• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

哈茨木霉A和B:两种源自珊瑚的真菌中的羟基蒽醌

Harzianumnones A and B: two hydroxyanthraquinones from the coral-derived fungus .

作者信息

Shi Ting, Hou Xue-Mei, Li Zhi-Yong, Cao Fei, Zhang Ya-Hui, Yu Jia-Yin, Zhao Dong-Lin, Shao Chang-Lun, Wang Chang-Yun

机构信息

Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China Qingdao 266003 People's Republic of China

Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology Qingdao 266071 People's Republic of China.

出版信息

RSC Adv. 2018 Aug 2;8(49):27596-27601. doi: 10.1039/c8ra04865g.

DOI:10.1039/c8ra04865g
PMID:35542739
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9083448/
Abstract

Two new hydroxyanthraquinones, harzianumnones A (1) and B (2), together with seven known analogs (3-9), were isolated from the soft coral-derived fungus (XS-20090075). Their chemical structures were elucidated by extensive spectroscopic investigation. The absolute configurations of 1 and 2 were determined by ECD calculation and single-crystal X-ray diffraction. Compounds 1 and 2 were identified as a pair of epimers, which are the first example of hydroanthraquinones from . Compounds 7 and 8 exhibited cytotoxicity against hepatoma cell line HepG2 with IC values of 2.10 and 9.39 μM, respectively. Compound 7 was still found to show cytotoxicity against cervical cancer cell line HeLa with an IC value of 8.59 μM.

摘要

从软珊瑚来源的真菌(XS - 20090075)中分离出两种新的羟基蒽醌,哈茨木醌A(1)和B(2),以及七种已知类似物(3 - 9)。通过广泛的光谱研究阐明了它们的化学结构。通过电子圆二色光谱(ECD)计算和单晶X射线衍射确定了1和2的绝对构型。化合物1和2被鉴定为一对差向异构体,这是来自该真菌的氢蒽醌的首个实例。化合物7和8对肝癌细胞系HepG2表现出细胞毒性,IC值分别为2.10和9.39 μM。还发现化合物7对宫颈癌细胞系HeLa表现出细胞毒性,IC值为8.59 μM。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/fe6a7a343275/c8ra04865g-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/c5067f27b734/c8ra04865g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/8a2b059528e5/c8ra04865g-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/14eca4c6311d/c8ra04865g-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/c30e0a859618/c8ra04865g-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/3ad8ae1c2886/c8ra04865g-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/c771d122eba3/c8ra04865g-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/fe6a7a343275/c8ra04865g-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/c5067f27b734/c8ra04865g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/8a2b059528e5/c8ra04865g-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/14eca4c6311d/c8ra04865g-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/c30e0a859618/c8ra04865g-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/3ad8ae1c2886/c8ra04865g-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/c771d122eba3/c8ra04865g-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d77/9083448/fe6a7a343275/c8ra04865g-f7.jpg

相似文献

1
Harzianumnones A and B: two hydroxyanthraquinones from the coral-derived fungus .哈茨木霉A和B:两种源自珊瑚的真菌中的羟基蒽醌
RSC Adv. 2018 Aug 2;8(49):27596-27601. doi: 10.1039/c8ra04865g.
2
Naphthalene derivatives and halogenate quinoline from the coral-derived fungus (XS-20090075) through OSMAC approach.通过 OSMAC 方法从珊瑚来源真菌(XS-20090075)中获得萘衍生物和卤代喹啉。
J Asian Nat Prod Res. 2021 Mar;23(3):250-257. doi: 10.1080/10286020.2020.1729752. Epub 2020 Feb 20.
3
Terpenoids From the Coral-Derived Fungus (XS-20090075) Induced by Chemical Epigenetic Manipulation.化学表观遗传操作诱导的源自珊瑚的真菌(XS - 20090075)中的萜类化合物
Front Microbiol. 2020 Apr 3;11:572. doi: 10.3389/fmicb.2020.00572. eCollection 2020.
4
Potent Phytotoxic Harziane Diterpenes from a Soft Coral-Derived Strain of the Fungus Trichoderma harzianum XS-20090075.一株哈茨木霉(Trichoderma harzianum)XS-20090075 来源的真菌中具有强除草活性的海生二萜类化合物。
Sci Rep. 2019 Sep 16;9(1):13345. doi: 10.1038/s41598-019-49778-7.
5
Discovery of Enzyme Inhibitors from Mangrove Sediment Derived Fungus Trichoderma harzianum SCSIO 41051.从红树林沉积物来源真菌哈茨木霉 SCSIO 41051 中发现的酶抑制剂。
Chem Biodivers. 2024 Apr;21(4):e202400070. doi: 10.1002/cbdv.202400070. Epub 2024 Mar 6.
6
Antifungal Nafuredin and Epithiodiketopiperazine Derivatives From the Mangrove-Derived Fungus D13.从红树林来源真菌D13中分离得到的抗真菌化合物萘呋地定和环(硫代二酮哌嗪)衍生物
Front Microbiol. 2020 Jun 26;11:1495. doi: 10.3389/fmicb.2020.01495. eCollection 2020.
7
Trichoketides A and B, two new protein tyrosine phosphatase 1B inhibitors from the marine-derived fungus Trichoderma sp.曲古菌素A和B,两种源自海洋真菌木霉属的新型蛋白酪氨酸磷酸酶1B抑制剂
J Antibiot (Tokyo). 2015 Oct;68(10):628-32. doi: 10.1038/ja.2015.44. Epub 2015 Apr 22.
8
Harzianolides B-G: Undescribed Butenolides isolated from the fungus Trichoderma harzianum ZN-4.哈茨烯内酯 B-G:从真菌哈茨木霉 ZN-4 中分离得到的未描述的丁烯内酯。
Fitoterapia. 2024 Jul;176:106039. doi: 10.1016/j.fitote.2024.106039. Epub 2024 May 25.
9
New Spirostane from a Fungus Neohelicomyces hyalosporus and Its Bioactivity.一种来源于真菌薄孔菌(Neohelicomyces hyalosporus)的新螺甾烷及其生物活性。
Chem Biodivers. 2023 May;20(5):e202300313. doi: 10.1002/cbdv.202300313. Epub 2023 May 5.
10
Cytotoxic Secondary Metabolites Isolated from the Marine Alga-Associated Fungus LD-201810.从海洋藻类相关真菌 LD-201810 中分离得到的细胞毒性次生代谢产物。
Mar Drugs. 2020 May 22;18(5):276. doi: 10.3390/md18050276.

引用本文的文献

1
Chemistry and biology of marine-derived Trichoderma metabolites.海洋来源的木霉菌代谢产物的化学与生物学
Nat Prod Bioprospect. 2024 Feb 2;14(1):14. doi: 10.1007/s13659-024-00433-3.
2
Marine Fungi: A Prosperous Source of Novel Bioactive Natural Products.海洋真菌:新型生物活性天然产物的丰富来源。
Curr Med Chem. 2025;32(5):992-1006. doi: 10.2174/0109298673266304231015070956.
3
Penazaphilones J-L, Three New Hydrophilic Azaphilone Pigments from and Their Anti-Inflammatory Activity.Penazaphilones J-L,Penazaphilones 家族的三个新亲水性氮杂菲酮类色素及其抗炎活性。

本文引用的文献

1
Direct Effects of Physcion, Chrysophanol, Emodin, and Pachybasin on Germination and Appressorium Formation of the Barley ( Hordeum vulgare L.) Powdery Mildew Fungus Blumeria graminis f. sp. hordei (DC.) Speer.大黄素、大黄酚、大黄素甲醚和掌叶防己碱对大麦白粉菌(Blumeria graminis f. sp. hordei (DC.) Speer.)萌发和附着胞形成的直接影响。
J Agric Food Chem. 2018 Apr 4;66(13):3393-3401. doi: 10.1021/acs.jafc.7b05977. Epub 2018 Mar 22.
2
Effect of Pachybasin on General Toxicity and Developmental Toxicity in Vivo.厚朴酚对体内一般毒性和发育毒性的影响。
J Agric Food Chem. 2017 Dec 6;65(48):10489-10494. doi: 10.1021/acs.jafc.7b03879. Epub 2017 Nov 20.
3
Molecules. 2023 Mar 31;28(7):3146. doi: 10.3390/molecules28073146.
4
Structures and Biological Activities of Secondary Metabolites from .从 中分离得到的次生代谢产物的结构和生物活性。
Mar Drugs. 2022 Nov 9;20(11):701. doi: 10.3390/md20110701.
5
Secondary Metabolites from Coral-Associated Fungi: Source, Chemistry and Bioactivities.来自珊瑚共生真菌的次生代谢产物:来源、化学性质及生物活性
J Fungi (Basel). 2022 Oct 3;8(10):1043. doi: 10.3390/jof8101043.
6
Chemical diversity, medicinal potentialities, biosynthesis, and pharmacokinetics of anthraquinones and their congeners derived from marine fungi: a comprehensive update.海洋真菌来源蒽醌及其类似物的化学多样性、药用潜力、生物合成和药代动力学:全面更新
RSC Adv. 2022 Sep 1;12(38):24887-24921. doi: 10.1039/d2ra03610j. eCollection 2022 Aug 30.
7
Anthraquinones and Their Analogues from Marine-Derived Fungi: Chemistry and Biological Activities.海洋源真菌中的蒽醌类化合物及其类似物:化学与生物活性。
Mar Drugs. 2022 Jul 25;20(8):474. doi: 10.3390/md20080474.
8
A thermodynamic and kinetic study of the antioxidant activity of natural hydroanthraquinones.天然氢蒽醌抗氧化活性的热力学与动力学研究
RSC Adv. 2020 May 27;10(34):20089-20097. doi: 10.1039/d0ra04013d. eCollection 2020 May 26.
9
Molecular methods unravel the biosynthetic potential of species.分子方法揭示了物种的生物合成潜力。
RSC Adv. 2021 Jan 18;11(6):3622-3635. doi: 10.1039/d0ra09627j. eCollection 2021 Jan 14.
10
Fungal Pigments: Potential Coloring Compounds for Wide Ranging Applications in Textile Dyeing.真菌色素:纺织染色中广泛应用的潜在着色化合物
J Fungi (Basel). 2020 May 20;6(2):68. doi: 10.3390/jof6020068.
Anthraquinones from the saline-alkali plant endophytic fungus Eurotium rubrum.
来自盐碱地植物内生真菌红色曲霉的蒽醌类化合物。
J Antibiot (Tokyo). 2017 Dec;70(12):1138-1141. doi: 10.1038/ja.2017.121. Epub 2017 Oct 11.
4
Discovery of DNA Topoisomerase I Inhibitors with Low-Cytotoxicity Based on Virtual Screening from Natural Products.基于天然产物虚拟筛选的低细胞毒性DNA拓扑异构酶I抑制剂的发现
Mar Drugs. 2017 Jul 9;15(7):217. doi: 10.3390/md15070217.
5
Marine natural products.海洋天然产物。
Nat Prod Rep. 2017 Mar 17;34(3):235-294. doi: 10.1039/c6np00124f.
6
Anti-HSV-1, antioxidant and antifouling phenolic compounds from the deep-sea-derived fungus Aspergillus versicolor SCSIO 41502.来自深海真菌杂色曲霉SCSIO 41502的抗单纯疱疹病毒1型、抗氧化和防污酚类化合物。
Bioorg Med Chem Lett. 2017 Feb 15;27(4):787-791. doi: 10.1016/j.bmcl.2017.01.032. Epub 2017 Jan 16.
7
Antioxidant Hydroanthraquinones from the Marine Algal-Derived Endophytic Fungus Talaromyces islandicus EN-501.来自海洋藻类内生真菌冰岛青霉EN-501的抗氧化性氢蒽醌
J Nat Prod. 2017 Jan 27;80(1):162-168. doi: 10.1021/acs.jnatprod.6b00797. Epub 2016 Dec 19.
8
Lentisone, a new phytotoxic anthraquinone produced by Ascochyta lentis, the causal agent of Ascochyta blight in Lens culinaris.菜豆壳球腔菌(Ascochyta lentis)所致豌豆叶枯病的病原菌,可产生一种新的植物毒性蒽醌 Lentisone。
J Agric Food Chem. 2013 Jul 31;61(30):7301-8. doi: 10.1021/jf4026663. Epub 2013 Jul 23.
9
A novel marine drug, SZ-685C, induces apoptosis of MMQ pituitary tumor cells by downregulating miR-200c.一种新型海洋药物 SZ-685C 通过下调 miR-200c 诱导 MMQ 垂体瘤细胞凋亡。
Curr Med Chem. 2013;20(16):2145-54. doi: 10.2174/0929867311320160007.
10
Structural and stereochemical studies of hydroxyanthraquinone derivatives from the endophytic fungus Coniothyrium sp.结构和立体化学研究内生真菌层出镰刀菌素属来源的羟基蒽醌衍生物
Chirality. 2013 Feb;25(2):141-8. doi: 10.1002/chir.22128. Epub 2012 Dec 18.