Cytosporones, coumarins, and an alkaloid from the endophytic fungus Pestalotiopsis sp. isolated from the Chinese mangrove plant Rhizophora mucronata

Chemical examination of the endophytic fungus Pestalotiopsis sp., isolated from the leaves of the Chinese mangrove Rhizophora mucronata, yielded 11 new compounds including cytosporones J-N (1-3, 5-6), five new coumarins pestalasins A-E (8-12), and a new alkaloid named pestalotiopsoid A (14), along with the known compounds cytosporone C (4), dothiorelone B (7), and 3-hydroxymethyl-6,8-dimethoxycoumarin (13). The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic data analysis.

Brominated Azaphilones from the Sponge-Associated Fungus Penicillium canescens Strain 4.14.6a

The fungus Penicillium canescens was isolated from the inner tissue of the Mediterranian sponge Agelas oroides. Fermentation of the fungus on solid rice medium yielded one new chlorinated diphenyl ether (1) and 13 known compounds (2-14). Addition of 5% NaBr to the rice medium increased the amounts of 4-6, while lowering the amounts of 8, 12, and 14. Furthermore, it induced the accumulation of 17 and two new brominated azaphilones, bromophilones A and B (15 and 16). Compounds 15 and 16 are the first example of azaphilones with the connection of a benzene moiety and the pyranoquinone core through a methylene group. The structures of the new compounds were elucidated based on the 1D and 2D NMR…

New bioactive alkaloids from the marine sponge Stylissa sp.

Abstract Chemical investigation of the Indonesian marine sponge Stylissa species, which was collected at 2008 from Derawan Islands, Berau, NE Kalimantan, Indonesia offered four new brominated alkaloids, including 12-N-methyl stevensine (1), 12-N-methyl-2-debromostevensine (2), 3-debromolatonduine B methyl ester (3), 3-debromolatonduine A (4) together with eight known alkaloids identified as Z-hymenialdisine, Z-debromohymenialdisine, Stevensine, 2-debromostevensine, 3-bromoaldizine, 3,4-dibromopyrrole-2-carbamide, latonduine A, and latonduine B methyl ester (5–12), respectively. The structures of all isolated compounds were unambiguously elucidated based on extensive 1D and 2D NMR spectrosco…

Polyketide Derivatives from Mangrove Derived Endophytic Fungus Pseudopestalotiopsis theae

Chemical investigation of secondary metabolites from the endophytic fungus Pseudopestalotiopsis theae led to the isolation of eighteen new polyketide derivatives, pestalotheols I&ndash

Expanding the chemical diversity of an endophytic fungus Bulgaria inquinans, an ascomycete associated with mistletoe, through an OSMAC approach

An endophytic fungus Bulgaria inquinans (isolate MSp3-1), isolated from mistletoe (Viscum album), was subjected to fermentation on solid Czapek medium. Chromatographic workup of the crude EtOAc extract yielded five new natural products (1–5). Subsequent application of the “One Strain, MAny Compounds” (OSMAC) strategy on this strain by the addition of a mixture of salts (MgSO4, NaNO3 and NaCl) to solid Czapek medium induced the accumulation of nine additional new secondary metabolites (6–13, 16), with most of them (8, 10–12) not detectable in cultures lacking the salt mixture. The structures of the new compounds were established on the basis of the 1D/2D NMR and HRESIMS data. The TDDFT-ECD m…

A new depsidone derivative from mangrove sediment derived fungus

A new depsidone derivative botryorhodine I (1), along with eight known compounds (2-9) were obtained from solid rice cultures of the fungal strain, Lasiodiplodia theobromae M4.2-2 isolated from a mangrove sediment sample. The structures of the isolated compounds were elucidated on the basis of 1 D and 2 D NMR analysis as well as by HRESIMS. All compounds were evaluated for their cytotoxic potential against the mouse lymphoma cell line L5178Y as well as for their antibacterial activities against a panel of Gram-positive and Gram-negative bacterial strains. Compound 3 revealed potent cytotoxic activity with an IC50 of 7.3 µM whereas compound 7 showed selective anti-bacterial activity against …

Sesterterpenes and macrolide derivatives from the endophytic fungus Aplosporella javeedii.

Abstract Five sesterterpenes (1–5) including two new compounds (1 and 2), as well as a new (6) and a known macrolide (7) were isolated from the endophytic fungus Aplosporella javeedii. The structures of the new compounds were elucidated by analysis of their 1D and 2D NMR and HRMS data as well as by comparison with the literature. Compound 4 and its acetyl derivatives 4a, 4b, 4c which were prepared by acetylation of 4 exhibited moderate cytotoxicity against the mouse lymphoma cell line L5178Y with IC50 values ranging from 6.2 to 12.8 μM, respectively. Moreover, 4a and 4c exhibited also cytotoxicity against human leukemia (Jurkat J16) and lymphoma (Ramos) cell lines. Compound 7 showed strong …

Cryptic Secondary Metabolites from the Sponge-Associated Fungus Aspergillus ochraceus

The fungus Aspergillus ochraceus was isolated from the Mediterranean sponge Agelas oroides. The initial fermentation of the fungus on solid rice medium yielded 16 known compounds (4&ndash

Indole Diterpenoids from an Endophytic Penicillium sp.

A chemical investigation of the endophyte Penicillium sp. (strain ZO-R1-1), isolated from roots of the medicinal plant Zingiber officinale, yielded nine new indole diterpenoids (1-9), together with 13 known congeners (10-22). The structures of the new compounds were elucidated by 1D and 2D NMR analysis in combination with HRESIMS data. The absolute configuration of the new natural products 1, 3, and 7 was determined using the TDDFT-ECD approach and confirmed for 1 by single-crystal X-ray determination through anomalous dispersion. The isolated compounds were tested for cytotoxicity against L5178Y, A2780, J82, and HEK-293 cell lines. Compound 1 was the most active metabolite toward L5178Y ce…

Trimeric Hemibastadin Congener from the Marine Sponge Ianthella basta

The first naturally occurring trimeric hemibastadin congener, sesquibastadin 1 (1), and the previously reported bastadins 3, 6, 7, 11, and 16 (2-6) were isolated from the marine sponge Ianthella basta, collected in Indonesia. The structure of 1 was elucidated on the basis of 1D and 2D NMR measurements and by HRMS. Among all the isolated compounds, the linear sesquibastadin 1 (1) and bastadin 3 (2) showed the strongest inhibition rates for at least 22 protein kinases (IC(50) = 0.1-6.5 μM), while the macrocyclic bastadins (3-6) demonstrated a strong cytotoxic potential against the murine lymphoma cell line L5178Y (IC(50) = 1.5-5.3 μM).

Azacoccones F-H, new flavipin-derived alkaloids from an endophytic fungus Epicoccum nigrum MK214079.

Abstract Three new flavipin-derived alkaloids, azacoccones F-H (1–3), along with six known compounds (4–9) were isolated from the endophytic fungus Epicoccum nigrum MK214079 associated with leaves of Salix sp. The structures of the new compounds were established by analysis of their 1D/2D nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectroscopy (HRESIMS) data. The absolute configuration of azacoccones F-H (1–3) was determined by comparison of experimental electronic circular dichroism (ECD) data with reported ones and biogenetic considerations. Epicocconigrone A (4), epipyrone A (5), and epicoccolide B (6) exhibited moderate antibacterial activity again…

Two new metabolites from the endophytic fungus Xylaria sp. isolated from the medicinal plant Curcuma xanthorrhiza

Abstract The endophytic fungus Xylaria sp. was isolated from healthy leaves of Curcuma xanthorrhiza, collected on the island of Timor, Indonesia. Two new compounds (1 and 2), together with the known resacetophenone (3), were isolated and their structures were elucidated on the basis of comprehensive NMR and mass spectral analyses. The enantiomers of rac-1 were separated by chiral HPLC and their HPLC-ECD spectra were recorded to determine the absolute configuration on the basis of TDDFT-ECD calculations. The (3R,3aR, 9aR) absolute configuration of the optically active 2 was established by comparing the experimental solution ECD spectrum with the TDDFT ones computed for the gas phase and solu…

Targeted solid phase fermentation of the soil dwelling fungus Gymnascella dankaliensis yields new brominated tyrosine-derived alkaloids

Seven new brominated tyrosine-derived alkaloids, gymnastatins T–Y (1–6) and dankastatin D (7), together with three known likewise brominated analogues gymnastatins I–K (8–10) were isolated from the soil fungus Gymnascella dankaliensis through fermentation on solid rice medium following addition of NaBr. None of these compounds were detected when the fungus was cultured on rice that either lacked NaBr or that contained NaCl instead, indicating a remarkable plasticity of the fungal secondary metabolism. All structures were elucidated on the basis of one and two dimensional NMR spectroscopic analyses and MS data. The absolute configuration of the new gymnastatin T (1) was determined by X-ray c…

Fusaristatins D–F and (7S,8R)-(−)-chlamydospordiol from Fusarium sp. BZCB-CA, an endophyte of Bothriospermum chinense

Abstract Three new lipodepsipeptides, fusaristatins D–F (1–3) and a new α-pyrone derivative, (7S,8R)-(−)-chlamydospordiol (5), together with eight known compounds (4, 6–12) were obtained from solid rice cultures of Fusarium sp. BZCB-CA, an endophyte of the Chinese medicinal plant, Bothriospermum chinense. The planar structures of the new metabolites (1–3, 5) were established by spectroscopic techniques (1D/2D NMR and HRESIMS). Marfey’s method was applied to determine the absolute configuration of 1, while the absolute configuration of 5 was determined by single-crystal X-ray crystallography analysis in addition to Mosher’s method. Crystallographic data of inflatin C (7) are also supplied he…

Alkaloids from the Sponge-Associated FungusAspergillussp.

Seven new alkaloids including tryptoquivaline K (1) and fumiquinazolines K–P (2–7), bearing a rare 1-aminocyclopropane-1-carboxylic acid residue, together with six known compounds (8–13), were isolated from the fungus Aspergillus sp. obtained from the Mediterranean sponge Tethya aurantium. The structures of the new compounds were determined by extensive analysis by 1D and 2D NMR spectroscopy and mass spectrometry. The absolute configurations of tryptoquivaline K (1) and fumiquinazolines K and L (2, 3) were determined by TDDFT ECD calculations of their solution conformers, and the configurational assignment of the related fumiquinazolines M–P (4–7) was achieved by comparison of their ECD spe…

Arthrinins A–D: Novel diterpenoids and further constituents from the sponge derived fungus Arthrinium sp.

Bioassay-guided fractionation of a methanolic extract of the fungus Arthrinium sp., isolated from the Mediterranean sponge Geodia cydonium, afforded 10 natural products including five new diterpenoids, arthrinins A-D (1-4) and myrocin D (5). In addition, five known compounds were obtained, which included myrocin A (6), norlichexanthone (7), anomalin A (8), decarboxycitrinone (9) and 2,5-dimethyl-7-hydroxychromone (10). The structures of all isolated compounds were unambiguously elucidated based on extensive 1D and 2D NMR and HR-MS analyzes. The absolute configuration of arthrinins A-D (1-4) was established by the convenient Mosher method performed in NMR tubes and by interpretation of the R…

Aaptamine Derivatives from the Indonesian Sponge Aaptos suberitoides

Four new aaptamine derivatives (1-4) along with aaptamine (5) and three related compounds (6-8) were isolated from the ethanol extract of the sponge Aaptos suberitoides collected in Indonesia. The structures of the new compounds were unambiguously determined by one- and two-dimensional NMR and by HRESIMS measurements. Compounds 3, 5, and 6 showed cytotoxic activity against the murine lymphoma L5178Y cell line, with IC(50) values ranging from 0.9 to 8.3 μM.

Hydroquinone derivatives from the marine-derived fungus Gliomastix sp.

Eight new hydroquinone derivatives, gliomastins A–D (1–4), 9-O-methylgliomastin C (5), acremonin A 1-O-β-D-glucopyranoside (6), gliomastin E 1-O-β-D-glucopyranoside (7), and 6′-O-acetyl-isohomoarbutin (8), together with seven known analogues were isolated from the marine-derived fungus Gliomastix sp. Their structures were elucidated by extensive spectroscopic analysis including 1D and 2D NMR measurements aided by DFT NMR calculations as well as MS data. TDDFT-ECD and OR calculations were performed to determine the absolute configurations of 1 and the aglycones of 6 and 7. Compound 1 features a novel skeleton, biogenetically derived from a Diels–Alder reaction between derivatives of 11 and 1…

Cytotoxic eudesmane sesquiterpenes from Crepis sancta

Abstract Chemical exploration of Crepis sancta (L.) Bornm. (Asteraceae) aerial parts afforded two new eudesmane sesquiterpenes (1 and 2) together with three known congeners (3-5) and two known methylated flavonoids (6 and 7). Structure elucidation of the new compounds was unambiguously performed based on HRESIMS, 1D and 2D NMR spectroscopic analyses. All isolated compounds were subjected to an in vitro cytotoxicity assay against mouse lymphoma (L5178Y) cells, revealing moderate activities with IC50 ranging from 7.9 to 21.0 μM.

New Acyclic Cytotoxic Jasplakinolide Derivative from the Marine Sponge Jaspis splendens

A new acylic jasplakinolide congener (2), another acyclic derivative requiring revision (4), together with two jasplakinolide derivatives including the parent compound jasplakinolide (1) were isolated from the Indonesian marine sponge Jaspis splendens. The chemical structures of the new and known compounds were unambiguously elucidated based on HRESIMS and exhaustive 1D and 2D NMR spectral analysis as well as a comparison of their NMR data with those of jasplakinolide (1). The isolated jasplakinolides inhibited the growth of mouse lymphoma (L5178Y) cells in vitro with IC50 values in the low micromolar to nanomolar range.

Cytotoxic Isomalabaricane Triterpenes from the Marine Sponge Rhabdastrella globostellata

Fourteen isomalabaricane triterpenes were isolated from the marine sponge Rhabdastrella globostellata. In addition to the known compounds globostellatic acids A (1) and D (4) and stelliferin riboside (13), 11 of the compounds were new natural products, which included globostelletin (3), eight new globostellatic acid congeners, F to M (2, 5-11), and two new stelliferin ribosides (12 and 14). The isolated compounds were tested against three different cancer cell lines, L5178Y (mouse lymphoma), HeLa (human cervix carcinoma), and PC-12 (rat pheochromocytoma). The isomalabaricane derivatives were found to be selectively active toward the mouse lymphoma cell line L5178Y. The structures were deter…

Cladosins L-O, new hybrid polyketides from the endophytic fungus Cladosporium sphaerospermum WBS017

Abstract The endophytic fungus Cladosporium sphaerospermum WBS017 was obtained from healthy bulbs of Fritillaria unibracteata var. wabuensis. Fermentation of C. sphaerospermum on solid rice medium yielded three new hybrid polyketides, cladosins L−N (1–3), and a known derivative cladodionen (4). Further cultivation of this fungus on white bean medium afforded an additional new hybrid polyketide, cladosin O (5) along with three known analogues (6–8). The structures of the new compounds were elucidated using a combination of NMR and HRESIMS data. The absolute configurations of compounds 2 and 3 were determined by Mosher’s method and TDDFT-ECD calculations. All isolated compounds were evaluated…

Pretrichodermamide C and N-methylpretrichodermamide B, two new cytotoxic epidithiodiketopiperazines from hyper saline lake derived Penicillium sp.

Abstract Two new epidithiodiketopiperazines, pretrichodermamide C (1) and N-methylpretrichodermamide B (2) were isolated from the fungus Penicillium sp., derived from the sediment of a hyper saline lake located at Wadi El-Natrun in Egypt. The structures of 1 and 2 were unambiguously determined on the basis of one- and two-dimensional NMR spectroscopy and by high-resolution mass spectrometry, as well as by comparison with the literature. Compound 2 showed pronounced cytotoxicity against the murine lymphoma L5178Y cell line with an IC50 value of 2 μM.

Cytotoxic and protein kinase inhibiting nakijiquinones and nakijiquinols from the sponge Dactylospongia metachromia.

Chemical investigation of the sponge Dactylospongia metachromia afforded five new sesquiterpene aminoquinones (1-5), two new sesquiterpene benzoxazoles (6 and 7), the known analogue 18-hydroxy-5-epi-hyrtiophenol (8), and a known glycerolipid. The structures of all compounds were unambiguously elucidated by one- and two-dimensional NMR and by MS analyses, as well as by comparison with the literature. Compounds 1-5 showed potent cytotoxicity against the mouse lymphoma cell line L5178Y with IC50 values ranging from 1.1 to 3.7 μM. When tested in vitro for their inhibitory potential against 16 different protein kinases, compounds 5, 6, and 8 exhibited the strongest inhibitory activity against AL…

Colletotrin: a sesquiterpene lactone from the endophytic fungus Colletotrichum gloeosporioides associated with Trichilia monadelpha

Abstract A new sesquiterpene lactone, namely colletotrin (1), together with two known fungal metabolites (2, 3), was obtained from a rice culture of Colletotrichum gloeosporioides, an endophytic fungus isolated from the stem bark of Cameroonian medicinal plant Trichilia monadelpha (Meliaceae). The structure of the new compound was established on the basis of extensive NMR analysis (1H, 13C, heteronuclear single-quantum coherence and heteronuclear multiple-bond correlation) completed by high-resolution electrospray ionization mass spectroscopy results and by comparison of these data with those of related compounds described in the literature. Their cytotoxic and antibacterial activities agai…

Secondary metabolites of the lichen-associated fungus Apiospora montagnei

Abstract The endolichenic fungus Apiospora montagnei isolated from the lichen Cladonia sp. was cultured on solid rice medium, yielding the new diterpenoid libertellenone L (1), the new pyridine alkaloid, 23-O-acetyl-N-hydroxyapiosporamide (2) and the new xanthone derivative 8-hydroxy-3-hydroxymethyl-9-oxo-9H-xanthene-1-carboxylic acid methyl ether (3) together with 19 known compounds (4–22). The structures of the new compounds were elucidated by 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of the new 6,7-seco-libertellenone derivative 1 was determined by single-crystal X-ray diffraction. Four additional known compounds 23–26 were isolated when NaCl or NH4Cl w…

Sesquiterpenoids from the Endophytic Fungus Rhinocladiella similis

Ten new sesquiterpenoid derivatives, rhinomilisins A-J (1-10), along with six known analogues (11-16), were isolated from the mangrove-derived endophytic fungus Rhinocladiella similis. The structures of the new compounds were elucidated by their NMR and MS data, while the absolute configuration of 3 and 6 was determined by X-ray crystallographic analysis and Mosher's method, respectively. All isolated compounds (1-16) were evaluated for their cytotoxicity against the mouse lymphoma cell line L5178Y, and compounds 1, 7, and 15 showed moderate activity with IC50 values of 5.0, 8.7, and 24.4 μM, respectively.

New 2-Methoxy Acetylenic Acids and Pyrazole Alkaloids from the Marine Sponge Cinachyrella sp.

Three new 2-methoxy acetylenic acids (1–3) and a known derivative (4), in addition to three new natural pyrazole alkaloids (5–7) were isolated from an Indonesian marine sponge of the genus Cinachyrella. Compounds 5 and 6 have previously been reported as synthetic compounds. The structures of the new compounds were established on the basis of one- and two-dimensional NMR spectroscopy as well as by mass spectrometric data. The absolute configuration of the new acetylenic acid derivatives (1–3) was established by ECD spectroscopy. All isolated compounds were evaluated for their cytotoxicity against L5178Y mouse lymphoma cells. Compounds 1–4 exhibited strong activity with an IC50 value of 0.3 µ…

Isolation and Molecular Docking of Cytotoxic Secondary Metabolites from Two Red Sea Sponges of the Genus Diacarnus

Bioactive metabolites from the endophytic fungus Ampelomyces sp. isolated from the medicinal plant Urospermum picroides

Extracts of cultures grown in liquid or on solid rice media of the fungal endophyte Ampelomyces sp. isolated from the medicinal plant Urospermum picroides exhibited considerable cytotoxic activity when tested in vitro against L5178Y cells. Chromatographic separation yielded 14 natural products that were unequivocally identified based on their 1H and 13C NMR as well as mass spectra and comparison with previously published data. Six compounds (2, 4, 5, 7, 9 and 11) were natural products. Both fungal extracts differed considerably in their secondary metabolites. The extract obtained from liquid cultures afforded a pyrone (2) and sulfated anthraquinones (7 and 9) along with the known compounds …

Lactones from the Sponge-Derived Fungus Talaromyces rugulosus.

The marine-derived fungus Talaromyces rugulosus isolated from the Mediterranean sponge Axinella cannabina and cultured on solid rice medium yielded seventeen lactone derivatives including five butenolides (1–5), seven (3S)-resorcylide derivatives (6–12), two butenolide-resorcylide dimers (13 and 14), and three dihydroisocoumarins (15–17). Among them, fourteen compounds (1–3, 6–16) are new natural products. The structures of the isolated compounds were elucidated by 1D and 2D NMR (Nuclear Magnetic Resonance) spectroscopy as well as by ESI-HRMS (ElectroSpray Ionization-High Resolution Mass Spectrometry). TDDFT-ECD (Time-Dependent Density Functional Theory-Electronic Circular Dichroism) calcul…

Cytotoxic 14-Membered Macrolides from a Mangrove-Derived Endophytic Fungus, Pestalotiopsis microspora.

Seven new 14-membered macrolides, pestalotioprolides C (2), D-H (4-8), and 7-O-methylnigrosporolide (3), together with four known analogues, pestalotioprolide B (1), seiricuprolide (9), nigrosporolide (10), and 4,7-dihydroxy-13-tetradeca-2,5,8-trienolide (11), were isolated from the mangrove-derived endophytic fungus Pestalotiopsis microspora. Their structures were elucidated by analysis of NMR and MS data and by comparison with literature data. Single-crystal X-ray diffraction analysis was used to confirm the absolute configurations of 1, 2, and 10, while Mosher's method and the TDDFT-ECD approach were applied to determine the absolute configurations of 5 and 6. Compounds 3-6 showed signif…

Bioactive pyrrole alkaloids isolated from the Red Sea : marine sponge Stylissa carteri

Abstract Fifteen pyrrole alkaloids were isolated from the Red Sea marine sponge Stylissa carteri and investigated for their biological activities. Four of them were dibrominated [(+) dibromophakelline, Z-3-bromohymenialdisine, (±) ageliferin and 3,4-dibromo-1H-pyrrole-2-carbamide], nine compounds were monobrominated [(−) clathramide C, agelongine, (+) manzacidin A, (−) 3-bromomanzacidin D, Z-spongiacidin D, Z-hymenialdisine, 2-debromostevensine, 2-bromoaldisine and 4-bromo-1H-pyrrole-2-carbamide)] and finally, two compounds were non-brominated derivatives viz., E-debromohymenialdisine and aldisine. The structure elucidations of isolated compounds were based on 1D & 2D NMR spectroscopic …

Tetrahydroanthraquinone Derivatives from the Endophytic Fungus Stemphylium globuliferm

Four new tetrahydroanthraquinone derivatives, namely, dihydroaltersolanol B (1), dihydroaltersolanol C (2), and the atropisomers acetylalterporriol D (3) and acetylalterporriol E (4), were obtained from the endophytic fungus Stemphylium globuliferum, which was isolated from Juncus acutus growing in Egypt. The structures of the new compounds were unambiguously elucidated on the basis of one- and two-dimensional NMR spectroscopy, as well as by high-resolution mass spectrometry and electronic circular dichroism (ECD) spectroscopy. In addition, seven known anthraquinone derivatives 5–11 were isolated and identified on the basis of their spectral characteristics and by comparison with literature…

Cytotoxic secondary metabolites from the endophytic fungus Aspergillus versicolor KU258497

Abstract Two new isocoumarin dimers (1 and 2) and one new dihydroquinolone derivative (3) were isolated from Aspergillus versicolor, an endophyte derived from leaves of the Egyptian water hyacinth Eichhornia crassipes (Pontederiaceae), together with ten other known metabolites. Chemical structures of the isolated metabolites were determined based on HRESIMS, extensive 1D and 2D NMR spectroscopy. The relative and absolute configurations of the new natural products were established by ROESY and electronic circular dichroism (ECD) spectroscopy, respectively. The axial chirality of the isocoumarin 7,7′-homodimers (1 and 2) was deduced by TDDFT-ECD calculations. All isolated compounds were asses…

A new depsidone derivative from mangrove sediment derived fungus Lasiodiplodia theobromae

A new depsidone derivative botryorhodine I (1), along with eight known compounds (2-9) were obtained from solid rice cultures of the fungal strain, Lasiodiplodia theobromae M4.2-2 isolated from a mangrove sediment sample. The structures of the isolated compounds were elucidated on the basis of 1 D and 2 D NMR analysis as well as by HRESIMS. All compounds were evaluated for their cytotoxic potential against the mouse lymphoma cell line L5178Y as well as for their antibacterial activities against a panel of Gram-positive and Gram-negative bacterial strains. Compound 3 revealed potent cytotoxic activity with an IC50 of 7.3 µM whereas compound 7 showed selective anti-bacterial activity against …

Ircinal E, a New Manzamine Derivative from the Indonesian Marine Sponge Acanthostrongylophora ingens

Chemical investigation of the MeOH extract of the sponge Acanthostrongylophora ingens afforded the new manzamine derivative ircinal E (1), in addition to six known metabolites (2–7). The structure of the new compound was unequivocally elucidated using one- and two-dimensional NMR spectroscopy, as well as high-resolution mass spectrometry. Compounds 1–6 exhibited strong to moderate cytotoxicity against the murine lymphoma L5178Y cell line with IC50 values ranging from 2.8 to 21.7 μM.

Dithiodiketopiperazine derivatives from endophytic fungi Trichoderma harzianum and Epicoccum nigrum

A new epidithiodiketopiperazine (ETP), pretrichodermamide G (1), along with three known (epi)dithiodiketopiparazines (2-4) were isolated from cultures of Trichoderma harzianum and Epicoccum nigrum, endophytic fungi associated with medicinal plants Zingiber officinale and Salix sp., respectively. The structure of the new compound (1) was established on the basis of spectroscopic data, including 1D/2D NMR and HRESIMS. The isolated compounds were investigated for their antifungal, antibacterial and cytotoxic potential against a panel of microorganisms and cell lines. Pretrichodermamide A (2) displayed antimicrobial activity towards the plant pathogenic fungus Ustilago maydis and the human path…

Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp.

Abstract Two new xanthone derivatives, 12-dimethoxypinselin ( 1 ) and 12- O -acetyl-AGI-B4 ( 2 ), as well as two new phenolic bisabolane-type sesquiterpenes, 11,12-dihydroxysydonic acid ( 15 ) and 1-hydroxyboivinianic acid ( 16 ), together with one new alkaloid, scopulamide ( 21 ) and one new α-pyrone derivative, scopupyrone ( 26 ), in addition to twenty-three known compounds ( 3 – 14 , 17 – 20 , 22 – 25 , 27 – 29 ) were isolated from solid rice cultures of the marine-derived fungus Scopulariopsis sp. obtained from the Red Sea hard coral Stylophora sp. All compounds were unambiguously identified through extensive NMR spectroscopic analyses, and by comparison with the literature. Marfey's re…

New amide and dioxopiperazine derivatives from leaves of Breynia nivosa

The first chemical investigation of leaves of Breynia nivosa from Nigeria resulted in the isolation of two new amide derivatives breynivosamides A and B (1 and 2) and two new dioxopiperazine derivatives breynivosines A and B (4 and 5) together with seven known compounds (3, 6-11). The structures of the new compounds were elucidated by 1D, 2D NMR and HRESIMS data as well as by comparison with the literature. All isolated compounds were tested for the cytotoxic and antimicrobial activities. Only cristatin A (6) showed cytotoxicity against the L5178Y mouse lymphoma cell line with an IC50 value of 13.9μM while breynivosamide A (1) exhibited moderate antimicrobial activity against Mycobacterium …

Chemical constituents from leaves and root bark of Trichilia monadelpha (Meliaceae)

Abstract Two new limonoid derivatives designated, monadelphin A (1) and monadelphin B (2) and two new sesquiterpene derivatives named trichins A (3) and B (4) were isolated together with six known compounds (5–10) from the mixture of methylene chloride/methanol (1:1) extract of leaves and root bark of Trichilia monadelpha (Meliaceae) collected in Cameroon. The structures of the new compounds were unambiguously established by detailed spectroscopic analysis including 1D and 2D NMR data in conjunction with high resolution mass spectrometry data and by comparison of these data with those of related compounds described in the literature. Compounds 1–4 were screened for their cytotoxic potential…

Induction of cryptic metabolites of the endophytic fungus Trichocladium sp. through OSMAC and co-cultivation

The endophytic fungus Trichocladium sp. isolated from roots of Houttuynia cordata was cultured on solid rice medium, yielding a new amidepsine derivative (1) and a new reduced spiro azaphilone derivative (3) together with eight known compounds (4–11). Co-cultivation of Trichocladium sp. with Bacillus subtilis resulted in induction of a further new compound (2) and a 10-fold increase of 11 compared to the axenic fungal culture. Moreover, when the fungus was cultivated on peas instead of rice, a new sesquiterpene derivative (13) and two known compounds (12 and 14) were obtained. Addition of 2% tryptophan to rice medium led to the isolation of a new bismacrolactone (15). The structures of the …

Polyketides from the marine-derived fungus Aspergillus falconensis: In silico and in vitro cytotoxicity studies.

Abstract Fermentation of the marine-derived fungus Aspergillus falconensis, isolated from sediment collected from the Red Sea, Egypt on solid rice medium containing 3.5% NaCl yielded a new dibenzoxepin derivative (1) and a new natural isocoumarin (2) along with six known compounds (3–8). Changes in the metabolic profile of the fungus were induced by replacing NaCl with 3.5% (NH4)2SO4 that resulted in the accumulation of three further known compounds (9–11), which were not detected when the fungus was cultivated in the presence of NaCl. The structures of the new compounds were elucidated by HRESIMS and 1D/2D NMR as well as by comparison with the literature. Molecular docking was conducted fo…

Didymellanosine, a new decahydrofluorene analogue, and ascolactone C from Didymella sp. IEA-3B.1, an endophyte of Terminalia catappa

Didymellanosine (1), the first analogue of the decahydrofluorene-class of natural products bearing a 13-membered macrocyclic alkaloid conjugated with adenosine, and a new benzolactone derivative, ascolactone C (4) along with eight known compounds (2, 3, 5–10), were isolated from a solid rice fermentation of the endophytic fungus Didymella sp. IEA-3B.1 derived from the host plant Terminalia catappa. In addition, ascochitamine (11) was obtained when (NH4)2SO4 was added to rice medium and is reported here for the first time as a natural product. Didymellanosine (1) displayed strong activity against the murine lymphoma cell line L5178Y, Burkitt's lymphoma B cells (Ramos) and adult lymphoblastic…

Tanzawaic acid derivatives from freshwater sediment-derived fungus Penicillium sp.

Abstract Chemical investigation of a freshwater sediment-derived fungus, Penicillium sp. (S1a1), led to the isolation of three new tanzawaic acid derivatives, including penitanzchroman (1), tanzawaic acids Y (2) and Z (3), along with six known tanzawaic acid analogues (4-9), three known isochromans (10-12) and two known benzoquinones (13 and 14). The structures of the new compounds were established based on high-resolution mass spectrometry, and detailed analysis of one- and two-dimensional NMR spectroscopy. The relative configuration of the new compounds was assigned on the basis of NMR spectroscopic data including ROESY spectra. The absolute configuration was determined based on the speci…

Dispacamide E and other bioactive bromopyrrole alkaloids from two Indonesian marine sponges of the genus Stylissa.

Chemical investigation of methanolic extracts of the two Indonesian marine sponges Stylissa massa and Stylissa flabelliformis yielded 25 bromopyrrole alkaloids including 2 new metabolites. The structures of all isolated compounds were unambiguously elucidated based on extensive 1D and 2D NMR, LR-MS and HR-MS analyses. All isolated compounds were assayed for their antiproliferative and protein kinase inhibitory activities. Several of the tested compounds revealed selective activity(ies) which suggested preliminary SARs of the isolated bromopyrrole alkaloids.

Indole alkaloids from the coprophilous fungus Aphanoascus fulvescens

Abstract The Ascomycete fungus Aphanoascus fulvescens isolated from goose dung was investigated for its secondary metabolites, yielding five new indole alkaloids okaramines V–Z (1–5) and eleven known derivatives (6–16). Their structures were determined by 1D, 2D NMR spectra and HRMS data. Compounds 6, 8, 11 and 12 showed significant to moderate cytotoxicity against the mouse lymphoma cell line L5178Y with IC50 values ranging from 4.0 to 14.7 μM. Preliminary structure-activity relationships are discussed.

Cladosporinone, a new viriditoxin derivative from the hypersaline lake derived fungus Cladosporium cladosporioides

A new cytotoxic viriditoxin derivative, cladosporinone (1), along with the known viriditoxin (2) and two viriditoxin derivatives (3 and 4) were obtained from the fungus C ladosporium cladosporioides isolated from the sediment of a hypersaline lake in Egypt. The structure of the new compound (1) was determined by 1D and 2D NMR measurements as well as by high-resolution ESIMS and electronic circular dichroism spectroscopy. All isolated compounds were studied for their cytotoxicity against the murine lymphoma cell line L5187Y and for their antibiotic activity against several pathogenic bacteria. Viriditoxin (2) was the most active compound in both bioassays. Compound 1 also exhibited strong cy…

Cytotoxic labdane diterpenes and bisflavonoid atropisomers from leaves of Araucaria bidwillii

Abstract Chemical investigation of a methanolic extract of leaves from Araucaria bidwillii (Araucariaceae) from Egypt afforded four new labdane diterpenoidal metabolites (1–4) together with one known diterpene, 7-oxocallitrisic acid (5), two triterpenoidal metabolites, 2-O-acetyl-11-keto-boswellic acid (6) and β-sitosterol-3-O-glucopyranoside (7), phloretic acid (8), and two methylated bisflavonoids, agathisflavone-4′,7,7″-trimethyl ether (9) and cupressuflavone-4′,7,7″-trimethyl ether (10). The new metabolites 1–4 were unambiguously identified by applying extensive 1D and 2D NMR spectroscopic studies as well as HRESIMS. The relative and absolute configurations of 1–4 were determined using …

Induction of new metabolites from sponge-associated fungus Aspergillus carneus by OSMAC approach.

Abstract A comparative study on the metabolic profile of the sponge-associated fungus Aspergillus carneus using the OSMAC approach was conducted. The fungal strain was fermented on three different media including solid rice medium with or without sea salt and modified Czapek medium. Three new natural products, isopropylchaetominine (1), isoterrelumamide A (2) and 5′-epi-averufanin (3), together with fourteen known compounds (4–17) were isolated. The structures of the new compounds were established by 1D and 2D NMR spectroscopic analysis as well as by HRESIMS. Compound 2 was only found when the fungus was cultivated on modified Czapek medium, whereas compounds 4, 7, 11, 12, and 14 were only …

Induction of ambuic acid derivatives by the endophytic fungus Pestalotiopsis lespedezae through an OSMAC approach

Abstract Ten new ambuic acid derivatives, pestallic acids H–Q including one new iodinated natural product along with two known compounds, ambuic acid and ambuic acid 18-acetate, were obtained through fermentation of the endophytic fungus Pestalotiopsis lespedezae on solid rice medium with 3.5% NaI. Pestallic acids H–Q were undetectable in cultures of the fungus grown on solid rice medium lacking NaI or in those where NaI had been replaced by NaCl or NaBr. The structures of the new metabolites were established on basis of 1D/2D NMR and HRESIMS data. Their absolute configurations were determined by Mosher’s method and TDDFT-ECD calculations. The compounds failed to show antibacterial activity…

New Austalides from the Sponge-Associated Fungus Aspergillus sp.

Chromatographic separation of a crude extract obtained from the fungus Aspergillus sp., isolated from the Mediterranean sponge Tethya aurantium, yielded five new meroterpenoid metabolites, austalides M–Q (1–5), together with nine known compounds (6–13). The structures of the new compounds were unambiguously elucidated on the basis of extensive 1D and 2D NMR methods and by mass spectral analysis. Furthermore, the absolute configurations of 1 and 4 were determined by time-dependent density functional theory electronic circular dichroism (TDDFT ECD) calculations, allowing the assignment of the absolute configuration of analogous compounds 2, 3, and 5. The calculations revealed that the conform…

Cytotoxic drimane meroterpenoids from the Indonesian marine sponge Dactylospongia elegans

Abstract Chemical investigation of the methanol extract of an Indonesian marine sponge Dactylospongia elegans (family Thorectidae) afforded two undescribed drimane meroterpenoidal metabolites, dactylospongenones G and H (1 and 2) together with thirteen known compounds (3–15) including pelorol, 5-epi-ilimaquinone, 5-epi-smenospongine, 5-epi-smenospongidine, nakijiquinone D, smenospongine C, isospongiaquinone, isosmenospongine, nakijiquinones A-C, G and 5-epi-nakijiquinone Q. The structures of the new metabolites were unambiguously determined by 1D and 2D NMR spectroscopy and by HRESIMS. All isolated compounds were assessed for their antimicrobial, antitubercular and cytotoxic activities. Sev…

Induction of Secondary Metabolites from the Marine-Derived Fungus Aspergillus versicolor through Co-cultivation with Bacillus subtilis

AbstractA new cyclic pentapeptide, cotteslosin C (1), a new aflaquinolone, 22-epi-aflaquinolone B (3), and two new anthraquinones (9 and 10), along with thirty known compounds (2, 4 – 8, 11 – 34) were isolated from a co-culture of the sponge-associated fungus Aspergillus versicolor with Bacillus subtilis. The new metabolites were only detected in the co-culture extract, but not when the fungus was grown under axenic conditions. Furthermore, the co-culture extract exhibited an enhanced accumulation of the known constituents versicolorin B (14), averufin (16), and sterigmatocyctin (19) by factors of 1.5, 2.0, and 4.7, respectively, compared to the axenic fungal culture. The structures of the …

Induced secondary metabolites from the endophytic fungus Aspergillus versicolor through bacterial co-culture and OSMAC approaches

Abstract Two new cryptic 3,4-dihydronaphthalen-(2H)-1-one (1-tetralone) derivatives, aspvanicin A (1) and its epimer aspvanicin B (2), as well as several known cryptic metabolites (3–8), were obtained from the ethyl acetate extract of the co-culture of the endophytic fungus Aspergillus versicolor KU258497 with the bacterium Bacillus subtilis 168 trpC2 on solid rice medium. When A. versicolor was cultured axenically in liquid Wickerham medium supplemented with 3.5% DMSO, an additional three known secondary metabolites (9–11) were isolated that were lacking when the fungus was fermented on rice medium. The structures of the new compounds were elucidated using one- and two-dimensional NMR spec…

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.

Metabolites from Combretum dolichopetalum and its associated endophytic fungus Nigrospora oryzae--Evidence for a metabolic partnership.

Abstract A new altersolanol derivative, 4-dehydroxyaltersolanol A ( 9 ), along with two known sesquiterpenoids, ( S )-7′-hydroxyabscisic acid ( 7 ) and ( S )-abscisic acid ( 8 ) were obtained from the endophytic fungus, Nigrospora oryzae , isolated from leaves of Combretum dolichopetalum . The host plant yielded six known compounds including ellagic acid ( 1 ), 3, 3′, 4-tri-O-methylellagic acid ( 2 ), arjunolic acid ( 3 ), 4′-dihydrophaseic acid ( 4 ), echinulin ( 5 ) and arestrictin B ( 6 ). Close structural similarities with regard to compounds 4 , 7 and 8 were observed between the metabolites from the host plant and those of the endophytic fungus. Furthermore compounds 5 and 6 are relate…

Cyclic heptapeptides from the soil-derived fungus Clonostachys rosea

Abstract Three new cyclic heptapeptides (1–3) together with three known compounds (4–6) were isolated from a solid rice culture of the soil-derived fungus Clonostachys rosea. Fermentation of the fungus on white beans instead of rice afforded a new γ-lactam (7) and a known γ-lactone (8) that were not detected in the former extracts. The structures of the new compounds were elucidated on the basis of 1D and 2D NMR spectra as well as by HRESIMS data. Compounds 1 and 4 exhibited significant cytotoxicity against the L5178Y mouse lymphoma cell line with IC50 values of 4.1 and 0.1 µM, respectively. Compound 4 also displayed cytotoxicity against the A2780 human ovarian cancer cell line with an IC50…

A New Tetrahydrofuran Derivative from the Endophytic Fungus Chaetomium sp. Isolated from Otanthus maritimus

1 A hitherto unidentified endophytic strain of the genus Chaetomium, isolated from the medicinal plant Otanthus maritimus, yielded a new tetrahydrofuran derivative, aureonitolic acid (), along with 5 known natural products, 2 - 6. The structure of 1 was determined by extensive spectroscopic analysis and comparison with reported data. Extracts of the fungus, grown either in liquid culture or on solid rice media, exhibited considerable cytotoxic activity when tested in vitro against L5178Y mouse lymphoma cells. Compounds 2 and 6 showed significant growth inhibition against L5178Y cells with EC50 values of 7.0 and 2.7 μg/mL, respectively, whereas 1 was inactive

A (1->3)-beta-D-glucan recognition protein from the sponge Suberites domuncula. Mediated activation of fibrinogen-like protein and epidermal growth factor gene expression

Sponges (phylum Porifera) live in a symbiotic relationship with microorganisms, primarily bacteria. Until now, molecular proof for the capacity of sponges to recognize fungi in the surrounding aqueous milieu has not been available. Here we demonstrate, for the demosponge Suberites domuncula (Porifera, Demospongiae, Hadromerida), a cell surface receptor that recognizes (1--3)-beta-D-glucans, e.g. curdlan or laminarin. This receptor, the (1--3)-beta-D-glucan-binding protein, was identified and its cDNA analysed. The gene coding for the 45 kDa protein was found to be upregulated in tissue after incubation with carbohydrate. Simultaneously with the increased expression of this gene, two further…

Farinomalein derivatives from an unidentified endophytic fungus isolated from the mangrove plant Avicennia marina

Five farinomalein derivatives including three new compounds, farinomaleins C–E (3–5), and one new isoindoline congener (6) were isolated from an unidentified endophytic fungus obtained from the inner tissues of healthy leaves of the mangrove plant Avicennia marina from Oman. The structures of the new compounds were unambiguously elucidated on the basis of their mass, as well as one and two dimensional NMR spectroscopic data.

From anti-fouling to biofilm inhibition: New cytotoxic secondary metabolites from two Indonesian Agelas sponges

Chemical investigation of Indonesian marine sponges Agelas linnaei and A. nakamurai afforded 24 alkaloid derivatives representing either bromopyrrole or diterpene alkaloids. A. linnaei yielded 16 bromopyrrole alkaloids including 11 new natural products with the latter exhibiting unusual functionalities. The new compounds include the first iodinated tyramine-unit bearing pyrrole alkaloids, agelanesins A-D. These compounds exhibited cytotoxic activity against L5178Y mouse lymphoma cells with IC(50) values between 9.25 and 16.76 muM. Further new compounds include taurine acid substituted bromopyrrole alkaloids and a new dibromophakellin derivative. A. nakamurai yielded eight alkaloids among th…

Bioactive polyketides and alkaloids from Penicillium citrinum , a fungal endophyte isolated from Ocimum tenuiflorum

Chemical investigation of the endophytic fungus Penicillium citrinum cultured on white beans or on rice led to the isolation of two new alkaloids (1 and 2), along with fourteen known polyketides (6-12, 14-20) and four known alkaloids (3-5, and 13). The structures of the isolated compounds were determined by extensive analysis of the 1D, 2D NMR, and MS data, and by comparison with the literature. Compound 13, which had been previously obtained only by chemical synthesis, was isolated as a natural product for the first time, while compound 6 was firstly reported as a fungal metabolite. A re-isolation of sclerotinin A (14) revealed it to be a diastereoisomeric mixture (14a and 14b), whose ster…

Polyketides and nitrogenous metabolites from the endophytic fungus Phomopsis sp. D15a2a

Abstract Three new polyketides, phomopones A−C (1–3), one new cyclic tetrapeptide, 18-hydroxydihydrotentoxin (4), and a new amide, 6-hydroxyenamidin (5) together with a known derivative, enamindin (6) were obtained from the endophytic fungus Phomopsis sp. D15a2a isolated from the plant Alternanthera bettzickiana. The structures of the new compounds were elucidated by 1D, 2D NMR and HRMS data. The absolute configurations of the isolated metabolites were determined either by X-ray crystallography, Marfey’s method or by converting the compounds to Mosher esters.

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