Shikimate-Derived Meroterpenoids from the Ascidian-Derived Fungus <i>Amphichorda felina</i> SYSU-MS7908 and Their Anti-Glioma Activity

Glioma is a clinically heterogeneous type of brain tumor with a poor prognosis. Current treatment approaches have limited effectiveness in treating glioma, highlighting the need for novel drugs. One approach is to explore marine natural products for their therapeutic potential. In this study, we isolated nine shikimate-derived diisoprenyl-cyclohexene/ane-type meroterpenoids (1–9), including four new ones, amphicordins A–D (1–4) from the ascidian-derived fungus Amphichorda felina SYSU-MS7908, and further semisynthesized four derivatives (10–13). Their structures were extensively characterized using 1D and 2D NMR, modified Mosher’s method, HR-ESIMS, NMR and ECD calculations, and X-ray crystallography. Notably, amphicordin C (3) possesses a unique benzo[g]chromene (6/6/6) skeleton in this meroterpenoid family. In an anti-glioma assay, oxirapentyn A (7) effectively inhibited the proliferation, migration, and invasion of glioma cells and induced their apoptosis. Furthermore, an in silico analysis suggested that oxirapentyn A has the potential to penetrate the blood–brain barrier. These findings highlight the potential of oxirapentyn A as a candidate for the development of novel anti-glioma drugs

Shikimate-Derived Meroterpenoids from the Ascidian-Derived Fungus <i>Amphichorda felina</i> SYSU-MS7908 and Their Anti-Glioma Activity

Glioma is a clinically heterogeneous type of brain tumor with a poor prognosis. Current treatment approaches have limited effectiveness in treating glioma, highlighting the need for novel drugs. One approach is to explore marine natural products for their therapeutic potential. In this study, we isolated nine shikimate-derived diisoprenyl-cyclohexene/ane-type meroterpenoids (1–9), including four new ones, amphicordins A–D (1–4) from the ascidian-derived fungus Amphichorda felina SYSU-MS7908, and further semisynthesized four derivatives (10–13). Their structures were extensively characterized using 1D and 2D NMR, modified Mosher’s method, HR-ESIMS, NMR and ECD calculations, and X-ray crystallography. Notably, amphicordin C (3) possesses a unique benzo[g]chromene (6/6/6) skeleton in this meroterpenoid family. In an anti-glioma assay, oxirapentyn A (7) effectively inhibited the proliferation, migration, and invasion of glioma cells and induced their apoptosis. Furthermore, an in silico analysis suggested that oxirapentyn A has the potential to penetrate the blood–brain barrier. These findings highlight the potential of oxirapentyn A as a candidate for the development of novel anti-glioma drugs

A new <i>α</i>-pyrone from the mangrove endophytic fungus <i>Phomopsis</i> sp. HNY29-2B

<p>A new <i>α</i>-pyrone derivative, phomopyrone A (<b>1</b>), together with two known compounds (<b>2</b>–<b>3</b>), was isolated from the culture of the mangrove endophytic fungus <i>Phomopsis</i> sp. HNY29-2B. Their structures were determined by detailed analysis of spectroscopic data. The configuration of <b>1</b> was further confirmed by X-ray diffraction. All isolated compounds were evaluated for antibacterial and antioxidative activities. Compound <b>2</b> exhibited antibacterial activities with minimal inhibition concentration (MIC) values of 25 and 50 μM against <i>Bacillus subtilis</i> and <i>Pseudomonas aeruginosa</i>, and compound <b>3</b> showed activities against <i>Staphylococcus aureus</i> and <i>B. subtilis</i> with MIC values of 25 and 50 μM, respectively.</p

Anti-inflammatory Mono- and Dimeric Sorbicillinoids from the Marine-Derived Fungus <i>Trichoderma reesei</i> 4670

Eight new dimeric sorbicillinoids (1–3, 5–9) and 12 new monomeric sorbicillinoids (10–20, 25), along with five known analogues (4 and 21–24), were isolated from the marine-derived fungus Trichoderma reesei 4670. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HR-ESIMS, and ECD) and X-ray crystallography. Compound 1, containing a pyrrolidin-2-one moiety, is reported for the first time in the sorbicillinoid family. Compounds 8 and 9 are the first examples of bisorbicillinoids possessing a benzofuro­[2,3-h]­chromene scaffold from a natural source. Compounds 3–11, 13–16, 18, 21, 22, 24, and 25 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50 values in the range from 0.94 to 38 μM. Structure–activity relationships of the sorbicillinoids were discussed

A new <i>β</i>-tetralonyl glucoside from the <i>Santalum album</i> derived endophytic fungus <i>Colletotrichum</i> sp. GDMU-1

<p>A new <i>β</i>-tetralonyl glucoside, methylberchemiaside (<b>1</b>), along with five known compounds (<b>2–6</b>) were isolated from a fungus <i>Colletotrichum</i> sp<i>.</i> GDMU-1 derived from the leaves of <i>Santalum album</i>. Their structures were determined by detailed analysis of spectroscopic data. All compounds were tested for the inhibitory effects on the nitric oxide (NO) production in lipopolysaccharide (LPS)-treated RAW264.7 cells. Among them, compounds <b>4</b> and <b>5</b> showed moderate anti-inflammatory activity with IC₅₀ value of 30.4 and 8.9 μM, respectively.</p

Targeted Discovery of Sorbicillinoid Pigments with Anti-Inflammatory Activity from the Sponge-Derived Fungus Stagonospora sp. SYSU-MS7888 Using the PMG Strategy

An effective identification and discovery of fungal pigments is very important to illustrate the role of fungal pigments in the life process and conduce to the discovery of new bioactive and edible pigments. The phenotype combined with metabolomic and genomic (PMG) strategy led to the discovery and characterization of three new sorbicillinoid pigments, stasorbicillinoids A–C (1–3), and five known analogues (4–8) from the sponge-derived fungus Stagonospora sp. SYSU-MS7888. Their structures were elucidated by the application of spectroscopic methods (NMR, MS, UV, IR, and ECD) and modified Mosher’s method. Compounds 1 and 2 featured novel naphthone nuclei linked by two alkyl side chains possibly undergoing inter- and intramolecular Michael reactions. Compounds 1–8 exhibited potent anti-inflammatory activity with IC50 values in the range of 3.56–22.8 μM. Furthermore, compound 2 inhibited the production of IL-1β, IL-6, and TNF-α in a dose-dependent manner. This study provides an effective strategy to accelerate the discovery of new fungal pigments and further exploration of their potential applications in different fields such as medicine and food industries

Peniisocoumarins A–J: Isocoumarins from <i>Penicillium commune</i> QQF-3, an Endophytic Fungus of the Mangrove Plant <i>Kandelia candel</i>

Ten new isocoumarins, named peniisocoumarins A–J (<b>1</b>–<b>9</b> and <b>11</b>), along with three known analogues (<b>10</b>, <b>12</b>, and <b>13</b>) were obtained from the fermentation of an endophytic fungus, <i>Penicillium commune</i> QQF-3, which was isolated from a fresh fruit of the mangrove plant <i>Kandelia candel.</i> Their structures were elucidated through extensive spectroscopic analysis. The absolute configurations of <b>1</b>–<b>7</b> were determined by single-crystal X-ray diffraction and modified Mosher’s method, and those of <b>8</b>, <b>9</b>, and <b>11</b> were assigned on the basis of experimental and calculated electronic circular dichroism data. Compounds <b>1</b> and <b>2</b> were unusual dimeric isocoumarins with a symmetric four-membered core. These isolated compounds (<b>1</b>–<b>13</b>) were evaluated for their cytotoxicity and enzyme inhibitory activities against α-glucosidase and <i>Mycobacterium tuberculosis</i> protein tyrosine phosphatase B (MptpB). Among them, compounds <b>3</b>, <b>7</b>, <b>9</b>, and <b>11</b> exhibited potent inhibitory effects against α-glucosidase with IC₅₀ values ranging from 38.1 to 78.1 μM, and compound <b>7</b> was found to inhibit MptpB with an IC₅₀ value of 20.7 μM

Shikimate-Derived Meroterpenoids from the Ascidian-Derived Fungus <i>Amphichorda felina</i> SYSU-MS7908 and Their Anti-Glioma Activity

Glioma is a clinically heterogeneous type of brain tumor with a poor prognosis. Current treatment approaches have limited effectiveness in treating glioma, highlighting the need for novel drugs. One approach is to explore marine natural products for their therapeutic potential. In this study, we isolated nine shikimate-derived diisoprenyl-cyclohexene/ane-type meroterpenoids (1–9), including four new ones, amphicordins A–D (1–4) from the ascidian-derived fungus Amphichorda felina SYSU-MS7908, and further semisynthesized four derivatives (10–13). Their structures were extensively characterized using 1D and 2D NMR, modified Mosher’s method, HR-ESIMS, NMR and ECD calculations, and X-ray crystallography. Notably, amphicordin C (3) possesses a unique benzo[g]chromene (6/6/6) skeleton in this meroterpenoid family. In an anti-glioma assay, oxirapentyn A (7) effectively inhibited the proliferation, migration, and invasion of glioma cells and induced their apoptosis. Furthermore, an in silico analysis suggested that oxirapentyn A has the potential to penetrate the blood–brain barrier. These findings highlight the potential of oxirapentyn A as a candidate for the development of novel anti-glioma drugs

Anti-inflammatory Mono- and Dimeric Sorbicillinoids from the Marine-Derived Fungus <i>Trichoderma reesei</i> 4670

Eight new dimeric sorbicillinoids (1–3, 5–9) and 12 new monomeric sorbicillinoids (10–20, 25), along with five known analogues (4 and 21–24), were isolated from the marine-derived fungus Trichoderma reesei 4670. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HR-ESIMS, and ECD) and X-ray crystallography. Compound 1, containing a pyrrolidin-2-one moiety, is reported for the first time in the sorbicillinoid family. Compounds 8 and 9 are the first examples of bisorbicillinoids possessing a benzofuro­[2,3-h]­chromene scaffold from a natural source. Compounds 3–11, 13–16, 18, 21, 22, 24, and 25 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50 values in the range from 0.94 to 38 μM. Structure–activity relationships of the sorbicillinoids were discussed

Peniisocoumarins A–J: Isocoumarins from <i>Penicillium commune</i> QQF-3, an Endophytic Fungus of the Mangrove Plant <i>Kandelia candel</i>

Ten new isocoumarins, named peniisocoumarins A–J (<b>1</b>–<b>9</b> and <b>11</b>), along with three known analogues (<b>10</b>, <b>12</b>, and <b>13</b>) were obtained from the fermentation of an endophytic fungus, <i>Penicillium commune</i> QQF-3, which was isolated from a fresh fruit of the mangrove plant <i>Kandelia candel.</i> Their structures were elucidated through extensive spectroscopic analysis. The absolute configurations of <b>1</b>–<b>7</b> were determined by single-crystal X-ray diffraction and modified Mosher’s method, and those of <b>8</b>, <b>9</b>, and <b>11</b> were assigned on the basis of experimental and calculated electronic circular dichroism data. Compounds <b>1</b> and <b>2</b> were unusual dimeric isocoumarins with a symmetric four-membered core. These isolated compounds (<b>1</b>–<b>13</b>) were evaluated for their cytotoxicity and enzyme inhibitory activities against α-glucosidase and <i>Mycobacterium tuberculosis</i> protein tyrosine phosphatase B (MptpB). Among them, compounds <b>3</b>, <b>7</b>, <b>9</b>, and <b>11</b> exhibited potent inhibitory effects against α-glucosidase with IC₅₀ values ranging from 38.1 to 78.1 μM, and compound <b>7</b> was found to inhibit MptpB with an IC₅₀ value of 20.7 μM