Charakterisierung zweier neuer antioxidativer Tetrahydroxyxanthone in Hypericum-Samen und rasterelektronenmikroskopische Untersuchung der Testa
Hypericum seeds have recently been identified as a natural source of different xanthone derivatives. Two main constituents, the tetrahydroxyxanthones THX-1 and -2, were identified in methanolic extracts of H. perforatum and H. tetrapterum by means of HPLC(DAD)-MS n methods. However, the exact config...
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Julius Kühn-Institut
2018-09-01
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| Online Access: | https://www.openagrar.de/receive/openagrar_mods_00078803 |
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| author | Lorenz, Peter Heller, Annerose Bunse, Marek Heinrich, Miriam Berger, Melanie Conrad, Jürgen Stintzing, Florian C. Kammerer, Dietmar R. |
| author_facet | Lorenz, Peter Heller, Annerose Bunse, Marek Heinrich, Miriam Berger, Melanie Conrad, Jürgen Stintzing, Florian C. Kammerer, Dietmar R. |
| author_sort | Lorenz, Peter |
| collection | DOAJ |
| description | Hypericum seeds have recently been identified as a natural source of different xanthone derivatives. Two main constituents, the tetrahydroxyxanthones THX-1 and -2, were identified in methanolic extracts of H. perforatum and H. tetrapterum by means of HPLC(DAD)-MS n methods. However, the exact configuration of both THX was unknown so far. For this reason, the two compounds were enriched by chromatography on polyamide and silica, and the corresponding fraction was investigated by 1D- and 2D-NMR techniques. Based on a tentative structural assignment a total synthesis of THX-1 and -2 was performed. Comparing the chromatographic and spectroscopic/spectrometric features of synthetic THX-1 and -2 with their natural counterparts their exact configuration was determined as 1,4,6,7-THX (THX-1) and 1,2,6,7-THX (THX-2), respectively. The novel compounds exhibited a threefold higher radical scavenging activity in the DPPH assay than the vitamin E derivative Trolox®. Hence, they are strong antioxidants. Furthermore, scanning electron microscopy (SEM) provided insights into the two-layer structure of the testa (seed coat), with the thick lignified sclerenchyma layer presumably being the depository of the xanthones. |
| first_indexed | 2024-03-10T09:00:45Z |
| format | Article |
| id | doaj.art-c96b709f1607463f88d149e7ef09ade3 |
| institution | Directory Open Access Journal |
| issn | 1868-9892 2199-921X |
| language | deu |
| last_indexed | 2024-03-10T09:00:45Z |
| publishDate | 2018-09-01 |
| publisher | Julius Kühn-Institut |
| record_format | Article |
| series | Julius-Kühn-Archiv |
| spelling | doaj.art-c96b709f1607463f88d149e7ef09ade32023-11-22T06:47:21ZdeuJulius Kühn-InstitutJulius-Kühn-Archiv1868-98922199-921X2018-09-01460454910.5073/jka.2018.460.014Charakterisierung zweier neuer antioxidativer Tetrahydroxyxanthone in Hypericum-Samen und rasterelektronenmikroskopische Untersuchung der TestaLorenz, Peter0Heller, Annerose1Bunse, Marek2Heinrich, Miriam3Berger, Melanie4Conrad, Jürgen5Stintzing, Florian C.6Kammerer, Dietmar R.7WALA Heilmittel GmbH, Abteilung Analytische Entwicklung & Forschung, Sektion Phytochemische Forschung, Bad Boll/Eckwälden, DeutschlandUniversität Hohenheim, Institut für Botanik (210), Stuttgart, DeutschlandWALA Heilmittel GmbH, Abteilung Analytische Entwicklung & Forschung, Sektion Phytochemische Forschung, Bad Boll/Eckwälden, DeutschlandWALA Heilmittel GmbH, Abteilung Analytische Entwicklung & Forschung, Sektion Phytochemische Forschung, Bad Boll/Eckwälden, DeutschlandWALA Heilmittel GmbH, Abteilung Analytische Entwicklung & Forschung, Sektion Phytochemische Forschung, Bad Boll/Eckwälden, DeutschlandUniversität Hohenheim, Institut für Botanik (210), Stuttgart, DeutschlandWALA Heilmittel GmbH, Abteilung Analytische Entwicklung & Forschung, Sektion Phytochemische Forschung, Bad Boll/Eckwälden, DeutschlandWALA Heilmittel GmbH, Abteilung Analytische Entwicklung & Forschung, Sektion Phytochemische Forschung, Bad Boll/Eckwälden, DeutschlandHypericum seeds have recently been identified as a natural source of different xanthone derivatives. Two main constituents, the tetrahydroxyxanthones THX-1 and -2, were identified in methanolic extracts of H. perforatum and H. tetrapterum by means of HPLC(DAD)-MS n methods. However, the exact configuration of both THX was unknown so far. For this reason, the two compounds were enriched by chromatography on polyamide and silica, and the corresponding fraction was investigated by 1D- and 2D-NMR techniques. Based on a tentative structural assignment a total synthesis of THX-1 and -2 was performed. Comparing the chromatographic and spectroscopic/spectrometric features of synthetic THX-1 and -2 with their natural counterparts their exact configuration was determined as 1,4,6,7-THX (THX-1) and 1,2,6,7-THX (THX-2), respectively. The novel compounds exhibited a threefold higher radical scavenging activity in the DPPH assay than the vitamin E derivative Trolox®. Hence, they are strong antioxidants. Furthermore, scanning electron microscopy (SEM) provided insights into the two-layer structure of the testa (seed coat), with the thick lignified sclerenchyma layer presumably being the depository of the xanthones.https://www.openagrar.de/receive/openagrar_mods_00078803hypericum perforatumh. tetrapterumseedsxanthonesdpphsem |
| spellingShingle | Lorenz, Peter Heller, Annerose Bunse, Marek Heinrich, Miriam Berger, Melanie Conrad, Jürgen Stintzing, Florian C. Kammerer, Dietmar R. Charakterisierung zweier neuer antioxidativer Tetrahydroxyxanthone in Hypericum-Samen und rasterelektronenmikroskopische Untersuchung der Testa Julius-Kühn-Archiv hypericum perforatum h. tetrapterum seeds xanthones dpph sem |
| title | Charakterisierung zweier neuer antioxidativer Tetrahydroxyxanthone in Hypericum-Samen und rasterelektronenmikroskopische Untersuchung der Testa |
| title_full | Charakterisierung zweier neuer antioxidativer Tetrahydroxyxanthone in Hypericum-Samen und rasterelektronenmikroskopische Untersuchung der Testa |
| title_fullStr | Charakterisierung zweier neuer antioxidativer Tetrahydroxyxanthone in Hypericum-Samen und rasterelektronenmikroskopische Untersuchung der Testa |
| title_full_unstemmed | Charakterisierung zweier neuer antioxidativer Tetrahydroxyxanthone in Hypericum-Samen und rasterelektronenmikroskopische Untersuchung der Testa |
| title_short | Charakterisierung zweier neuer antioxidativer Tetrahydroxyxanthone in Hypericum-Samen und rasterelektronenmikroskopische Untersuchung der Testa |
| title_sort | charakterisierung zweier neuer antioxidativer tetrahydroxyxanthone in hypericum samen und rasterelektronenmikroskopische untersuchung der testa |
| topic | hypericum perforatum h. tetrapterum seeds xanthones dpph sem |
| url | https://www.openagrar.de/receive/openagrar_mods_00078803 |
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