Neopetrosiamine A，一种来自加勒比海海绵 Neopetrosia proxima 的具有生物活性的双哌啶生物碱。
Neopetrosiamine A, biologically active bis-piperidine alkaloid from the Caribbean sea sponge Neopetrosia proxima.
机构信息
Department of Chemistry, University of Puerto Rico, PO Box 23346, UPR Station, San Juan 00931-3346, Puerto Rico.
出版信息
Bioorg Med Chem Lett. 2010 Oct 1;20(19):5905-8. doi: 10.1016/j.bmcl.2010.07.084. Epub 2010 Jul 24.
Abstract
A new tetracyclic bis-piperidine alkaloid, neopetrosiamine A (1), has been extracted from the marine sponge Neopetrosiaproxima collected off the west coast of Puerto Rico. The structure of compound 1 was elucidated by analysis of spectroscopic data coupled with careful comparisons of its (1)H and (13)C NMR data with those of a well-known 3-alkylbis-piperidine alkaloid model. The new alkaloid displayed strong in vitro cytotoxic activity against a panel of cancer cell lines as well as in vitro inhibitory activity against the pathogenic microbes Mycobacterium tuberculosis and Plasmodium falciparum.
摘要
一种新的四环双哌啶生物碱，新海绵胺 A（1），已从波多黎各西海岸采集的海洋海绵 Neopetrosiaproxima 中提取出来。通过分析光谱数据并仔细比较其 1H 和 13C NMR 数据与已知的 3-烷基双哌啶生物碱模型的 1H 和 13C NMR 数据，确定了化合物 1 的结构。新的生物碱对一系列癌细胞系具有很强的体外细胞毒性活性，并且对致病微生物结核分枝杆菌和疟原虫具有体外抑制活性。
相似文献
1
Neopetrosiamine A, biologically active bis-piperidine alkaloid from the Caribbean sea sponge Neopetrosia proxima.Neopetrosiamine A，一种来自加勒比海海绵 Neopetrosia proxima 的具有生物活性的双哌啶生物碱。
Bioorg Med Chem Lett. 2010 Oct 1;20(19):5905-8. doi: 10.1016/j.bmcl.2010.07.084. Epub 2010 Jul 24.
2
Xestoproxamines A-C from Neopetrosia proxima. Assignment of absolute stereostructure of bis-piperidine alkaloids by integrated degradation-CD analysis.来自 Neopetrosia proxima 的 Xestoproxamines A-C。通过综合降解-CD 分析对双哌啶生物碱的绝对立体结构进行指定。
J Nat Prod. 2011 Mar 25;74(3):430-40. doi: 10.1021/np1008637. Epub 2011 Feb 22.
3
Calyxamines A and B, novel piperidine alkaloids from the Caribbean sea sponge Calyx podatypa.萼胺A和B，来自加勒比海绵萼囊皮海绵的新型哌啶生物碱。
J Nat Prod. 1997 Dec;60(12):1331-3. doi: 10.1021/np970328e.
4
Cytotoxic alkylpiperidine alkaloids from the Brazilian marine sponge Pachychalina alcaloidifera.来自巴西海洋海绵生物碱产厚皮海绵的细胞毒性烷基哌啶生物碱。
J Nat Prod. 2007 Apr;70(4):538-43. doi: 10.1021/np060450q. Epub 2007 Mar 9.
5
Tetradehydrohalicyclamine A and 22-hydroxyhalicyclamine A, new cytotoxic bis-piperidine alkaloids from a marine sponge Amphimedon sp.来自海洋海绵Amphimedon sp.的新型细胞毒性双哌啶生物碱——四脱氢卤代环胺A和22-羟基卤代环胺A
J Nat Prod. 2004 Oct;67(10):1758-60. doi: 10.1021/np049824a.
6
Halichondramine, a new tetracyclic bipiperidine alkaloid from the marine sponge Halichondria sp.卤海绵胺，一种从海洋海绵Halichondria sp.中提取的新型四环双哌啶生物碱。
J Nat Prod. 2002 Nov;65(11):1738-41. doi: 10.1021/np0200663.
7
Haliclonacyclamines, tetracyclic alkylpiperidine alkaloids, as anti-dormant mycobacterial substances from a marine sponge of Haliclona sp.卤代环胺类，四环烷基哌啶生物碱，作为来自Haliclona属海洋海绵的抗休眠分枝杆菌物质。
Chem Pharm Bull (Tokyo). 2009 Oct;57(10):1136-8. doi: 10.1248/cpb.57.1136.
8
Plakinamine M, a steroidal alkaloid from the marine sponge Corticium sp.普卡灵碱 M，一种来源于海洋海绵 Corticium sp. 的甾体生物碱。
J Nat Prod. 2013 Nov 22;76(11):2150-2. doi: 10.1021/np400649e. Epub 2013 Nov 6.
9
3,4'-Linked bis(piperidines) related to the haliclonacyclamine class of marine alkaloids: synthesis using crossed-aldol chemistry and preliminary biological evaluations.与海洋生物碱哈立克纳昔胺类相关的 3,4'-连接的双(哌啶): 使用交叉羟醛缩合化学合成和初步的生物学评价。
Org Biomol Chem. 2012 Jan 7;10(1):154-61. doi: 10.1039/c1ob06418e. Epub 2011 Nov 8.
10
Renieramycin J, a highly cytotoxic tetrahydroisoquinoline alkaloid, from a marine sponge Neopetrosia sp.瑞尼霉素J，一种具有高度细胞毒性的四氢异喹啉生物碱，源自海洋海绵新岩海绵属物种。
J Nat Prod. 2003 Aug;66(8):1136-9. doi: 10.1021/np030092g.
引用本文的文献
1
Tetracyclic Bis-Piperidine Alkaloids: Structures, Bioinspired Synthesis, Synthesis, and Bioactivities.四环双哌啶生物碱：结构、仿生合成、合成及生物活性
Molecules. 2025 Jul 9;30(14):2907. doi: 10.3390/molecules30142907.
2
Marine Natural Products as Novel Treatments for Parasitic Diseases.海洋天然产物作为寄生虫病的新型治疗方法。
Handb Exp Pharmacol. 2025;287:325-393. doi: 10.1007/164_2024_712.
3
Identification of Antimycobacterial Natural Products from a Library of Marine Invertebrate Extracts.从海洋无脊椎动物提取物文库中鉴定抗分枝杆菌天然产物。
Medicines (Basel). 2022 Jan 28;9(2):9. doi: 10.3390/medicines9020009.
4
Marine alkaloids as bioactive agents against protozoal neglected tropical diseases and malaria.海洋生物碱作为抗原生动物性 neglected 热带病和疟疾的生物活性物质。
Nat Prod Rep. 2021 Dec 15;38(12):2214-2235. doi: 10.1039/d0np00078g.
5
Antimicrobial Potential and Phytochemical Screening of sp. 1 and () Sponge Crude Extracts Obtained from the South East Coast of South Africa.南非东南海岸 1 和 () 海绵粗提物的抗菌潜力和植物化学成分筛查。
Biomed Res Int. 2021 Feb 26;2021:6697944. doi: 10.1155/2021/6697944. eCollection 2021.
6
Cytotoxic Alkaloids Derived from Marine Sponges: A Comprehensive Review.海洋海绵来源的细胞毒素生物碱：全面综述。
Biomolecules. 2021 Feb 10;11(2):258. doi: 10.3390/biom11020258.
7
Attenuation of Rat Colon Carcinogenesis by Styela plicata Aqueous Extract. Modulation of NF-κB Pathway and Cytoplasmic Sod1 Gene Expression.海鞘提取物对大鼠结肠癌发生的抑制作用。NF-κB 通路和细胞质 Sod1 基因表达的调节。
Asian Pac J Cancer Prev. 2020 Sep 1;21(9):2739-2750. doi: 10.31557/APJCP.2020.21.9.2739.
8
A newly isolated strain of Halomonas sp. (HA1) exerts anticancer potential via induction of apoptosis and G/M arrest in hepatocellular carcinoma (HepG2) cell line.一株新分离的盐单胞菌（HA1）通过诱导肝癌（HepG2）细胞系凋亡和 G/M 期阻滞发挥抗癌潜力。
Sci Rep. 2020 Aug 21;10(1):14076. doi: 10.1038/s41598-020-70945-8.
9
Marine-Derived Macrocyclic Alkaloids (MDMAs): Chemical and Biological Diversity.海洋来源的大环生物碱（MDMAs）：化学和生物多样性。
Mar Drugs. 2020 Jul 17;18(7):368. doi: 10.3390/md18070368.
10
Total Synthesis of (-)-Anaferine: A Further Ramification in a Diversity-Oriented Approach.(-)-阿纳非林的全合成：多样性导向方法的进一步分支。
Molecules. 2020 Feb 27;25(5):1057. doi: 10.3390/molecules25051057.
本文引用的文献
1
Dolabellane-type diterpenoids with antiprotozoan activity from a southwestern Caribbean gorgonian octocoral of the genus Eunicea.来源于加勒比海西南部柳珊瑚属 Eunicea 的一种具有抗原生动物活性的 dolabellane 型二萜类化合物。
J Nat Prod. 2010 May 28;73(5):925-34. doi: 10.1021/np100074r.
2
Concise access to a model of the marine alkaloid halicyclamine A through macrocycle-forming addition of a 5-aminopenta-2,4-dienal onto a 2,3-dihydropyridinium salt.通过将5-氨基戊-2,4-二烯醛进行大环化加成到2,3-二氢吡啶盐上，简洁地获得海洋生物碱哈利环胺A的模型。
Chemistry. 2010 Mar 22;16(12):3594-7. doi: 10.1002/chem.201000142.
3
Total synthesis of (+/-)-haliclonacyclamine C.（±）-海兔环胺C的全合成
Angew Chem Int Ed Engl. 2010 Feb 22;49(9):1599-602. doi: 10.1002/anie.200905732.
4
Marine natural products.海洋天然产物。
Nat Prod Rep. 2010 Feb;27(2):165-237. doi: 10.1039/b906091j. Epub 2010 Jan 7.
5
Marine sponges: potential sources of new antimicrobial drugs.海洋海绵：新型抗菌药物的潜在来源。
Curr Pharm Biotechnol. 2009 Jan;10(1):86-105. doi: 10.2174/138920109787048625.
6
Total synthesis of (+)-sarain A.(+)-沙林 A 的全合成。
J Am Chem Soc. 2007 Oct 3;129(39):11987-2002. doi: 10.1021/ja074300t. Epub 2007 Sep 12.
7
Cytotoxic alkylpiperidine alkaloids from the Brazilian marine sponge Pachychalina alcaloidifera.来自巴西海洋海绵生物碱产厚皮海绵的细胞毒性烷基哌啶生物碱。
J Nat Prod. 2007 Apr;70(4):538-43. doi: 10.1021/np060450q. Epub 2007 Mar 9.
8
Tetradehydrohalicyclamine A and 22-hydroxyhalicyclamine A, new cytotoxic bis-piperidine alkaloids from a marine sponge Amphimedon sp.来自海洋海绵Amphimedon sp.的新型细胞毒性双哌啶生物碱——四脱氢卤代环胺A和22-羟基卤代环胺A
J Nat Prod. 2004 Oct;67(10):1758-60. doi: 10.1021/np049824a.
9
Halichondramine, a new tetracyclic bipiperidine alkaloid from the marine sponge Halichondria sp.卤海绵胺，一种从海洋海绵Halichondria sp.中提取的新型四环双哌啶生物碱。
J Nat Prod. 2002 Nov;65(11):1738-41. doi: 10.1021/np0200663.
10
Synthesis of the cytotoxic sponge metabolite haliclamine A.细胞毒性海绵代谢物哈利克拉明A的合成。
J Org Chem. 2002 Sep 6;67(18):6474-8. doi: 10.1021/jo025650v.
Zotero 插件