A tetrahydrobenzofuran derivative from the fermentation broth of Lentinus squarrosulus BCC 22366

Isaka, Masahiko; Sappan, Malipan; Rachtawee, Pranee; Boonpratuang, Thitiya

doi:10.1016/j.phytol.2010.12.002

Cited by 14 publications

(9 citation statements)

References 14 publications

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“…The fruit body, if harvested within 3 days of fruiting, is used as a meat substitute. It was not until recently that research started to emerge on its application in food [2], medicine [3] [4] and bioremediation [5]. Proximate analysis shows that both the cap and stipe are rich in proteins, sugars, fiber, lipids, amino acids, vitamins B, C, and D, and minerals [6].…”

Section: Introductionmentioning

confidence: 99%

Nutrient Requirements and Fermentation Conditions for Mycelia and Crude Exo-Polysaccharides Production by <i>Lentinus squarrosulus</i>

Anike¹,

Isikhuemhen²,

Blum³

et al. 2015

ABB

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Lentinus squarrosulus Mont. is an emerging tropical white rot basidiomycete, with nutritional and medicinal benefits. Low levels of commercial cultivation of the mushrooms limit their availability for use as food and medicine. Mycelia from submerged fermentation are a suitable alternative to the mushroom from L. squarrosulus. Three strains, 340, 339 and 218, were studied to determine optimum growth conditions for mycelia mass and crude exo-polysaccharides (CEPS) production. The experiments were conducted in a completely randomized design (CRD) with a factorial structure. Nutrients involving 8 carbon and 8 nitrogen sources were screened, and concentrations of the best sources were optimized. Optimized nutrients, interaction between strains and other parameters such as agitation and medium volume were investigated to obtain optimum fermentation conditions for biomass and CEPS production. Biomass yield varied among strains depending on carbon or nitrogen nutrient sources. Starch and yeast extract at 30 and 25 g/L were identified as the most important nutrients in mycelia and CEPS production. Nutrient optimization resulted in a 3-fold increase in mycelia mass: 12.8, 10.0 and 15.3 g/L in strains 340, 339 and 218 respectively. There was a significant interaction between strain, agitation, and volume (p < 0.001). Mycelia mass increased with volume under shake conditions, while polysaccharides decreased. There was a weak and negative correlation between mycelia mass and polysaccharides (p = 0.02). Static conditions favored more polysaccharide production. Optimized fermentation conditions resulted in very high increase in biomass: 238.1, 266.9 and 185.0 g/L in strains 340, 339 and 218 respectively. Results obtained could be useful in modeling fermentation systems for large-scale production of mycelia mass, CEPS and other bio-products from L. squarrosulus.

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Section: Introductionmentioning

confidence: 99%

Nutrient Requirements and Fermentation Conditions for Mycelia and Crude Exo-Polysaccharides Production by <i>Lentinus squarrosulus</i>

Anike¹,

Isikhuemhen²,

Blum³

et al. 2015

ABB

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“…The 1 H-1 H COSY correlation between H-4 and H-5 in combination with HMBC correlations (l " Fig. 3) revealed a similar structure with the known compound (6S,7S)-6,7-dihydroxy-3,6-dimethyl-2-isovaleroyl-4,5,6,7-tetrahydrobenzofuran isolated from the mushroom Lentinus squarrosulus [19]. The ROESY correlation of H 3 -14 with H-7 indicated a cis-configuration of H 3 -14 and H-7 in 3.…”

Section: Resultsmentioning

confidence: 53%

“…The sign of the Cotton effect observed in the induced spectrum comes from the chirality of the vicinal-diol moiety, as indicated by the sign of the O-C-C-O torsion angle. According to the empirical rule [19], the negative Cotton effects observed at about 321 nm assigned the absolute configurations of 6 S and 7R in 3 (Supporting Information). The molecular formula of pleurotin C (4) was assigned as C 15 H 20 O 5 (six degrees of unsaturation) by HRTOFMS.…”

Section: Resultsmentioning

confidence: 99%

Sesquiterpenoids with PTP1B Inhibitory Activity and Cytotoxicity from the Edible Mushroom Pleurotus citrinopileatus

Tao

et al. 2016

Planta Med

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One new perhydrobenzannulated 5,5-spiroketal sesquiterpene, pleurospiroketal F (1), as well as six new modified bisabolene sesquiterpenes pleurotins A-F (2-7) were isolated from solid-state fermentation of Pleurotus citrinopileatus. The structures of compounds 1-7 were determined by NMR and MS spectroscopic analysis. The absolute configuration of 1 was determined by X-ray diffraction analysis, while the absolute configurations of 3-7 were assigned using the in situ dimolybdenum circular dichroism method and circular dichroism data comparison. Protein tyrosine phosphatase 1B plays a crucial role as a negative regulator of the insulin-dependent signal cascades. Therefore, the protein tyrosine phosphatase 1B inhibitor can be used for treating type 2 diabetes mellitus and obesity. Compounds 2 and 6 showed moderate inhibitory effects on protein tyrosine phosphatase 1B with IC50 s of 32.1 µM and 30.5 µM, respectively. The kinetic study confirmed compound 2 to be a noncompetitive inhibitor. Compounds 1-7 did not show cytotoxic activity against cancer cell lines (IC50 > 50 µM).

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“…The 13 C and HSQC NMR spectra ( Figure 2 ) of 4 revealed 16 carbon resonances, comprising four methyls (δ C 22.5, 22.4, 20.4, and 24.9), four methylenes (δ C 17.6, 32.8, 47.1, and 56.9), two methines (δ C 24.1 and one oxygenated at δ C 68.6), four sp 2 quaternary carbons (δ C 147.6, 126.4, 121.6, and 154.8), an oxygenated quaternary carbon (δ C 70.4), and a conjugated ketone (δ C 190.4). The aforementioned information, along with the reported (6S,7S)-6,7-dihydroxy-3,6-dimethyl-2-isovaleroyl-4,5,6,7-tetrahydrobenzofuran, suggested that 4 was closely related to tetrahydrobenzofuran-type [ 17 ]. Then, one nitrogen atom in the molecular formula was identified as an amide (at δ C 170.1) among the carbonyl group, as supported by the HMBC correlation from H-15 to δ C 126.4 (C-3), 147.6 (C-2), and 121.6 (C-9).…”

Section: Resultsmentioning

confidence: 99%

Five New Terpenes with Cytotoxic Activity from Pestalotiopsis sp.

Zhao

et al. 2021

Molecules

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Five new compounds called Pestalotis A–E (1–5), comprising three monoterpene-lactone compounds (1–3), one tetrahydrobenzofuran derivative (4), and one sesquiterpene (5), were isolated from the EtOAc extract of Pestalotiopsis sp. The structures of the new compounds were elucidated by analysis of their NMR, HRMS, and ECD spectra, and the absolute configurations were established through the comparison of experimental and calculated ECD spectra. All compounds were tested for antitumor activity against SW-480, LoVo, HuH-7, and MCF-7. The results showed that compounds 2 and 4 exhibited potent antitumor activity against SW-480, LoVo, and HuH-7 cell lines. Furthermore, compound 4 was assessed against HuH-7, and the results indicated that the rate of apoptosis was dose-dependent.

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A tetrahydrobenzofuran derivative from the fermentation broth of Lentinus squarrosulus BCC 22366

Cited by 14 publications

References 14 publications

Nutrient Requirements and Fermentation Conditions for Mycelia and Crude Exo-Polysaccharides Production by <i>Lentinus squarrosulus</i>

Nutrient Requirements and Fermentation Conditions for Mycelia and Crude Exo-Polysaccharides Production by <i>Lentinus squarrosulus</i>

Sesquiterpenoids with PTP1B Inhibitory Activity and Cytotoxicity from the Edible Mushroom Pleurotus citrinopileatus

Five New Terpenes with Cytotoxic Activity from Pestalotiopsis sp.

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A tetrahydrobenzofuran derivative from the fermentation broth of Lentinus squarrosulus BCC 22366

Cited by 14 publications

References 14 publications

Nutrient Requirements and Fermentation Conditions for Mycelia and Crude Exo-Polysaccharides Production by &lt;i&gt;Lentinus squarrosulus&lt;/i&gt;

Nutrient Requirements and Fermentation Conditions for Mycelia and Crude Exo-Polysaccharides Production by &lt;i&gt;Lentinus squarrosulus&lt;/i&gt;

Sesquiterpenoids with PTP1B Inhibitory Activity and Cytotoxicity from the Edible Mushroom Pleurotus citrinopileatus

Five New Terpenes with Cytotoxic Activity from Pestalotiopsis sp.

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Nutrient Requirements and Fermentation Conditions for Mycelia and Crude Exo-Polysaccharides Production by <i>Lentinus squarrosulus</i>

Nutrient Requirements and Fermentation Conditions for Mycelia and Crude Exo-Polysaccharides Production by <i>Lentinus squarrosulus</i>