Bioactive polyketides and tryptophol alkaloids from the endophytic fungus Botryosphaeria dothidea LE-07 of Chinese tulip tree

IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Fitoterapia Pub Date : 2024-09-24 DOI:10.1016/j.fitote.2024.106229
Xiao-Rui Liu , Ke-Xin Li , Hao-Wei Chen , Yu-Hang He , Hai-Yan Wang , Yi-Cheng Mao , Ji-Yang Li , Jin-Feng Hu , Juan Xiong
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Abstract

Two new tetraketide-derived phenol rhamnosides [botryrhamnosides A (1) and B (2)] and a new rhamnosylated tryptophol alkaloid (botryrhamnoside C, 3), along with seven related known compounds (410) were isolated from the solid culture of Botryosphaeria dothidea LE-07, an endophytic fungus residing in the leaves of the rare medicinal plant Chinese tulip tree (Liriodendron chinense). Their structures with the absolute configurations were determined by a combination of spectroscopy methods, comparing specific rotations, electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. Compounds 1 and 2 are rare tetraketide-derived resorcinols incorporating a l-rhamnose moiety, while 3 represents the first example of rhamnose-bound tryptophol derivatives produced by microorganisms. These metabolites were evaluated in vitro for their antimicrobial and anti-neuroinflammation activities. The rhamnosylated derivatives 15 displayed potent antibacterial activity against Escherichia coli, with MIC values in the range of 8–16 μg/mL. Compound 2 attenuated neuroinflammation in lipopolysaccharide (LPS)-induced BV-2 microglial cells, by decreasing the level of pro-inflammatory mediators [nitric oxide (NO), tumor necrosis factor-α (TNF-α), and interleukin 6 (IL-6)] and down-regulating the mRNA expression of inducible nitric oxide synthase (iNOS). In addition, compound 8 exhibited remarkable inhibitory effect against the ATP-citrate lyase (ACL), an emerging drug target for hyperlipidemia and related glycolipid metabolic disorders, with an IC50 value of 5.32 μM.

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中国郁金香树内生真菌 Botryosphaeria dothidea LE-07 的生物活性多酮和色醇生物碱
研究人员从寄生在珍稀药用植物中国郁金香树(Liriodendron chinense)叶片中的内生真菌 Botryosphaeria dothidea LE-07 的固体培养物中分离出了两种新的四酮类苯酚鼠李糖苷(botryrhamnosides A (1) 和 B (2))和一种新的鼠李糖基化色酚生物碱(botryrhamnoside C, 3),以及七种相关的已知化合物(4-10)。它们的绝对构型结构是通过光谱学方法、比较特定旋转、电子圆二色性(ECD)计算和单晶 X 射线衍射分析相结合确定的。化合物 1 和 2 是罕见的含有鼠李糖分子的四酮衍生间苯二酚,而化合物 3 则是微生物产生的鼠李糖结合色醇衍生物的第一个实例。对这些代谢物的抗菌和抗神经炎症活性进行了体外评估。鼠李糖基化衍生物 1-5 对大肠杆菌具有很强的抗菌活性,MIC 值在 8-16 μg/mL 之间。化合物 2 通过降低促炎介质[一氧化氮(NO)、肿瘤坏死因子-α(TNF-α)和白细胞介素 6(IL-6)]的水平以及下调诱导型一氧化氮合酶(iNOS)的 mRNA 表达,减轻了脂多糖(LPS)诱导的 BV-2 小胶质细胞的神经炎症。此外,化合物 8 对高脂血症和相关糖脂代谢紊乱的新兴药物靶点 ATP 柠檬酸酶(ACL)具有显著的抑制作用,IC50 值为 5.32 μM。
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来源期刊
Fitoterapia
Fitoterapia 医学-药学
CiteScore
5.80
自引率
2.90%
发文量
198
审稿时长
1.5 months
期刊介绍: Fitoterapia is a Journal dedicated to medicinal plants and to bioactive natural products of plant origin. It publishes original contributions in seven major areas: 1. Characterization of active ingredients of medicinal plants 2. Development of standardization method for bioactive plant extracts and natural products 3. Identification of bioactivity in plant extracts 4. Identification of targets and mechanism of activity of plant extracts 5. Production and genomic characterization of medicinal plants biomass 6. Chemistry and biochemistry of bioactive natural products of plant origin 7. Critical reviews of the historical, clinical and legal status of medicinal plants, and accounts on topical issues.
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