Monoterpene Hydroxy Lactones Isolated from Thalassiosira sp. Microalga and Their Antibacterial and Antioxidant Activities.

IF 4.2 2区化学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Molecules Pub Date : 2024-10-31 DOI:10.3390/molecules29215175

Alcina M M B Morais, Decha Kumla, Valter F R Martins, Ana Alves, Luis Gales, Artur M S Silva, Paulo M Costa, Sharad Mistry, Anake Kijjoa, Rui M S C Morais

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Abstract

Two monoterpenoid lactones, loliolide (1) and epi-loliolide (2), were isolated from the crude dichloromethane extract of a microalga, Thalassiosira sp.). The structures of loliolide (1) and epi-loliolide (2) were elucidated by 1D and 2D NMR analysis, as well as a comparison of their ¹H or/and ¹³C NMR data with those reported in the literature. In the case of loliolide (1), the absolute configurations of its stereogenic carbons were confirmed by X-ray analysis, whereas those of epi-loliolide (2) were determined by NOESY correlations. Loliolide (1) and epi-loliolide (2) were tested for their growth inhibitory activity against two Gram-positive (Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212) and two Gram-negative (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853) bacteria, as well as one clinical isolate (E. coli SA/2, an extended-spectrum β-lactamase producer-ESBL) and two environmental isolates, S. aureus 74/24, a methicillin-resistant (MRSA), and E. faecalis B3/101, a vancomycin-resistant (VRE) isolates. The results showed that none of the tested compounds exhibited antibacterial activity at the highest concentrations tested (325 μM), and both revealed low antioxidant activity, with ORAC values of 2.786 ± 0.070 and 2.520 ± 0.319 µmol TE/100 mg for loliolide (1) and epi-loliolide (2), respectively.

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从Thalassiosira sp.微藻中分离出的单萜羟基内酯及其抗菌和抗氧化活性。

从一种微藻（Thalassiosira sp.）的二氯甲烷粗提取物中分离出了两种单萜内酯，即 loliolide (1) 和 epi-loliolide (2)。通过一维和二维核磁共振分析，以及将它们的 1H 或/和 13C 核磁共振数据与文献报道的数据进行比较，阐明了 loliolide (1) 和 epi-loliolide (2) 的结构。对于 loliolide (1)，其立体碳的绝对构型是通过 X 射线分析确认的，而对于 epi-loliolide (2)，其立体碳的绝对构型是通过 NOESY 关联测定的。测试了 Loliolide (1) 和 epi-loliolide (2) 对两种革兰氏阳性菌（金黄色葡萄球菌 ATCC 29213、粪肠球菌 ATCC 29212）和两种革兰氏阴性菌（大肠埃希菌 ATCC 25922、铜绿假单胞菌 ATCC 27853）以及一种临床分离菌（大肠埃希菌 SA/2，一种扩展的大肠杆菌）的生长抑制活性。大肠杆菌 SA/2，一种广谱 β-内酰胺酶生产者-ESBL）和两种环境分离物：金黄色葡萄球菌 74/24，一种耐甲氧西林（MRSA）分离物；粪大肠杆菌 B3/101，一种耐万古霉素（VRE）分离物。结果表明，在测试的最高浓度（325 μM）下，所有受测化合物均未表现出抗菌活性，而且两种化合物的抗氧化活性都很低，loliolide（1）和 epi-loliolide （2）的 ORAC 值分别为 2.786 ± 0.070 和 2.520 ± 0.319 µmol TE/100 mg。

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来源期刊

Molecules 化学-有机化学

CiteScore

7.40

自引率

8.70%

发文量

7524

审稿时长

1.4 months

期刊介绍： Molecules (ISSN 1420-3049, CODEN: MOLEFW) is an open access journal of synthetic organic chemistry and natural product chemistry. All articles are peer-reviewed and published continously upon acceptance. Molecules is published by MDPI, Basel, Switzerland. Our aim is to encourage chemists to publish as much as possible their experimental detail, particularly synthetic procedures and characterization information. There is no restriction on the length of the experimental section. In addition, availability of compound samples is published and considered as important information. Authors are encouraged to register or deposit their chemical samples through the non-profit international organization Molecular Diversity Preservation International (MDPI). Molecules has been launched in 1996 to preserve and exploit molecular diversity of both, chemical information and chemical substances.