Paenibacillin A,a new 2(1H)-pyrazinone ring-containing natural product from the endophytic bacterium Paenibacillus sp. Xy-2

A new 2(1H)-pyrazinone ring-containing natural product, paenibacillin A (1), together with five known diketopiperazine derivatives 2–6 and two known isoflavones 7–8, was isolated from the culture of an endophytic bacterium Paenibacillus sp. Xy-2. The structure of compound 1 was elucidated by extensive spectral methods, including UV, IR, HR-ESI-MS, 1D and 2D NMR and ECD experiments. Compound 1 exhibited moderate cytotoxicity against HL-60 cell line with IC₅₀ value of 50.48 μM.     

Xanthones isolated from Gentianella acuta and their protective effects against H2O2-induced myocardial cell injury

In the present study, two new xanthones, (5′S,8′S)-1,3,5,8-tetrahydroxyxanthone(7→2′)-1,3,5,8-tetrahydroxy-5′,6′,7′,8′-tetrahydroxanthone (1), 5-hydroxy-3,4,6-trimethoxyxanthone-1-O-β-D-glucopyranoside (2), and eight known xanthones (3–10) were isolated from the whole plants of Gentianella acuta. Their structures were identified by the spectroscopic analyses (HR-ESI-MS, and 1D and 2D NMR). Meanwhile, cell-protective effects against H₂O₂-induced H9c2 cardiomyocyte injury and cytotoxic activities of compounds 1–10 were also determined.     

One new 19-nor cucurbitane-type triterpenoid from the stems of Momordica charantia

One new 19-nor cucurbitane-type triterpenoid (3β,9β,25-trihydroxy-7β-methoxy-19-nor-cucurbita-5,23(E)-diene) (1), together with other six known cucurbitane-type triterpenoids (2–7), were isolated from the stems of Momordica charantia L. The chemical structure of 1 was elucidated by extensive 1D NMR and 2D NMR (HSQC, HMBC, COSY and ROESY), MS experiments. Using MTT assay, compound 1 exhibited weak cytotoxicity against HL-60, A-549, and SK-BR-3 cell lines with the IC₅₀ values at 27.3, 32.7 and 26.6 μM, respectively.     

Cytotoxic withanolides from Physalis angulata

A new withanolide (1), physagulide P, together with five known withanolides (2–6), was isolated from the aerial parts of Physalis angulata L. The structure of new compound was elucidated on the basis of extensive spectroscopic techniques, including 1D, 2D NMR and HRESIMS. The activity screening indicated that compound 1 showed significant cytotoxicities against the human osteosarcoma cell line MG-63, HepG-2 hepatoma cells and breast cancer cells MDA-MB-231 with the IC₅₀ value of 3.50, 4.22 and 15.74 μM.     

Noralashinol A,a new norlignan from stem barks of Syringa pinnatifolia

One new norlignan, namely noralashinol A (1), one known analogue (2), together with seven known lignans (3–9) were isolated from the stem barks of Syringa pinnatifolia. Their structures were elucidated extensively by spectroscopic methods, including mass spectrometry and 1D and 2D NMR spectroscopies. Compound 8 significantly inhibited NO production in LPS-induced BV-2 murine microglia cells with its IC₅₀ value of 20.7 μM, compared to a positive control quercetin with its IC₅₀ value of 15.3 μM.     

A new fatty acid ester from Nigella sativa var. hispidula Boiss showing potent anti-protein tyrosine phosphatase 1B activity

A new fatty acid ester (1) and seven known phenolic compounds, i.e. salfredin B₁₁ (2), nigephenol C (3), nigephenol B (4), acetovanillion (5), p-hydroxybenzoic acid (6), p-hydroxy-acetophenone (7) and p-hydroxybenzaldehyde (8), were isolated from the seeds of Nigella sativa var. hispidula. Among them, compounds 5, 7 and 8 were isolated from Nigella for the first time. Their structures were elucidated with HR-ESI-MS, 1D and 2D NMR spectra. Evaluation of the isolated compounds on protein tyrosine phosphatase (PTP1B) assay indicated that although compounds 2–8 show no promising anti-PTP1B activities, compound 1 possess anti-PTP1B activity with an IC₅₀ value of 7.38 ± 0.14 μM in vitro.     

A new di-C-prenylated coumarin from Sophora interrupta

A new di-C-prenylated coumarin, 7-methoxy-6,8-bis-(2,3-dihydroxy-3-methylbutyl)-coumarin (1), together with seven known compounds, isopimpinellin (2), an arylbenzofuran (3), three flavonoids (4–6), (+)-maackianin (7) and echinoisoflavanone (8), were isolated from the leaves of Sophora interrupta Bedd. The structure of the new compound 1 as well as known compounds was elucidated by extensive 1D and 2D NMR spectral studies.     

A new abietane diterpenoid glycoside from ajuga ovalifolia var. calantha

A new abietane diterpenoid glycoside, ajugaside B (1), along with three known compounds (2–4), were isolated from the whole plants of Ajuga ovalifolia var. calantha. The structure of the new compound (1) was elucidated by means of spectroscopic analyses (HRESIMS, IR, NMR and ECD). All of the isolated compounds were evaluated for their antitumor activities against MGC803, MCF-7, A549, HT29 and HepG2 cell lines. Compounds 3–4 showed moderate cytotoxicity against all tested cell lines with IC₅₀ values of 1.8–7.3?μM.     

New p-terphenyl and benzoquinone metabolites from the bioluminescent mushroom Neonothopanus nambi

Abstract

Two new p-terphenyls, neonambiterphenyls A and B (1–2), a new benzoquinone, neonambiquinone A (3), together with six known sesquiterpenes (4–9), were isolated from the bioluminescent mushroom Neonothopanus nambi PW3. The isolated compounds were identified by mass, IR and spectroscopic analyses (1D and 2D NMR). Compounds 1–3 and 5–7 showed cytotoxicity against cancer cell lines such as KB, NCI-H187 and MCF-7 with IC₅₀ values ranging from 1.45 to 49.31?µg/mL. In addition, compounds 1 and 5 showed cytotoxicity against Vero cells with IC₅₀ values of 38.72 and 32.90?µg/mL, respectively.     

Three new polyketides from the marine sponge-derived fungus Trichoderma sp. SCSIO41004

Three new polyketides named trichbenzoisochromen A (1), 5,7-dihydroxy-3-methyl -2-(2-oxopropyl)naphthalene-1,4-dione (2) and 7-acetyl-1,3,6-trihydroxyanthracene-9,10- dione (3) together with six known compounds (4–9) were isolated from a sponge-derived fungus Trichoderma sp. SCSIO41004. The structures of three new polyketides (1–3) were determined by the extensive spectroscopic analysis, including 1D, 2D NMR and HRESIMS data. The absolute configuration of compound 1 was confirmed by the specific optical rotation value and CD spectra analyses. Compound 4 exhibited significant inhibitory activity against EV71 with the IC₅₀ value of 25.7 μM.     

Two novel compounds from the root bark of Morus alba L.

Chemical investigation of the root bark of Morus alba led to the isolation of a new flavone, dioxycudraflavone A (1) and a new 2-arylbenzofuran, 5-hydroxyethyl moracin M (2), together with seven known compounds namely sanggenon V (3), morusin (4), morusignin L (5), licoflavone C (6), moracin C (7), alfafuran (8) and mulberrofuran G (9). The structure elucidation of these compounds was based on analyses of spectroscopic data including 1D, 2D NMR and HR-ESI-MS. All compounds were evaluated for the α-glucosidase inhibitory and cytotoxic activities. Compounds 2–4, 8 and 9 exhibited strong α-glucosidase inhibitory activities with IC₅₀ less than 10 μM, while only 4 and 9 showed moderate cytotoxic effects against lung cancer cells.     

A New Lycopodine-type Alkaloid from Lycopodium japonicum

A new lycopodine-type alkaloid, 12β-hydroxy-acetylfawcettiine N-oxide (1), together with seven known analogues, acetyllycoposerramine M (2), lycopodine (3), lycoclavine (4), diphaladine A (5), lycoposerramine K (6), 11β-hydroxy-12-epilycodoline (7) and fawcettiine (8), were isolated from Lycopodium japonicum. Their structures were established by mass spectrometry and 1D and 2D NMR techniques. The isolated alkaloids were assayed for their inhibition activities against acetylcholinesterase, but no inhibitory activities for the compounds were detected.     

Penicindopene A,a new indole diterpene from the deep-sea fungus Penicillium sp. YPCMAC1

A new indole diterpene, named penicindopene A (1), together with seven known compounds (2?–?8), was isolated from the deep-sea fungus Penicillium sp. YPCMAC1. The structure of penicindopene A was elucidated by extensive spectroscopic analyses (1?D and 2?D NMR, and HRESIMS data), in addition to the ECD calculations for the assignments of its absolute configuration. Penicindopene A represented the first example of indole diterpenes possessing a 3-hydroxyl-2-indolone moiety, and it exhibited moderate cytotoxicities against A549 and HeLa cell lines with IC₅₀ values of 15.2 and 20.5?µM, respectively.     

Terrenolide S,a new antileishmanial butenolide from the endophytic fungus Aspergillus terreus

Terrenolide S, a new butenolide derivative (6), together with six known compounds: (22E,24R)-stigmasta-5,7,22-trien-3-β-ol (1), stigmast-4-ene-3-one (2), stigmasta-4,6,8(14),22-tetraen-3-one (3), terretonin A (4), terretonin (5) and butyrolactone VI (7) have been isolated from the endophytic fungus Aspergillus terreus isolated from the roots of Carthamus lanatus (Asteraceae). Their structures were established by extensive spectroscopic analyses (1D, 2D NMR and HRESIMS), as well as optical rotation measurement and comparison with literature data. Compound 1 displayed a potent activity towards methicillin-resistant Staphylococcus aureus (MRSA) and Cryptococcus neoformans with IC₅₀ values of 2.29 and 10.68 µM, respectively. Moreover, 1, 2 and 6 exhibited antileishmanial activity towards Leishmania donovani with IC₅₀ values of 11.24, 15.32 and 27.27 µM, respectively and IC₉₀ values of 14.68, 40.56 and 167.03 µM, respectively.     

A new flavane acid from the fruits of Illicium verum

A new compound, illiciumflavane acid (1), along with 13 known compounds (2–14), were isolated from the fruits of Illicium verum Hook. F. Their structures were elucidated through various spectroscopic methods, including 1D NMR (¹H NMR, ¹³C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centres was determined using CD spectrum as well as analyses of coupling constants and optical rotation data. Cytotoxicity evaluation of four compounds showed that illiciumflavane acid and (E)-1,2-bis(4-methoxyphenyl)ethene exhibited potential against A549 activities with IC₅₀ values of 4.63 μM and 9.17 μM, respectively.     

Insecticidal,cytotoxic and anti-phytopathogenic fungal activities of chemical constituents from the aerial parts of Ferula sinkiangensis

Abstract

A new rare monoterpene coumarin (1) and its two known analogues (2–3), together with two sesquiterpenes (6–7) and ferulic acid (8) were isolated from the aerial parts of Ferula sinkiangensis. The structure of new compound was established on the basis of 1D and 2D NMR data and HRESIMS data interpretation. Insecticidal, cytotoxic and anti-phytopathogenic fungal activities of isolated compounds were evaluated against third-instar larvae of Spodoptera exigua and its cell line, and three plant pathogenic fungi respectively. Compounds 1–3 and 6–7 were found to be more effective contact toxicity to S. exigua with the corrected mortality values of 38.89%-58.89% at 10?μg/larva doses for 24?h. Further studies showed that compounds 3 and 6 exhibited cell growth inhibitory activity against S. exigua cell line with the EC₅₀ values of 22.78 and 14.64?µM for 72?h. In addition, compound 6 exhibited potent antifungal activity with MICs?=?16–32?µg/mL.     

Preparative separation of six coumarins from the pummelo (Citrus maxima (Burm.) Merr. Cv. Shatian Yu) peel by high-speed countercurrent chromatography

In this work, six coumarins, including two new ones, 8-(3-hydroxy-2,2-dimethylpropyl)-7-methoxy-2H-chromen-2-one (2) and 5-[(7′,8′-dihydroxy-3′,8′-dimethyl-2-nonadienyl)oxy] psoralen (4), as well as four known ones, 5-[(6′,7′-dihydroxy-3′,7′-dimethyl-2-octenyl) oxy] psoralen (1), marmin (3), epoxybergamottin (5), and aurapten (6) were successfully separated from the crude extract of pummelo (Citrus maxima (Burm.) Merr. Cv. Shatian Yu) peel by high-speed countercurrent chromatography in a single run with petroleum-ether–ethyl acetate–methanol–water (4:6:6:4, v/v). The structures of these six coumarins were elucidated by ESI-MS, extensive 1D and 2D NMR spectroscopy.     

Eudesmane and aromadendrane sesquiterpenoids from the Vietnamese soft coral Sinularia erecta

Using various chromatographic separations, eight sesquiterpenoids (1–8), including one new compound 3β,5α-dihydroxyeudesma-4(15),11-diene (1), were isolated from the MeOH extract of the Vietnamese soft coral Sinularia erecta. The structure elucidation was confirmed by spectroscopic experiments including 1D and 2D NMR and HR-ESI-MS. The cytotoxic activities against three human cancer cell lines (A-549, HeLa and PANC-1) of all isolated compounds were evaluated by MTT-based colorimetric assays. Compound 1 exhibited selective cytotoxicity against the A549 cell line with IC₅₀ of 14.79 ± 0.91 μM.     

Bioactive xanthoquinodins and epipolythiodioxopiperazines from Chaetomium globosum 7s-1, an endophytic fungus isolated from Rhapis cochinchinensis (Lour.) Mart

Abstract

A new xanthoquinodin B9 (1), together with two known xanthoquinodins, xanthoquinodin A1 (2) and xanthoquinodin A3 (3), three epipolythiodioxopiperazines, chetomin (4), chaetocochin C (5) and dethio-tetra(methylthio)chetomin (6), and four other compounds, chrysophanol (7), emodin (8), alatinone (9), and ergosterol (10) were isolated from the endophytic fungus Chaetomium globosum 7s-1, isolated from Rhapis cochinchinensis (Lour.) Mart. All isolated structures were established based on their spectroscopic data analyses. Compounds 1–6 showed antibacterial activity against Gram positive bacteria with MICs ranging from 0.02?pM to 10.81 µM. Compounds 1–6 also exhibited cytotoxicity against KB, MCF-7 and NCI-H187 cancer cell lines (IC₅₀ 0.04–18.40 µM). However, they were cytotoxic towards a normal cell line (Vero cell) with IC₅₀ values ranging from 0.04 to 3.86 µM.     

Six new metabolites produced by Colletotrichum aotearoa 09F0161, an endophytic fungus isolated from Bredia oldhamii

Six new compounds, colletobredins A–D (1–4) and colletomelleins A and B (5 and 6), along with 12 previously identified compounds, were isolated from the culture broth of Colletotrichum aotearoa BCRC 09F0161, a fungal endophyte residing in the leaves of an endemic Formosan plant Bredia oldhamii Hook. f. (Melastomataceae). The structures of the new compounds were established by spectroscopic methods, including UV, IR, HR-ESIMS and extensive 1D and 2D NMR techniques. The effects of some isolates on the inhibition of nitric oxide (NO) production in lipopolysaccharide-activated murine macrophage RAW264.7 cells were evaluated. All these compounds inhibited NO production in activated macrophages without any cytotoxicity at a concentration of 100 μM. Of these isolates, 1 showed weak NO inhibitory activity with IC₅₀ value of 182.2 μM. To the best of our knowledge, this is the first report on isochroman glycoside metabolites (1–4) from the genus Colletotrichum.