Antibacterial Ilicicolinic Acids C and D and Ilicicolinal from <i>Neonectria discophora</i> SNB-CN63 Isolated from a Termite Nest

Ilicicolinic acids A, C, and D (<b>1</b>–<b>3</b>) and ilicicolinal (<b>4</b>) were isolated from a fungus isolated from a <i>Nasutitermes corniger</i> nest in French Guiana. The structures of ilicicolinic acids C and D and ilicicolinal were elucidated using 1D and 2D NMR spectroscopic data as well as MS data. Ilicicolinic acids show antibacterial activity <i>in vitro</i>

Antifungal Agents from <i>Pseudallescheria boydii</i> SNB-CN73 Isolated from a <i>Nasutitermes</i> sp. Termite

Defense mutualisms between social insects and microorganisms have been described in the literature. The present article describes the discovery of a <i>Pseudallescheria boydii</i> strain isolated from <i>Nasutitermes</i> sp. The microbial symbiont produces two antifungal metabolites: tyroscherin and <i>N</i>-methyltyroscherin, a compound not previously described in the literature. Methylation of tyroscherin has confirmed the structure of <i>N</i>-methyltyroscherin. Both compounds are effective antifungal agents with favorable selectivity indices for <i>Candida albicans</i> and <i>Trichophyton rubrum</i>

Pseudallicins A–D: Four Complex Ovalicin Derivatives from <i>Pseudallescheria boydii</i> SNB-CN85

The isolation and complete structural elucidation of four complex ovalicin analogues, named pseudallicins A–D, from the fungus <i>Pseudallescheria boydii</i> strain SNB-CN85 are described. On the basis of structural similarities and information from the literature, a joint biosynthetic pathway for the pseudallicins is proposed

Mucorolactone, a Macrolactone from Mucor sp. SNB-VECD13A, a Fungus Isolated from the Cuticle of a Vespidae Species

The newly discovered macrolactone, mucorolactone, along with eight known compounds, was isolated from an ethyl acetate extract of the insect-borne fungus Mucor sp. All structures were elucidated using 1D and 2D NMR and MS spectroscopic experiments. Relative and absolute configurations of the original skeleton of mucorolactone was deduced from NOESY experiments, from the ¹³C NMR chemical shift calculation based on the DP4 probability method, and from the comparison of experimental and calculated electronic circular dichroism spectra

Structurally Diverse Diterpenoids from Sandwithia guyanensis

Bioassay-guided fractionation of an EtOAc extract of the trunk bark of Sandwithia guyanensis, using a chikungunya virus (CHIKV)-cell-based assay, afforded 17 new diterpenoids <b>1</b>–<b>17</b> and the known jatrointelones A and C (<b>18</b> and <b>19</b>). The new compounds included two tetranorditerpenoids <b>1</b> and <b>2</b>, a trinorditerpenoid <b>3</b>, euphoractines P-W (<b>4</b>–<b>11</b>), and euphactine G (<b>13</b>) possessing the rare 5/6/7/3 (<b>4</b>–<b>7</b>), 5/6/6/4 (<b>8</b>–<b>11</b>), and 5/6/8 (<b>13</b>) fused ring skeletons, sikkimenoid E (<b>12</b>), and jatrointelones J-M (<b>14</b>–<b>17</b>) possessing jatropholane and lathyrane carbon skeletons, respectively. Jatrointelones J (<b>14</b>) and M (<b>17</b>) represent the first naturally occurring examples of C-15 nonoxidized lathyrane-type diterpenoids. The structures of the new compounds were elucidated by NMR spectroscopic data analysis. The relative configuration of compound <b>16</b> and the absolute configurations of compounds <b>3</b>–<b>6</b> and <b>14</b> were determined by single-crystal X-ray diffraction analysis. In addition, jatrointelone K (<b>15</b>) was chemically transformed to euphoractine T (<b>8</b>) supporting the biosynthetic relationships between the two types of diterpenoids. Only compound <b>15</b> showed a moderate anti-CHIKV activity with an EC₅₀ value of 14 μM. Finally, using a molecular networking-based dereplication strategy, several close analogues of 12-<i>O</i>-tetradecanoylphorbol-13-acetate (TPA), one of the most potent inhibitors of CHIKV replication, were dereplicated

Structurally Diverse Diterpenoids from Sandwithia guyanensis

Bioassay-guided fractionation of an EtOAc extract of the trunk bark of Sandwithia guyanensis, using a chikungunya virus (CHIKV)-cell-based assay, afforded 17 new diterpenoids <b>1</b>–<b>17</b> and the known jatrointelones A and C (<b>18</b> and <b>19</b>). The new compounds included two tetranorditerpenoids <b>1</b> and <b>2</b>, a trinorditerpenoid <b>3</b>, euphoractines P-W (<b>4</b>–<b>11</b>), and euphactine G (<b>13</b>) possessing the rare 5/6/7/3 (<b>4</b>–<b>7</b>), 5/6/6/4 (<b>8</b>–<b>11</b>), and 5/6/8 (<b>13</b>) fused ring skeletons, sikkimenoid E (<b>12</b>), and jatrointelones J-M (<b>14</b>–<b>17</b>) possessing jatropholane and lathyrane carbon skeletons, respectively. Jatrointelones J (<b>14</b>) and M (<b>17</b>) represent the first naturally occurring examples of C-15 nonoxidized lathyrane-type diterpenoids. The structures of the new compounds were elucidated by NMR spectroscopic data analysis. The relative configuration of compound <b>16</b> and the absolute configurations of compounds <b>3</b>–<b>6</b> and <b>14</b> were determined by single-crystal X-ray diffraction analysis. In addition, jatrointelone K (<b>15</b>) was chemically transformed to euphoractine T (<b>8</b>) supporting the biosynthetic relationships between the two types of diterpenoids. Only compound <b>15</b> showed a moderate anti-CHIKV activity with an EC₅₀ value of 14 μM. Finally, using a molecular networking-based dereplication strategy, several close analogues of 12-<i>O</i>-tetradecanoylphorbol-13-acetate (TPA), one of the most potent inhibitors of CHIKV replication, were dereplicated

Structurally Diverse Diterpenoids from Sandwithia guyanensis

Bioassay-guided fractionation of an EtOAc extract of the trunk bark of Sandwithia guyanensis, using a chikungunya virus (CHIKV)-cell-based assay, afforded 17 new diterpenoids <b>1</b>–<b>17</b> and the known jatrointelones A and C (<b>18</b> and <b>19</b>). The new compounds included two tetranorditerpenoids <b>1</b> and <b>2</b>, a trinorditerpenoid <b>3</b>, euphoractines P-W (<b>4</b>–<b>11</b>), and euphactine G (<b>13</b>) possessing the rare 5/6/7/3 (<b>4</b>–<b>7</b>), 5/6/6/4 (<b>8</b>–<b>11</b>), and 5/6/8 (<b>13</b>) fused ring skeletons, sikkimenoid E (<b>12</b>), and jatrointelones J-M (<b>14</b>–<b>17</b>) possessing jatropholane and lathyrane carbon skeletons, respectively. Jatrointelones J (<b>14</b>) and M (<b>17</b>) represent the first naturally occurring examples of C-15 nonoxidized lathyrane-type diterpenoids. The structures of the new compounds were elucidated by NMR spectroscopic data analysis. The relative configuration of compound <b>16</b> and the absolute configurations of compounds <b>3</b>–<b>6</b> and <b>14</b> were determined by single-crystal X-ray diffraction analysis. In addition, jatrointelone K (<b>15</b>) was chemically transformed to euphoractine T (<b>8</b>) supporting the biosynthetic relationships between the two types of diterpenoids. Only compound <b>15</b> showed a moderate anti-CHIKV activity with an EC₅₀ value of 14 μM. Finally, using a molecular networking-based dereplication strategy, several close analogues of 12-<i>O</i>-tetradecanoylphorbol-13-acetate (TPA), one of the most potent inhibitors of CHIKV replication, were dereplicated

Structurally Diverse Diterpenoids from Sandwithia guyanensis

Bioassay-guided fractionation of an EtOAc extract of the trunk bark of Sandwithia guyanensis, using a chikungunya virus (CHIKV)-cell-based assay, afforded 17 new diterpenoids <b>1</b>–<b>17</b> and the known jatrointelones A and C (<b>18</b> and <b>19</b>). The new compounds included two tetranorditerpenoids <b>1</b> and <b>2</b>, a trinorditerpenoid <b>3</b>, euphoractines P-W (<b>4</b>–<b>11</b>), and euphactine G (<b>13</b>) possessing the rare 5/6/7/3 (<b>4</b>–<b>7</b>), 5/6/6/4 (<b>8</b>–<b>11</b>), and 5/6/8 (<b>13</b>) fused ring skeletons, sikkimenoid E (<b>12</b>), and jatrointelones J-M (<b>14</b>–<b>17</b>) possessing jatropholane and lathyrane carbon skeletons, respectively. Jatrointelones J (<b>14</b>) and M (<b>17</b>) represent the first naturally occurring examples of C-15 nonoxidized lathyrane-type diterpenoids. The structures of the new compounds were elucidated by NMR spectroscopic data analysis. The relative configuration of compound <b>16</b> and the absolute configurations of compounds <b>3</b>–<b>6</b> and <b>14</b> were determined by single-crystal X-ray diffraction analysis. In addition, jatrointelone K (<b>15</b>) was chemically transformed to euphoractine T (<b>8</b>) supporting the biosynthetic relationships between the two types of diterpenoids. Only compound <b>15</b> showed a moderate anti-CHIKV activity with an EC₅₀ value of 14 μM. Finally, using a molecular networking-based dereplication strategy, several close analogues of 12-<i>O</i>-tetradecanoylphorbol-13-acetate (TPA), one of the most potent inhibitors of CHIKV replication, were dereplicated

Structurally Diverse Diterpenoids from Sandwithia guyanensis

Bioassay-guided fractionation of an EtOAc extract of the trunk bark of Sandwithia guyanensis, using a chikungunya virus (CHIKV)-cell-based assay, afforded 17 new diterpenoids <b>1</b>–<b>17</b> and the known jatrointelones A and C (<b>18</b> and <b>19</b>). The new compounds included two tetranorditerpenoids <b>1</b> and <b>2</b>, a trinorditerpenoid <b>3</b>, euphoractines P-W (<b>4</b>–<b>11</b>), and euphactine G (<b>13</b>) possessing the rare 5/6/7/3 (<b>4</b>–<b>7</b>), 5/6/6/4 (<b>8</b>–<b>11</b>), and 5/6/8 (<b>13</b>) fused ring skeletons, sikkimenoid E (<b>12</b>), and jatrointelones J-M (<b>14</b>–<b>17</b>) possessing jatropholane and lathyrane carbon skeletons, respectively. Jatrointelones J (<b>14</b>) and M (<b>17</b>) represent the first naturally occurring examples of C-15 nonoxidized lathyrane-type diterpenoids. The structures of the new compounds were elucidated by NMR spectroscopic data analysis. The relative configuration of compound <b>16</b> and the absolute configurations of compounds <b>3</b>–<b>6</b> and <b>14</b> were determined by single-crystal X-ray diffraction analysis. In addition, jatrointelone K (<b>15</b>) was chemically transformed to euphoractine T (<b>8</b>) supporting the biosynthetic relationships between the two types of diterpenoids. Only compound <b>15</b> showed a moderate anti-CHIKV activity with an EC₅₀ value of 14 μM. Finally, using a molecular networking-based dereplication strategy, several close analogues of 12-<i>O</i>-tetradecanoylphorbol-13-acetate (TPA), one of the most potent inhibitors of CHIKV replication, were dereplicated

Structurally Diverse Diterpenoids from Sandwithia guyanensis

Bioassay-guided fractionation of an EtOAc extract of the trunk bark of Sandwithia guyanensis, using a chikungunya virus (CHIKV)-cell-based assay, afforded 17 new diterpenoids <b>1</b>–<b>17</b> and the known jatrointelones A and C (<b>18</b> and <b>19</b>). The new compounds included two tetranorditerpenoids <b>1</b> and <b>2</b>, a trinorditerpenoid <b>3</b>, euphoractines P-W (<b>4</b>–<b>11</b>), and euphactine G (<b>13</b>) possessing the rare 5/6/7/3 (<b>4</b>–<b>7</b>), 5/6/6/4 (<b>8</b>–<b>11</b>), and 5/6/8 (<b>13</b>) fused ring skeletons, sikkimenoid E (<b>12</b>), and jatrointelones J-M (<b>14</b>–<b>17</b>) possessing jatropholane and lathyrane carbon skeletons, respectively. Jatrointelones J (<b>14</b>) and M (<b>17</b>) represent the first naturally occurring examples of C-15 nonoxidized lathyrane-type diterpenoids. The structures of the new compounds were elucidated by NMR spectroscopic data analysis. The relative configuration of compound <b>16</b> and the absolute configurations of compounds <b>3</b>–<b>6</b> and <b>14</b> were determined by single-crystal X-ray diffraction analysis. In addition, jatrointelone K (<b>15</b>) was chemically transformed to euphoractine T (<b>8</b>) supporting the biosynthetic relationships between the two types of diterpenoids. Only compound <b>15</b> showed a moderate anti-CHIKV activity with an EC₅₀ value of 14 μM. Finally, using a molecular networking-based dereplication strategy, several close analogues of 12-<i>O</i>-tetradecanoylphorbol-13-acetate (TPA), one of the most potent inhibitors of CHIKV replication, were dereplicated