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链霉菌来源的含γ-吡喃酮骨架的天然产物。

Natural products with γ-pyrone scaffold from Streptomyces.

机构信息

Department of Life Science and Biochemical Engineering, Sun Moon University, 70 Sun Moon-Ro 221, Tangjeong-Myeon, Asan-Si, 31460, Chungnam, Korea.

Department of Pharmaceutical Engineering and Biotechnology, Sun Moon University, 70 Sun Moon-Ro 221, Tangjeong-Myeon, Asan-Si, 31460, Chungnam, Korea.

出版信息

Appl Microbiol Biotechnol. 2024 Sep 24;108(1):471. doi: 10.1007/s00253-024-13296-y.

Abstract

The Streptomyces sp. is considered the vast reservoir of bioactive natural products belonging to different classes like polyketides, terpenoids, lanthipeptides, and non-ribosomal peptides to name a few. The ubiquitous distribution of the genus makes them capable of producing distinct compounds. Many of those compounds contain a unique γ-pyrone with various chemical structures and exhibit different bioactivities. One such class, nitrophenyl-γ-pyrone, constitutes different bioactive compounds isolated from Streptomyces sp. from different sources ranging from soil to marine environments. In addition, such compounds have antinematodal, cytotoxicity activities, and inhibition of adipogenesis. These compounds include aureothin (3), spectinabilin (7), and their derivatives. Moreover, there are other compounds like actinopyrones (11-16), benwamycins (22-23), and peucemycin and its derivatives (24-26) that also have antibacterial and anticancer activities. The other group classified as anthra-γ-pyrone has various bioactive natural products. For instance, tetrahydroanthra-γ-pyrone, shellmycin A-D (27-30) possess antibacterial as well as anticancer activities. In addition, the pluramycin family compounds belonging to anthra-γ-pyrone group also possess cytotoxic activity, for instance, kidamycin (31), rubiflavin, and their derivatives (33-37). Xanthones are another important group of natural products that also contain γ-pyrone ring producing different bioactivities. Albofungin (42) and its derivatives (43-46) belong to subgroup polycyclic tetrahydro xanthones that possess antibacterial, anticancer, and antibiofilm, antimacrofouling activities. Similarly, other compounds, belonging to this subgroup, exhibit different bioactivities like antifungal, antimalarial, and antibacterial activities and block transient receptor potential vanilloid 1 (TRPV1). These compounds include cervinomycins (48-55), citreamycins (56-57), sattahipmycin (59), and chrexanthomycins (60-63). This review gives succinct information on the γ-pyrone containing natural products isolated from Streptomyces sp. focusing on their structure and bioactivities. KEY POINTS: • The Streptomyces sp. is the producer of various bioactive natural products including the one with γ-pyrone ring. • These γ-pyrone compounds are structurally different and possess different bioactivities. • The Streptomyces has the potential to produce such compounds and the reservoir of these compounds is expected to increase in the future.

摘要

链霉菌属被认为是生物活性天然产物的巨大资源库,属于不同类别,如聚酮、萜类、硫肽和非核糖体肽等。该属的广泛分布使其能够产生不同的化合物。其中许多化合物含有独特的γ-吡喃酮,具有各种化学结构,并表现出不同的生物活性。其中一类,硝基苯基-γ-吡喃酮,由不同来源的链霉菌属分离得到的不同生物活性化合物组成,这些化合物的来源从土壤到海洋环境不等。此外,这些化合物具有抗线虫、细胞毒性活性和抑制脂肪生成。这些化合物包括 Aureothin(3)、Spectinabilin(7)及其衍生物。此外,还有其他化合物,如 Actinopyrones(11-16)、Benwamycins(22-23)和 Peucemycin 及其衍生物(24-26),也具有抗菌和抗癌活性。另一类被归类为蒽-γ-吡喃酮的化合物具有各种生物活性天然产物。例如,四氢蒽-γ-吡喃酮、Shellmycin A-D(27-30)具有抗菌和抗癌活性。此外,属于蒽-γ-吡喃酮组的 Pluramycin 家族化合物也具有细胞毒性活性,例如,Kidamycin(31)、Rubiflavin 及其衍生物(33-37)。黄烷酮是另一类重要的天然产物,也含有γ-吡喃酮环,产生不同的生物活性。Albofungin(42)及其衍生物(43-46)属于多环四氢黄烷酮亚组,具有抗菌、抗癌、抗生物膜、抗污损活性。同样,属于该亚组的其他化合物具有不同的生物活性,如抗真菌、抗疟原虫和抗菌活性,并阻断瞬时受体电位香草醛 1(TRPV1)。这些化合物包括 Cervinomycins(48-55)、Citreamycins(56-57)、Sattahipmycin(59)和 Chrexanthomycins(60-63)。本综述简要介绍了从链霉菌属中分离得到的含γ-吡喃酮的天然产物,重点介绍了它们的结构和生物活性。要点:

  1. 链霉菌属是各种生物活性天然产物的生产者,包括含γ-吡喃酮环的天然产物。

  2. 这些γ-吡喃酮化合物结构不同,具有不同的生物活性。

  3. 链霉菌属具有产生此类化合物的潜力,预计未来这些化合物的储备量将会增加。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3486/11422467/283c6e473319/253_2024_13296_Fig1_HTML.jpg

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