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热胁迫下的化学变化以及树突内酯的鉴定,一种来自南极海洋海绵的具有罕见重排海绵烷骨架的新型二萜衍生物

Chemical Changes Under Heat Stress and Identification of Dendrillolactone, a New Diterpene Derivative with a Rare Rearranged Spongiane Skeleton from the Antarctic Marine Sponge .

作者信息

Prófumo Andrea, Avila Conxita, Cutignano Adele

机构信息

Departament de Biologia Evolutiva, Ecologia i Ciències Ambientals (BEECA), Facultat de Biologia, Universitat de Barcelona (UB), Av. Diagonal 643, 08028 Barcelona, Catalonia, Spain.

Institut de Recerca de la Biodiversitat (IRBio), Universitat de Barcelona (UB), 08028 Barcelona, Catalonia, Spain.

出版信息

Mar Drugs. 2024 Dec 28;23(1):10. doi: 10.3390/md23010010.

DOI:10.3390/md23010010
PMID:39852512
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11767012/
Abstract

The waters around the western Antarctic Peninsula are experiencing fast warming due to global change, being among the most affected regions on the planet. This polar area is home to a large and rich community of benthic marine invertebrates, such as sponges, tunicates, corals, and many other animals. Among the sponges, the bright yellow is commonly known for using secondary diterpenoids as a defensive mechanism against local potential predators. From the dichloromethane extract of sponge samples from Deception Island collected in January 2023, we isolated a novel derivative with an unusual β-lactone diterpene skeleton here named dendrillolactone (), along with seven previously described diterpenes, including deceptionin (), a gracilane norditerpene (), cadlinolide C (), a glaciolane norditerpene (), membranolide (), aplysulphurin (), and tetrahydroaplysulphurine-1 (). Here, we also report our studies on the changes in the chemical arsenal of this sponge by slow temperature increase in aquaria experiments. Despite being a species capable of inhabiting volcanically active areas, with frequent water temperature fluctuations due to the existing fumaroles, the results show that diterpenes such as deceptionin, cadlinolide C, membranolide, and tetrahydroaplysulphurin-1 seem to be susceptible to the temperature increase, resulting in a trend to higher concentrations. However, temperatures above 4 °C severely affected sponge metabolism, causing its death much earlier than expected. Further research on the roles of these natural products in and their relationship to the sponge's resilience to environmental changes should help to better understand the defensive mechanisms of Antarctic marine benthos in the context of global change.

摘要

由于全球变化,南极半岛西部周围的水域正在迅速变暖,是地球上受影响最严重的地区之一。这个极地地区是大量丰富的底栖海洋无脊椎动物群落的家园,如海绵、被囊动物、珊瑚和许多其他动物。在海绵中,亮黄色的[海绵名称未给出]通常以使用次生二萜类化合物作为抵御当地潜在捕食者的防御机制而闻名。从2023年1月在欺骗岛采集的海绵样本的二氯甲烷提取物中,我们分离出一种具有不寻常β-内酯二萜骨架的新型衍生物,在此命名为树突内酯(),以及七种先前描述的二萜类化合物,包括欺骗菌素()、一种细枝烷降二萜()、卡德内酯C()、一种冰川烷降二萜()、膜内酯()、海兔硫素()和四氢海兔硫素-1()。在这里,我们还报告了我们通过水族箱实验中缓慢升温对这种海绵化学武器库变化的研究。尽管该物种能够栖息在火山活动活跃的地区,由于现有的喷气孔,水温频繁波动,但结果表明,欺骗菌素、卡德内酯C、膜内酯和四氢海兔硫素-1等二萜类化合物似乎对温度升高敏感,导致浓度有升高趋势。然而,高于4°C的温度严重影响海绵的新陈代谢,导致其比预期更早死亡。对这些天然产物在[具体作用未明确]中的作用及其与海绵对环境变化恢复力的关系进行进一步研究,应有助于更好地理解全球变化背景下南极海洋底栖生物的防御机制。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a98/11767012/95fe9ef65b21/marinedrugs-23-00010-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a98/11767012/a502da930617/marinedrugs-23-00010-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a98/11767012/d36a29f40dcf/marinedrugs-23-00010-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a98/11767012/b4227304f528/marinedrugs-23-00010-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a98/11767012/95fe9ef65b21/marinedrugs-23-00010-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a98/11767012/a502da930617/marinedrugs-23-00010-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a98/11767012/d36a29f40dcf/marinedrugs-23-00010-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a98/11767012/b4227304f528/marinedrugs-23-00010-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a98/11767012/95fe9ef65b21/marinedrugs-23-00010-g004.jpg

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本文引用的文献

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Handb Exp Pharmacol. 2025;287:325-393. doi: 10.1007/164_2024_712.
2
A Comprehensive Review of the Classification, Sources, Phytochemistry, and Pharmacology of Norditerpenes.北二萜的分类、来源、植物化学和药理学的全面综述。
Molecules. 2023 Dec 21;29(1):60. doi: 10.3390/molecules29010060.
3
A Chemo-Ecological Investigation of Topsent, 1905: Identification of Deceptionin and the Effects of Heat Stress and Predation Pressure on Its Terpene Profiles.
托彭特 1905 年的化学生态学研究:欺骗性的识别以及热应激和捕食压力对其萜烯图谱的影响。
Mar Drugs. 2023 Sep 19;21(9):499. doi: 10.3390/md21090499.
4
From Antarctica to cancer research: a novel human DNA topoisomerase 1B inhibitor from Antarctic sponge .从南极洲到癌症研究:一种新型的人源 DNA 拓扑异构酶 1B 抑制剂来自南极海绵。
J Enzyme Inhib Med Chem. 2022 Dec;37(1):1404-1410. doi: 10.1080/14756366.2022.2078320.
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Marine Demospongiae: A Challenging Treasure of Bioactive Compounds.海洋寻常海绵:生物活性化合物的挑战性宝藏。
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Antifouling Diterpenoids from the Sponge Dendrilla antarctica.南极海绵来源的防污二萜。
Chem Biodivers. 2022 Feb;19(2):e202100618. doi: 10.1002/cbdv.202100618. Epub 2021 Dec 29.
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Discovery of cytotoxic natural products from Red Sea sponges: Structure and synthesis.从红海海绵中发现细胞毒性天然产物:结构与合成。
Eur J Med Chem. 2021 Aug 5;220:113491. doi: 10.1016/j.ejmech.2021.113491. Epub 2021 Apr 24.
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