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10 pages, 1536 KiB

Open AccessArticle

Anverenes B–E, New Polyhalogenated Monoterpenes from the Antarctic Red Alga Plocamium cartilagineum

by Andrew J. Shilling, Jacqueline L. von Salm, Anthony R. Sanchez, Younghoon Kee, Charles D. Amsler, James B. McClintock and Bill J. Baker

Mar. Drugs 2019, 17(4), 230; https://doi.org/10.3390/md17040230 - 17 Apr 2019

Cited by 19 | Viewed by 5929

Abstract

The subtidal red alga Plocamium cartilagineum was collected from the Western Antarctic Peninsula during the 2011 and 2017 austral summers. Bulk collections from specific sites corresponded to chemogroups identified by Young et al. in 2013. One of the chemogroups yielded several known acyclic [...] Read more.

The subtidal red alga Plocamium cartilagineum was collected from the Western Antarctic Peninsula during the 2011 and 2017 austral summers. Bulk collections from specific sites corresponded to chemogroups identified by Young et al. in 2013. One of the chemogroups yielded several known acyclic halogenated monoterpenes (2–5) as well as undescribed compounds of the same class, anverenes B–D (6–8). Examination of another chemogroup yielded an undescribed cyclic halogenated monoterpene anverene E (9) as its major secondary metabolite. Elucidation of structures was achieved through one-dimensional (1D) and 2D nuclear magnetic resonance (NMR) spectroscopy and negative chemical ionization mass spectrometry. Compounds 1–9 show moderate cytotoxicity against cervical cancer (HeLa) cells. Full article

(This article belongs to the Special Issue Terpenoids from Marine Organisms)

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9 pages, 2969 KiB

Open AccessArticle

New Furanocembranoids from Briareum violaceum

by Pin-Chang Huang, Wen-Sou Lin, Bo-Rong Peng, Yu-Chia Chang, Lee-Shing Fang, Guo-Qiang Li, Tsong-Long Hwang, Zhi-Hong Wen and Ping-Jyun Sung

Mar. Drugs 2019, 17(4), 214; https://doi.org/10.3390/md17040214 - 5 Apr 2019

Cited by 8 | Viewed by 3289

Abstract

Three new furanocembranoids—briaviodiol F (1) and briaviotriols A (2) and B (3)—along with a known analogue, briaviodiol A (4), were obtained from a cultured-type octocoral Briareum violaceum. The structures of cembranoids 1–3 [...] Read more.

Three new furanocembranoids—briaviodiol F (1) and briaviotriols A (2) and B (3)—along with a known analogue, briaviodiol A (4), were obtained from a cultured-type octocoral Briareum violaceum. The structures of cembranoids 1–3 were elucidated by using spectroscopic methods. In vitro study demonstrated that compounds 2 and 4 exerted inhibition effects on inducible nitric oxide synthase (iNOS) release from RAW 264.7, 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)

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10 pages, 1352 KiB

Open AccessArticle

UPLC–MS/MS Identification of Sterol Sulfates in Marine Diatoms

by Genoveffa Nuzzo, Carmela Gallo, Giuliana D’Ippolito, Emiliano Manzo, Nadia Ruocco, Ennio Russo, Ylenia Carotenuto, Maria Costantini, Valerio Zupo, Angela Sardo and Angelo Fontana

Mar. Drugs 2019, 17(1), 10; https://doi.org/10.3390/md17010010 - 24 Dec 2018

Cited by 18 | Viewed by 5587

Abstract

Diatoms are unicellular eukaryotic organisms that play a key ecological and biogeochemical role in oceans as major primary producers. Recently, these microalgae have also attracted interest as a promising source of functional products with widespread relevance. Progress in the knowledge of cell and [...] Read more.

Diatoms are unicellular eukaryotic organisms that play a key ecological and biogeochemical role in oceans as major primary producers. Recently, these microalgae have also attracted interest as a promising source of functional products with widespread relevance. Progress in the knowledge of cell and molecular biology of diatoms is envisaged as a key step to understanding regulation of their life cycle in marine environments as well as facilitating their full and profitable exploitation by biotechnological platforms. Recently, we identified sterol sulfates (StS) as regulatory molecules of cell death in the diatom Skeletonema marinoi. As these compounds may have a general role in diatom physiology and chemical signals in aquatic systems, we investigated a suitable tool for their analysis in laboratory and field samples. Herein, we describe a sensitive, fast, and efficient ultra performance liquid chromatography–mass spectrometry (UPLC–MS) method for qualitative and quantitative analysis of StS from crude extract of diatoms and other microalgae. The method was applied to 13 different strains of our collection of marine protists. This first study suggested a species-specific distribution of StS and identified the sulfated derivatives of 24-methylene cholesterol and 24-methyl cholesterol as the most common members in diatoms. Full article

(This article belongs to the Special Issue Terpenoids from Marine Organisms)

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10 pages, 4225 KiB

Open AccessArticle

Eutypellenoids A–C, New Pimarane Diterpenes from the Arctic Fungus Eutypella sp. D-1

by Hao-Bing Yu, Xiao-Li Wang, Wei-Heng Xu, Yi-Xin Zhang, Yi-Sen Qian, Jian-Peng Zhang, Xiao-Ling Lu and Xiao-Yu Liu

Mar. Drugs 2018, 16(8), 284; https://doi.org/10.3390/md16080284 - 16 Aug 2018

Cited by 26 | Viewed by 4478

Abstract

Three new pimarane diterpenes, eutypellenoids A–C (1–3), together with a known compound, eutypenoid C (4), were isolated from the culture extract of Eutypella sp. D-1 derived from the Arctic region. Compounds 1–3 possessed an uncommon [...] Read more.

Three new pimarane diterpenes, eutypellenoids A–C (1–3), together with a known compound, eutypenoid C (4), were isolated from the culture extract of Eutypella sp. D-1 derived from the Arctic region. Compounds 1–3 possessed an uncommon tetrahydrofuran-fused pimarane diterpene skeleton. The structures of all compounds were determined by detailed spectroscopic analysis, electronic circular dichroism (ECD) analysis, as well as a comparison with the literature data. Antibacterial, antifungal, and cytotoxic activities of these compounds were evaluated. Compound 2 displayed antibacterial activity against Staphylococcus aureus and Escherichia coli with MIC values of 8 and 8 μg/mL, respectively. Additionally, compound 2 showed antifungal activity against Candida parapsilosis, Candida albicans, Candida glabrata, and Candida tropicalis with MIC values of 8, 8, 16, and 32 μg/mL, respectively. Furthermore, compound 2 exhibited moderate cytotoxic activity against HCT-116 cell line with IC₅₀ value of 3.7 μM. Full article

(This article belongs to the Special Issue Terpenoids from Marine Organisms)

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17 pages, 3348 KiB

Open AccessArticle

New Cembranoids and a Biscembranoid Peroxide from the Soft Coral Sarcophyton cherbonnieri

by Chia-Chi Peng, Chiung-Yao Huang, Atallah F. Ahmed, Tsong-Long Hwang, Chang-Feng Dai and Jyh-Horng Sheu

Mar. Drugs 2018, 16(8), 276; https://doi.org/10.3390/md16080276 - 6 Aug 2018

Cited by 22 | Viewed by 4784

Abstract

Six new cembranoids, cherbonolides A−E (1–5) and bischerbolide peroxide (6), along with one known cembranoid, isosarcophine (7), were isolated from the Formosan soft coral Sarcophyton cherbonnieri. The structures of these compounds were elucidated by [...] Read more.

Six new cembranoids, cherbonolides A−E (1–5) and bischerbolide peroxide (6), along with one known cembranoid, isosarcophine (7), were isolated from the Formosan soft coral Sarcophyton cherbonnieri. The structures of these compounds were elucidated by detailed spectroscopic analysis and chemical methods. Compound 6 was discovered to be the first example of a molecular skeleton formed from two cembranoids connected by a peroxide group. Compounds 1–7 were shown to have the ability of inhibiting the production of superoxide anions and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced human neutrophils. Full article

(This article belongs to the Special Issue Terpenoids from Marine Organisms)

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13 pages, 2858 KiB

Open AccessCommunication

Asperversins A and B, Two Novel Meroterpenoids with an Unusual 5/6/6/6 Ring from the Marine-Derived Fungus Aspergillus versicolor

by Huaqiang Li, Weiguang Sun, Mengyi Deng, Changxing Qi, Chunmei Chen, Hucheng Zhu, Zengwei Luo, Jianping Wang, Yongbo Xue and Yonghui Zhang

Mar. Drugs 2018, 16(6), 177; https://doi.org/10.3390/md16060177 - 23 May 2018

Cited by 25 | Viewed by 4378

Abstract

Asperversins A (1) and B (2), two novel meroterpenoids featuring an uncommon 5/6/6/6 ring system, along with five new analogues (3–7) and a known compound asperdemin (8), were obtained from the marine-derived fungus [...] Read more.

Asperversins A (1) and B (2), two novel meroterpenoids featuring an uncommon 5/6/6/6 ring system, along with five new analogues (3–7) and a known compound asperdemin (8), were obtained from the marine-derived fungus Aspergillus versicolor. Their structures and absolute configurations were confirmed by extensive spectroscopic analyses, single-crystal X-ray diffraction studies, and electronic circular dichroism (ECD) calculation. All new compounds were tested for their acetylcholinesterase enzyme (AChE) inhibitory activities and cytotoxic activities, of which compound 7 displayed moderate inhibitory activity against the AChE with an IC₅₀ value of 13.6 μM. Full article

(This article belongs to the Special Issue Terpenoids from Marine Organisms)

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15 pages, 12771 KiB

Open AccessArticle

Anticancer Activity of Euplotin C, Isolated from the Marine Ciliate Euplotes crassus, Against Human Melanoma Cells

by Sara Carpi, Beatrice Polini, Giulio Poli, Gabriela Alcantara Barata, Stefano Fogli, Antonella Romanini, Tiziano Tuccinardi, Graziano Guella, Francesco Paolo Frontini, Paola Nieri and Graziano Di Giuseppe

Mar. Drugs 2018, 16(5), 166; https://doi.org/10.3390/md16050166 - 16 May 2018

Cited by 23 | Viewed by 4836

Abstract

Cutaneous melanoma is the most serious type of skin cancer, so new cytotoxic weapons against novel targets in melanoma are of great interest. Euplotin C (EC), a cytotoxic secondary metabolite of the marine ciliate Euplotes crassus, was evaluated in the present study [...] Read more.

Cutaneous melanoma is the most serious type of skin cancer, so new cytotoxic weapons against novel targets in melanoma are of great interest. Euplotin C (EC), a cytotoxic secondary metabolite of the marine ciliate Euplotes crassus, was evaluated in the present study on human cutaneous melanoma cells to explore its anti-melanoma activity and to gain more insight into its mechanism of action. EC exerted a marked cytotoxic effect against three different human melanoma cell lines (A375, 501Mel and MeWo) with a potency about 30-fold higher than that observed in non-cancer cells (HDFa cells). A pro-apoptotic activity and a decrease in melanoma cell migration by EC were also observed. At the molecular level, the inhibition of the Erk and Akt pathways, which control many aspects of melanoma aggressiveness, was shown. EC cytotoxicity was antagonized by dantrolene, a ryanodine receptor (RyR) antagonist, in a concentration-dependent manner. A role of RyR as a direct target of EC was also suggested by molecular modelling studies. In conclusion, our data provide the first evidence of the anti-melanoma activity of EC, suggesting it may be a promising new scaffold for the development of selective activators of RyR to be used for the treatment of melanoma and other cancer types. Full article

(This article belongs to the Special Issue Terpenoids from Marine Organisms)

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Review

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17 pages, 2097 KiB

Open AccessReview

Triterpenoids in Echinoderms: Fundamental Differences in Diversity and Biosynthetic Pathways

by Emily J. S. Claereboudt, Guillaume Caulier, Corentin Decroo, Emmanuel Colson, Pascal Gerbaux, Michel R. Claereboudt, Hubert Schaller, Patrick Flammang, Magali Deleu and Igor Eeckhaut

Mar. Drugs 2019, 17(6), 352; https://doi.org/10.3390/md17060352 - 13 Jun 2019

Cited by 21 | Viewed by 6386

Abstract

Echinoderms form a remarkable phylum of marine invertebrates that present specific chemical signatures unique in the animal kingdom. It is particularly the case for essential triterpenoids that evolved separately in each of the five echinoderm classes. Indeed, while most animals have Δ⁵ [...] Read more.

Echinoderms form a remarkable phylum of marine invertebrates that present specific chemical signatures unique in the animal kingdom. It is particularly the case for essential triterpenoids that evolved separately in each of the five echinoderm classes. Indeed, while most animals have Δ⁵-sterols, sea cucumbers (Holothuroidea) and sea stars (Asteroidea) also possess Δ⁷ and Δ⁹⁽¹¹⁾-sterols, a characteristic not shared with brittle stars (Ophiuroidea), sea urchins (Echinoidea), and crinoids (Crinoidea). These particular Δ⁷ and Δ⁹⁽¹¹⁾ sterols emerged as a self-protection against membranolytic saponins that only sea cucumbers and sea stars produce as a defense mechanism. The diversity of saponins is large; several hundred molecules have been described in the two classes of these saponins (i.e., triterpenoid or steroid saponins). This review aims to highlight the diversity of triterpenoids in echinoderms by focusing on sterols and triterpenoid glycosides, but more importantly to provide an updated view of the biosynthesis of these molecules in echinoderms. Full article

(This article belongs to the Special Issue Terpenoids from Marine Organisms)

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15 pages, 3421 KiB

Open AccessReview

Terpenoids from Marine Soft Coral of the Genus Lemnalia: Chemistry and Biological Activities

by Qihao Wu, Jiadong Sun, Jianwei Chen, Huawei Zhang, Yue-Wei Guo and Hong Wang

Mar. Drugs 2018, 16(9), 320; https://doi.org/10.3390/md16090320 - 9 Sep 2018

Cited by 30 | Viewed by 6210

Abstract

Lemnalia is one of the most widely-distributed marine soft coral in tropical oceans and is known to produce novel terpenoids with a broad spectrum of biological activities. This review provides the first comprehensive overview of terpenoids produced by soft coral Lemnalia since their [...] Read more.

Lemnalia is one of the most widely-distributed marine soft coral in tropical oceans and is known to produce novel terpenoids with a broad spectrum of biological activities. This review provides the first comprehensive overview of terpenoids produced by soft coral Lemnalia since their first discovery in 1974. Full article

(This article belongs to the Special Issue Terpenoids from Marine Organisms)

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