Microbial Transformation of Yakuchinone A and Cytotoxicity Evaluation of Its Metabolites
Yakuchinone A (<b>1</b>) is a bioactive diarylheptanoid isolated from the dried fruits of <i>Alpinia oxyphylla.</i> Microbial transformation has been recognized as an efficient method to produce new biologically active derivatives from natural products. In the present study,...
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MDPI AG
2022-04-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/23/7/3992 |
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| author | Chen Huo Fubo Han Yina Xiao Hyun Jung Kim Ik-Soo Lee |
| author_facet | Chen Huo Fubo Han Yina Xiao Hyun Jung Kim Ik-Soo Lee |
| author_sort | Chen Huo |
| collection | DOAJ |
| description | Yakuchinone A (<b>1</b>) is a bioactive diarylheptanoid isolated from the dried fruits of <i>Alpinia oxyphylla.</i> Microbial transformation has been recognized as an efficient method to produce new biologically active derivatives from natural products. In the present study, microbial transformation of yakuchinone A was performed with the fungus <i>Mucor hiemalis</i> KCTC 26779, which led to the isolation of nine new metabolites (<b>2</b>, <b>3a</b>, <b>3b</b>, and <b>4</b>–<b>9</b>). Their structures were elucidated as (3<i>S</i>)-oxyphyllacinol (<b>2</b>), (3<i>S,7R</i>)- and (3<i>S,7S</i>)-7-hydroxyoxyphyllacinol (<b>3a</b> and <b>3b</b>), (3<i>S</i>)-oxyphyllacinol-4′-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>4</b>), (3<i>S</i>)-4″-hydroxyoxyphyllacinol (<b>5</b>), (3<i>S</i>)-3″-hydroxyoxyphyllacinol (<b>6</b>), (3<i>S</i>)-2″-hydroxyoxyphyllacinol (<b>7</b>), (3<i>S</i>)-2″-hydroxyoxyphyllacinol-2″-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>8</b>), and (3<i>S</i>)-oxyphyllacinol-3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>9</b>) based on the comprehensive spectroscopic analyses and the application of modified Mosher’s method. All compounds were evaluated for their cytotoxic activities against melanoma, as well as breast, lung, and colorectal cancer cell lines. Compound <b>9</b>, which was <i>O</i>-glucosylated on the diarylheptanoid alkyl chain, exhibited the most selective cytotoxic activities against melanoma cell lines with the IC<sub>50</sub> values ranging from 6.09 to 9.74 μM, indicating that it might be considered as a possible anti-cancer lead compound. |
| first_indexed | 2024-03-09T11:44:30Z |
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| language | English |
| last_indexed | 2024-03-09T11:44:30Z |
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| spelling | doaj.art-69f4c573023d4b7c9f38ae27057475e32023-11-30T23:25:04ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-04-01237399210.3390/ijms23073992Microbial Transformation of Yakuchinone A and Cytotoxicity Evaluation of Its MetabolitesChen Huo0Fubo Han1Yina Xiao2Hyun Jung Kim3Ik-Soo Lee4College of Pharmacy, Chonnam National University, Gwangju 61186, KoreaCollege of Pharmacy, Chonnam National University, Gwangju 61186, KoreaCollege of Pharmacy, Chonnam National University, Gwangju 61186, KoreaCollege of Pharmacy and Natural Medicine Research Institute, Mokpo National University, Muan-gun 58554, Jeonnam, KoreaCollege of Pharmacy, Chonnam National University, Gwangju 61186, KoreaYakuchinone A (<b>1</b>) is a bioactive diarylheptanoid isolated from the dried fruits of <i>Alpinia oxyphylla.</i> Microbial transformation has been recognized as an efficient method to produce new biologically active derivatives from natural products. In the present study, microbial transformation of yakuchinone A was performed with the fungus <i>Mucor hiemalis</i> KCTC 26779, which led to the isolation of nine new metabolites (<b>2</b>, <b>3a</b>, <b>3b</b>, and <b>4</b>–<b>9</b>). Their structures were elucidated as (3<i>S</i>)-oxyphyllacinol (<b>2</b>), (3<i>S,7R</i>)- and (3<i>S,7S</i>)-7-hydroxyoxyphyllacinol (<b>3a</b> and <b>3b</b>), (3<i>S</i>)-oxyphyllacinol-4′-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>4</b>), (3<i>S</i>)-4″-hydroxyoxyphyllacinol (<b>5</b>), (3<i>S</i>)-3″-hydroxyoxyphyllacinol (<b>6</b>), (3<i>S</i>)-2″-hydroxyoxyphyllacinol (<b>7</b>), (3<i>S</i>)-2″-hydroxyoxyphyllacinol-2″-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>8</b>), and (3<i>S</i>)-oxyphyllacinol-3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>9</b>) based on the comprehensive spectroscopic analyses and the application of modified Mosher’s method. All compounds were evaluated for their cytotoxic activities against melanoma, as well as breast, lung, and colorectal cancer cell lines. Compound <b>9</b>, which was <i>O</i>-glucosylated on the diarylheptanoid alkyl chain, exhibited the most selective cytotoxic activities against melanoma cell lines with the IC<sub>50</sub> values ranging from 6.09 to 9.74 μM, indicating that it might be considered as a possible anti-cancer lead compound.https://www.mdpi.com/1422-0067/23/7/3992yakuchinone Amicrobial transformationcytotoxicityMosher’s method |
| spellingShingle | Chen Huo Fubo Han Yina Xiao Hyun Jung Kim Ik-Soo Lee Microbial Transformation of Yakuchinone A and Cytotoxicity Evaluation of Its Metabolites International Journal of Molecular Sciences yakuchinone A microbial transformation cytotoxicity Mosher’s method |
| title | Microbial Transformation of Yakuchinone A and Cytotoxicity Evaluation of Its Metabolites |
| title_full | Microbial Transformation of Yakuchinone A and Cytotoxicity Evaluation of Its Metabolites |
| title_fullStr | Microbial Transformation of Yakuchinone A and Cytotoxicity Evaluation of Its Metabolites |
| title_full_unstemmed | Microbial Transformation of Yakuchinone A and Cytotoxicity Evaluation of Its Metabolites |
| title_short | Microbial Transformation of Yakuchinone A and Cytotoxicity Evaluation of Its Metabolites |
| title_sort | microbial transformation of yakuchinone a and cytotoxicity evaluation of its metabolites |
| topic | yakuchinone A microbial transformation cytotoxicity Mosher’s method |
| url | https://www.mdpi.com/1422-0067/23/7/3992 |
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