Terpenoids from Marine Organisms II

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

Deadline for manuscript submissions: closed (31 December 2020) | Viewed by 15063

Special Issue Editors

Special Issue Information

Dear Colleagues,

Marine natural products have attracted the attention of biologists and chemists all over the world for the last six decades. The marine environment provides different biosynthetic conditions to organisms that live in it, influencing the “art” by which marine organisms elaborate their fascinating bioactive metabolites, including molecules that have been approved as drugs, as well as an array of compounds that are currently into clinical trials.

Terpenes, one of the most diverse classes of natural products produced by a variety of organisms, are vital for most organisms, exerting metabolic control and mediating intra- and interspecies interactions. Marine organisms produce a wide array of fascinating terpenoid structures, characterized by unique structural features. The biological and ecochemical functions of terpenes include chemical communication, pollination, chemical protection, growth regulation, among others, but even though numerous studies have been reported on this subject, the full spectrum of their ecological roles has not yet been fully clarified.

The Special Issue will include studies focusing on the challenges and future directions involved in the advancement of these promising natural compounds, encompassing isolation–structure elucidation of new molecules, metabolomic studies, evaluation of bioactivities, elucidation of mechanisms of action, recent developments in their biosynthesis, total synthesis, semisynthesis, and biotransformation, as well as pharmaceutical applications.

Prof. Vassilios Roussis
Ass. Prof. Efstathia Ioannou
Guest Editors

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Keywords

  • Terpenes
  • Bioactivity
  • Metabolites
  • Synthesis
  • Biotransformations
  • Pharmaceutical applications

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Related Special Issue

Published Papers (4 papers)

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Research

19 pages, 3196 KiB  
Article
Cytotoxic Scalarane Sesterterpenes from the Sponge Hyrtios erectus
by Oh-Seok Kwon, Donghwa Kim, Chang-Kwon Kim, Jeongyoon Sun, Chung J. Sim, Dong-Chan Oh, Sang Kook Lee, Ki-Bong Oh and Jongheon Shin
Mar. Drugs 2020, 18(5), 253; https://doi.org/10.3390/md18050253 - 13 May 2020
Cited by 12 | Viewed by 3588
Abstract
Twelve new sesterterpenes along with eight known sesterterpenes were isolated from the marine sponge Hyrtios erectus collected off the coast of Chuuk Island, the Federated State of Micronesia. Based upon a combination of spectroscopic and computational analyses, these compounds were determined to be [...] Read more.
Twelve new sesterterpenes along with eight known sesterterpenes were isolated from the marine sponge Hyrtios erectus collected off the coast of Chuuk Island, the Federated State of Micronesia. Based upon a combination of spectroscopic and computational analyses, these compounds were determined to be eight glycine-bearing scalaranes (18), a 3-keto scalarane (9), two oxidized-furan-bearing scalaranes (10 and 11), and a salmahyrtisane (12). Several of these compounds exhibited weak antiproliferation against diverse cancer cell lines as well as moderate anti-angiogenesis activities. The antiproliferative activity of new compound 4 was found to be associated with G0/G1 arrest in the cell cycle. Full article
(This article belongs to the Special Issue Terpenoids from Marine Organisms II)
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17 pages, 2358 KiB  
Article
Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral Lobophytum varium
by Chuan-Hsiang Chang, Atallah F. Ahmed, Tian-Sheng Yang, You-Cheng Lin, Chiung-Yao Huang, Tsong-Long Hwang and Jyh-Horng Sheu
Mar. Drugs 2020, 18(4), 223; https://doi.org/10.3390/md18040223 - 22 Apr 2020
Cited by 10 | Viewed by 3538
Abstract
Further chemical investigation of the EtOAc extract of the soft coral Lobophytum varium resulted in the discovery of eleven new diterpenoids lobovarols F–P (111) of lobane– and prenyleudesmane–types, along with two known metabolites (12 and 13). The [...] Read more.
Further chemical investigation of the EtOAc extract of the soft coral Lobophytum varium resulted in the discovery of eleven new diterpenoids lobovarols F–P (111) of lobane– and prenyleudesmane–types, along with two known metabolites (12 and 13). The structures of the new metabolites were established by spectroscopic analyses, including 2D NMR experiments. The absolute configuration of 1 was determined using Mosher’s method. The complete assignment of 1H and 13C NMR spectroscopic data of 12 and 13 and the identification of pyran-derived moieties in the prenyleudesmanes were reported for the first time. Anti-inflammatory activities of the isolated compounds in suppressing elastase release and superoxide anion generation in human neutrophils were disclosed for 1, 2, 4, 12, and 13. A stereospecific biosynthesis for lobanes and prenyleudesmanes from the related prenylgermacranes could explain the coexistence of lobanes and prenylgermacranes in L. varium. Full article
(This article belongs to the Special Issue Terpenoids from Marine Organisms II)
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16 pages, 2431 KiB  
Article
Halogenated Diterpenes with In Vitro Antitumor Activity from the Red Alga Sphaerococcus coronopifolius
by Vangelis Smyrniotopoulos, Anna Cláudia de Andrade Tomaz, Maria de Fátima Vanderlei de Souza, Emídio Vasconcelos Leitão da Cunha, Robert Kiss, Véronique Mathieu, Efstathia Ioannou and Vassilios Roussis
Mar. Drugs 2020, 18(1), 29; https://doi.org/10.3390/md18010029 - 29 Dec 2019
Cited by 13 | Viewed by 3364
Abstract
Eight new (18) structurally diverse diterpenes featuring five different carbocycles were isolated from the organic extracts of the red alga Sphaerococcus coronopifolius collected from the coastline of the Ionian Sea in Greece. The structures of the new natural products, [...] Read more.
Eight new (18) structurally diverse diterpenes featuring five different carbocycles were isolated from the organic extracts of the red alga Sphaerococcus coronopifolius collected from the coastline of the Ionian Sea in Greece. The structures of the new natural products, seven of which were halogenated, and the relative configuration of their stereocenters were determined on the basis of comprehensive spectroscopic analyses, including NMR and HRMS data. Compounds 5 and 8 were found to possess in vitro antitumor activity against one murine and five human cancer cell lines with mean IC50 values 15 and 16 μM, respectively. Full article
(This article belongs to the Special Issue Terpenoids from Marine Organisms II)
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9 pages, 5178 KiB  
Article
New 8-Hydroxybriaranes from the Gorgonian Coral Junceella fragilis (Ellisellidae)
by You-Ying Chen, Lee-Shing Fang, Yu-Hsin Chen, Bo-Rong Peng, Tung-Pin Su, Thanh-Hao Huynh, Feng-Yu Lin, Chiung-Chin Hu, Nai-Cheng Lin, Zhi-Hong Wen, Jih-Jung Chen, Chieh-Yu Lee, Jin-Wei Wang and Ping-Jyun Sung
Mar. Drugs 2019, 17(9), 534; https://doi.org/10.3390/md17090534 - 14 Sep 2019
Cited by 7 | Viewed by 3594
Abstract
Three new 8-hydroxybriaranes—fragilides R–T (13) were obtained from a sea whip gorgonian coral Junceella fragilis. The structures of briaranes 13 were elucidated by using spectroscopic methods, including 1D (1H and 13C NMR), 2D [...] Read more.
Three new 8-hydroxybriaranes—fragilides R–T (13) were obtained from a sea whip gorgonian coral Junceella fragilis. The structures of briaranes 13 were elucidated by using spectroscopic methods, including 1D (1H and 13C NMR), 2D (COSY, HSQC, HMBC, and NOESY experiments) NMR studies, and (+)-HRESIMS. Fragilides S and T (2 and 3) are the only briaranes known to possess 8α-hydroxy and 17β-methyl groups, respectively. Briarane 2 exerted an inhibition effect on iNOS release from RAW264.7; a macrophage cell line that originated from a mouse monocyte macrophage, stimulated with lipopolysaccharides. Full article
(This article belongs to the Special Issue Terpenoids from Marine Organisms II)
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