New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis
Latrunculia sponges represent a rich source of discorhabdin-type pyrroloiminoquinone alkaloids, a few of which comprise a dimeric structure. The anticancer-activity-guided isolation of the n -hexane subextract of the Antarctic deep-sea sponge Latrunculia biformis yielded the known compound (−)-(1 R...
| Published in: | Marine Drugs |
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| Main Authors: | , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
MDPI AG
2020
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| Subjects: | |
| Online Access: | https://doi.org/10.3390/md18020107 https://doaj.org/article/da3bccc13c214677891e291489598d52 |
| Summary: | Latrunculia sponges represent a rich source of discorhabdin-type pyrroloiminoquinone alkaloids, a few of which comprise a dimeric structure. The anticancer-activity-guided isolation of the n -hexane subextract of the Antarctic deep-sea sponge Latrunculia biformis yielded the known compound (−)-(1 R ,2 R ,6 R ,8 S ,6’ S )-discorhabdin B dimer ( 1 ) and two new derivatives, (−)-(1 S ,2 R ,6 R ,8 S ,6’ S )-discorhabdin B dimer ( 2 ) and (−)-(1 R ,2 R ,6 R ,8 S ,6’ S )-16’,17’-dehydrodiscorhabdin B dimer ( 3 ). The chemical structures of compounds 1 − 3 were elucidated by means of HR-ESIMS, NMR, [α] D , ECD spectroscopy, and a comparison with the previously reported discorhabdin analogs. Compounds 1 and 2 showed significant in vitro anticancer activity against the human colon cancer cell line (HCT-116), with IC 50 values of 0.16 and 2.01 µM, respectively. Compared to monomeric discorhabdins, dimeric discorhabdins are very rare in Nature. This study adds two new discorhabdin dimers ( 2 and 3 ) to this small pyrroloiminoquinone subfamily. This is also the first report of compound 1 as a natural product and the first assessment of its in vitro anticancer activity. |
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