卡里巴二醇，一种从海洋海绵卡里巴属中提取的细胞毒性大环内酯。
Callyspongiolide, a cytotoxic macrolide from the marine sponge Callyspongia sp.
机构信息
Institute of Pharmaceutical Biology and Biotechnology and §Institute of Molecular Medicine, Heinrich-Heine University , 40225 Düsseldorf, Germany.
出版信息
Org Lett. 2014 Jan 3;16(1):266-9. doi: 10.1021/ol403241v. Epub 2013 Dec 13.
Abstract
A novel macrolide, callyspongiolide, whose structure was determined by comprehensive analysis of the NMR and HRMS spectra, was isolated from the marine sponge Callyspongia sp. collected in Indonesia. The compound features a carbamate-substituted 14-membered macrocyclic lactone ring with a conjugated structurally unprecedented diene-ynic side chain terminating at a brominated benzene ring. Callyspongiolide showed strong cytotoxicity against human Jurkat J16 T and Ramos B lymphocytes.
摘要
一种新型大环内酯类化合物 callyspongiolide 从印度尼西亚采集的海绵 Callyspongia sp. 中分离得到，其结构通过 NMR 和高分辨率质谱（HRMS）谱的综合分析确定。该化合物具有一个氨甲酰基取代的 14 元大环内酯环，带有一个共轭的前所未有的二烯-炔侧链，末端为溴化苯环。Callyspongiolide 对人 Jurkat J16 T 和 Ramos B 淋巴细胞具有很强的细胞毒性。
相似文献
1
Callyspongiolide, a cytotoxic macrolide from the marine sponge Callyspongia sp.卡里巴二醇，一种从海洋海绵卡里巴属中提取的细胞毒性大环内酯。
Org Lett. 2014 Jan 3;16(1):266-9. doi: 10.1021/ol403241v. Epub 2013 Dec 13.
2
Enantioselective formal synthesis of the marine macrolide (-)-callyspongiolide.对海洋大环内酯（-）-卡利什海绵内酯的对映选择性形式合成。
Chem Commun (Camb). 2020 May 21;56(41):5536-5539. doi: 10.1039/d0cc01978j.
3
Iriomoteolides-10a and 12a, Cytotoxic Macrolides from Marine Dinoflagellate Amphidinium Species.来自海洋双鞭毛藻裸甲藻属物种的细胞毒性大环内酯类化合物——西表岛内酯-10a和12a
Chem Pharm Bull (Tokyo). 2016;64(7):1019-23. doi: 10.1248/cpb.c16-00026.
4
Tedanolide C: a potent new 18-membered-ring cytotoxic macrolide isolated from the Papua New Guinea marine sponge Ircinia sp.泰德内酯C：一种从巴布亚新几内亚海洋海绵Ircinia sp.中分离出的强效新型18元环细胞毒性大环内酯类化合物。
J Org Chem. 2006 Mar 17;71(6):2510-3. doi: 10.1021/jo052285+.
5
The Synthesis and Bioactivity of the Marine Macrolide Callyspongiolide.海洋大环内酯 Callyspongiolide 的合成与生物活性。
Chemistry. 2021 Feb 5;27(8):2589-2611. doi: 10.1002/chem.202003898. Epub 2020 Dec 14.
6
Saccharothriolides A-C, novel phenyl-substituted 10-membered macrolides isolated from a rare actinomycete Saccharothrix sp.甜三内酯A - C，从罕见放线菌糖丝菌属中分离出的新型苯基取代的10元大环内酯类化合物
Chem Commun (Camb). 2015 May 11;51(38):8074-7. doi: 10.1039/c5cc01953b. Epub 2015 Apr 14.
7
Sulfated meroterpenoids from the Brazilian sponge Callyspongia sp. are inhibitors of the antileishmaniasis target adenosine phosphoribosyl transferase.来自巴西海绵Callyspongia sp.的硫酸化杂萜类化合物是抗利什曼病靶点腺苷磷酸核糖基转移酶的抑制剂。
J Org Chem. 2006 Nov 10;71(23):8685-90. doi: 10.1021/jo060295k.
8
Callyspongiamides A and B, sterol O-acyltransferase inhibitors, from the Indonesian marine sponge Callyspongia sp.Callyspongiamides A 和 B，一种固醇 O-酰基转移酶抑制剂，来源于印度尼西亚海洋海绵 Callyspongia sp.
Bioorg Med Chem Lett. 2018 Jun 1;28(10):1911-1914. doi: 10.1016/j.bmcl.2018.03.077. Epub 2018 Mar 30.
9
Structure and Stereochemistry of Amphidinolide N Congeners from Marine Dinoflagellate Amphidinium Species.海洋甲藻属 Amphidinium 种中 Amphidinolide N 同系物的结构和立体化学。
Chem Pharm Bull (Tokyo). 2021;69(1):141-149. doi: 10.1248/cpb.c20-00745.
10
Structure, synthesis, and biological activity of a C-20 bisacetylenic alcohol from a marine sponge Callyspongia sp.一种海洋海绵 Callyspongia sp. 的 C-20 双炔醇的结构、合成及生物活性
J Nat Prod. 2013 Jul 26;76(7):1337-42. doi: 10.1021/np400297p. Epub 2013 Jul 15.
引用本文的文献
1
Indonesian marine and its medicinal contribution.印度尼西亚的海洋及其医学贡献。
Nat Prod Bioprospect. 2023 Oct 16;13(1):38. doi: 10.1007/s13659-023-00403-1.
2
Naturally Occurring Organohalogen Compounds-A Comprehensive Review.天然有机卤代化合物综述。
Prog Chem Org Nat Prod. 2023;121:1-546. doi: 10.1007/978-3-031-26629-4_1.
3
Chemical and biological diversity of new natural products from marine sponges: a review (2009-2018).海洋海绵新天然产物的化学与生物多样性综述（2009 - 2018年）
Mar Life Sci Technol. 2022 Aug 1;4(3):356-372. doi: 10.1007/s42995-022-00132-3. eCollection 2022 Aug.
4
spp.: Secondary Metabolites, Pharmacological Activities, and Mechanisms.物种：次生代谢产物、药理活性及作用机制。
Metabolites. 2023 Feb 1;13(2):217. doi: 10.3390/metabo13020217.
5
Palladium-Catalyzed Carbonylations: Application in Complex Natural Product Total Synthesis and Recent Developments.钯催化羰基化反应：在复杂天然产物全合成中的应用及最新进展。
J Org Chem. 2023 Apr 21;88(8):4925-4941. doi: 10.1021/acs.joc.2c02746. Epub 2023 Jan 27.
6
Metabolities from Marine Sponges of the Genus : Occurrence, Biological Activity, and NMR Data.海洋海绵属代谢产物：分布、生物活性和 NMR 数据。
Mar Drugs. 2021 Nov 26;19(12):663. doi: 10.3390/md19120663.
7
Callyspongiolide kills cells by inducing mitochondrial dysfunction via cellular iron depletion.卡利海绵素内酯通过细胞铁耗竭诱导线粒体功能障碍杀死细胞。
Commun Biol. 2021 Sep 23;4(1):1123. doi: 10.1038/s42003-021-02643-8.
8
Marine-Derived Macrolides 1990-2020: An Overview of Chemical and Biological Diversity.海洋来源大环内酯类化合物 1990-2020：化学和生物多样性概述。
Mar Drugs. 2021 Mar 25;19(4):180. doi: 10.3390/md19040180.
9
Chemical Diversity and Biological Activity of Secondary Metabolites Isolated from Indonesian Marine Invertebrates.从印度尼西亚海洋无脊椎动物中分离得到的次生代谢产物的化学多样性和生物活性。
Molecules. 2021 Mar 27;26(7):1898. doi: 10.3390/molecules26071898.
10
Mitochondrial dysfunction induced by callyspongiolide promotes autophagy-dependent cell death.钙调神经磷酸酶抑制剂诱导的线粒体功能障碍促进自噬依赖性细胞死亡。
BMB Rep. 2021 Apr;54(4):227-232. doi: 10.5483/BMBRep.2021.54.4.037.
本文引用的文献
1
New cytotoxic 1,2,4-thiadiazole alkaloids from the ascidian Polycarpa aurata.从多棘海盘车中分离得到的新型细胞毒素 1,2,4-噻二唑生物碱。
Org Lett. 2013 May 3;15(9):2230-3. doi: 10.1021/ol400791n. Epub 2013 Apr 12.
2
Tetrahydrofuran-containing macrolides: a fascinating gift from the deep sea.含四氢呋喃的大环内酯类化合物：来自深海的迷人馈赠。
Chem Rev. 2013 Jul 10;113(7):4567-610. doi: 10.1021/cr3004778. Epub 2013 Mar 18.
3
Aaptamine derivatives from the Indonesian sponge Aaptos suberitoides.从印度尼西亚海绵 Aaptos suberitoides 中分离得到的阿朴菲类生物碱衍生物。
J Nat Prod. 2013 Jan 25;76(1):103-6. doi: 10.1021/np300794b. Epub 2013 Jan 2.
4
Marine natural products.海洋天然产物。
Nat Prod Rep. 2013 Feb;30(2):237-323. doi: 10.1039/c2np20112g.
5
Trimeric hemibastadin congener from the marine sponge Ianthella basta.来自海洋海绵 Ianthella basta 的三聚半巴卡丁同系物。
J Nat Prod. 2013 Jan 25;76(1):121-5. doi: 10.1021/np300764u. Epub 2012 Dec 18.
6
New candidaspongiolides, tedanolide analogues that selectively inhibit melanoma cell growth.新型候选海绵二醇类化合物，特达诺内酯类似物，选择性抑制黑色素瘤细胞生长。
Org Lett. 2011 Jul 1;13(13):3518-21. doi: 10.1021/ol201329p. Epub 2011 Jun 6.
7
Leiodermatolide, a potent antimitotic macrolide from the marine sponge Leiodermatium sp.利奥蝶呤，一种来自海洋海绵 Leiodermatium sp. 的强效抗有丝分裂大环内酯。
Angew Chem Int Ed Engl. 2011 Mar 28;50(14):3219-23. doi: 10.1002/anie.201007719. Epub 2011 Mar 4.
8
Callyaerins A-F and H, new cytotoxic cyclic peptides from the Indonesian marine sponge Callyspongia aerizusa.卡里埃林 A-F 和 H，来自印度尼西亚海洋海绵 Callyspongia aerizusa 的新型细胞毒性环状肽。
Bioorg Med Chem. 2010 Jul 15;18(14):4947-56. doi: 10.1016/j.bmc.2010.06.012. Epub 2010 Jun 11.
9
Marine macrolides, a promising source of antitumor compounds.海洋大环内酯类化合物，一种有前景的抗肿瘤化合物来源。
Anticancer Agents Med Chem. 2009 Feb;9(2):122-37. doi: 10.2174/187152009787313800.
10
Niphatoxin C, a cytotoxic tripyridine alkaloid from Callyspongia sp.尼帕毒素C，一种来自加勒比海绵属物种的具有细胞毒性的三吡啶生物碱
J Nat Prod. 2007 Dec;70(12):2040-1. doi: 10.1021/np070366q. Epub 2007 Nov 21.
Zotero 插件