Novel Compounds from the Mycelia and Fruiting Bodies of Climacodon septentrionalis
Abstract and Figures
A novel ester (1) along with a known compound (2) were isolated from the mycelia of Climacodon septentrionalis. A novel furanone (3) and a known compound (4) were purified from the fruiting bodies of the fungus. The respective structures of 1 and 3 were determined as those of (S)-3-p-tolylbutyl 2-hydroxy-2-methylpropanoate and (-)-5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one by interpreting the spectroscopic data.
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... (6H, m). Compound II was identified as 5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one, agreeing with the data of Wu et al. [35] ( Figure 4B). ...
... The 5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one is a 2(5H)-furanone (commonly known as butenolide) derivative and has been identified in the fungus Climacodon septentrionalis [35]. This compound has also been isolated from various plants and sea corals: Rosa roxburghii [54], Tricyrtis maculate [55], and Suberosa subergorgia [56]. ...
Using plant-based allelopathic compounds might be a potent substitute to help mitigate the effects of synthetic herbicides. Annona reticulata L. is often planted for its fruit in residential gardens. This plant is well-documented for its diverse ethnomedicinal uses. However, there is no information in the literature on the allelopathic potential of A. reticulata leaves. Therefore, the allelopathic potential and relevant allelopathic compounds of A. reticulata leaves were investigated in this study. The bioassays were carried out using a completely randomized experimental layout (CRD), and the resulting data were analyzed using one-way ANOVA at p ≤ 0.05. Aqueous methanol extracts of A. reticulata leaves significantly inhibited the growth of three dicots and three monocots (Lepidium sativum L., Medicago sativa L., Lactuca sativa L., Echinochloa crus-galli (L.) P. Beauv., Lolium multiflorum Lam., and Phleum pratense L., respectively). The level of growth inhibition was proportional to the A. reticulata extract concentration. Three compounds were purified through different chromatographic steps, and their structures were determined using spectroscopy and identified as loliolide, 5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one, and 3,4-dihydroxyphenylethanol. The 5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one had the greatest effect on suppressing cress root growth, while loliolide had the greatest effect on suppressing timothy shoot growth. The values for 50% seedling growth suppression showed that the compound with the maximum inhibitory activity was loliolide, followed by 5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one and 3,4-dihydroxyphenylethanol. Therefore, this result suggests that the three compounds might be responsible for the allelopathic effects of A. reticulata leaf extracts, and these compounds have the potential to be used to develop effective bioherbicides.
... Its biological activity and isolation of it from fungi have not been reported yet. Compound 2, (S)-3-hydroxy-4-butanolide, has been isolated from a mushroom, Climacodon septentrionalis, and was evaluated for cytotoxicity against human lung cancer cells, but no effects were exhibited [16]. Compound 4 was identified as catathelasmol D, which has been isolated from the fruiting bodies of Catathelasma imperiale, and it has inhibitory activities against two isozymes, 11β-hydroxysteroid dehydrogenases (11β -HSD1 and 11β -HSD2) [17]. ...
A novel compound, (R)-4-ethoxy-2-hydroxy-4-oxobutanoic acid (1), and six known compounds (2–7) were isolated from the fruiting bodies of the wild edible mushroom Leucopaxillus giganteus. The planar structure of 1 was determined by the interpretation of spectroscopic data analysis. The absolute configuration of 1 was determined by comparing specific rotation of the synthetic compounds. In the plant regulatory assay, the isolated compounds (1–7) and the chemically prepared compounds (8–10) were evaluated their biological activity against the lettuce (Lactuca sativa) growth. Compounds 1 and 3–10 showed the significant regulatory activity of lettuce growth. 1 showed the strongest inhibition activity among the all the compounds tested. In the lung cancer assay, all the compounds were assessed the mRNA expression of Axl and immune checkpoints (PD-L1, PD-L2) in the human A549 alveolar epithelial cell line by RT-PCR. Compounds 1–10 showed significant inhibition activity against Axl and/or immune checkpoint.
... The 95% EtOH extract of L. crustacea (LC) was subsequently partitioned by different solvents to yield n-hexane (LC-H), EtOAc (LC-Et), n-BuOH (LC-B), and H 2 O (LC-W) fractions. The EtOAc fraction was subjected to chromatographic methods, leading to the isolation of 33 compounds, including phytol (1) (Xiong et al., 2013), aloe-emodin (2) (Kametani et al., 2007), aloe-emodin 1-methyl ester (3) (Alexander et al., 1980), digiferruginol (4) (Chang and Lee, 1984), fallacinol (5) (Bloomer et al., 1993), (6R,7E,9R)-3-oxo-α-ionol-β-D-glucopyranoside (6) (Pabst et al., 1992), byzantionoside B (7) (Matsunami et al., 2010), a mixture of trans-martynoside (8) and cis-martynoside (9) (Calis et al., 1984), a mixture of trans-isomartynoside (10) and cis-isomartynoside (11) (Calis et al., 1984), (Colombo et al., 1999), 5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one (31) (Wu et al., 2011), p-coumaric acid ethyl ester (32) (Sathish Kumar et al., 2014), and ferulic acid methyl ester (33) (Wang et al., 2015). The structures were established by spectroscopic analysis and comparison with the reported spectral data (Fig. 2). ...
Ethnopharmacological relevance:
Lindernia crustacea (L.) F.Muell. (Scrophulariaceae) was selected for phytochemical investigation owing to its traditional use against human herpes virus infection and its anti-Epstein-Barr virus (EBV) effect.
Aims of the study:
The present study focused on the phytochemical investigation of L. crustacea including the isolation and structure determination of its biologically active compounds. Compounds with anti-EBV effects were also investigated.
Materials and methods:
The EtOH extract of L. crustacea was subsequently partitioned using different solvents. The EtOAc fraction was subjected to several chromatographic methods to obtain pure compounds. The structures of all isolates were established by spectroscopic analysis and compared with previously reported physical data. The anti-EBV effect was evaluated in an EBV-containing Burkitt's lymphoma cell line (P3HR1) to study the expression of EBV lytic proteins.
Results:
Thirty-three compounds, including one diterpene (1), four anthraquinones (2-5), two ionones (6 and 7), fourteen phenylpropanoid glycosides (8-21), five flavonoids (22-26), one lignan glycoside (27), one phenethyl alcohol glycoside (28), one phenylpropene glycoside (29), one glucosyl glycerol derivative (30), one furanone (31), and two cinnamic acid derivatives (32 and 33), were isolated from the ethanolic extract of the plant. All isolated compounds were obtained for the first time from Lindernia sp. The evaluation of the anti-EBV activity of L. crustacea crude extract, partitioned fractions, and constituents was performed for the first time. Phytol (1), aloe-emodin (2), byzantionoside B (7), a mixture of trans-martynoside (8) and cis-martynoside (9), a mixture of trans-isomartynoside (10) and cis-isomartynoside (11), luteolin-7-O-β-D-glucopyranoside (24), and apigenin-7-O-[β-D-apiofuranosyl (1 → 6)-β-D-glucopyranoside] (25) exhibited significant inhibitory effects on the EBV lytic cycle at 20 μg/mL in the immunoblot analysis. On the other hand, (6R,7E,9R)-3-oxo-α-ionol-β-D-glucopyranoside (6) and a mixture of trans-dolichandroside A (12) and cis-dolichandroside A (13) showed moderate anti-EBV activity at 20 μg/mL.
Conclusions:
L. crustacea and its active isolates could be developed as potential candidates against EBV. Our findings provide scientific evidence for the traditional use of L. crustacea for its antiviral effects.
... After that, by dehydration, the smaller but most abundant fragment ion m/z 111.0086 [M -80 − H] -was produced from the fragment m/z 129.0192, or by the secondary decarboxylation at a higher collision energy, the fragment m/z 82.0295 [M -62 − H] -was formed. In this way, other 22 organic acids were identified, including mevalonic acid (peak 7) [57], methylsuccinic acid (peak 8) [58], 3-methylglutaric acid (peak 9) [59], suberic acid (peak 26) [60], 3-tertbutyladipic acid (peak 38) [61], 9-hydroxy-10,14-octadecadien-12-ynoic acid (peak 43) [62], 9,12,13-trihydroxy-15-octadecenoic acid (peak 48) [63], moroctic acid (peak 49) [64], 5,8-dihydroxy-9,12-octadecadienoic acid (peak 55) [63], 3-hydroxy-(4,2-hydroxy-6-methyl)-2 heptanyl benzoic acid (peak 57) [65], porrigenic acid (peak 58) [66], 12-oxo-phytodienoic acid (peak 60) [67], 3-methyl-5-pentyl-2-furanundecanoic acid (peak 63) [68], 10-hydroxy-8,12-octadecadienoic acid (peak 67), α-eleostearic acid (peak 68) [69], 8-oxo-9-octadecenoic acid (peak 69) [70], 6,7-epoxystearic acid (peak 71) [63], 9-oxo-octadecadienoic acid (peak 73) [71], 2,3-seco-2,3-dicarboxyplatanic acid (peak 74) [72], diroleuton (peak 83) [73], linoleic acid (peak 93) [74], and 1-(hydroxymethyl)-2[(1-oxohexadecyl)oxy]ethyl-ester-9,12-heptadecadienoic acid (peak 108) [75]. All these organic acids were identified from the genus of Sparassis for the first time. ...
Sparassis crispa is a kind of edible fungus widely grows in the north temperate zone, which shows various medicinal properties. Due to the complexity of chemical constitutes of this species, few investigations have acquired a comprehensive configuration for the chemical profile of it. In this study, a strategy based on ultra-high performance liquid chromatography (UPLC) combined with Orbitrap mass spectrometer (MS) was established for rapidly characterizing various chemical components in S. crispa. Through the summarized MS/MS fragmentation patterns of reference compounds and systematic identification strategy, a total of 110 components attributed to six categories were identified for the first time. Moreover, allergic rhinitis (AR) is a worldwide inflammatory disease seriously affecting human health, and the development of drugs to treat AR has been a topic of interest. It has been reported that the extracts of S. crispa showed obvious inhibitory effects on degranulation of mast cell-and allergen-induced IgE and proinflammatory mediators, but the active components and specific mechanism were still not clear. Src family kinases (SFKs) participate in the initial stage of allergy occurrence, which are considered the targets of AR treatment. Herein, on the basis of that self-built chemical database, virtual screening was applied to predict the potential SFKs inhibitors in S. crispa, using known crystal structures of Hck, Lyn, Fyn, and Syk as receptors, followed by the anti-inflammatory activity evaluation for screened hits by intracellular calcium mobilization assay. As results, sparoside A was directly confirmed to have strong anti-inflammatory activity with an IC 50 value of 5.06 ± 0.60 µM. This study provides a useful elucidation for the chemical composition of S. crispa, and demonstrated its potential inhibitory effects on AR, which could promote the research and development of effective agents from natural resources.
... The pentyl side chain is connected to the hydroxyl-dimethyl-2-furanone moiety at C(4), a deduction from the HMBC results with the observation of 2 J correlation from C(4) to H(5), hence completing the structure of 2 as 5-hydroxy-3,4dimethyl-5-pentylfuran-2(5H)-one. Compound 2 has been previously isolated from microorganism (Koshino et al. 1989;Wu et al. 2011;Yuan et al. 2016) and named as hydroxydihydrobovolide and was reported to show mild antimicrobial activity. The experiment data were similar with those reported and this is the first isolation report of hydroxydihydrobovolide from a plant source (Figure 3). ...
Crotalaria pallida Aiton is an herbaceous legume from the family Fabaceae. In the present study, one new cyclopentyliene, crotolidene (1) and seven known compounds, i.e. hydroxydihydrobovolide (2), octacosane (3), trans-phytyl palmitate (4), linoleic acid (5), methyl oleate (6), ethyl palmitate (7), and palmitic acid (8) were isolated from the C. pallida collected from Perak, Malaysia. These compounds were isolated and characterized using extensive chromatographic and spectroscopic methods.
... The fruiting body was found to have nematicidal ability, 12 and 2 novel compounds were isolated and identified. 13 However, little is known about the cultivation requirements and bioactivities of this species. The aim of this study was to identify the optimal submerged conditions for EPS production by C. septentrionalis, characterize the composition of the isolated pure EPS, and evaluate the antioxidant activities of the EPS in vitro. ...
The optimization, purification, and characterization of exopolysaccharide (EPS) from Climacodon septentrionalis were investigated. The results showed that the optimal incubation time was 8 days for EPS production by C. septentrionalis; maltose and soy extract were the best carbon and nitrogen sources, respectively. One kind of EPS fraction was purified; it had a molecular weight of about 3.4 × 105 Da and mainly comprised glucose (98%). The main structure of EPS is α-glucopyranose. In addition, the EPS showed good antioxidant properties in vitro. The thermal stability of EPS also was investigated, and the results suggest that to maintain its bioactivity the processing temperature of EPS should not be more than 200°C. The structural characteristics of EPS, such as molecular weight, functional groups, monosaccharide constituents, and configuration of the glycosidic bond give EPS great potential for application as a natural antioxidant material in health, food, and therapeutics.
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Mushrooms are a fascinating modern-day food item due to their negligible toxicity and highly beneficial health properties. Nowadays, mushrooms are considered to be potent nutraceuticals and dietary supplements. Mushrooms have become a potential source of various bioactive compounds as well as protein, minerals, amino acids, vitamins, and crude fiber, which make them important nutraceuticals. Leucopaxillus giganteus (Sowerby) Singer, also known as the giant funnel or giant leucopax, is a well-known type of wild mushroom belonging to the Tricholomataceae family. Generally, this mushroom is native to Portugal but can also be found in Turkey, Rajasthan, and the Himalayan region of Asia. This mushroom species has been traditionally used to treat asthma, cardiovascular disease, boost the immune system, and strengthen bones. The most important bioactive compound of this mushroom is clitocine, alongside other therapeutically important phytoconstituents such as galactomannoglucan, catathelasmol D, (R)-4-ethoxy-2-hydroxy-4-oxobutanoic acid, (S)-4-hydroxydihydrofuran-2(3H)-one, and (S)-5-(hydroxymethyl)dihydrofuran-2(3H)-one. The different phytoconstituents in L. giganteus are responsible for its different pharmacological attributes, such as antioxidant, antimicrobial, and anti-tumour properties. Although, L. giganteus has been exploited as a food supplement, the further exploration of its pharmacological potential will help in the development of efficient therapies.
Nineteen metabolites with diverse structures, including the rare pyrroloindoline alkaloid verrupyrroloindoline (1), the unprecedented highly fused benzosesquiterpenoid verrubenzospirolactone (2), the new asteriscane-type sesquiterpenoid 10-deoxocapillosanane D (3), and the two new cyclopentenone derivatives (4S*,5S*)-4-hydroxy-5-(hydroxymethyl)-2,3-dimethyl-4-pentylcyclopent-2-en-1-one (4) and (S)-4-hydroxy-5-methylene-2,3-dimethyl-4-pentylcyclopent-2-en-1-one (5), were isolated from a South China Sea collection of the soft coral Sinularia verruca. Eleven previously described marine metabolites (7-15, 18, and 19) were also obtained as well as three new EtOH-adduct artifacts (6, 16, and 17). The structures of the new compounds were elucidated by extensive spectroscopic analysis and by comparison with previously reported data. Compounds 4, 5, and 16 showed protection against the cytopathic effects of HIV-1 infection with EC50 values of 5.8-34 μM, and 4, 6, and 16 exhibited inhibition against LPS-induced NO production with IC50 values of 24-28 μM.
An enantioselective synthesis of (R)-, (S)-turmerone and (7S,9R)-bisacumol is described. The enantiomerically pure key intermediates, a substituted butanoate ester and acid are utilized in the synthesis of both enantiomers of turmerone. The lipase catalyzed resolution studies of the acetate of bisacumol have been exploited towards the total synthesis of the naturally occurring cytotoxic sesquiterpene, (7S,9R)-bisacumol with high diastereoselectivity (94% de).
Five fatty acid derivatives including three novel compounds were isolated from the mushroom Clitocybe clavipe. Their structures were elucidated by spectral analyses. These compounds inhibited aldehyde dehydrogenase in vitro.
A plant growth inhibitor was isolated from blue light-illuminated cressseedlings and identified as 4-hydroxy-2,3-dimethyl-2-nonen-4-olide from1H and 13C NMR and ESI-MS spectra. It inhibited thehypocotyl growth of cress seedlings at concentrations higher than 100M.
Five fatty acid derivatives including three novel compounds were isolated from the mushroom Clitocybe clavipe. Their structures were elucidated by spectral analyses. These compounds inhibited aldehyde dehydrogenase in vitro.
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