Circumdatin-Aspyrone Conjugates from the Coral-Associated <i>Aspergillus ochraceus</i> LCJ11-102
Ochrazepines A−D (<b>1</b>−<b>4</b>), four new conjugates dimerized from 2-hydroxycircumdatin C (<b>5</b>) and aspyrone (<b>6</b>) by a nucleophilic addition to epoxide, were isolated from the fermentation broth of the coral-associa...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2019-07-01
|
| Series: | Marine Drugs |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1660-3397/17/7/400 |
| _version_ | 1811262664189411328 |
|---|---|
| author | Yaqin Fan Yalin Zhou Yuqi Du Yi Wang Peng Fu Weiming Zhu |
| author_facet | Yaqin Fan Yalin Zhou Yuqi Du Yi Wang Peng Fu Weiming Zhu |
| author_sort | Yaqin Fan |
| collection | DOAJ |
| description | Ochrazepines A−D (<b>1</b>−<b>4</b>), four new conjugates dimerized from 2-hydroxycircumdatin C (<b>5</b>) and aspyrone (<b>6</b>) by a nucleophilic addition to epoxide, were isolated from the fermentation broth of the coral-associated <i>Aspergillus ochraceus</i> strain LCJ11-102. Their structures including absolute configurations were determined based on spectroscopic analysis and chemical methods. Compounds <b>1</b>−<b>4</b> were also obtained by the semisynthesis from a nucleophilic addition of 2-hydroxycircumdatin C (<b>5</b>) to aspyrone (<b>6</b>). New compound <b>1</b> exhibited cytotoxic activity against 10 human cancer cell lines while new compounds <b>2</b> and <b>4</b> selectively inhibited U251 (human glioblastoma cell line) and compound <b>3</b> was active against A673 (human rhabdomyoma cell line), U87 (human glioblastoma cell line), and Hep3B (human liver cancer cell line) with IC<sub>50</sub> (half maximal inhibitory concentration) values of 2.5−11.3 μM among 26 tested human cancer cell lines. |
| first_indexed | 2024-04-12T19:30:30Z |
| format | Article |
| id | doaj.art-6765baee200c4443a6082bc7a4eba325 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-12T19:30:30Z |
| publishDate | 2019-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-6765baee200c4443a6082bc7a4eba3252022-12-22T03:19:21ZengMDPI AGMarine Drugs1660-33972019-07-0117740010.3390/md17070400md17070400Circumdatin-Aspyrone Conjugates from the Coral-Associated <i>Aspergillus ochraceus</i> LCJ11-102Yaqin Fan0Yalin Zhou1Yuqi Du2Yi Wang3Peng Fu4Weiming Zhu5Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaOchrazepines A−D (<b>1</b>−<b>4</b>), four new conjugates dimerized from 2-hydroxycircumdatin C (<b>5</b>) and aspyrone (<b>6</b>) by a nucleophilic addition to epoxide, were isolated from the fermentation broth of the coral-associated <i>Aspergillus ochraceus</i> strain LCJ11-102. Their structures including absolute configurations were determined based on spectroscopic analysis and chemical methods. Compounds <b>1</b>−<b>4</b> were also obtained by the semisynthesis from a nucleophilic addition of 2-hydroxycircumdatin C (<b>5</b>) to aspyrone (<b>6</b>). New compound <b>1</b> exhibited cytotoxic activity against 10 human cancer cell lines while new compounds <b>2</b> and <b>4</b> selectively inhibited U251 (human glioblastoma cell line) and compound <b>3</b> was active against A673 (human rhabdomyoma cell line), U87 (human glioblastoma cell line), and Hep3B (human liver cancer cell line) with IC<sub>50</sub> (half maximal inhibitory concentration) values of 2.5−11.3 μM among 26 tested human cancer cell lines.https://www.mdpi.com/1660-3397/17/7/400ochrazepinesconjugatessemisynthesiscytotoxic activity<i>Aspergillus ochraceus</i> |
| spellingShingle | Yaqin Fan Yalin Zhou Yuqi Du Yi Wang Peng Fu Weiming Zhu Circumdatin-Aspyrone Conjugates from the Coral-Associated <i>Aspergillus ochraceus</i> LCJ11-102 Marine Drugs ochrazepines conjugates semisynthesis cytotoxic activity <i>Aspergillus ochraceus</i> |
| title | Circumdatin-Aspyrone Conjugates from the Coral-Associated <i>Aspergillus ochraceus</i> LCJ11-102 |
| title_full | Circumdatin-Aspyrone Conjugates from the Coral-Associated <i>Aspergillus ochraceus</i> LCJ11-102 |
| title_fullStr | Circumdatin-Aspyrone Conjugates from the Coral-Associated <i>Aspergillus ochraceus</i> LCJ11-102 |
| title_full_unstemmed | Circumdatin-Aspyrone Conjugates from the Coral-Associated <i>Aspergillus ochraceus</i> LCJ11-102 |
| title_short | Circumdatin-Aspyrone Conjugates from the Coral-Associated <i>Aspergillus ochraceus</i> LCJ11-102 |
| title_sort | circumdatin aspyrone conjugates from the coral associated i aspergillus ochraceus i lcj11 102 |
| topic | ochrazepines conjugates semisynthesis cytotoxic activity <i>Aspergillus ochraceus</i> |
| url | https://www.mdpi.com/1660-3397/17/7/400 |
| work_keys_str_mv | AT yaqinfan circumdatinaspyroneconjugatesfromthecoralassociatediaspergillusochraceusilcj11102 AT yalinzhou circumdatinaspyroneconjugatesfromthecoralassociatediaspergillusochraceusilcj11102 AT yuqidu circumdatinaspyroneconjugatesfromthecoralassociatediaspergillusochraceusilcj11102 AT yiwang circumdatinaspyroneconjugatesfromthecoralassociatediaspergillusochraceusilcj11102 AT pengfu circumdatinaspyroneconjugatesfromthecoralassociatediaspergillusochraceusilcj11102 AT weimingzhu circumdatinaspyroneconjugatesfromthecoralassociatediaspergillusochraceusilcj11102 |