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Marine Drugs
Special Issues
Terpenoids of Marine Origin
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Terpenoids of Marine Origin

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (30 September 2014) | Viewed by 102294

Special Issue Editor

Dr. RuAngelie Edrada-Ebel

E-Mail Website
Guest Editor
Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, Glasgow G4 0RE, UK
Interests: marine natural products chemistry; secondary metabolomics; NMR- and MS-based metabolomics; marine biotechnology
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The last review published on marine-derived terpenoids was in 2006. It is about time to collate and update the work done on this group of compounds in the last decade. This special issue will focus on the chemistry of terpenoids from diverse marine sources ranging from sponges, soft corals, molluscs, and other marine invertebrates. This will also include studies done on their biosyntheses, ecological significance, and biological activity.

Dr. RuAngelie Edrada-Ebel
Guest Editor

Keywords

  • sesquiterpenes
  • diterpenes
  • triterpenes
  • Alcyonaria
  • Porifera
  • Mollusca
  • ecology

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Published Papers (9 papers)

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Research

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24 pages, 974 KiB  
Article
New Insights on the Terpenome of the Red Seaweed Laurencia dendroidea (Florideophyceae, Rhodophyta)
by Louisi Souza De Oliveira, Diogo Antonio Tschoeke, Aline Santos De Oliveira, Lilian Jorge Hill, Wladimir Costa Paradas, Leonardo Tavares Salgado, Cristiane Carneiro Thompson, Renato Crespo Pereira and Fabiano L. Thompson
Mar. Drugs 2015, 13(2), 879-902; https://doi.org/10.3390/md13020879 - 10 Feb 2015
Cited by 39 | Viewed by 10646
Abstract
The red seaweeds belonging to the genus Laurencia are well known as halogenated secondary metabolites producers, mainly terpenoids and acetogennins. Several of these chemicals exhibit important ecological roles and biotechnological applications. However, knowledge regarding the genes involved in the biosynthesis of these compounds [...] Read more.
The red seaweeds belonging to the genus Laurencia are well known as halogenated secondary metabolites producers, mainly terpenoids and acetogennins. Several of these chemicals exhibit important ecological roles and biotechnological applications. However, knowledge regarding the genes involved in the biosynthesis of these compounds is still very limited. We detected 20 different genes involved in the biosynthesis of terpenoid precursors, and 21 different genes coding for terpene synthases that are responsible for the chemical modifications of the terpenoid precursors, resulting in a high diversity of carbon chemical skeletons. In addition, we demonstrate through molecular and cytochemical approaches the occurrence of the mevalonate pathway involved in the biosynthesis of terpenes in L. dendroidea. This is the first report on terpene synthase genes in seaweeds, enabling further studies on possible heterologous biosynthesis of terpenes from L. dendroidea exhibiting ecological or biotechnological interest. Full article
(This article belongs to the Special Issue Terpenoids of Marine Origin)
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12 pages, 603 KiB  
Article
New Meroterpenoids from the Endophytic Fungus Aspergillus flavipes AIL8 Derived from the Mangrove Plant Acanthus ilicifolius
by Zhi-Qiang Bai, Xiuping Lin, Junfeng Wang, Xuefeng Zhou, Juan Liu, Bin Yang, Xianwen Yang, Shengrong Liao, Lishu Wang and Yonghong Liu
Mar. Drugs 2015, 13(1), 237-248; https://doi.org/10.3390/md13010237 - 7 Jan 2015
Cited by 42 | Viewed by 8612
Abstract
Four new meroterpenoids (2–5), along with three known analogues (1, 6, and 7) were isolated from mangrove plant Acanthus ilicifolius derived endophytic fungus Aspergillus flavipes. The structures of these compounds were elucidated by NMR and [...] Read more.
Four new meroterpenoids (2–5), along with three known analogues (1, 6, and 7) were isolated from mangrove plant Acanthus ilicifolius derived endophytic fungus Aspergillus flavipes. The structures of these compounds were elucidated by NMR and MS analysis, the configurations were assigned by CD data, and the stereochemistry of 1 was confirmed by X-ray crystallography analysis. A possible biogenetic pathway of compounds 1–7 was also proposed. All compounds were evaluated for antibacterial and cytotoxic activities. Full article
(This article belongs to the Special Issue Terpenoids of Marine Origin)
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8 pages, 410 KiB  
Communication
Rumphellaoic Acid A, a Novel Sesquiterpenoid from the Formosan Gorgonian Coral Rumphella antipathies
by Hsu-Ming Chung, Wei-Hsien Wang, Tsong-Long Hwang, Lee-Shing Fang, Zhi-Hong Wen, Jih-Jung Chen, Yang-Chang Wu and Ping-Jyun Sung
Mar. Drugs 2014, 12(12), 5856-5863; https://doi.org/10.3390/md12125856 - 4 Dec 2014
Cited by 18 | Viewed by 6574
Abstract
A novel sesquiterpenoid, rumphellaoic acid A (1), was isolated from the gorgonian coral Rumphella antipathies, and was found to possess a carbon skeleton that was obtained for the first time from a natural sources. The structure of 1 was elucidated [...] Read more.
A novel sesquiterpenoid, rumphellaoic acid A (1), was isolated from the gorgonian coral Rumphella antipathies, and was found to possess a carbon skeleton that was obtained for the first time from a natural sources. The structure of 1 was elucidated by spectroscopic methods and this compound and was found to exert a moderate inhibitory effect on the release of elastase by human neutrophils. Full article
(This article belongs to the Special Issue Terpenoids of Marine Origin)
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9 pages, 553 KiB  
Article
Oxygenated Eremophilane- and Neolemnane-Derived Sesquiterpenoids from the Soft Coral Lemnalia philippinensis
by Yun-Jie Xio, Jui-Hsin Su, Yen-Ju Tseng, Bo-Wei Chen, Wangta Liu and Jyh-Horng Sheu
Mar. Drugs 2014, 12(8), 4495-4503; https://doi.org/10.3390/md12084495 - 15 Aug 2014
Cited by 13 | Viewed by 6124
Abstract
Five sesquiterpene-related metabolites (1–5), including two new eremophilane-type compounds, philippinlins C and D (1 and 2) and a 4,5-seconeolemnane philippinlin E (3), were isolated from the organic extract of a Taiwanese soft coral Lemnalia philippinensis [...] Read more.
Five sesquiterpene-related metabolites (1–5), including two new eremophilane-type compounds, philippinlins C and D (1 and 2) and a 4,5-seconeolemnane philippinlin E (3), were isolated from the organic extract of a Taiwanese soft coral Lemnalia philippinensis. The structures of the new metabolites were determined on the basis of extensive spectroscopic analysis and by comparison of NMR data with those of related metabolites. Compound 3 was suggested to be derived from the neolemnane skeleton. Full article
(This article belongs to the Special Issue Terpenoids of Marine Origin)
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12 pages, 447 KiB  
Article
Scopararanes C–G: New Oxygenated Pimarane Diterpenes from the Marine Sediment-Derived Fungus Eutypella scoparia FS26
by Li Sun, Dongli Li, Meihua Tao, Yuchan Chen, Feijun Dan and Weimin Zhang
Mar. Drugs 2012, 10(3), 539-550; https://doi.org/10.3390/md10030539 - 27 Feb 2012
Cited by 54 | Viewed by 9340
Abstract
Five new oxygenated pimarane diterpenes, named scopararanes C–G (1–5) were isolated from the culture of a marine sediment-derived fungus Eutypella scoparia FS26 obtained from the South China Sea. The structures of these compounds were established on the basis of [...] Read more.
Five new oxygenated pimarane diterpenes, named scopararanes C–G (1–5) were isolated from the culture of a marine sediment-derived fungus Eutypella scoparia FS26 obtained from the South China Sea. The structures of these compounds were established on the basis of extensive spectroscopic analysis. The absolute configurations of compounds 1–5, were determined by CD spectroscopic analysis and comparison with literature data. All isolated compounds (1–5) were evaluated for their cytotoxic activities against MCF-7, NCI-H460, and SF-268 tumor cell lines by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) method. Full article
(This article belongs to the Special Issue Terpenoids of Marine Origin)
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Review

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27 pages, 2174 KiB  
Review
Bioactive Terpenes from Marine-Derived Fungi
by Ahmed M. Elissawy, Mohamed El-Shazly, Sherif S. Ebada, AbdelNasser B. Singab and Peter Proksch
Mar. Drugs 2015, 13(4), 1966-1992; https://doi.org/10.3390/md13041966 - 3 Apr 2015
Cited by 58 | Viewed by 10897
Abstract
Marine-derived fungi continue to be a prolific source of secondary metabolites showing diverse bioactivities. Terpenoids from marine-derived fungi exhibit wide structural diversity including numerous compounds with pronounced biological activities. In this review, we survey the last five years’ reports on terpenoidal metabolites from [...] Read more.
Marine-derived fungi continue to be a prolific source of secondary metabolites showing diverse bioactivities. Terpenoids from marine-derived fungi exhibit wide structural diversity including numerous compounds with pronounced biological activities. In this review, we survey the last five years’ reports on terpenoidal metabolites from marine-derived fungi with particular attention on those showing marked biological activities. Full article
(This article belongs to the Special Issue Terpenoids of Marine Origin)
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29 pages, 417 KiB  
Review
Terpenes from Marine-Derived Fungi
by Rainer Ebel
Mar. Drugs 2010, 8(8), 2340-2368; https://doi.org/10.3390/md8082340 - 13 Aug 2010
Cited by 86 | Viewed by 16162
Abstract
Terpenes from marine-derived fungi show a pronounced degree of structural diversity, and due to their interesting biological and pharmacological properties many of them have aroused interest from synthetic chemists and the pharmaceutical industry alike. The aim of this paper is to give an [...] Read more.
Terpenes from marine-derived fungi show a pronounced degree of structural diversity, and due to their interesting biological and pharmacological properties many of them have aroused interest from synthetic chemists and the pharmaceutical industry alike. The aim of this paper is to give an overview of the structural diversity of terpenes from marine-derived fungi, highlighting individual examples of chemical structures and placing them in a context of other terpenes of fungal origin. Wherever possible, information regarding the biological activity is presented. Full article
(This article belongs to the Special Issue Terpenoids of Marine Origin)
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37 pages, 1870 KiB  
Review
Structures, Biological Activities and Phylogenetic Relationships of Terpenoids from Marine Ciliates of the Genus Euplotes
by Graziano Guella, Danielle Skropeta, Graziano Di Giuseppe and Fernando Dini
Mar. Drugs 2010, 8(7), 2080-2116; https://doi.org/10.3390/md8072080 - 8 Jul 2010
Cited by 27 | Viewed by 13740
Abstract
In the last two decades, large scale axenic cell cultures of the marine species comprising the family Euplotidae have resulted in the isolation of several new classes of terpenoids with unprecedented carbon skeletons including the (i) euplotins, highly strained acetylated sesquiterpene hemiacetals; (ii) [...] Read more.
In the last two decades, large scale axenic cell cultures of the marine species comprising the family Euplotidae have resulted in the isolation of several new classes of terpenoids with unprecedented carbon skeletons including the (i) euplotins, highly strained acetylated sesquiterpene hemiacetals; (ii) raikovenals, built on the bicyclo[3.2.0]heptane ring system; (iii) rarisetenolides and focardins containing an octahydroazulene moiety; and (iv) vannusals, with a unique C30 backbone. Their complex structures have been elucidated through a combination of nuclear magnetic resonance spectroscopy, mass spectrometry, molecular mechanics and quantum chemical calculations. Despite the limited number of biosynthetic experiments having been performed, the large diversity of ciliate terpenoids has facilitated the proposal of biosynthetic pathways whereby they are produced from classical linear precursors. Herein, the similarities and differences emerging from the comparison of the classical chemotaxonomy approach based on secondary metabolites, with species phylogenesis based on genetic descriptors (SSU-rDNA), will be discussed. Results on the interesting ecological and biological properties of ciliate terpenoids are also reported. Full article
(This article belongs to the Special Issue Terpenoids of Marine Origin)
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Graphical abstract

34 pages, 495 KiB  
Review
Bioactive Sesterterpenes and Triterpenes from Marine Sponges: Occurrence and Pharmacological Significance
by Sherif S. Ebada, WenHan Lin and Peter Proksch
Mar. Drugs 2010, 8(2), 313-346; https://doi.org/10.3390/md8020313 - 23 Feb 2010
Cited by 147 | Viewed by 18238
Abstract
Marine ecosystems (>70% of the planet's surface) comprise a continuous resource of immeasurable biological activities and immense chemical entities. This diversity has provided a unique source of chemical compounds with potential bioactivities that could lead to potential new drug candidates. Many marine-living organisms [...] Read more.
Marine ecosystems (>70% of the planet's surface) comprise a continuous resource of immeasurable biological activities and immense chemical entities. This diversity has provided a unique source of chemical compounds with potential bioactivities that could lead to potential new drug candidates. Many marine-living organisms are soft bodied and/or sessile. Consequently, they have developed toxic secondary metabolites or obtained them from microorganisms to defend themselves against predators [1]. For the last 30–40 years, marine invertebrates have been an attractive research topic for scientists all over the world. A relatively small number of marine plants, animals and microbes have yielded more than 15,000 natural products including numerous compounds with potential pharmaceutical potential. Some of these have already been launched on the pharmaceutical market such as Prialt® (ziconotide; potent analgesic) and Yondelis® (trabectedin or ET-743; antitumor) while others have entered clinical trials, e.g., alpidin and kahalalide F. Amongst the vast array of marine natural products, the terpenoids are one of the more commonly reported and discovered to date. Sesterterpenoids (C25) and triterpenoids (C30) are of frequent occurrence, particularly in marine sponges, and they show prominent bioactivities. In this review, we survey sesterterpenoids and triterpenoids obtained from marine sponges and highlight their bioactivities. Full article
(This article belongs to the Special Issue Terpenoids of Marine Origin)
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