New diterpene alkaloids from the marine sponge Agelas mauritiana

Hong, Li-Li; Sun, Jia-Bao; Yang, Fan; Liu, Man; Tang, Jie; Sun, Fan; Lin, Hou‐Wen; Wang, Shuping; Zhang, Wei

doi:10.1039/c7ra02547e

Cited by 21 publications

(25 citation statements)

References 30 publications

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“…Unfortunately, the scarcity of the compounds-due to repeated purification of agelasine type compounds and their isomeric nature-prevented us from confirming the activity of agelasines B and D against the test bacteria. Nevertheless, previous studies on antimicrobial activity of agelasines B and D showed that both compounds had potent antimicrobial activity against S. aureus (Vik et al 2006;Hong et al 2017). Also, agelasine D had a strong and broad-spectrum antimicrobial activity against Mycobacterium tuberculosis and both aerobic and anaerobic Gram-positive and negative bacteria (Hong et al 2017).…”

Section: Antimicrobial Screeningmentioning

confidence: 93%

“…Over the years, agelasines have been reported to exhibit a broad range of bioactivities including antifungal against Cryptococcus neoformans, antileishmanial against Leishmania donovani and antibacterial against S. aureus and methicillin S. aureus (Yang et al 2012), antiprotozoal against Leishmania infantum and Trypanosoma cruzi (Vik et al 2009), antimalarial against Plasmodium falciparum (Appenzeller et al 2008), antifungal against Candida albicans, antimicrobials against Staphylococcus aureus, Bacillus subtilis (Capon and Faulkner 1984), Micrococcus luteus (Vik et al 2006), antimycobacterial against both dormant and active mycobacterium (Arai et al 2014) and an inhibitor of Na + and K + ATPase (Nakamura et al 1984). In particular, both agelasines B and D were reported to have anticancer against PC9, A549, HepG2, MCF-7, and U937 cancer cell lines (Hong et al, 2017) and a potent antimicrobial activity against S. aureus (Vik et al 2006). To date, however, almost nothing is known about antimicrobial potential of agelasines against both Gramnegative ESKAPE (A. baumanii and K. pneumoniae) and fish pathogenic (V. parahaemoliticus, E. tarda and V. salmonicida) bacteria.…”

Section: Introductionmentioning

confidence: 99%

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Agelasines B, D and antimicrobial extract of a marine sponge Agelas sp. from Tahuna Bay, Sangihe Islands, Indonesia

Balansa¹,

Wodi²,

Rieuwpassa³

et al. 2020

Biodiversitas

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Abstract. Balansa W, Wodi SIM, Rieuwpassa FJ, Ijong FG. 2020. Agelasines B, D and antimicrobial extract of Agelas sp. from Tahuna Bay, Sangihe Islands, Indonesia. Biodiversitas 21: 699-706. The alarming growth of antibiotic-resistant bacteria necessitates the discovery of new antibiotics including those for combating life-threatening ESKAPE (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa and Enterobacter sp) and fish pathogenic bacteria. This study aimed to identify antimicrobial compounds from an extract of a marine sponge collected from Enepahembang coral reef, Sangihe Islands, North Sulawesi, Indonesia. The sponge was identified by DNA barcoding as Agelas sp. and its extract was evaluated against three ESKAPE bacteria (S. aureus, K. pneumoniae, and A. baumannii) and three fish pathogenic bacteria (A. hydrophila, Edwardsiella tarda and Vibrio parahaemolyticus), using the standard disk diffusion method. It showed moderate to strong antimicrobial activity against S. aureus (25.3 mm), K. pneumoniae (15.5 mm), A. baumannii (20.2 mm), A. hydrophila (20.5 mm), E. tarda (22.4 mm) and A. salmonicida (21.2 mm). The extract was isolated by chromatographic techniques (column chromatography, flash chromatography, and high-performance liquid chromatography). The structures and relative stereochemistry of the two compounds were elucidated by HRESIMS, 1D and 2D NMR data analysis as well as by comparison with reported values. Unfortunately, limited amount of the pure compounds prevented us from further evaluating their antimicrobial activity against the test bacteria. Nevertheless, the crude extract's strong antimicrobial activity, especially against the test Gram-negative bacteria, suggests the importance of this finding in light of the recent antimicrobial drug scarcity but rapid antimicrobial resistance and the emerging paradigm of antimicrobial drug modification, redirection and/or repurposing for discovering new antibiotics particularly against the life-threatening Gram-negative bacteria.

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Section: Antimicrobial Screeningmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Agelasines B, D and antimicrobial extract of a marine sponge Agelas sp. from Tahuna Bay, Sangihe Islands, Indonesia

Balansa¹,

Wodi²,

Rieuwpassa³

et al. 2020

Biodiversitas

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“…30 In this group, the Euphorbiaceae, 78,108,109,[111][112][113][114] Cistaceae, 17,26,27,29,30,110,[115][116][117][118] Leguminoseae, 48,119,120 Compositae, 21,24 Jungermanniaceae, 121 Velloziaceae 52 and Annonaceae 122,123 plant families have been studied together with marine organisms of genus Spurilla 124 and Agelas. 74,125 The most numerous compounds of this group (Fig. 4) are those that show a carboxylic function at C18 and among them the most frequent possess an unsaturated or polyfunctionalized side chain.…”

Section: Scheme 10mentioning

confidence: 99%

“…124 8 0 -Oxoagelasine C (86) is a novel purine diterpene that was recently isolated from Agelas nakamurai and it is the only halimane purine presenting a carbonyl group at adenine C8. 125 Compounds of this type, usually known as agelasines, have been isolated from genus Agelas sponges and are very interesting owing to their antimicrobial and antispasmodic activities and their action as Na,K-ATPase enzyme inhibitors. 126 Although this group is quite numerous, only six furohalimane derivatives (38, 63-66 and 75) and a halimanolide (85) are known.…”

Section: Scheme 10mentioning

confidence: 99%

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Halimane diterpenoids: sources, structures, nomenclature and biological activities

et al. 2018

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Covering: 1970 to 2017 Diterpenes with a halimane skeleton constitute a small group of natural products that can be biogenetically considered as being between labdane and clerodane diterpenoids. Some of these compounds show biological activities, such as antitumour, mosquito repellency, germination inhibition and antimicrobial, as well as being biomarkers for tuberculosis. To the best of our knowledge, there are no reviews on these compounds. In this review, halimane skeleton diterpenoids are classified according to their biogenetic origin, characterization and/or the enzymes involved in their biosynthesis. Herein, a review of their synthesis or synthetic approaches is communicated.

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Recent Advances on Marine Alkaloids from Sponges

Bian

Wang

Zhou

et al. 2020

Chemistry & Biodiversity

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Alkaloids from marine secondary metabolites have received extensive attention from pharmacists in recent years. Miscellaneous alkaloids derived from marine sponges possessed various pharmacological activities including cytotoxicity, antimicrobial, antioxidant, and so on. Herein, we summarized 149 marine alkaloids from sponges based on their structures and bioactivities reported from 2015 to 2020 and analyzed the production environment of marine sponges with rich alkaloids. Moreover, we discussed biosynthesis routes of pyrrole and guanidine alkaloids from marine sponges Agelas and Monanchora. This article will be beneficial for future research on drugs from marine natural products.

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New diterpene alkaloids from the marine sponge Agelas mauritiana

Cited by 21 publications

References 30 publications

Agelasines B, D and antimicrobial extract of a marine sponge Agelas sp. from Tahuna Bay, Sangihe Islands, Indonesia

Agelasines B, D and antimicrobial extract of a marine sponge Agelas sp. from Tahuna Bay, Sangihe Islands, Indonesia

Halimane diterpenoids: sources, structures, nomenclature and biological activities

Recent Advances on Marine Alkaloids from Sponges

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