Novel alkaloids of the aaptamine class from an Indonesian marine sponge of the genus Xestospongia

Calcul, Laurent; Longeon, Arlette; Al‐Mourabit, Ali; Guyot, Michèle; Bourguet‐Kondracki, Marie‐Lise

doi:10.1016/s0040-4020(03)01069-x

Cited by 84 publications

(63 citation statements)

References 17 publications

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“…Detail examination of spectroscopic data (IR, MS, 1D, and 2D NMR) of compound (1) readily established indentity with aaptamine (1) previously described from the Indonesian Xestospongia sp. (Calcul et al, 2003) and Aaptos aaptos (Rosmiati, 2013).…”

Section: Resultsmentioning

confidence: 99%

MARINE SPONGE Aaptos suberitoides, IT’S POTENTIAL SOURCE OF NATURAL ANTIBACTERIAL FOR CONTROLLING Vibrio harveyi ON TIGER SHRIMP (Penaeus monodon) CULTURE

Rosmiati

Parenrengi

Suryati

2015

Indonesian Aquaculture Journal

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The study aims to isolate and identify the natural antibacterial compounds potential from Aaptos suberitoides for Vibrio harveyi control on tiger shrimp (Penaeus monodon) culture. The agar diffusion method using paper discs was used to determine the antibacterial activity of extracts (diethyl ether (DEE), butanol (BUE) and aqueous (HOE) and compounds successfully isolated against Vibrio harveyi. Findings showed that the antibacterial activity was concentrated in BUE with the inhibition zone of 17.2±0.1 mm. Meanwhile, two other extracts (DEE and HOE) did not exhibit any antibacterial activity against V. harveyi. From the active BUE, it was successfully isolated two compounds giving a strong anti-vibrio activity with the inhibition zone of 22±0.1 mm. The IR, 1 H, 13 C, COSY, HMQC, HMBC, and MS spectrum analysis indicated that both active compounds identified as aaptamine (1) and 9-demethyloxyaaptamine (2). The study suggested that marine sponge A. suberitoides may have potential compounds source for controlling of V. harveyi on tiger shrimp culture.

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Section: Resultsmentioning

confidence: 99%

MARINE SPONGE Aaptos suberitoides, IT’S POTENTIAL SOURCE OF NATURAL ANTIBACTERIAL FOR CONTROLLING Vibrio harveyi ON TIGER SHRIMP (Penaeus monodon) CULTURE

Rosmiati

Parenrengi

Suryati

2015

Indonesian Aquaculture Journal

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“…According to our findings, the aaptamine analogs have significant potential to be utilized in practical AF applications. These previously undescribed and novel AF compounds from abundant and unfouled sponges of the genus Aaptos are reasonable synthetic targets and may be of microbial origin owing to their identification from samples of unrelated genera (Calcul et al, 2003). The ability to produce compounds from Aaptos sponges through microbial fermentation could enhance the cost-effectiveness of these AF compounds for practical use.…”

Section: Discussionmentioning

confidence: 99%

Zebra Mussel Antifouling Activity of the Marine Natural Product Aaptamine and Analogs

et al. 2006

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Several aaptamine derivatives were selected as potential zebra mussel (Dreissena polymorpha) antifoulants because of the noteworthy absence of fouling observed on Aaptos sponges. Sponges of the genus Aaptos collected in Manado, Indonesia consistently produce aaptamine-type alkaloids. To date, aaptamine and its derivatives have not been carefully evaluated for their antifoulant properties. Structure-activity relationship studies were conducted using several aaptamine derivatives in a zebra mussel antifouling assay. From these data, three analogs have shown significant antifouling activity against zebra mussel attachment. Aaptamine, isoaaptamine, and the demethylated aaptamine compounds used in the zebra mussel assay produced EC 50 values of 24.2, 11.6, and 18.6 μM, respectively. In addition, neither aaptamine nor isoaaptamine produced a phytotoxic response (as high as 300 μM) toward a nontarget organism, Lemna pausicostata, in a 7-day exposure. The use of these aaptamine derivatives from Aaptos sp. as potential environmentally benign antifouling alternatives to metal-based paints and preservatives is significant, not only as a possible control of fouling organisms, but also to highlight the ecological importance of these and similar biochemical defenses.

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“…In general, a compound that is heterocyclic, nitrogenous (at least one nitrogen derived from an amino acid) and has limited distribution within a plant is considered as an alkaloid. Among all screened alkaloids, the aaptamine, agelasine, indole, indolizidine, isoquinoline, piperazine, polyamine and quinolone exhibit antimicrobial potential [90][91][92][93]. However, alkaloids are not widely used for disease therapy because most of the compounds mentioned exhibit carcinogenic properties and may cause severe toxicity to humans [94][95].…”

Section: Alkaloidsmentioning

confidence: 99%

Untitled

2019

Org.Commun.

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Antibiotic resistance had first been reported not long after the discovery of the first antibiotic and has remained a major public health issue ever since. Challenges are constantly encountered during the mitigation process of antibiotic resistance in the clinical setting; especially with the emergence of the formidable superbug, a bacteria with multiple resistance towards different antibiotics; this resulted in the term multidrug resistant (MDR) bacteria. This rapid evolution of the resistance phenomenon has propelled researchers to continuously uncover new antimicrobial agents in a bid to hopefully, downplay the rate of evolution despite a drying pipeline. Recently, there has been a paradigm shift in the mining of potential antimicrobials; in the past, targets for drug discovery were from microorganisms and at current, the focus has moved onto plants, this is mainly due to the beneficial attributes that plants are able to confer over that of microorganisms. This review will briefly discuss antibiotic resistance mechanisms employed by resistant bacteria followed by a detailed expository regarding the use of secondary metabolites from plants as a potential solution to the MDR pathogen. Finally, future prospects recommending enhancements to the usage of plant secondary metabolites to directly target antibiotic resistant pathogens will be discussed.

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Novel alkaloids of the aaptamine class from an Indonesian marine sponge of the genus Xestospongia

Cited by 84 publications

References 17 publications

MARINE SPONGE Aaptos suberitoides, IT’S POTENTIAL SOURCE OF NATURAL ANTIBACTERIAL FOR CONTROLLING Vibrio harveyi ON TIGER SHRIMP (Penaeus monodon) CULTURE

MARINE SPONGE Aaptos suberitoides, IT’S POTENTIAL SOURCE OF NATURAL ANTIBACTERIAL FOR CONTROLLING Vibrio harveyi ON TIGER SHRIMP (Penaeus monodon) CULTURE

Zebra Mussel Antifouling Activity of the Marine Natural Product Aaptamine and Analogs

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