Theonellapeptolide Id: Structure Identification of Cytotoxic Constituent from Kaliapsis sp. Sponge (Bowerbank) Collected from West Bali Sea Indonesia

Setyowati, Erna P.; Jenie, Umar Anggara; Sudarsono, Sudarsono; Kardono, L.B.S.; Rahmat, Rachmaniar

doi:10.3923/jbs.2009.29.36

Cited by 4 publications

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“…v Lamellomorpha strongylata, která je hojná v okolí Nového Zélandu (Li et al, 1998), nebo v Kaliapsis sp. z Indonésie (Setyowati et al, 2009).…”

Section: Theonellapeptolidyunclassified

Natural derivatives of beta-alanine

Patočka¹

2009

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Jihočeská univerzita v Českých Budějovicích, Zdravotně sociální fakulta, katedra radiologie a toxikologie Summary Amino acids are molecules having amino groups (-NH2), carboxylic groups (-COOH) and side chains. Amino acids play a central role as structural blocks of proteins and as intermediate metabolism products. Twenty amino acids present in proteins are carriers of their enormous chemical diversity. Natural amino acids in proteins are alpha-amino acids, which means that their amino group is located at the carbon atom bearing the carboxylic group, referred to as alpha position. However, there are also amino acids, whose amino group is located at more distant carbon atoms: beta, gamma, etc. This type of amino acid is also beta-alanine. Beta-alanine is a natural amino acid, which is, however, not used in the biosynthesis of important proteins and enzymes. In spite of this, betaalanine is the most frequently occurring beta-amino acid. It was found in animals, plants, fungi and bacteria, since it is incorporated into substances of their primary and secondary metabolism. In mammals, beta-alanine is a part of natural dipeptides carnosine and anserine, which are important molecules in their primary metabolism and also in pantothenic acid (vitamin B5), which is a part of coenzyme A. Certain secondary metabolites of beta-alanine are biologically highly active compounds, which were first found in fungi and terrestrial bacteria and later, starting from 1980, in sponges and cyanobacteria, which became considerable subjects of research. These organisms very frequently contain cyclic and acyclic peptides and depsipeptides with unusual amino acids. Natural compounds with incorporated beta-alanine are substances, which are of interest to academic as well as industrial chemists, pharmacologists and toxicologists. These substances are very important for all the specialists who are interested in bioorganic and biological chemistry.

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“…v Lamellomorpha strongylata, která je hojná v okolí Nového Zélandu (Li et al, 1998), nebo v Kaliapsis sp. z Indonésie (Setyowati et al, 2009).…”

Section: Theonellapeptolidyunclassified

Natural derivatives of beta-alanine

Patočka¹

2009

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“…Although there have been several reports on chemical studies of marine sponges and sponge-associated fungi collected from West Bali [6][7], this is an early study carried out of specimens from East Bali including Tulamben. A single specimen of sponge Aplysinella strongylata and two nudibranch extracts including Hypselodoris infucata and Glossodoris hikuerensis were investigated.…”

Section: Introductionmentioning

confidence: 99%

Bioprospecting of the Balinese marine sponges and nudibranchs

Mudianta

2018

J. Phys.: Conf. Ser.

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Abstract. Secondary metabolites play an invaluable role as a starting point in drug discovery process. Among marine organisms, sponges and nudibranch mollusc (Mollusca: Gastropoda: Nudibranchia) have been the prolific sources of bioactive secondary metabolites with diverse chemical structures and promising bioactivities. This report presents the isolation and structure elucidation of bioactive natural products from the Balinese marine sponge Aplysinella strongylata and the nudibranchs Hypselodoris infucata and Glossodoris hikuerensis. The samples were collected from Tulamben beach Bali, an unexplored site but rich in marine biodiversity. The separation and purification of the metabolites were achieved by mean of NPflash column chromatography and HPLC. Structure elucidations of the isolated compounds were completed by analysis of spectroscopic dataset including 1 H and 2D NMR. A series of bromotyrosine-derived alkaloid possessing a spirooxepinisoxazoline moiety were identified from the extract of A. strongylata. One of the metabolites, 19-hydroxypsammaplysin E (1), showed the best antimalarial activity, with an IC50 value of 6.4 μM. The absolute configuration of psammaplysin series compounds has been assigned as (6R, 7R) using experimental and calculated electronic circular dichroism (ECD) data and NMR analysis of MPA esters prepared from the acetamide derivative of psammaplysin A. A furanosesquiterpen, (-)-furodysinin (2), was identified for the first time from the nudibranch H. infucata. The compound inhibited the growth of HeLa cell line at IC50 102.7 µg/mL. Two new scalarane sesterterpenes (3-4) were characterised from an organic extract of a single specimen of the nudibranch G. hikuerensis.

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