Hemiacetalmeroterpenoids A–C and Astellolide Q with Antimicrobial Activity from the Marine-Derived Fungus <i>Penicillium</i> sp. N-5
Four new compounds including three andrastin-type meroterpenoids hemiacetalmeroterpenoids A-C (<b>1</b>–<b>3</b>), and a drimane sesquiterpenoid astellolide Q (<b>15</b>), together with eleven known compounds (<b>4</b>–<b>14</b>) were isola...
Main Authors: | , , , , , , |
---|---|
Format: | Article |
Language: | English |
Published: |
MDPI AG
2022-08-01
|
Series: | Marine Drugs |
Subjects: | |
Online Access: | https://www.mdpi.com/1660-3397/20/8/514 |
_version_ | 1797443807598346240 |
---|---|
author | Tao Chen Wencong Yang Taobo Li Yihao Yin Yufeng Liu Bo Wang Zhigang She |
author_facet | Tao Chen Wencong Yang Taobo Li Yihao Yin Yufeng Liu Bo Wang Zhigang She |
author_sort | Tao Chen |
collection | DOAJ |
description | Four new compounds including three andrastin-type meroterpenoids hemiacetalmeroterpenoids A-C (<b>1</b>–<b>3</b>), and a drimane sesquiterpenoid astellolide Q (<b>15</b>), together with eleven known compounds (<b>4</b>–<b>14</b>) were isolated from the cultures of the marine-derived fungus <i>Penicillium</i> sp. N-5, while compound <b>14</b> was first isolated from a natural source. The structures of the new compounds were determined by analysis of detailed spectroscopic data, and the absolute configurations were further decided by a comparison of the experimental and calculated ECD spectra. Hemiacetalmeroterpenoid A (<b>1</b>) possesses a unique and highly congested 6,6,6,6,5,5-hexa-cyclic skeleton. Moreover, the absolute configuration of compound <b>14</b> was also reported for the first time. Compounds <b>1</b>, <b>5</b> and <b>10</b> exhibited significant antimicrobial activities against <i>Penicillium italicum</i> and <i>Colletrichum gloeosporioides</i> with MIC values ranging from 1.56 to 6.25 μg/mL. |
first_indexed | 2024-03-09T13:02:23Z |
format | Article |
id | doaj.art-0c218147b23e4fdfbc9b019c275e0027 |
institution | Directory Open Access Journal |
issn | 1660-3397 |
language | English |
last_indexed | 2024-03-09T13:02:23Z |
publishDate | 2022-08-01 |
publisher | MDPI AG |
record_format | Article |
series | Marine Drugs |
spelling | doaj.art-0c218147b23e4fdfbc9b019c275e00272023-11-30T21:51:53ZengMDPI AGMarine Drugs1660-33972022-08-0120851410.3390/md20080514Hemiacetalmeroterpenoids A–C and Astellolide Q with Antimicrobial Activity from the Marine-Derived Fungus <i>Penicillium</i> sp. N-5Tao Chen0Wencong Yang1Taobo Li2Yihao Yin3Yufeng Liu4Bo Wang5Zhigang She6School of Chemistry, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Chemistry, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Chemistry, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Chemistry, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Chemistry, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Chemistry, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Chemistry, Sun Yat-sen University, Guangzhou 510275, ChinaFour new compounds including three andrastin-type meroterpenoids hemiacetalmeroterpenoids A-C (<b>1</b>–<b>3</b>), and a drimane sesquiterpenoid astellolide Q (<b>15</b>), together with eleven known compounds (<b>4</b>–<b>14</b>) were isolated from the cultures of the marine-derived fungus <i>Penicillium</i> sp. N-5, while compound <b>14</b> was first isolated from a natural source. The structures of the new compounds were determined by analysis of detailed spectroscopic data, and the absolute configurations were further decided by a comparison of the experimental and calculated ECD spectra. Hemiacetalmeroterpenoid A (<b>1</b>) possesses a unique and highly congested 6,6,6,6,5,5-hexa-cyclic skeleton. Moreover, the absolute configuration of compound <b>14</b> was also reported for the first time. Compounds <b>1</b>, <b>5</b> and <b>10</b> exhibited significant antimicrobial activities against <i>Penicillium italicum</i> and <i>Colletrichum gloeosporioides</i> with MIC values ranging from 1.56 to 6.25 μg/mL.https://www.mdpi.com/1660-3397/20/8/514andrastin-type meroterpenoidsdrimane sesquiterpenoidmarine-derived fungusantimicrobials activities |
spellingShingle | Tao Chen Wencong Yang Taobo Li Yihao Yin Yufeng Liu Bo Wang Zhigang She Hemiacetalmeroterpenoids A–C and Astellolide Q with Antimicrobial Activity from the Marine-Derived Fungus <i>Penicillium</i> sp. N-5 Marine Drugs andrastin-type meroterpenoids drimane sesquiterpenoid marine-derived fungus antimicrobials activities |
title | Hemiacetalmeroterpenoids A–C and Astellolide Q with Antimicrobial Activity from the Marine-Derived Fungus <i>Penicillium</i> sp. N-5 |
title_full | Hemiacetalmeroterpenoids A–C and Astellolide Q with Antimicrobial Activity from the Marine-Derived Fungus <i>Penicillium</i> sp. N-5 |
title_fullStr | Hemiacetalmeroterpenoids A–C and Astellolide Q with Antimicrobial Activity from the Marine-Derived Fungus <i>Penicillium</i> sp. N-5 |
title_full_unstemmed | Hemiacetalmeroterpenoids A–C and Astellolide Q with Antimicrobial Activity from the Marine-Derived Fungus <i>Penicillium</i> sp. N-5 |
title_short | Hemiacetalmeroterpenoids A–C and Astellolide Q with Antimicrobial Activity from the Marine-Derived Fungus <i>Penicillium</i> sp. N-5 |
title_sort | hemiacetalmeroterpenoids a c and astellolide q with antimicrobial activity from the marine derived fungus i penicillium i sp n 5 |
topic | andrastin-type meroterpenoids drimane sesquiterpenoid marine-derived fungus antimicrobials activities |
url | https://www.mdpi.com/1660-3397/20/8/514 |
work_keys_str_mv | AT taochen hemiacetalmeroterpenoidsacandastellolideqwithantimicrobialactivityfromthemarinederivedfungusipenicilliumispn5 AT wencongyang hemiacetalmeroterpenoidsacandastellolideqwithantimicrobialactivityfromthemarinederivedfungusipenicilliumispn5 AT taoboli hemiacetalmeroterpenoidsacandastellolideqwithantimicrobialactivityfromthemarinederivedfungusipenicilliumispn5 AT yihaoyin hemiacetalmeroterpenoidsacandastellolideqwithantimicrobialactivityfromthemarinederivedfungusipenicilliumispn5 AT yufengliu hemiacetalmeroterpenoidsacandastellolideqwithantimicrobialactivityfromthemarinederivedfungusipenicilliumispn5 AT bowang hemiacetalmeroterpenoidsacandastellolideqwithantimicrobialactivityfromthemarinederivedfungusipenicilliumispn5 AT zhigangshe hemiacetalmeroterpenoidsacandastellolideqwithantimicrobialactivityfromthemarinederivedfungusipenicilliumispn5 |