Colletoindole A from the Mangrove Plant Endophytic Fungus Colletotrichum tropicale SCSIO 41022

A new indole derivative colletoindole A ( 1 ), along with two new indole derivatives ( 2 and 3 ) and one known compound acropyrone ( 4 ) were isolated from cultures of Colletotrichum tropicale SCSIO 41022 derived from a mangrove plant Kandelia candel. The structures of 1 – 4 were determined by analysis of NMR and MS data. The cytotoxicity of 1 , 2 and 4 , and the COX‐2 inhibitory activity of 1 and 2 were evaluated.     

New Furanone Derivatives and Alkaloids from the Co‐Culture of Marine‐Derived Fungi Aspergillus sclerotiorum and Penicillium citrinum

Six new compounds including two furanone derivatives sclerotiorumins A and B ( 1 and 2 ), one novel oxadiazin derivative sclerotiorumin C ( 3 ), one pyrrole derivative 1‐(4‐benzyl‐1H‐pyrrol‐3‐yl)ethanone ( 4 ), and two complexes of neoaspergillic acid aluminiumneohydroxyaspergillin ( 5 ) and ferrineohydroxyaspergillin ( 6 ) were isolated from the co‐culture of marine‐derived fungi Aspergillus sclerotiorum and Penicillium citrinum. Compound 3 was the first natural 1,2,4‐oxadiazin‐6‐one. Compound 5 showed significant and selective cytotoxicity against human histiocytic lymphoma U937 cell line (IC₅₀ = 4.2 μm ) and strong toxicity towards brine shrimp (LC₅₀ = 6.1 μm ), and oppositely increased the growth and biofilm formation of Staphylococcus aureus.     

Microsphaerol and Seimatorone: Two New Compounds Isolated from the Endophytic Fungi,Microsphaeropsis sp. and Seimatosporium sp.

A new polychlorinated triphenyl diether named microsphaerol ( 1 ), has been isolated from the endophtic fungus Microsphaeropsis sp. An intensive phytochemical investigation of the endophytic fungus Seimatosporium sp., led to the isolation of a new naphthalene derivative named seimatorone ( 2 ) and eight known compounds, i.e., 1‐(2,6‐dihydroxyphenyl)‐3‐hydroxybutan‐1‐one ( 3 ), 1‐(2,6‐dihydroxyphenyl)butan‐1‐one ( 4 ), 1‐(2‐hydroxy‐6‐methoxyphenyl)butan‐1‐one ( 5 ), 5‐hydroxy‐2‐methyl‐4H‐chromen‐4‐one ( 6 ), 2,3‐dihydro‐5‐hydroxy‐2‐methyl‐4H‐chromen‐4‐one ( 7 ), 8‐methoxynaphthalen‐1‐ol ( 8 ), nodulisporins A and B ( 9 and 10 , resp.), and daldinol ( 11 ). The structures of 1 and 2 were elucidated by detailed spectroscopic analysis including ¹H‐ and ¹³C‐NMR, COSY, HMQC, HMBC, and HR‐EI‐MS, while the structures of the known compounds were deduced from comparison of their spectral data with those in the literature. Preliminary studies revealed that microsphaerol ( 1 ) showed good antibacterial activities against B. Megaterium and E. coli, and good antilagal and antifungal activities against C. fusca, M. violaceum, respectively. On the other hand, seimatorone ( 2 ) exhibited moderate antibacterial, antialgal, and antifungal activities.     

Cytotoxic Compounds from the Leaves of Garcinia polyantha

A new compound, named banganxanthone C (=12‐(1,1‐dimethylprop‐2‐en‐1‐yl)‐5,10‐dihydroxy‐9‐methoxy‐2‐methyl‐2‐(4‐methylpent‐3‐en‐1‐yl)‐2H,6H‐pyrano[3,2‐b]xanthen‐6‐one; 4 ), together with five known compounds, were isolated from the leaves of Garcinia polyantha. The structures of the compounds were elucidated on the basis of 1D‐ and 2D‐NMR spectroscopy. Among the known compounds, two were xanthones, one was a pentacyclic triterpene, one sterol, and one benzophenone derivative. Isoxanthochymol ( 2 ) and 4‐[(2E)‐3,7‐dimethylocta‐2,6‐dien‐1‐yl]‐1,5,8‐trihydroxy‐3‐methoxy‐9H‐xanthen‐9‐one ( 3 ) exhibited significant antiproliferative activity against the leukemia cell line TPH‐1 with IC₅₀ inhibition values of 1.5 and 2.8 μg/ml, respectively. The cytotoxic activity was found to be related to apoptosis induction.     

A new ferulic acid ester, a new ellagic acid derivative, and other constituents from pachycentria formosana: effects on neutrophil pro-inflammatory responses

A new ferulic acid ester derivative, tetracosane‐1,24‐diyl di[(Z)‐ferulate] ( 1 ), and a new ellagic acid derivative, 3,4 : 3′,4′‐bis(O,O‐methylene)ellagic acid ( 2 ), have been isolated from leaves and twigs of Pachycentria formosana, together with eight known compounds. Their structures were determined by in‐depth spectroscopic and mass‐spectrometric analyses. Among the isolated compounds, oleanolic acid ( 6 ), ursolic acid acetate ( 7 ), and 3‐epibetulinic acid ( 9 ) exhibited potent inhibition (IC₅₀ values ≤21.8 μM ) of O₂^⋅− generation by human neutrophils in response to N‐formyl‐L ‐methionyl‐L ‐leucyl‐L ‐phenylalanine/cytochalasin B (fMLP/CB). In addition, oleanolic acid ( 6 ), 3‐O‐[(E)‐feruloyl]ursolic acid ( 8 ), 3‐epibetulinic acid ( 9 ), and lawsonic acid ( 10 ) also inhibited fMLP/CB‐induced elastase release with IC₅₀ values ≤18.6 μM .     

Chemical Constituents from a Mangrove-Derived Actinobacteria Isoptericola chiayiensis BCRC 16888 and Evaluation of Their Anti-NO Activity

Cultivation of the actinobacteria strain Isoptericola chiayiensis, a mangrove - derived actinobacteria that was isolated from a mangrove soil collected in Chiayi County, resulted in the isolation of one new 2-furanone derivative, isopterfuranone ( 1 ), one new sesquiterpenoid, isopterchiayione ( 2 ), one new benzenoid derivative, isopterinoid ( 3 ), five new flavonoids, chiayiflavans A−E ( 4 – 8 ), and 4 metabolites isolated for the first time from nature source, methyl 3-(4-methyl-2,5-dioxopyrrolidin-3-yl)propanoate ( 9 ), 3-ethyl-4-methylpyrrolidine-2,5-dione ( 10 ), chiayiensol ( 11 ) and chiayiensic acid ( 12 ). Their structures were determined through in-depth spectroscopic and mass-spectrometric analyses. Most of the isolates showed potent inhibitory effects on NO production in LPS-stimulated RAW 264.7 murine macrophages cells with IC₅₀ values ranging from 9.36 to 40.02 μM. Of these isolates, 4 and 5 showed NO inhibitory activity with IC₅₀ values of 17.14 and 9.36 μM, stronger than the positive control quercetin (IC₅₀=36.95 μM). This is the first report on flavan metabolites from the genus Isoptericola.     

Indole Alkaloids from the Sea Anemone Heteractis aurora and Homarine from Octopus cyanea

The two new indole alkaloids 2‐amino‐1,5‐dihydro‐5‐(1H‐indol‐3‐ylmethyl)‐4H‐imidazol‐4‐one ( 1 ), 2‐amino‐5‐[(6‐bromo‐1H‐indol‐3‐yl)methyl]‐3,5‐dihydro‐3‐methyl‐4H‐imidazol‐4‐one ( 2 ), and auramine ( 3 ) have been isolated from the sea anemone Heteractis aurora. Both indole alkaloids were synthesized for the confirmation of the structures. Homarine ( 4 ), along with uracil ( 5 ), hypoxanthine ( 6 ), and inosine ( 7 ) have been obtained from Octopus cyanea.     

Four New Acylated Iridoid Glycosides from the Aerial Part of Veronicastrum sibiricum and Their Antioxidant Response Element‐Inducing Activity

Four new ( 1 – 4 ) and one known ( 5 ) acylated iridoid glycosides were isolated from the aerial parts of Veronicastrum sibiricum (L.) Pennell . The chemical structures of the isolated compounds were determined to be 3″,4″‐dicinnamoyl‐6‐O‐rhamnopyranosyl‐10‐O‐bergaptol‐5,7‐bisdeoxycynanchoside ( 1 ), 3″,4″‐dicinnamoyl‐6‐O‐rhamnopyranosylpaulownioside ( 2 ), 2″,4″‐dicinnamoyl‐6‐O‐rhamnopyranosylcatalpol ( 3 ), 3″,4″‐dicinnamoyl‐6‐O‐rhamnopyranosylaucubin ( 4 ), and 3″,4″‐dicinnamoyl‐6‐O‐rhamnopyranosylcatalpol ( 5 ) using spectroscopic techniques. Among these compounds, compound 5 increased antioxidant response element (ARE) luciferase activity.     

A New Anti‐Inflammatory Alkaloid from Roots of Heracleum dissectum

Using various chromatographic methods, a new piperidinone alkaloid, (3S)‐3‐{4‐[(1E)‐3‐hydroxyprop‐1‐en‐1‐yl]‐2‐methoxyphenoxy}piperidin‐2‐one ( 1 ), together with 10 known compounds, bergapten ( 2 ), xanthotoxol ( 3 ), isopimpinellin ( 4 ), isobergapten ( 5 ), heratomol‐6‐O‐β‐d ‐glucopyranoside ( 6 ), scopoletin ( 7 ), apterin ( 8 ), 3‐methoxy‐4‐β‐d ‐glucopyranosyloxypropiophenone, (praeroside; 9 ), tachioside ( 10 ) and coniferin ( 11 ), were isolated from roots of Heracleum dissectum Ledeb . Their structures were elucidated on the basis of physicochemical properties and the detailed interpretation of various spectroscopic data. All the isolated compounds were screened for anti‐inflammatory activity in vitro. As the results, compound 1 and 8 showed significantly inhibitory activity on nitric oxide production in RAW264.7 cells.     

Sesquiterpenoids from Chloranthus henryi and Their Anti‐neuroinflammatory Activities

Five new and seven known mono‐sesquiterpenoids ( 1 – 5 and 6 – 12 , resp.) together with five known lindenane‐type disesquiterpenoids, 13 – 17 , were isolated from the whole plant of Chloranthus henryi. Based on spectroscopic methods, the new structures were established to be (5S,6R,8S,10R)‐6‐hydroxyeudesma‐4(15),7(11)‐diene‐12,8‐olide ( 1 ), 6α‐hydroxyeudesma‐4(15),7(11),8(9)‐triene‐12,8‐olide ( 2 ), 8,12‐epoxy‐1β‐hydroxyeudesma‐4(15),7,11‐trien‐6‐one ( 3 ), 12‐oxochloraniolide A ( 4 ), and (4α)‐8‐hydroxy‐12‐norcardina‐6,8,10‐trien‐11‐one ( 5 ), respectively. Among the isolates, compound 2 , zederone epoxide ( 8 ), spicachlorantin G ( 13 ), chloramultilide A ( 14 ), shizukaol B ( 15 ), and spicachlorantin B ( 17 ) showed significant anti‐neuroinflammatory effects by inhibiting nitric‐oxide (NO) production in lipopolysaccharide (LPS)‐stimulated murine BV‐2 microglial cells with relatively low cytotoxicity.     

Chemical Constituents from a Soil‐Derived Actinomycete,Actinomadura miaoliensis BCRC 16873, and Their Inhibitory Activities on Lipopolysaccharide‐Induced Tumor Necrosis Factor Production

An investigation on the secondary metabolites from the BuOH extract of the fermentation broth of the thermotolerant polyester‐degrading actinomycete Actinomadura miaoliensis BCRC 16873 was carried out. One previously undescribed α‐pyrone (=pyran‐2‐one) derivative, designated as miaolienone ( 1 ), and a new butanolide, miaolinolide ( 2 ), together with 13 known compounds, 3 – 15 , were obtained. Their structures were established on the basis of extensive 1D‐ and 2D‐NMR analyses in combination with HR‐MS experiments. In addition, the isolated compounds 1 – 15 were evaluated for the inhibitory effects of the isolates on the production of tumor necrosis factor (TNF‐α) induced by lipopolysaccharide (LPS). Among the isolates, 1 and 2 significantly inhibited TNF‐α production in U937 cells in vitro, and the IC₅₀ values were 0.59 and 0.76 μM , respectively. Compounds 3 – 5 displayed moderate inhibitory activities on LPS‐induced TNF‐α production.     

Butanolides from Methanolic Extract of Litsea glutinosa

Phytochemical investigations of a MeOH extract obtained from the heartwoods of the Litsea glutinosa (Lauraceae) led to the isolation and characterization of four new butenolides, (3R,4S,5S)‐2‐hexadecyl‐3‐hydroxy‐4‐methylbutanolide 1 , litsealactone C ( 2 ), and litsealactone D ( 4 ), litsealactone G ( 5 ), and a new benzoic acid derivative named eusmoside C ( 3 ). The structures of these compounds were elucidated on the basis of spectral studies.     

New Isoprenylated Phenolic Compounds from Morus laevigata

Two new isoprenylated flavonoids, laevigasins A and B ( 1 and 2 , resp.), and one new isoprenylated 2‐arylbenzofuran, leavigasin C ( 3 ), together with eight known compounds, 4 – 11 , were isolated from the twigs of Morus laevigata. Their structures were elucidated by spectroscopic methods. Laevigasin A ( 1 ) showed significant inhibitory effect on α‐glucosidase in vitro. Notabilisin E ( 5 ), taxifolin ( 10 ), and hultenin ( 11 ) inhibited PTP1B phosphatase activity in vitro.     

The Chemical Constituents of Endophytic Fungus Trichoderma sp. MFF‐1

A fungal strain named MFF‐1 was isolated from the flower of Pyrethrum cinerariifolium. Based on the sequence at the internal transcribed spacer (ITS) region, this strain was identified as a Trichoderma sp. Two new compounds, including a mitorubrin derivative and its potential biogenetic precursor, together with a known compound, were isolated from the cultures of the endophytic fungus. Their structures were established by spectroscopic methods and determined to be (3S*,6R*,7R*)‐3,4,5,6,7,8‐hexahydro‐7‐hydroxy‐7‐methyl‐8‐oxo‐3‐[(E)‐prop‐1‐enyl]‐1H‐isochromen‐6‐yl 2,4‐dihydroxy‐6‐methylbenzoate ( 1 ), named deacetylisowortmin, (E)‐2‐(hydroxymethyl)‐3‐(2‐hydroxypent‐3‐enyl)phenol ( 2 ), and wortmannin ( 3 ). All compounds were assayed for antimicrobial activity. Compound 3 showed activity against Candida albicans and Bacillus cereus.     

Chemical Constituents from the Whole Plant of Gaultheria itoana Hayata

Two new diterpenoids, 14,18‐dihydroxyabieta‐8,11,13‐trien‐7‐one ( 1 ) and 13‐acetyl‐14,18‐dihydroxy‐podocarpa‐8,11,13‐triene ( 2 ), together with eight known compounds, i.e., gaultheric acid ( 3 ), vanillic acid ( 4 ), 4‐hydroxybenzoic acid ( 5 ), cinnamic acid ( 6 ), stearic acid ( 7 ), palmitic acid ( 8 ), β‐sitosterol ( 9 ), and stigmasterol ( 10 ), were isolated from the MeOH extract of the whole plant of Gaultheria itoana Hayata (Ericaceae). The structures of the new constituents were elucidated by spectroscopic methods (UV, IR, and 1D‐ and 2D‐NMR) and by mass spectrometry (HR‐ESI‐MS). Among them, 1 and 2 were demonstrated to exhibit significant cytotoxic activity against the LNCaP cell line.     

Cochlioquinone Derivatives with Apoptosis‐Inducing Effects on HCT116 Colon Cancer Cells from the Phytopathogenic Fungus Bipolaris luttrellii L439

A new cochlioquinone derivative, cochlioquinone F ( 1 ), as well as three known compounds, anhydrocochlioquinone A ( 2 ), isocochlioquinone A ( 3 ), and isocochlioquinone C ( 4 ), were isolated from the PDB (potato dextrose broth) culture of the phytopathogenic fungus Bipolaris luttrellii. The structure of 1 was elucidated on the basis of NMR techniques. The apoptosis‐inducing effects of compounds 1 – 4 were evaluated against HCT116 cancer cells. Compound 2 exhibited the strongest activity in inducing apoptosis on HCT116 cells within the range of 10–30 μM . In addition, the caspase activation, the release of cytochrome c from mitochondria, and the downregulation of Bcl‐2 protein in HCT116 cells treated with compound 2 were detected.     

Novel Flavones from the Root of Phytolacca acinosa Roxb.

Two new flavones, 6,7‐methylenedioxy‐4‐hydroxypeltogynan‐7′‐one ( 1 ), cochliophilin B ( 2 ), as well as two known ones, cochliophilin A ( 3 ) and 6‐methoxy‐7‐hydroxy flavone ( 4 ), were isolated from the ethanol extract of the root of Phytolacca acinosa Roxb . Compound 1 is a flavanol framework with one δ‐lactone unit, which is rather rare in nature. The structures of the new compounds were determined on the basis of extensive spectroscopic (IR, MS, 1D‐ and 2D‐NMR) analyses, the absolute configuration of 1 was established by comparing experimental and calculated electronic circular dichroism spectra. The structures of known compounds were fixed by comparison with literatures data. Compounds 2 and 4 showed modest inhibitory activities against BEL‐7402 cell line, with IC₅₀ values of 28.22 and 39.16 μmol/L, respectively.     

Chemical Constituents of Daphne giraldii Nitsche

In a search for structurally interesting substances from traditional Chinese medicines, eight compounds were isolated from an ethanolic extract of the stem bark of Daphne giraldii Nitsche. On the basis of one- and two-dimensional nuclear magnetic resonance and mass spectrometry data, and chemical methods, their structures were determined to be 2H-1-benzopyran-2-one-8-hydroxy-7-O-β-D-glucopyranosyl-5-（2-oxo- 2H-1-benzopyran-7-hydroxy-8-yloxy） （compound 1）, 1-pentanone, 1-（4-hydroxyphenyl）-5-phenyl （compound 2）, octadecyl caffeate （compound 3）, （＋）syringaresinol-4,4＇-diglycoside （compound 4）, daphnetin-8-O-β-D- glucopyranoside （compound 5）, p-hydroxybenzoic acid （compound 6）, 7,7＇-dihydroxy-[6, 8＇-bi-2H-benzopyran]- 2, 2＇-dione （compound 7）, and daphnorin （compound 8）, respectively. Of the compounds isolated, compounds 1 and 2, which we named daphnolin and daphnolon, respectively, were new, and the others were obtained from this plant for the first time.     

Four New Chromone Derivatives from Colletotrichum gloeosporioides

Four previously unreported chromones, 5‐hydroxy‐2‐(hydroxymethyl)‐8‐methoxy‐4H‐chromen‐4‐one ( 1 ), (5R,7S)‐5,7‐dihydroxy‐2‐propyl‐5,6,7,8‐tetrahydro‐4H‐chromen‐4‐one ( 2 ), (5R,7S)‐5,7‐dihydroxy‐2‐methyl‐5,6,7,8‐tetrahydro‐4H‐chromen‐4‐one ( 3 ), and (5R,7S)‐5,7‐dihydroxy‐2‐[(E)‐prop‐1‐en‐1‐yl]‐5,6,7,8‐tetrahydro‐4H‐chromen‐4‐one ( 4 ), as well as one known analogue 5‐hydroxy‐2‐methyl‐4H‐chromen‐4‐one ( 5 ) were isolated from the fermentation broth of the endophytic fungus Colletotrichum gloeosporioides derived from the mangrove Ceriops tagal. Their structures were elucidated based on extensive spectroscopic analyses. The absolute configurations of 2 – 4 were determined by comparison the experimental and calculated electronic circular dichroism (ECD) spectra. Compound 2 showed cytotoxic activity against A549 cell line with the IC₅₀ value of 0.094 mm .     

Hispanane‐Type Diterpenoid and Secoiridoid Glucosides from Viburnum cylindricum

Three hitherto unknown compounds, including one new hispanane‐type diterpenoid glucoside, namely viburnumoside ( 1 ), two new secoiridoid glucosides, 7α‐galloyloxysweroside ( 2 ), and 7β‐galloyloxysweroside ( 3 ), together with ten known compounds ( 4 – 13 ) were isolated from the ethanol extract of twigs and leaves of Viburnum cylindricum. Their structures were elucidated on the basis of extensive spectroscopic studies, and the absolute configuration of compound 1 was confirmed by the experimental and calculated electronic circular dichroism (ECD) data.