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Special Issue "Terpenoids of Marine Origin"

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

Deadline for manuscript submissions: closed (30 September 2014)

Special Issue Editor

Guest Editor
Dr. RuAngelie Edrada-Ebel (Website)

Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, The John Arbuthnott Building, 161 Cathedral Street, Glasgow G4 0RE, UK
Fax: +44 141 552 2562
Interests: natural products; drug discovery; NMR spectroscopy; metabolomics

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

Published Papers (9 papers)

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Research

Jump to: Review

Open AccessArticle New Insights on the Terpenome of the Red Seaweed Laurencia dendroidea (Florideophyceae, Rhodophyta)
Mar. Drugs 2015, 13(2), 879-902; doi:10.3390/md13020879
Received: 14 September 2014 / Revised: 17 December 2014 / Accepted: 12 January 2015 / Published: 10 February 2015
Cited by 5 | PDF Full-text (974 KB) | HTML Full-text | XML Full-text | Supplementary Files
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 [...] 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 Ldendroidea exhibiting ecological or biotechnological interest. Full article
(This article belongs to the Special Issue Terpenoids of Marine Origin)
Open AccessArticle New Meroterpenoids from the Endophytic Fungus Aspergillus flavipes AIL8 Derived from the Mangrove Plant Acanthus ilicifolius
Mar. Drugs 2015, 13(1), 237-248; doi:10.3390/md13010237
Received: 26 August 2014 / Accepted: 22 December 2014 / Published: 7 January 2015
Cited by 3 | PDF Full-text (603 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Four new meroterpenoids (25), 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 [...] Read more.
Four new meroterpenoids (25), 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 17 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)
Open AccessCommunication Rumphellaoic Acid A, a Novel Sesquiterpenoid from the Formosan Gorgonian Coral Rumphella antipathies
Mar. Drugs 2014, 12(12), 5856-5863; doi:10.3390/md12125856
Received: 9 September 2014 / Revised: 4 November 2014 / Accepted: 21 November 2014 / Published: 4 December 2014
Cited by 4 | PDF Full-text (410 KB) | HTML Full-text | XML Full-text | Supplementary Files
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 [...] 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)
Open AccessArticle Oxygenated Eremophilane- and Neolemnane-Derived Sesquiterpenoids from the Soft Coral Lemnalia philippinensis
Mar. Drugs 2014, 12(8), 4495-4503; doi:10.3390/md12084495
Received: 8 April 2014 / Revised: 29 July 2014 / Accepted: 31 July 2014 / Published: 15 August 2014
Cited by 2 | PDF Full-text (553 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Five sesquiterpene-related metabolites (15), 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 [...] Read more.
Five sesquiterpene-related metabolites (15), 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)
Open AccessArticle Scopararanes C–G: New Oxygenated Pimarane Diterpenes from the Marine Sediment-Derived Fungus Eutypella scoparia FS26
Mar. Drugs 2012, 10(3), 539-550; doi:10.3390/md10030539
Received: 29 November 2011 / Revised: 16 February 2012 / Accepted: 20 February 2012 / Published: 27 February 2012
Cited by 14 | PDF Full-text (447 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Five new oxygenated pimarane diterpenes, named scopararanes C–G (15) 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 [...] Read more.
Five new oxygenated pimarane diterpenes, named scopararanes C–G (15) 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 15, were determined by CD spectroscopic analysis and comparison with literature data. All isolated compounds (15) 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)

Review

Jump to: Research

Open AccessReview Bioactive Terpenes from Marine-Derived Fungi
Mar. Drugs 2015, 13(4), 1966-1992; doi:10.3390/md13041966
Received: 4 December 2014 / Revised: 25 February 2015 / Accepted: 14 March 2015 / Published: 3 April 2015
Cited by 3 | PDF Full-text (2174 KB) | HTML Full-text | XML Full-text
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 [...] 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)
Open AccessReview Terpenes from Marine-Derived Fungi
Mar. Drugs 2010, 8(8), 2340-2368; doi:10.3390/md8082340
Received: 6 July 2010 / Revised: 21 July 2010 / Accepted: 9 August 2010 / Published: 13 August 2010
Cited by 28 | PDF Full-text (417 KB) | HTML Full-text | XML Full-text
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 [...] 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)
Open AccessReview Structures, Biological Activities and Phylogenetic Relationships of Terpenoids from Marine Ciliates of the Genus Euplotes
Mar. Drugs 2010, 8(7), 2080-2116; doi:10.3390/md8072080
Received: 1 June 2010 / Revised: 6 July 2010 / Accepted: 6 July 2010 / Published: 8 July 2010
Cited by 13 | PDF Full-text (1870 KB) | HTML Full-text | XML Full-text
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; [...] 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)
Figures

Open AccessReview Bioactive Sesterterpenes and Triterpenes from Marine Sponges: Occurrence and Pharmacological Significance
Mar. Drugs 2010, 8(2), 313-346; doi:10.3390/md8020313
Received: 20 January 2010 / Revised: 5 February 2010 / Accepted: 20 February 2010 / Published: 23 February 2010
Cited by 53 | PDF Full-text (495 KB) | HTML Full-text | XML Full-text
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 [...] 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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