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来自……的类固醇和表可可碱

Steroids and Epicoccarines from .

作者信息

Lindsay Charmaine A, Tan Choon Y, Krishnan Deepa, Uchenik Dmitriy, Eugenio Gerardo D Anaya, Salinas Eric D, de Blanco Esperanza J Carcache, Kinghorn A Douglas, Rakot Ondraibe Harinantenaina L

机构信息

Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA.

Instrumentation Facility, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA.

出版信息

Phytochem Lett. 2024 Oct;63:79-86. doi: 10.1016/j.phytol.2024.08.008. Epub 2024 Aug 16.

DOI:10.1016/j.phytol.2024.08.008
PMID:39280884
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11391924/
Abstract

Lichens are symbiotic organisms comprised of mycobionts and photobiont partners. They are known to produce bioactive secondary metabolites and most of these are biosynthesized by mycobionts. Investigations of cultures of isolated lichen-associated fungi have shown promise for the discovery of cytotoxic compounds. Thus, the lichen-associated fungus was studied for its potential to produce novel compounds and the new sterols (20*)-hydroxy-24(28)-dehydrocampesterol (), 7α-methoxy-8β-hydroxypaxisterol (), 14--epicoccarine A () and 14--epicoccarine B (), as well as the known compound PF1140 (), were isolated. The structures of these compounds were elucidated using methods including nuclear magnetic resonance (NMR) spectroscopy and high-resolution electrospray ionization mass spectrometry (HRESIMS). Following cytotoxicity assays, compound demonstrated activity against the pancreatic adenocarcinoma epithelial HPAC cell line at 17.76 ± 5.35 μM. Since the structures of compounds and were very similar to tetramic acid derivatives that were reported to be biosynthesized from a polyketide synthase- non-ribosomal peptide synthetase (PKS-NRPS) hybrid pathway, a plausible biosynthetic route for production in is proposed herein.

摘要

地衣是由真菌共生体和光合生物共生伙伴组成的共生生物。已知它们能产生生物活性次生代谢产物,其中大部分是由真菌共生体生物合成的。对分离出的与地衣相关真菌的培养物进行的研究显示出发现细胞毒性化合物的潜力。因此,对与地衣相关的真菌进行了研究,以探讨其产生新化合物的潜力,并分离出了新的甾醇(20*)-羟基-24(28)-脱氢麦角甾醇()、7α-甲氧基-8β-羟基派司甾醇()、14--表棒曲霉素A()和14--表棒曲霉素B(),以及已知化合物PF1140()。这些化合物的结构通过核磁共振(NMR)光谱和高分辨率电喷雾电离质谱(HRESIMS)等方法得以阐明。经过细胞毒性试验,化合物在17.76±5.35μM浓度下对胰腺腺癌上皮HPAC细胞系表现出活性。由于化合物和的结构与据报道通过聚酮合酶-非核糖体肽合成酶(PKS-NRPS)杂交途径生物合成的四胺酸衍生物非常相似,本文提出了在中产生的一种可能的生物合成途径。

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本文引用的文献

1
Evolutionary biology of lichen symbioses.地衣共生的进化生物学
New Phytol. 2022 Jun;234(5):1566-1582. doi: 10.1111/nph.18048. Epub 2022 Mar 18.
2
Antimicrobial Compounds Isolated from Endolichenic Fungi: A Review.内生真菌中分离得到的抗菌化合物:综述。
Molecules. 2021 Jun 25;26(13):3901. doi: 10.3390/molecules26133901.
3
Lichens as a repository of bioactive compounds: an open window for green therapy against diverse cancers.地衣作为生物活性化合物的储存库:针对多种癌症的绿色治疗的开放窗口。
Semin Cancer Biol. 2022 Nov;86(Pt 2):1120-1137. doi: 10.1016/j.semcancer.2021.05.028. Epub 2021 May 27.
4
The Lichens' Microbiota, Still a Mystery?地衣的微生物群,仍是一个谜?
Front Microbiol. 2021 Mar 30;12:623839. doi: 10.3389/fmicb.2021.623839. eCollection 2021.
5
Biosynthetic strategies for tetramic acid formation.四氢酸生物合成策略。
Nat Prod Rep. 2021 Sep 23;38(9):1555-1566. doi: 10.1039/d0np00099j.
6
Cytotoxic Heptaketides from the Endolichenic Fungus .细胞毒性七环倍半萜类化合物来自内生菌真菌。
J Nat Prod. 2020 May 22;83(5):1623-1633. doi: 10.1021/acs.jnatprod.0c00108. Epub 2020 May 12.
7
α-Pyrone and Sterol Constituents of , a Fungal Associate of the Lichen .与地衣共生的真菌 的α-吡喃酮和甾醇成分。
J Nat Prod. 2019 Sep 27;82(9):2529-2536. doi: 10.1021/acs.jnatprod.9b00340. Epub 2019 Aug 29.
8
Isocoumarindole A, a Chlorinated Isocoumarin and Indole Alkaloid Hybrid Metabolite from an Endolichenic Fungus Aspergillus sp.异香豆素 A,一种来源于内生真菌 Aspergillus sp 的含氯异香豆素和吲哚生物碱混合代谢产物
Org Lett. 2019 Mar 1;21(5):1530-1533. doi: 10.1021/acs.orglett.9b00385. Epub 2019 Feb 20.
9
Molecular phylogeny and bioprospecting of Endolichenic Fungi (ELF) inhabiting in the lichens collected from a mangrove ecosystem in Sri Lanka.分子系统发育与生物勘探斯里兰卡红树林生态系统中内生真菌(ELF)
PLoS One. 2018 Aug 29;13(8):e0200711. doi: 10.1371/journal.pone.0200711. eCollection 2018.
10
Tetramic Acids and Pyridone Alkaloids from the Endolichenic Fungus Tolypocladium cylindrosporum.来自内生地衣真菌柱孢束丝放线菌的四嗪酸和吡啶酮生物碱。
J Nat Prod. 2015 Sep 25;78(9):2155-60. doi: 10.1021/np501018w. Epub 2015 Sep 10.