A new diterpene from the fungal mycelia of Hericium erinaceus

One new diterpene (1) and new compound (2), along with four known compounds (3–6) were isolated from the fungal mycelia of Hericium erinaceus by the tracking method of antibacterial activity. The structures of compounds (1–6) were elucidated on the basis of spectral data. Compound (3) showed strong antibacterial activity against Helicobacter pylori (ATCC43504) and compounds (1), (2) and (4) showed moderate antibacterial activity. Compound (1) exhibited good cytotoxicity against three human cancer cell lines (K562, LANCAP, HEP2).     

Three new koninginins from Trichoderma neokongii 8722

Three new fungal metabolites, named koninginins I (1), J (2) and K (3) together with four known koninginins A (4), B (5), D (6) and E (7), were isolated from solid fermentation products of Trichoderma neokongii 8722. Three new structures were elucidated by extensive spectroscopic methods, including 1D NMR and 2D NMR, and HR-ESI–MS experiments.     

Novel bioactive molecules from Lentzea violacea strain AS 08 using one strain-many compounds (OSMAC) approach

A new eudesmane sesquiterpenoid (1), and a new homologue of virginiae butanolide E (2) along with butyl isobutyl phthalate (3) were isolated from, actinomycete-Lentzea violacea strain AS08 isolated from north western Himalayas by stressing on modified one strain-many compounds (OSMAC) method. The structures of the new compounds were elucidated by extensive spectroscopic analyses including 1D, 2D NMR along with HR-ESI-MS and FT-IR data. Herein, a distinctive method was added for inspecting secretory profile of the strain by quantification of extract value of cell free supernatant in different types of culture media fallowed by HPLC profiling of respective extracts, which revealed a highly altered metabolic profile of the strain and formed the base for the selection of media. The compounds 1 and 2 showed moderate activity against Gram negative (MIC ～32–64 µg ml^?1) in comparison to Gram positive bacterial pathogens. Compound 1 exhibited significant activity in human cancerous cell lines (IC₅₀ ～19.2 µM).     

Koninginins L and M,two polyketides from Trichoderma koningii 8662

Two new fungal metabolites, named koninginins L (1) and M (2), together with three known koninginins A (3), E (4), and trichodermaketone C (5), were isolated from solid fermentation products of Trichoderma koningii 8662. Koninginins L (1) and M (2) were elucidated by extensive spectroscopic methods, including 1D and 2D NMR, HR-EI-MS experiments, and the absolute configuration of compound 1 was confirmed by single-crystal X-ray diffraction analysis using the anomalous scattering of Cu Kα radiation.     

(±)-Meliviticines A and B: Rearranged prenylated acetophenone derivatives from Melicope viticina and their antimicrobial activity

Two new prenylated acetophenone derivatives racemates, meliviticines A (1) and B (2) with unprecedented rearranged skeletons, were isolated from Melicope viticina. Subsequent chiral resolution led to the separation of two pairs of enantiomers, (±)-meliviticines A (1a/1b) and (±)-meliviticines B (2a/2b). Their structures including absolute configurations were elucidated by extensive spectroscopic data, electronic circular dichroism analysis, and X-ray crystallography. A plausible biosynthetic pathway of 1 and 2, involving ring cleavage and rearrangement of the prenylated acetophenone backbone was proposed. All the isolates showed moderate antimicrobial activities with MIC values of 25–50 μg/mL against several bacterial and fungal strains.     

Diphenyl ether and benzophenone derivatives from the marine mangrove-derived fungus Penicillium sp. MA-37

Further investigation of the marine mangrove-derived fungal strain Penicillium sp. MA-37 led to the isolation of one new benzophenone, iso-monodictyphenone (1), two new diphenyl ether derivatives penikellides A (2) and B (3), and two known analogs monodictyphenone (4) and 6-[2-hydroxy-6-(hydroxymethyl)-4-methylphenoxy]-2-methoxy-3-(1-methoxy-3-methylbutyl)benzoic acid (5). The structures of these compounds were elucidated by spectroscopic analyses including 1D- and 2D-NMR and mass spectrometry. The brine shrimp lethality and antibacterial activity against five aquaculture pathogens were evaluated.     

Phenol derivatives from the cold-seep fungus Aspergillus sydowii 10–31

Two bisabolane-type sesquiterpenoid phenols inclusive of the known (7 S)-flavilane A (1) and the new (7 S)− 4-iodo-flavilane A (2), along with a new tetraphenyl ether, bisviolaceol II (3), were isolated from the cold-seep fungus Aspergillus sydowii 10–31. Their structures were identified through spectroscopic methods, such as MS, IR, and NMR, and the absolute configurations of 1 and 2 were ascertained by comparison of ECD curves. Compounds 1 and 2 represent rarely encountered sulfur-bearing sesquiterpenes in nature, and the iodination in 2 makes it unique in particular. Additionally, 3 is the first tetraphenyl ether derivative from the fungal species A. sydowii. Compounds 1-3 inhibited the growth of several Vibrio bacteria and harmful microalgae.     

Two new spirooxindole alkaloids from rhizosphere strain Streptomyces sp. xzqh-9

Two new spirooxindole alkaloids spindomycins A (1) and B (2) were isolated from rhizosphere strain Streptomyces sp. xzqh-9. Their structures were elucidated by comprehensive spectroscopic analyses of NMR and MS data. The absolute configurations of 1 and 2 were determined by experimental and theoretical calculation of electronic circular dichroism (ECD). Antitumor, lactate dehydrogenase, and tyrosine kinase inhibitory activities of two compounds were evaluated, while only spindomycin B (2) exhibited weak inhibitory activity against tyrosine kinase Bcr-Abl.     

Hypocreaterpenes A and B,cadinane-type sesquiterpenes from a marine-derived fungus,Hypocreales sp.

Two new cadinane-type sesquiterpenes, hypocreaterpenes A (1) and B (2), along with five known compounds (3–7) were isolated from a marine-derived fungus Hypocreales sp. strain HLS-104 isolated from a sponge Gelliodes carnosa. Their structures were determined by a combination of spectroscopic methods. All compounds were tested for the inhibitory effects on the nitric oxide (NO) production in lipopolysaccharide (LPS)-treated RAW264.7 cells. Among them, compounds 3 and 6 showed moderate anti-inflammatory activity with average maximum inhibition (E_max) values of 10.22% and 26.46% at 1 μM, respectively.     

Two new sesquiterpene derivatives from soil actinomycete Streptomyces albospinus 15-4-2

Two new sesquiterpene derivatives, 4α,10β-dimethyl-decahydronaphthalene-1β,3β,5α,8α-tetraol (1) and 5β H-eudesmane-1β,6α,11-triol (2) were isolated from the soil actinomycete Streptomyces albospinus 15-4-2. Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 exhibited antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) strain in vitro.     

Guanacastane-type diterpenoids from Coprinus radians

Thirteen diterpenoids, named radianspenes A–M (1–13), including three lactams radianspenes J (10), K (11) and L (12) and one dimer radianspene M (13), were isolated from fermentation products of the higher fungal strain Coprinus radians M65. All these compounds possessing guanacastane skeleton were evaluated for antitumor activity using MDA-MB-435 cell line. Radianspene C exhibited inhibitory activity with IC₅₀ of 0.91 μM.     

Secondary metabolites from the endophytic fungus Biscogniauxia formosana and their antimycobacterial activity

Two new azaphilone derivatives, namely, biscogniazaphilones A (1) and B (2), along with ten known compounds (3–12), were isolated from the n-BuOH-soluble fraction of the 95% EtOH extract of long-grain rice fermented with the endophytic fungus Biscogniauxia formosana BCRC 33718, derived from the bark of medicinal plant Cinnamomum species. Their structures were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR as well as HRESIMS, ESIMS, UV, and IR, and comparison with literature data. In addition, the isolated compounds (1–12) were evaluated for their antimycobacterial activity. Two new constituents, biscogniazaphilones A (1) and B (2), exhibited the strongest antimycobacterial activities against Mycobacterium tuberculosis strain H₃₇Rv, with MIC values of 5.12 and 2.52 μg/mL, respectively.     

Inducing secondary metabolite production by the soil-dwelling fungus Aspergillus terreus through bacterial co-culture

The soil-dwelling fungus Aspergillus terreus was isolated from sediment collected from the lake of Wadi EI Natrun in Egypt. Co-cultivation of A. terreus with the bacteria Bacillus subtilis and Bacillus cereus on solid rice medium resulted in an up to 34-fold increase in the accumulation of constitutively present fungal natural products (4–15) compared to axenic cultures of A. terreus. The fungal products included two new butyrolactone derivatives, isobutyrolactone II (1) and 4-O-demethylisobutyrolactone II (2), together with the known N-(carboxymethyl)anthranilic acid (3) that were not present in axenic fungal controls and were only detected during co-cultivation with B. subtilis or with B. cereus. The structures of all compounds were unambiguously elucidated by 1D and 2D NMR spectroscopy, and by HRESIMS measurements, as well as by comparison with the literature. In a second set of experiments, A. terreus was co-cultured with Streptomyces lividans and with Streptomyces coelicolor. These co-cultivation experiments failed to induce fungal natural product accumulation in contrast to co-cultures with Bacillus sp. Compounds 5 and 14 showed weak inhibition of B. cereus with minimal inhibitory concentrations (MICs) of 64 μg/mL, whereas only 8 showed moderate cytotoxicity against the murine lymphoma (L5178Y) cell line with inhibition of 80% at a dose of 10 μg/mL.     

Pochonicine,a polyhydroxylated pyrrolizidine alkaloid from fungus Pochonia suchlasporia var. suchlasporia TAMA 87 as a potent β-N-acetylglucosaminidase inhibitor

A new polyhydroxylated pyrrolizidine alkaloid designated as pochonicine (1) was isolated from a solid fermentation culture of the fungal strain Pochonia suchlasporia var. suchlasporia TAMA 87. The structure of 1 was determined using NMR and MS techniques as (1R*, 3S*, 5S*, 6S*, 7R*, 7a S*)-5-acetamidomethyl-3-hydroxymethyl-1,6,7-trihydroxypyrrolizidine. Pochonicine (1) showed potent inhibition against β-N-acetylglucosaminidases (GlcNAcases) of various organisms including insects, fungi, mammals, and a plant but no inhibition against β-glucosidase of almond, α-glucosidase of yeast, or chitinase of Bacillus sp. The GlcNAcase inhibitory activity of pochonicine (1) was comparable to nagstatin, a potent GlcNAcase inhibitor of natural origin.     

Two novel saponins from Cephalaria davisiana (Dipsacaceae)

Two novel hederagenin type triterpene saponins, namely davisianoside A (1) and davisianoside B (2) together with ten known compounds (3–12) were isolated from the aerial parts of Cephalaria davisiana (Dipsacaceae). One new prosapogenin (1a) was also obtained after the alkaline hydrolysis of compound 1. The chemical structures of all compounds were established mainly by 1D-, 2D-NMR and HR-ESI/MS analysis as well as chemical methods.The antibacterial and antifungal effects of compounds 1–2 were evaluated against Gram-positive, Gram-negative bacteria and unicellular yeast C. albicans by MIC method.     

New sesquiterpene lactone glucosides from the roots of Ferula varia

Five new eudesmane- (1–5), two new guaiane- (6 and 7) and one new germacrane-type (8) sesquiterpene lactone glucosides were isolated from the H₂O-soluble fraction of the roots of Ferula varia. Their structures were elucidated by extensive spectroscopic analyses. The absolute configuration of 1 was determined by modified Mosher's method.     

Three new jacaranone derivatives from the aerial parts of Senecio chrysanoides DC. with their cytotoxic activity

Three new jacaranone derivatives, namely, (1R)-ethyl 1-hydroxy-4-oxo-2-cyclohexenylacetate (1), (1R, 6S)-ethyl 6-ethoxy-1-hydroxy-4-oxo-2-cyclohexenylacetate (2) and (1R, 6R)-ethyl 6-ethoxy-1-hydroxy-4-oxo-2-cyclohexenylacetate (3), along with a known jacaranone derivative, ethyl 1-hydroxy-4-oxocyclohexylacetate (4) were isolated from the aerial parts of Senecio chrysanoides DC.. Their structures were elucidated by spectroscopic methods, optical rotation calculations and CD analyses. All the isolated compounds were evaluated for their cytotoxicity against three human cancer cell lines in vitro. Compound 2 exhibited moderate inhibitory effects against these cancer cell lines.     

Aureolic acids from a marine-derived Streptomyces sp. WBF16

A marine-derived actinomycete (Streptomyces sp. WBF16) exhibiting antitumor activities was investigated. The strain was identified using morphological, biochemical and genetic techniques. 16S rDNA sequence of the isolate indicated that it was most closely related to Streptomyces coelicolor A3 (2). Furthermore, a new aureolic acid (Chromomycin B, 1), along with Chromomycin A₂ (2) and Chromomycin A₃ (3) were isolated from its secondary metabolites. Their structures were determined by chemical and spectroscopic methods including 1D, 2D NMR and HRMS. Compounds 1–3 showed strong cytotoxicity against SGC7901, HepG2, A549, HCT116 and COC1 and HUVEC.     

Two new diterpenoids from the roots of Pygmacopremna herbacea

Two new diterpenoids, neobharangi-δ-lactone (1) and bharangi quinone (2) along with two known compounds neobharangin (3) and bharangin (4) were isolated from the ethyl acetate extract of root nodules of Pygmacopremna herbacea. The structures of the new compounds were established by 1D and 2D NMR spectroscopic data.     

Antifungal cinnamic acid derivatives from Persian leek (Allium ampeloprasum Subsp. Persicum)

A cinnamic imidate, (1Z,2E)-methyl 3-(-p-hydroxy-m-methoxyphenyl)-N-(-p-hydroxyphenethyl) acrylimidate, named persicoimidate (1), has been isolated and characterized from bulbs and seeds of Persian leek, Allium ampeloprasum Subsp. Persicum. Two cinnamic acid derivatives, N-feruloyl tyramine (2) and N-caffeoyl tyramine (3) were isolated from bulbs and seeds. Compound 2 has been previously reported from garlic and leek, while compound 3 is described in Allium plants for the first time. The chemical structures of the isolated compounds have been elucidated unambiguously by spectroscopic methods, including 2D NMR and MS. The isolated compounds were evaluated for their antifungal activity against four fungal pathogens, the soil-borne pathogen Penicillium italicum, the air-borne pathogens Aspergillus niger and Botrytis cinerea, and the antagonistic fungi Trichoderma harzianum to evaluate the possible involvement of such compounds in resistance to pathogen attack.