Hybrid Polyketides from a <i>Hydractinia</i>-Associated <i>Cladosporium sphaerospermum</i> SW67 and Their Putative Biosynthetic Origin
Five hybrid polyketides (<b>1a</b>, <b>1b</b>, and <b>2</b>−<b>4</b>) containing tetramic acid core including a new hybrid polyketide, cladosin L (<b>1</b>), were isolated from the marine fungus <i>Cladosporium sphaerospermu...
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| Format: | Article |
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MDPI AG
2019-10-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/17/11/606 |
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| author | Seoung Rak Lee Dahae Lee Hee Jeong Eom Maja Rischer Yoon-Joo Ko Ki Sung Kang Chung Sub Kim Christine Beemelmanns Ki Hyun Kim |
| author_facet | Seoung Rak Lee Dahae Lee Hee Jeong Eom Maja Rischer Yoon-Joo Ko Ki Sung Kang Chung Sub Kim Christine Beemelmanns Ki Hyun Kim |
| author_sort | Seoung Rak Lee |
| collection | DOAJ |
| description | Five hybrid polyketides (<b>1a</b>, <b>1b</b>, and <b>2</b>−<b>4</b>) containing tetramic acid core including a new hybrid polyketide, cladosin L (<b>1</b>), were isolated from the marine fungus <i>Cladosporium sphaerospermum</i> SW67, which was isolated from the marine hydroid polyp of <i>Hydractinia echinata</i>. The hybrid polyketides were isolated as a pair of interconverting geometric isomers. The structure of <b>1</b> was determined based on 1D and 2D NMR spectroscopic and HR-ESIMS analyses. Its absolute configuration was established by quantum chemical electronic circular dichroism (ECD) calculations and modified Mosher’s method. Tetramic acid-containing compounds are reported to be derived from a hybrid PKS-NRPS, which was also proved by analyzing our <sup>13</sup>C-labeling data. We investigated whether compounds <b>1</b>−<b>4</b> could prevent cell damage induced by cisplatin, a platinum-based anticancer drug, in LLC-PK1 cells. Co-treatment with <b>2</b> and <b>3</b> ameliorated the damage of LLC-PK1 cells induced by 25 μM of cisplatin. In particular, the effect of compound <b>2</b> at 100 μM (cell viability, 90.68 ± 0.81%) was similar to the recovered cell viability of 88.23 ± 0.25% with 500 μM <i>N</i>-acetylcysteine (NAC), a positive control. |
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| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T14:01:04Z |
| publishDate | 2019-10-01 |
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| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-07dea24e153248e394289acbdde2f7b82022-12-22T04:20:07ZengMDPI AGMarine Drugs1660-33972019-10-01171160610.3390/md17110606md17110606Hybrid Polyketides from a <i>Hydractinia</i>-Associated <i>Cladosporium sphaerospermum</i> SW67 and Their Putative Biosynthetic OriginSeoung Rak Lee0Dahae Lee1Hee Jeong Eom2Maja Rischer3Yoon-Joo Ko4Ki Sung Kang5Chung Sub Kim6Christine Beemelmanns7Ki Hyun Kim8School of Pharmacy, Sungkyunkwan University, Suwon 16419, KoreaSchool of Pharmacy, Sungkyunkwan University, Suwon 16419, KoreaSchool of Pharmacy, Sungkyunkwan University, Suwon 16419, KoreaLeibniz Institute for Natural Product Research and Infection Biology e.V., Hans-Knöll-Institute (HKI), 07745 Jena, GermanyLaboratory of Nuclear Magnetic Resonance, National Center for Inter-University Research Facilities (NCIRF), Seoul National University, Gwanak-gu, Seoul 08826, KoreaCollege of Korean Medicine, Gachon University, Seongnam 13120, KoreaDepartment of Chemistry, Yale University, New Haven, CT 06520, USALeibniz Institute for Natural Product Research and Infection Biology e.V., Hans-Knöll-Institute (HKI), 07745 Jena, GermanySchool of Pharmacy, Sungkyunkwan University, Suwon 16419, KoreaFive hybrid polyketides (<b>1a</b>, <b>1b</b>, and <b>2</b>−<b>4</b>) containing tetramic acid core including a new hybrid polyketide, cladosin L (<b>1</b>), were isolated from the marine fungus <i>Cladosporium sphaerospermum</i> SW67, which was isolated from the marine hydroid polyp of <i>Hydractinia echinata</i>. The hybrid polyketides were isolated as a pair of interconverting geometric isomers. The structure of <b>1</b> was determined based on 1D and 2D NMR spectroscopic and HR-ESIMS analyses. Its absolute configuration was established by quantum chemical electronic circular dichroism (ECD) calculations and modified Mosher’s method. Tetramic acid-containing compounds are reported to be derived from a hybrid PKS-NRPS, which was also proved by analyzing our <sup>13</sup>C-labeling data. We investigated whether compounds <b>1</b>−<b>4</b> could prevent cell damage induced by cisplatin, a platinum-based anticancer drug, in LLC-PK1 cells. Co-treatment with <b>2</b> and <b>3</b> ameliorated the damage of LLC-PK1 cells induced by 25 μM of cisplatin. In particular, the effect of compound <b>2</b> at 100 μM (cell viability, 90.68 ± 0.81%) was similar to the recovered cell viability of 88.23 ± 0.25% with 500 μM <i>N</i>-acetylcysteine (NAC), a positive control.https://www.mdpi.com/1660-3397/17/11/606hybrid polyketidestetramic acid<i>cladosporium sphaerospermum</i>hybrid pks-nrpsllc-pk1 cells |
| spellingShingle | Seoung Rak Lee Dahae Lee Hee Jeong Eom Maja Rischer Yoon-Joo Ko Ki Sung Kang Chung Sub Kim Christine Beemelmanns Ki Hyun Kim Hybrid Polyketides from a <i>Hydractinia</i>-Associated <i>Cladosporium sphaerospermum</i> SW67 and Their Putative Biosynthetic Origin Marine Drugs hybrid polyketides tetramic acid <i>cladosporium sphaerospermum</i> hybrid pks-nrps llc-pk1 cells |
| title | Hybrid Polyketides from a <i>Hydractinia</i>-Associated <i>Cladosporium sphaerospermum</i> SW67 and Their Putative Biosynthetic Origin |
| title_full | Hybrid Polyketides from a <i>Hydractinia</i>-Associated <i>Cladosporium sphaerospermum</i> SW67 and Their Putative Biosynthetic Origin |
| title_fullStr | Hybrid Polyketides from a <i>Hydractinia</i>-Associated <i>Cladosporium sphaerospermum</i> SW67 and Their Putative Biosynthetic Origin |
| title_full_unstemmed | Hybrid Polyketides from a <i>Hydractinia</i>-Associated <i>Cladosporium sphaerospermum</i> SW67 and Their Putative Biosynthetic Origin |
| title_short | Hybrid Polyketides from a <i>Hydractinia</i>-Associated <i>Cladosporium sphaerospermum</i> SW67 and Their Putative Biosynthetic Origin |
| title_sort | hybrid polyketides from a i hydractinia i associated i cladosporium sphaerospermum i sw67 and their putative biosynthetic origin |
| topic | hybrid polyketides tetramic acid <i>cladosporium sphaerospermum</i> hybrid pks-nrps llc-pk1 cells |
| url | https://www.mdpi.com/1660-3397/17/11/606 |
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