potential antinematodal activity. Among the isolated compounds, 7‐epiisogarcinol ( 2 ) was the most active against Candida albicans.     

Two New Spirostanol Saponins from Reineckia carnea

Two new spirostanol saponins, (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐(β‐D ‐xylopyranoside) ( 1 ) and (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐[α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐fucopyranoside] ( 2 ), along with two known compounds, (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐[α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐xylopyranoside] ( 3 ) and (1β,3β,4β,5β,25S)‐spirostan‐1,3,4,5‐tetrol 5‐(β‐D ‐glucopyranoside) ( 4 ) were isolated from the whole plant of Reineckia carnea. The structures of the new steroids were determined by detailed analysis of their 1D‐ and 2D‐NMR spectra and chemical methods, and by comparison with spectral data of known compounds. Compounds 3 and 4 were isolated from the genus Reineckia for the first time.