Isolation of Sesquiterpenoids and Steroids from the Soft Coral <i>Sinularia brassica</i> and Determination of Their Absolute Configuration
Two undescribed rearranged cadinane-type sesquiterpenoids (<b>1</b>–<b>2</b>), named sinulaketol A-B, together with one new chlorinated steroid (<b>3</b>), one new gorgosterol (<b>4</b>), one known sesquiterpene (<b>5</b>), one known dibrom...
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MDPI AG
2021-09-01
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| Series: | Marine Drugs |
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| author | Giang Nam Pham Da Yeun Kang Min Ju Kim Se Jong Han Jun Hyuck Lee MinKyun Na |
| author_facet | Giang Nam Pham Da Yeun Kang Min Ju Kim Se Jong Han Jun Hyuck Lee MinKyun Na |
| author_sort | Giang Nam Pham |
| collection | DOAJ |
| description | Two undescribed rearranged cadinane-type sesquiterpenoids (<b>1</b>–<b>2</b>), named sinulaketol A-B, together with one new chlorinated steroid (<b>3</b>), one new gorgosterol (<b>4</b>), one known sesquiterpene (<b>5</b>), one known dibromoditerpene (<b>6</b>) and two known polyhydroxylated steroids (<b>7</b>–<b>8</b>) were isolated from the soft coral <i>Sinularia brassica</i>. The structures of these compounds were established by extensive spectroscopic analysis, including HRESIMS, 1D, and 2D NMR spectroscopy. Their absolute configurations were also determined by the ECD calculations and DP4+ probability analysis. Antileishmanial activity of compounds <b>1</b>–<b>8</b> was evaluated in vitro against the amastigote forms of <i>Leishmania donovani</i>, in which compounds <b>3</b>, <b>6</b>, and <b>7</b> inhibited the growth of <i>L. donovani</i> by 58.7, 74.3, 54.7%, respectively, at a concentration of 50 μM. Antimicrobial effect of the isolated compounds were also evaluated against <i>Candida albicans</i>, <i>Staphylococcus aureus</i>, and <i>Escherichia coli.</i> Compound <b>6</b>, a brominated diterpene, exhibited antimicrobial effect against <i>S</i>. <i>aureus</i>. |
| first_indexed | 2024-03-10T07:29:54Z |
| format | Article |
| id | doaj.art-5735864a96ac488d8a50bb2f570fbbcf |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T07:29:54Z |
| publishDate | 2021-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-5735864a96ac488d8a50bb2f570fbbcf2023-11-22T13:59:04ZengMDPI AGMarine Drugs1660-33972021-09-0119952310.3390/md19090523Isolation of Sesquiterpenoids and Steroids from the Soft Coral <i>Sinularia brassica</i> and Determination of Their Absolute ConfigurationGiang Nam Pham0Da Yeun Kang1Min Ju Kim2Se Jong Han3Jun Hyuck Lee4MinKyun Na5College of Pharmacy, Chungnam National University, Daejeon 34134, KoreaCollege of Pharmacy, Chungnam National University, Daejeon 34134, KoreaDivision of Life Sciences, Korea Polar Research Institute, Incheon 21990, KoreaDivision of Life Sciences, Korea Polar Research Institute, Incheon 21990, KoreaDepartment of Polar Sciences, University of Science and Technology, Incheon 21990, KoreaCollege of Pharmacy, Chungnam National University, Daejeon 34134, KoreaTwo undescribed rearranged cadinane-type sesquiterpenoids (<b>1</b>–<b>2</b>), named sinulaketol A-B, together with one new chlorinated steroid (<b>3</b>), one new gorgosterol (<b>4</b>), one known sesquiterpene (<b>5</b>), one known dibromoditerpene (<b>6</b>) and two known polyhydroxylated steroids (<b>7</b>–<b>8</b>) were isolated from the soft coral <i>Sinularia brassica</i>. The structures of these compounds were established by extensive spectroscopic analysis, including HRESIMS, 1D, and 2D NMR spectroscopy. Their absolute configurations were also determined by the ECD calculations and DP4+ probability analysis. Antileishmanial activity of compounds <b>1</b>–<b>8</b> was evaluated in vitro against the amastigote forms of <i>Leishmania donovani</i>, in which compounds <b>3</b>, <b>6</b>, and <b>7</b> inhibited the growth of <i>L. donovani</i> by 58.7, 74.3, 54.7%, respectively, at a concentration of 50 μM. Antimicrobial effect of the isolated compounds were also evaluated against <i>Candida albicans</i>, <i>Staphylococcus aureus</i>, and <i>Escherichia coli.</i> Compound <b>6</b>, a brominated diterpene, exhibited antimicrobial effect against <i>S</i>. <i>aureus</i>.https://www.mdpi.com/1660-3397/19/9/523<i>Sinularia brassica</i>sesquiterpenoidssteroidsantileishmanial activityantimicrobial activity |
| spellingShingle | Giang Nam Pham Da Yeun Kang Min Ju Kim Se Jong Han Jun Hyuck Lee MinKyun Na Isolation of Sesquiterpenoids and Steroids from the Soft Coral <i>Sinularia brassica</i> and Determination of Their Absolute Configuration Marine Drugs <i>Sinularia brassica</i> sesquiterpenoids steroids antileishmanial activity antimicrobial activity |
| title | Isolation of Sesquiterpenoids and Steroids from the Soft Coral <i>Sinularia brassica</i> and Determination of Their Absolute Configuration |
| title_full | Isolation of Sesquiterpenoids and Steroids from the Soft Coral <i>Sinularia brassica</i> and Determination of Their Absolute Configuration |
| title_fullStr | Isolation of Sesquiterpenoids and Steroids from the Soft Coral <i>Sinularia brassica</i> and Determination of Their Absolute Configuration |
| title_full_unstemmed | Isolation of Sesquiterpenoids and Steroids from the Soft Coral <i>Sinularia brassica</i> and Determination of Their Absolute Configuration |
| title_short | Isolation of Sesquiterpenoids and Steroids from the Soft Coral <i>Sinularia brassica</i> and Determination of Their Absolute Configuration |
| title_sort | isolation of sesquiterpenoids and steroids from the soft coral i sinularia brassica i and determination of their absolute configuration |
| topic | <i>Sinularia brassica</i> sesquiterpenoids steroids antileishmanial activity antimicrobial activity |
| url | https://www.mdpi.com/1660-3397/19/9/523 |
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