Neoengleromycin,a Novel Compound from Engleromyces goetzii

A novel N‐containing compound, neoengleromycin ( 1 ) was isolated from the fruiting bodies of the ascomycete Engleromyces goetzii together with two known cytochalasins: cytochalasin D ( 2 ) and 19,20‐epoxycytochalasin D ( 3 ). Structures were established by spectroscopic (including 2D‐NMR) and chemical means. Neoengleromycin ( 1 ) possesses the rare structure of an N‐substituted hydroxamic acid and represents a new type of natural products.     

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.     

Two New Phenolic Compounds from Artemisia iwayomogi

Two new phenolic compounds, (Z)‐5′‐hydroxyjasmone 5′‐O‐{6″‐O‐[(E)‐caffeoyl]‐β‐D ‐glucopyranoside} ( 1 ) and quercetin‐7‐O‐β‐D ‐glucuronide methyl ester ( 2 ), along with ten known phenolic compounds, 3 – 12 , were isolated from the aerial parts of Artemisia iwayomogi. Their structures were elucidated by spectroscopic methods, including 1D‐ and 2D‐NMR, and HR‐ESI‐TOF‐MS techniques. The inhibitory effects of compounds 1 – 12 on the LPS‐stimulated production of IL‐12 p40, IL‐6, and TNF‐α in bone marrow‐derived dendritic cells were evaluated.     

Four New Nor‐Diterpenoid Alkaloids from Aconitum brachypodum

Four new C₁₉‐nor‐diterpenoid alkaloids, named brachyaconitines A–D ( 1 – 4 ), were isolated from the roots of Aconitum brachypodum Diels. Their structures were elucidated as 3‐O‐acetyl‐20‐deethyl‐20‐formylaconitine ( 1 ), 3‐O‐acetyl‐19,20‐didehydro‐20‐deethylaconitine ( 2 ), 3‐O‐acetyl‐8‐de(acetyloxy)‐7,8,17,20‐tetradehydro‐20‐deethyl‐7,17‐secoaconitine ( 3 ), and 1‐O‐methylflavaconitine ( 4 ) by means of MS, IR, 1D‐ and 2D‐NMR analyses. The structure of compound 1 was confirmed by an X‐ray diffraction experiment.     

Iridoid Glycosides from Gardenia jasminoides Ellis

Three new iridoid glycosides, 4″‐O‐[(E)‐p‐coumaroyl]gentiobiosylgenipin ( 1 ), 6′‐O‐[(E)‐caffeoyl]deacetylasperulosidic acid methyl ester ( 2 ), and 6′‐O‐[(E)‐sinapoyl]gardoside ( 3 ), together with seven analogues, 4 – 10 , were isolated from the BuOH extract of the fruits of Gardenia jasminoides Ellis . Their structures were determined by means of spectroscopic analyses, including HR‐ESI‐MS, IR, and ¹H‐ and ¹³C‐NMR, and 2D experiments (COSY, HSQC, and HMBC), and comparison with known related compounds.     

New Cytotoxic Myrsinane‐Type Diterpenes from Euphorbia prolifera

Four new myrsinol diterpenes, proliferins A–D ( 1 – 4 , resp.) were isolated from the EtOH extracts of the roots of Euphorbia prolifera, along with four known compounds, euphorprolitherin B ( 5 ), euphorprolitherin D ( 6 ), SPr5 ( 7 ), and 14‐desoxo‐3‐O‐propionyl‐5,15‐di‐O‐acetyl‐7‐O‐nicotinoylmyrsinol‐14β‐acetate ( 8 ). Their structures were established on the basis of spectroscopic methods, including HR‐ESI‐MS, and 1D‐ and 2D‐NMR techniques. The cytotoxicity of compounds 1, 3 , and 4 against cancer cells was evaluated, with compound 1 being active against A2780 cancer cells.     

C21 Steroidal Glycosides from Cynanchum wilfordii

Eight new C₂₁ steroidal glycosides, named wilfosides A–H ( 1 – 8 , resp.), along with one known compound wilfoside KIN ( 9 ), were isolated from the roots of Cynanchum wilfordii. The structures of the new glycosides were determined on the basis of spectroscopic analysis, including 1D‐ and 2D‐NMR, and ESI‐MS techniques, as well as by comparison of the spectral data with those of related compounds.     

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.     

Tumor‐Promoting Diterpene Esters from Latex of Euphorbia cauducifolia L.

Tumor‐promoting characteristics of seven esters, 1 – 7 , obtained from the latex of Euphorbia cauducifolia L. was appraised by carrying out NMRI mice back skin. The structures of 1 – 7 were elucidated by spectroscopic techniques like ¹H‐ and ¹³C‐NMR, 2D‐NMR (HMQC, HMBC, HOHAHA (homonuclear Hartmann–Hahn), NOESY, and NOE), FT‐IR, UV, and MS as esters of 17‐hydroxyingenol, namely 17‐[(2Z,4E,6Z)‐deca‐2,4,6‐trienoyloxy]ingenol ( 1 ), 3‐O‐angeloyl‐17‐[(2Z,4E,6Z)‐deca‐2,4,6‐trienoyloxy]ingenol ( 2 ), 3‐O‐acetyl‐20‐O‐angeloyl‐17‐hydroxyingenol ( 3 ), 17‐(acetyloxy)‐3‐O‐angelyl‐ingenol ( 4 ), 20‐O‐acetyl‐3‐O‐angeloyl‐17‐hydroxyingenol ( 5 ), 3‐O‐angelyl‐17‐(benzoyloxy)ingenol ( 6 ) and 20‐O‐acetyl‐3‐O‐angelyl‐17‐(benzoyloxy)ingenol ( 7 ). Compounds 1 – 4 were isolated for the first time, whereas 5 – 7 are known metabolites but detected for the first time in this plant. Biological investigations revealed that these compounds are tumor promoters.     

New Highly Oxidized Formamidobisabolene‐Derived Sesquiterpenes from a Hainan Sponge Axinyssa variabilis

Two new highly oxidized formamidobisabolene sesquiterpenes ( 1 and 2 ), together with seven known related analogues ( 3 – 9 ), were isolated from a Hainan sponge Axinyssa variabilis. Their structures were determined by extensive 1D‐ and 2D‐NMR and MS spectra analyses, and by comparison of their spectroscopic data with those of the related model compounds. The plausible biosynthetic relationship between compounds 1 – 9 has also been described.     

Phochinenins A – F,Dimeric 9,10‐Dihydrophenanthrene Derivatives,from Pholidota chinensis

Six new compounds, phochinenins A–F ( 1 – 6 ), dimerized from 9,10‐dihydrophenanthrene and dihydrostilbene through direct coupling or an oxygen bridge, along with eight known compounds, were isolated from the whole plants of Pholidota chinensis. Their structures were elucidated on the basis of extensive spectroscopic investigations (1D‐, 2D‐NMR, and HR‐EI‐MS).     

Two New Pentacyclic Triterpenoids from Centella asiatica

Two new pentacyclic triterpenoids, named centelloside D ( 1 ) and centelloside E ( 9 ), together with the seven known compounds 2 – 8 , were isolated from the whole plants of Centella asiatica. Compound 5 was reported for the first time from this genus. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D ‐ and 2D ‐NMR, and HR‐MS experiments, and by comparison with literature data. Compounds 1 – 4, 6 , and 8 did not show any cytotoxicity against L929 (mouse embryonic fibroblast).     

Five New Steroidal Alkaloid Glycosides from Solanum tuberosum

Five new steroidal alkaloid glycosides, 1 – 5 , along with the known analog 6 , have been isolated from the aerial parts of Solanum tuberosum. The structures of the new compounds were elucidated by spectroscopic methods, including 1D‐ and 2D‐NMR and HR‐ESI‐MS techniques, as well as by comparison of the spectral data with those of related compounds. Only compound 6 showed significant cytotoxicity.     

Eupatozansins A – C,Sesquiterpene Lactones from Eupatorium chinense var. tozanense

Phytochemical investigation of Eupatorium chinense var. tozanense has resulted in the isolation of three new germacranolides, designated as eupatozansins A–C ( 1 – 3 ), along with five known compounds, (5S,6R,7R,8R)‐8‐angeloyloxy‐2‐oxoguaia‐1(10),3,11(13)‐trien‐12,6‐olide ( 4 ), costunolide ( 5 ), leptocarpin ( 6 ), 2α‐hydroxyeupatolide 8‐O‐angelate ( 7 ), and quercetin ( 8 ). The structures of the new compounds were identified by 1D and 2D NMR experiments, as well as high‐resolution mass spectrometry. The in vitro cytotoxic activities of compounds 1 – 8 were evaluated.     

Six New C21 Steroidal Glycosides from Cynanchum bungei Decne

Six new C₂₁ steroidal glycosides 1 – 6 were isolated from the stem parts of Cynanchum bungei Decne . The structures of the new glycosides were determined on the basis of spectroscopic analysis, including 1D‐ and 2D‐NMR and HR‐ESI‐MS techniques as well as by comparison of their spectral data with those of related compounds.     

New Triterpenoid Saponins from the Roots of Gypsophila paniculata L.

The seven new triterpenoid saponins 1 – 7 were isolated from the roots of Gypsophila paniculata L. Their structures were established by 1D ‐ and 2D‐NMR techniques, HR‐MS, and acid hydrolysis. The isolated compounds include 3,28‐O‐bidesmosides with or without a 4‐methoxycinnamoyl group (see 1 vs. 2 and 3 ), and 3‐O‐monoglucosides 4 – 7 . All isolated saponins 1 – 7 and their aglycones were evaluated for their α‐glucosidase inhibition activity. Compound 1 showed inhibitory activity against yeast α‐glucosidase with an IC₅₀ value of 100.9±3.3 μM , whereas compounds 2 – 7 were inactive.     

Four Novel Diterpenoids from Crinipellis sp. 113

Four novel diterpenoids, namely (4β)‐4,4‐O‐dihydrocrinipellin A ( 1 ), (4β,8α)‐4,4‐O,8,8‐O‐tetrahydrocrinipellin B ( 2 ), crinipellin C ( 3 ), and crinipellin D ( 4 ), along with three known ones, (3β,4β)‐3,3‐C,4,4‐O‐tetrahydrocrinipellin A ( 5 ), (4β)‐4,4‐O‐dihydrocrinipellin B ( 6 ), and phlebiakauranol alcohol, were isolated from the fungal strain Crinipellis sp. 113. Their structures were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR experiments, and by HR‐Q‐TOF mass spectrometry. Antitumor and antibacterial assays with the novel compounds 1 – 4 were carried out, showing moderate activities against HeLa cells and no effects on the growth of tested bacteria or yeast.     

New Pentacyclic Triterpenoids from Centella asiatica

Three new pentacyclic triterpenoids, named centellasaponins G, H, and F ( 1 – 3 , resp.), together with four known compounds, 4 – 7 , were isolated from the whole plants of Centella asiatica. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D‐ and 2D‐NMR and HR‐MS experiments, and by comparison with literature data.     

Two New Limonoids from the Root Bark of Chinese Medicinal Plant Dictamnus dasycarpus

Two new limonoids, kihadanin C ( 1 ) and 23‐methoxydasylactone A ( 2 ), together with seven related known ones, 3 – 9 , were isolated from the root bark of the plant Dictamnus dasycarpus. The structures of the new compounds were elucidated on the basis of extensive analyses of their spectroscopic data (1D‐ and 2D‐NMR, MS) and by comparison of their NMR data with those reported in the literature. To the best of our knowledge, 1 presents the first example of A,D‐seco limonoid with an unusual 3,4‐dihydroxy‐2,5‐dimethoxytetrahydrofuran moiety as ring E. In the bioassay in vitro, 7 showed moderate antibacterial activity against Staphylococcus aureus, while 8 and 9 displayed neuroprotective activities against H₂O₂‐induced injury in SH‐SY5Y cells.     

Ophiobolin Sesterterpenoids and Pyrrolidine Alkaloids from the Sponge‐Derived Fungus Aspergillus ustus

Chemical examination of the fungus Aspergillus ustus isolated from the Mediterranean sponge Suberites domuncula yielded the five new ophiobolin‐type sesterterpenoids 1 – 5 and the two new pyrrolidine alkaloids 6 and 7 , together with the known compound aurantiamine and cerebroside D. The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic‐data analysis (1D‐ and 2D‐NMR, MS, and UV) and comparison with literature data. All compounds were evaluated for their cytotoxicity against murine lymphoma cell line L5178Y.