Toxic Indole Diterpenes from Endophyte-Infected Perennial Ryegrass Lolium perenne L.: Isolation and Stability
The most potent of the indole diterpenes, lolitrem B, is found in perennial ryegrass (Lolium perenne L.) infected with the endophyte Epichloë festucae var. lolii (also termed LpTG-1). Ingestion causes a neurological syndrome in grazing livestock called ryegrass staggers disease. To enable t...
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| Format: | Article |
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MDPI AG
2019-01-01
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| Series: | Toxins |
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| Online Access: | http://www.mdpi.com/2072-6651/11/1/16 |
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| author | Priyanka Reddy Myrna A. Deseo Vilnis Ezernieks Kathryn Guthridge German Spangenberg Simone Rochfort |
| author_facet | Priyanka Reddy Myrna A. Deseo Vilnis Ezernieks Kathryn Guthridge German Spangenberg Simone Rochfort |
| author_sort | Priyanka Reddy |
| collection | DOAJ |
| description | The most potent of the indole diterpenes, lolitrem B, is found in perennial ryegrass (Lolium perenne L.) infected with the endophyte Epichloë festucae var. lolii (also termed LpTG-1). Ingestion causes a neurological syndrome in grazing livestock called ryegrass staggers disease. To enable the rapid development of new forage varieties, the toxicity of lolitrem B and its biosynthetic intermediates needs to be established. However, most of these indole diterpenes are not commercially available; thus, isolation of these compounds is paramount. A concentrated endophyte-infected perennial ryegrass seed extract was subjected to silica flash chromatography followed by preparative HPLC and purification by crystallization resulting in lolitrem B and the intermediate compounds lolitrem E, paspaline and terpendole B. The four-step isolation and purification method resulted in a 25% yield of lolitrem B. After isolation, lolitrem B readily degraded to its biosynthetic intermediate, lolitriol. We also found that lolitrem B can readily degrade depending on the solvent and storage conditions. The facile method which takes into consideration the associated instability of lolitrem B, led to the purification of indole diterpenes in quantities sufficient for use as analytical standards for identification in pastures, and/or for toxicity testing in pasture development programs. |
| first_indexed | 2024-04-11T13:03:44Z |
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| issn | 2072-6651 |
| language | English |
| last_indexed | 2024-04-11T13:03:44Z |
| publishDate | 2019-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Toxins |
| spelling | doaj.art-6a549547da8c4f0baefc49c0599d15f22022-12-22T04:22:50ZengMDPI AGToxins2072-66512019-01-011111610.3390/toxins11010016toxins11010016Toxic Indole Diterpenes from Endophyte-Infected Perennial Ryegrass Lolium perenne L.: Isolation and StabilityPriyanka Reddy0Myrna A. Deseo1Vilnis Ezernieks2Kathryn Guthridge3German Spangenberg4Simone Rochfort5Agriculture Victoria, AgriBio, Centre for AgriBioscience, Bundoora, Victoria 3083, AustraliaAgriculture Victoria, AgriBio, Centre for AgriBioscience, Bundoora, Victoria 3083, AustraliaAgriculture Victoria, AgriBio, Centre for AgriBioscience, Bundoora, Victoria 3083, AustraliaAgriculture Victoria, AgriBio, Centre for AgriBioscience, Bundoora, Victoria 3083, AustraliaAgriculture Victoria, AgriBio, Centre for AgriBioscience, Bundoora, Victoria 3083, AustraliaAgriculture Victoria, AgriBio, Centre for AgriBioscience, Bundoora, Victoria 3083, AustraliaThe most potent of the indole diterpenes, lolitrem B, is found in perennial ryegrass (Lolium perenne L.) infected with the endophyte Epichloë festucae var. lolii (also termed LpTG-1). Ingestion causes a neurological syndrome in grazing livestock called ryegrass staggers disease. To enable the rapid development of new forage varieties, the toxicity of lolitrem B and its biosynthetic intermediates needs to be established. However, most of these indole diterpenes are not commercially available; thus, isolation of these compounds is paramount. A concentrated endophyte-infected perennial ryegrass seed extract was subjected to silica flash chromatography followed by preparative HPLC and purification by crystallization resulting in lolitrem B and the intermediate compounds lolitrem E, paspaline and terpendole B. The four-step isolation and purification method resulted in a 25% yield of lolitrem B. After isolation, lolitrem B readily degraded to its biosynthetic intermediate, lolitriol. We also found that lolitrem B can readily degrade depending on the solvent and storage conditions. The facile method which takes into consideration the associated instability of lolitrem B, led to the purification of indole diterpenes in quantities sufficient for use as analytical standards for identification in pastures, and/or for toxicity testing in pasture development programs.http://www.mdpi.com/2072-6651/11/1/16mycotoxinsterpendolelolitremneurotoxinalkaloidendophyte |
| spellingShingle | Priyanka Reddy Myrna A. Deseo Vilnis Ezernieks Kathryn Guthridge German Spangenberg Simone Rochfort Toxic Indole Diterpenes from Endophyte-Infected Perennial Ryegrass Lolium perenne L.: Isolation and Stability Toxins mycotoxins terpendole lolitrem neurotoxin alkaloid endophyte |
| title | Toxic Indole Diterpenes from Endophyte-Infected Perennial Ryegrass Lolium perenne L.: Isolation and Stability |
| title_full | Toxic Indole Diterpenes from Endophyte-Infected Perennial Ryegrass Lolium perenne L.: Isolation and Stability |
| title_fullStr | Toxic Indole Diterpenes from Endophyte-Infected Perennial Ryegrass Lolium perenne L.: Isolation and Stability |
| title_full_unstemmed | Toxic Indole Diterpenes from Endophyte-Infected Perennial Ryegrass Lolium perenne L.: Isolation and Stability |
| title_short | Toxic Indole Diterpenes from Endophyte-Infected Perennial Ryegrass Lolium perenne L.: Isolation and Stability |
| title_sort | toxic indole diterpenes from endophyte infected perennial ryegrass lolium perenne l isolation and stability |
| topic | mycotoxins terpendole lolitrem neurotoxin alkaloid endophyte |
| url | http://www.mdpi.com/2072-6651/11/1/16 |
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