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11 pages, 3569 KiB

Open AccessArticle

New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis

by Fengjie Li, Dorte Janussen and Deniz Tasdemir

Mar. Drugs 2020, 18(2), 107; https://doi.org/10.3390/md18020107 - 11 Feb 2020

Cited by 15 | Viewed by 3867

Abstract

Latrunculia sponges represent a rich source of discorhabdin-type pyrroloiminoquinone alkaloids, a few of which comprise a dimeric structure. The anticancer-activity-guided isolation of the n-hexane subextract of the Antarctic deep-sea sponge Latrunculia biformis yielded the known compound (−)-(1R,2R,6R [...] Read more.

Latrunculia sponges represent a rich source of discorhabdin-type pyrroloiminoquinone alkaloids, a few of which comprise a dimeric structure. The anticancer-activity-guided isolation of the n-hexane subextract of the Antarctic deep-sea sponge Latrunculia biformis yielded the known compound (−)-(1R,2R,6R,8S,6’S)-discorhabdin B dimer (1) and two new derivatives, (−)-(1S,2R,6R,8S,6’S)-discorhabdin B dimer (2) and (−)-(1R,2R,6R,8S,6’S)-16’,17’-dehydrodiscorhabdin B dimer (3). The chemical structures of compounds 1–3 were elucidated by means of HR-ESIMS, NMR, [α]_D, ECD spectroscopy, and a comparison with the previously reported discorhabdin analogs. Compounds 1 and 2 showed significant in vitro anticancer activity against the human colon cancer cell line (HCT-116), with IC₅₀ values of 0.16 and 2.01 µM, respectively. Compared to monomeric discorhabdins, dimeric discorhabdins are very rare in Nature. This study adds two new discorhabdin dimers (2 and 3) to this small pyrroloiminoquinone subfamily. This is also the first report of compound 1 as a natural product and the first assessment of its in vitro anticancer activity. Full article

(This article belongs to the Special Issue Advances in Marine Alkaloids)

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10 pages, 1616 KiB

Open AccessArticle

Penicamide A, A Unique N,N′-Ketal Quinazolinone Alkaloid from Ascidian-Derived Fungus Penicillium sp. 4829

by Senhua Chen, Minghua Jiang, Bin Chen, Jintana Salaenoi, Shah-Iram Niaz, Jianguo He and Lan Liu

Mar. Drugs 2019, 17(9), 522; https://doi.org/10.3390/md17090522 - 5 Sep 2019

Cited by 24 | Viewed by 3636

Abstract

Previously unreported N,N′-ketal quinazolinone enantiomers [(−)-1 and (+)-1] and a new biogenetically related compound (2), along with six known compounds, 2-pyrovoylaminobenzamide (3), N-(2-hydroxypropanoyl)-2 amino benzoic acid amide (4), pseurotin A [...] Read more.

Previously unreported N,N′-ketal quinazolinone enantiomers [(−)-1 and (+)-1] and a new biogenetically related compound (2), along with six known compounds, 2-pyrovoylaminobenzamide (3), N-(2-hydroxypropanoyl)-2 amino benzoic acid amide (4), pseurotin A (5), niacinamide (6), citreohybridonol (7), citreohybridone C (8) were isolated from the ascidian-derived fungus Penicillium sp. 4829 in wheat solid-substrate medium culture. Their structures were elucidated by a combination of spectroscopic analyses (1D and 2D NMR and Electron Circular Dichroism data) and X-ray crystallography. The enantiomeric pair of 1 is the first example of naturally occurring N,N′-ketal quinazolinone possessing a unique tetracyclic system having 4-quinazolinone fused with tetrahydroisoquinoline moiety. The enantiomeric mixtures of 1 displayed an inhibitory effect on NO production in lipopolysaccharide-activated RAW264.7 cells, while the optically pure (–)-1 showed better inhibitory effect than (+)-1. Full article

(This article belongs to the Special Issue Advances in Marine Alkaloids)

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12 pages, 1216 KiB

Open AccessCommunication

Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues

by Maxim E. Zhidkov, Polina A. Smirnova, Oleg A. Tryapkin, Alexey V. Kantemirov, Yuliya V. Khudyakova, Olesya S. Malyarenko, Svetlana P. Ermakova, Valeria P. Grigorchuk, Moritz Kaune, Gunhild von Amsberg and Sergey A. Dyshlovoy

Mar. Drugs 2019, 17(9), 496; https://doi.org/10.3390/md17090496 - 25 Aug 2019

Cited by 22 | Viewed by 5449

Abstract

A simple approach toward the synthesis of the marine sponge derived pigment fascaplysin was used to obtain the marine alkaloids 3-bromofascaplysin and 3,10-dibromofascaplysin. These compounds were used for first syntheses of the alkaloids 14-bromoreticulatate and 14-bromoreticulatine. Preliminary bioassays showed that 14-bromoreticulatine has a [...] Read more.

A simple approach toward the synthesis of the marine sponge derived pigment fascaplysin was used to obtain the marine alkaloids 3-bromofascaplysin and 3,10-dibromofascaplysin. These compounds were used for first syntheses of the alkaloids 14-bromoreticulatate and 14-bromoreticulatine. Preliminary bioassays showed that 14-bromoreticulatine has a selective antibiotic (to Pseudomonas aeruginosa) activity and reveals cytotoxicity toward human melanoma, colon, and prostate cancer cells. 3,10-Dibromofascaplysin was able to target metabolic activity of the prostate cancer cells, without disrupting cell membrane’s integrity and had a wide therapeutic window amongst the fascaplysin alkaloids. Full article

(This article belongs to the Special Issue Advances in Marine Alkaloids)

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14 pages, 2305 KiB

Open AccessArticle

α-Conotoxin TxIB: A Uniquely Selective Ligand for α6/α3β2β3 Nicotinic Acetylcholine Receptor Attenuates Nicotine-Induced Conditioned Place Preference in Mice

by Shen You, Xiaodan Li, Jian Xiong, Xiaoyu Zhu, Dongting Zhangsun, Xiaopeng Zhu and Sulan Luo

Mar. Drugs 2019, 17(9), 490; https://doi.org/10.3390/md17090490 - 22 Aug 2019

Cited by 18 | Viewed by 3405

Abstract

α-Conotoxin TxIB is a specific antagonist of α6/α3β2β3(α6β2*) nicotinic acetylcholine receptor (nAChR) with an IC₅₀ of 28 nM. Previous studies have shown that α6β2* nAChRs are abundantly expressed in midbrain dopaminergic neurons and play an important role in mediating the mechanism of [...] Read more.

α-Conotoxin TxIB is a specific antagonist of α6/α3β2β3(α6β2*) nicotinic acetylcholine receptor (nAChR) with an IC₅₀ of 28 nM. Previous studies have shown that α6β2* nAChRs are abundantly expressed in midbrain dopaminergic neurons and play an important role in mediating the mechanism of nicotine and other drugs reward effect. It provided important targets for the development of anti-addiction drugs. The present study evaluated the pharmacological activity of TxIB in vivo with conditioned place preference (CPP) model, which were induced by subcutaneous injection (s.c.) of nicotine (NIC, 0.5 mg/kg). α-Conotoxin TxIB inhibited the expression and reinstatement of CPP in mice dose-dependently, but had no significant effect on locomotor activity. The concentrations of dopamine (DA), γ-aminobutyric acid (GABA) and noradrenaline (NE) in different brain regions were measured by enzyme-linked immunosorbent assay (ELISA). We found that TxIB could inhibit the concentrations of DA, GABA and NE in different brain regions (such as nucleus accumbens (NAc), hippocampus (HIP) and prefrontal cortex (PFC)) in NIC-induced mice. The concentrations of DA and NE were decreased in ventral tegmental area (VTA), while GABA had little change. The current work described the inhibition activity of TxIB in NIC-induced CPP, suggesting that α6β2* nAChR-targeted compound may be a promising drug for nicotine addiction treatment. Full article

(This article belongs to the Special Issue Advances in Marine Alkaloids)

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14 pages, 1632 KiB

Open AccessArticle

Tersone A-G, New Pyridone Alkaloids from the Deep-Sea Fungus Phomopsis tersa

by Shan-Chong Chen, Zhao-Ming Liu, Hai-Bo Tan, Yu-Chan Chen, Sai-Ni Li, Hao-Hua Li, Heng Guo, Shuang Zhu, Hong-Xin Liu and Wei-Min Zhang

Mar. Drugs 2019, 17(7), 394; https://doi.org/10.3390/md17070394 - 3 Jul 2019

Cited by 25 | Viewed by 4008

Abstract

Four phenylfuropyridone racemates, (±)-tersones A-C and E (1–3, 5), one phenylpyridone racemate, (±)-tersone D (4), one new pyridine alkaloid, tersone F (6), single new phenylfuropyridone, tersone G (7) and two known analogs [...] Read more.

Four phenylfuropyridone racemates, (±)-tersones A-C and E (1–3, 5), one phenylpyridone racemate, (±)-tersone D (4), one new pyridine alkaloid, tersone F (6), single new phenylfuropyridone, tersone G (7) and two known analogs 8 and 9 were isolated from the deep-sea fungus Phomopsis tersa. Their structures and absolute configurations were characterized on the basis of comprehensive spectroscopic analyses, single-crystal X-ray diffraction experiments, and electronic circular dichroism (ECD) calculations. Moreover, compounds 1–9 were evaluated for in vitro antimicrobial and cytotoxic activity. Compounds 5b and 8b exhibited antibacterial activity against S. aureus with the MIC value of 31.5 μg/mL, while compound 5b showed cytoxic activities against SF-268, MCF-7, HepG-2 and A549 cell lines with IC₅₀ values of 32.0, 29.5, 39.5 and 33.2 μM, respectively. Full article

(This article belongs to the Special Issue Advances in Marine Alkaloids)

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18 pages, 2858 KiB

Open AccessFeature PaperArticle

Bromotryptamine and Bromotyramine Derivatives from the Tropical Southwestern Pacific Sponge Narrabeena nigra

by Maria Miguel-Gordo, Sandra Gegunde, Kevin Calabro, Laurence K. Jennings, Amparo Alfonso, Grégory Genta-Jouve, Jean Vacelet, Luis M. Botana and Olivier P. Thomas

Mar. Drugs 2019, 17(6), 319; https://doi.org/10.3390/md17060319 - 30 May 2019

Cited by 12 | Viewed by 6084

Abstract

So far, the Futuna Islands located in the Central Indo-Pacific Ocean have not been inventoried for their diversity in marine sponges and associated chemical diversity. As part of the Tara Pacific expedition, the first chemical investigation of the sponge Narrabeena nigra collected around [...] Read more.

So far, the Futuna Islands located in the Central Indo-Pacific Ocean have not been inventoried for their diversity in marine sponges and associated chemical diversity. As part of the Tara Pacific expedition, the first chemical investigation of the sponge Narrabeena nigra collected around the Futuna Islands yielded 18 brominated alkaloids: seven new bromotryptamine derivatives 1–7 and one new bromotyramine derivative 8 together with 10 known metabolites of both families 9–18. Their structures were deduced from extensive analyses of nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS) data. In silico metabolite anticipation using the online tool MetWork revealed the presence of a key and minor biosynthetic intermediates. These 18 compounds showed almost no cytotoxic effect up to 10 µM on human neuroblastoma SH-SY5Y and microglia BV2 cells, and some of them exhibited an interesting neuroprotective activity by reducing oxidative damage. Full article

(This article belongs to the Special Issue Advances in Marine Alkaloids)

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10 pages, 1364 KiB

Open AccessArticle

Synergistic Anti-Candida Activity of Bengazole A in the Presence of Bengamide A

by Matthew T. Jamison, Xiao Wang, Tina Cheng and Tadeusz F. Molinski

Mar. Drugs 2019, 17(2), 102; https://doi.org/10.3390/md17020102 - 7 Feb 2019

Cited by 7 | Viewed by 3280

Abstract

Bengazoles A–G from the marine sponge Jaspis sp. exhibit potent in vitro antifungal activity against Candida spp. and other pathogenic fungi. The mechanism of action (MOA) of bengazole A was explored in Candida albicans under both liquid culture and surface culture on Mueller-Hinton [...] Read more.

Bengazoles A–G from the marine sponge Jaspis sp. exhibit potent in vitro antifungal activity against Candida spp. and other pathogenic fungi. The mechanism of action (MOA) of bengazole A was explored in Candida albicans under both liquid culture and surface culture on Mueller-Hinton agar. Pronounced dose-dependent synergistic antifungal activity was observed with bengazole A in the presence of bengamide A, which is also a natural product from Jaspis sp. The MOA of bengazole A was further explored by monitoring the sterol composition of C. albicans in the presence of sub-lethal concentrations of bengazole A. The GCMS of solvent extracts prepared from liquid cultures of C. albicans in the presence of clotrimazole―a clinically approved azole antifungal drug that suppresses ergosterol biosynthesis by the inhibition of 14α-demethylase―showed reduced cellular ergosterol content and increased concentrations of lanosterol and 24-methylenedihydrolanosterol (a shunt metabolite of ergosterol biosynthesis). No change in relative sterol composition was observed when C. albicans was cultured with bengazole A. These results eliminate an azole-like MOA for the bengazoles, and suggest that another as-yet unidentified mechanism is operative. Full article

(This article belongs to the Special Issue Advances in Marine Alkaloids)

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Review

Jump to: Research

17 pages, 2402 KiB

Open AccessReview

Marine Alkaloids with Anti-Inflammatory Activity: Current Knowledge and Future Perspectives

by Cássio R. M. Souza, Wallace P. Bezerra and Janeusa T. Souto

Mar. Drugs 2020, 18(3), 147; https://doi.org/10.3390/md18030147 - 2 Mar 2020

Cited by 69 | Viewed by 7812

Abstract

Alkaloids are nitrogenous compounds with various biological activities. Alkaloids with anti-inflammatory activity are commonly found in terrestrial plants, but there are few records of the identification and characterization of the activity of these compounds in marine organisms such as fungi, bacteria, sponges, ascidians, [...] Read more.

Alkaloids are nitrogenous compounds with various biological activities. Alkaloids with anti-inflammatory activity are commonly found in terrestrial plants, but there are few records of the identification and characterization of the activity of these compounds in marine organisms such as fungi, bacteria, sponges, ascidians, and cnidarians. Seaweed are a source of several already elucidated bioactive compounds, but few studies have described and characterized the activity of seaweed alkaloids with anti-inflammatory properties. In this review, we have gathered the current knowledge about marine alkaloids with anti-inflammatory activity and suggest future perspectives for the study and bioprospecting of these compounds. Full article

(This article belongs to the Special Issue Advances in Marine Alkaloids)

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22 pages, 9065 KiB

Open AccessReview

Recent Discovery of Heterocyclic Alkaloids from Marine-Derived Aspergillus Species

by Kuo Xu, Xiao-Long Yuan, Chen Li and and Xiao-Dong Li

Mar. Drugs 2020, 18(1), 54; https://doi.org/10.3390/md18010054 - 14 Jan 2020

Cited by 36 | Viewed by 6448

Abstract

Nitrogen heterocycles have drawn considerable attention due to of their significant biological activities. The marine fungi residing in extreme environments are among the richest sources of these basic nitrogen-containing secondary metabolites. As one of the most well-known universal groups of filamentous fungi, marine-derived [...] Read more.

Nitrogen heterocycles have drawn considerable attention due to of their significant biological activities. The marine fungi residing in extreme environments are among the richest sources of these basic nitrogen-containing secondary metabolites. As one of the most well-known universal groups of filamentous fungi, marine-derived Aspergillus species produce a large number of structurally unique heterocyclic alkaloids. This review attempts to provide a comprehensive summary of the structural diversity and biological activities of heterocyclic alkaloids that are produced by marine-derived Aspergillus species. Herein, a total of 130 such structures that were reported from the beginning of 2014 through the end of 2018 are included, and 75 references are cited in this review, which will benefit future drug development and innovation. Full article

(This article belongs to the Special Issue Advances in Marine Alkaloids)

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13 pages, 3321 KiB

Open AccessReview

Bioactive Nitrogenous Secondary Metabolites from the Marine Sponge Genus Haliclona

by Jiaying Zhu, Yang Liu, Zijun Liu, Hao Wang and Huawei Zhang

Mar. Drugs 2019, 17(12), 682; https://doi.org/10.3390/md17120682 - 3 Dec 2019

Cited by 13 | Viewed by 3953

Abstract

Marine sponge genus Haliclona, one of the most prolific sources of natural products, contains over 600 species but only a small part of them had been classified and chemically investigated. On the basis of extensive literature search, this review firstly summarizes 112 [...] Read more.

Marine sponge genus Haliclona, one of the most prolific sources of natural products, contains over 600 species but only a small part of them had been classified and chemically investigated. On the basis of extensive literature search, this review firstly summarizes 112 nitrogenous secondary metabolites from classified and unclassified Haliclona sponges as well as from their symbiotic microorganisms. Most of these substances have only been found in Haliclona sponges, and display diverse bioactive properties with potential applications in new drug discovery. Full article

(This article belongs to the Special Issue Advances in Marine Alkaloids)

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