ChemInform Abstract: Novel Naturally Occurring α‐Methoxy Acids from the Phospholipids of Caribbean Sponges

Carballeira, Néstor M.; Negrón, Vilmary; Reyes, Elba D.

doi:10.1002/chin.199223268

Cited by 2 publications

(2 citation statements)

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“…( Z )-16-pentacosenoic acid ( 129 ) and ( Z )-18-pentacosenoic acid ( 130 ) were isolated from the hydrolyzed phospholipids of the Caribbean sponge M. laevis [ 56 ], while (5 Z )-2-methoxy-5-hexadeconic acid ( 131 ) ( Figure 12 ) was reported from M. laxissima [ 57 ]. Chemical investigation of the Red Sea M. euplectellioides led to the identification of hexacosa-(6 Z ,10 Z )-dienoic acid methyl ester ( 132 ), hexacosa-(6 Z ,10 Z )-dienoic acid ( 133 ) and icosa-(8 Z ,11 Z )-dienoic acid methyl ester ( 134 ) ( Figure 12 ).…”

Section: Chemistry and Biological Activities Of The Secondary Metamentioning

confidence: 99%

Chemistry and Biological Activities of the Marine Sponges of the Genera Mycale (Arenochalina), Biemna and Clathria

et al. 2018

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Over the past seven decades, particularly since the discovery of the first marine-derived nucleosides, spongothymidine and spongouridine, from the Caribbean sponge Cryptotethya crypta in the early 1950s, marine natural products have emerged as unique, renewable and yet under-investigated pools for discovery of new drug leads with distinct structural features, and myriad interesting biological activities. Marine sponges are the most primitive and simplest multicellular animals, with approximately 8900 known described species, although more than 15,000 species are thought to exist worldwide today. These marine organisms potentially represent the richest pipeline for novel drug leads. Mycale (Arenochalina) and Clathria are recognized marine sponge genera belonging to the order Poecilosclerida, whereas Biemna was more recently reclassified, based on molecular genetics, as a new order Biemnida. Together, these sponge genera contribute to the production of physiologically active molecular entities with diverse structural features and a wide range of medicinal and therapeutic potentialities. In this review, we provide a comprehensive insight and up-to-date literature survey over the period of 1976–2018, focusing on the chemistry of the isolated compounds from members of these three genera, as well as their biological and pharmacological activities, whenever available.

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Section: Chemistry and Biological Activities Of The Secondary Metamentioning

confidence: 99%

Chemistry and Biological Activities of the Marine Sponges of the Genera Mycale (Arenochalina), Biemna and Clathria

et al. 2018

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“…A selected group of marine sponges, such as Calyx podatypa , Tropsentia roquensis or Higginsia tethyoides , biosynthesize unusual α-methoxylated fatty acids with saturated, monounsaturated, and diunsaturated alkyl chains [ 1 ]. The most ubiquitous monounsaturated α-methoxylated fatty acids in the phospholipids of sponges are those with a Δ 6 double bond, while among the diunsaturated α-methoxylated fatty acids the Δ 5,9 double bonds predominate akin with the propensity of sponges to biosynthesize very long-chain Δ 5,9 fatty acids [ 2 , 3 ]. More recently, the anticancer activity of this interesting group of fatty acids has received renewed attention, and there is substantial evidence indicating that α-methoxylation increases the anticancer properties of fatty acids by probably decreasing the fatty acid critical micelle concentration (CMC) [ 4 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Marine α-Methoxylated Fatty Acid Analogs that Effectively Inhibit the Topoisomerase IB from Leishmania donovani with a Mechanism Different from that of Camptothecin

et al. 2013

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Sponges biosynthesize α-methoxylated fatty acids with unusual biophysical and biological properties and in some cases they display enhanced anticancer activities. However, the antiprotozoal properties of the α-methoxylated fatty acids have been less studied. In this work, we describe the total synthesis of (5Z,9Z)-(±)-2-methoxy-5,9-eicosadienoic acid (1) and its acetylenic analog (±)-2-methoxy-5,9-eicosadiynoic acid (2), and report that they inhibit (EC50 values between 31 and 22 µM) the Leishmania donovani DNA topoisomerase IB enzyme (LdTopIB). The inhibition of LdTopIB (EC50 = 53 µM) by the acid (±)-2-methoxy-6-icosynoic acid (12) was studied as well. The potency of LdTopIB inhibition followed the trend 2 > 1 > 12, indicating that the effectiveness of inhibition depends on the degree of unsaturation. All of the studied α-methoxylated fatty acids failed to inhibit the human topoisomerase IB enzyme (hTopIB) at 100 µM. However, the α-methoxylated fatty acids were capable of inhibiting an active but truncated LdTopIB with which camptothecin (CPT) cannot interact suggesting that the methoxylated fatty acids inhibit LdTopIB with a mechanism different from that of CPT. The diunsaturated fatty acids displayed low cytotoxicity towards Leishmania infantum promastigotes (EC50 values between 260 and 240 µM), but 12 displayed a better cytotoxicity towards Leishmania donovani promastigotes (EC50 = 100 µM) and a better therapeutic index.

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ChemInform Abstract: Novel Naturally Occurring α‐Methoxy Acids from the Phospholipids of Caribbean Sponges

Cited by 2 publications

References 1 publication

Chemistry and Biological Activities of the Marine Sponges of the Genera Mycale (Arenochalina), Biemna and Clathria

Chemistry and Biological Activities of the Marine Sponges of the Genera Mycale (Arenochalina), Biemna and Clathria

Synthesis of Marine α-Methoxylated Fatty Acid Analogs that Effectively Inhibit the Topoisomerase IB from Leishmania donovani with a Mechanism Different from that of Camptothecin

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