Monanchocidin: A New Apoptosis-Inducing Polycyclic Guanidine Alkaloid from the Marine Sponge <i>Monanchora pulchra</i>

Guzii, Alla G.; Makarieva, Tatyana N.; Денисенко, В. А.; Dmitrenok, Pavel S.; Kuzmich, Alexandra S.; Dyshlovoy, Sergey A.; Krasokhin, Vladimir B.; Stonik, Valentin A.

doi:10.1021/ol101716x

Cited by 83 publications

(106 citation statements)

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“…Renieramycins are members of the tetrahydroiso-quinoline family that were isolated from marine sponges belonging to genera Reniera induces apoptosis through p53-dependent pathway and may inhibit progression and metastasis of lung cancer cells [28]. Monanchocidin is a novel polycyclic guanidine alkaloid isolated from the marine sponge Monanchora pulchra that promote cell death in human monocytic leukemia (THP-1), human cervical cancer (HeLa) and mouse epidermal (JB6 Cl41) cells [29]. Smenospongine, a sesquiterpene aminoquinone, from the sponge Smenospongia sp.…”

Section: Spongesmentioning

confidence: 99%

Introduction to Anticancer Drugs from Marine Origin

Kim

Kalimuthu

2014

Handbook of Anticancer Drugs From Marine Origin

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The chemical and biological diversity of the marine environment is extraordinary resource for the discovery of new anticancer drugs. Recent technological and methodological advances in elucidation of structure, synthesis, and biological assay have resulted in the isolation and clinical evaluation of various novel anticancer agents from marine pipeline. To understanding the marine derived anticancer compounds are useful in pharmaceutical industry and clinical applications. The marine sponges, algae, microbes, tunicates and other species from the marine pipeline are the important sources for biological active compounds. The past decade has seen a dramatic increase in the number of preclinical anticancer lead compounds from diverse marine life enter human clinical trials.Keywords Anticancer · Algae · Sponges · Marine · Bioactive compounds IntroductionCancer is a dreadful human disease, increasing with changing life style, nutrition, and global warming. A report released by the World Health Organization (WHO) showed that an estimated 12.7 million people were diagnosed with cancer globally and about 7.6 million people died of it in 2008. As estimated in this report, more than 21 million new cancer cases and 13 million deaths are expected by 2030. Although cancer accounts for around 13 % of all deaths in the world, more than 30 % of cancer deaths can be prevented by modifying or avoiding key risk factors [1]. However, almost all of the chemotherapy drugs currently in the market cause serious side effects. Natural products and their derivatives represent more than 50 % of all the drugs in clinical use of the world. Higher plants contribute not less than 25 % of the total. Almost 60 % of drugs approved for cancer treatment are of natural origin.S.-K. Kim and S. Kalimuthu 2 Although marine compounds are underrepresented in current pharmacopoeia, it is anticipated that the marine environment will become an invaluable source of novel compounds in the future [2].Marine nutraceuticals can be derived from a vast array of sources, including marine plants, microorganisms, and sponges. Marine nutraceutical products currently promoted to various countries include fish oil, chitin, chitosan, marine enzymes and chondroitin from shark cartilage, sea cucumbers and mussels. Polysaccharides derived from alga, including alginate, carrageenan and agar are widely used as thickeners and stabilizers in a variety of food ingredients. In addition, Omega PUFA (Polyunsaturated fatty acid) is an important ingredient to the nutraceutical industry [3]. It has been proven that Omega-PUFA, especially eicosapentaenoic acid (EPA) and docosahexenoic acid (DHA) play a significant role in number of aspects of human health [4].More than 70 % of our planet's surface is covered by oceans. An exciting "marine pipeline" of new anticancer clinical and preclinical agents has emerged from intense efforts over the past decade to more effectively explore the rich chemical diversity offered by marine life. The chemical adaptations generally take the form of ...

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Section: Spongesmentioning

confidence: 99%

Introduction to Anticancer Drugs from Marine Origin

Kim

Kalimuthu

2014

Handbook of Anticancer Drugs From Marine Origin

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“…Structurally, monanchomycalin B ( 1 ) contains the same pentacyclic core as monanchocidin A [3], but a hydrophobic moiety with spermidine residue as previously found in ptilomycalin A [25]. The urupocidin A ( 2 ) possesses a trisubstituted hydrocarbon chain bicyclic system with three different alkyl substituents.…”

Section: Resultsmentioning

confidence: 99%

“…In recent years it has been shown that the far-eastern marine sponge Monanchora pulchra is also a rich source of novel pentacyclic [3,4,5,6,7], bicyclic [8] and acyclic guanidine alkaloids [9,10]. It is interesting that alkaloids produced in the sponges from different locations and depths had a variety of structures.…”

Section: Introductionmentioning

confidence: 99%

“…The reasons for these differences are not clear. The alkaloids from the sponge M. pulchra demonstrate a broad spectrum of biological activities, including potent cytotoxic effects [4,5,6], induction of cellular autophagy and lysosomal membrane permeabilization [11], apoptosis [3], as well as inhibition of some cellular receptors [9,10,12,13]. For instance, it was shown earlier that the pentacyclic guanidine alkaloid monanchocidin A demonstrated inhibitory activities in electrophysiology experiments on the mouse muscle and rat α7 nAChRs [13], while acyclic guanidine alkaloids pulchranins A–C inhibited the TRPV1 receptor [9,10,12].…”

Section: Introductionmentioning

confidence: 99%

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Marine Cyclic Guanidine Alkaloids Monanchomycalin B and Urupocidin A Act as Inhibitors of TRPV1, TRPV2 and TRPV3, but not TRPA1 Receptors

et al. 2017

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Abstract:Marine sponges contain a variety of low-molecular-weight compounds including guanidine alkaloids possessing different biological activities. Monanchomycalin B and urupocidin A were isolated from the marine sponge Monanchora pulchra. We found that they act as inhibitors of the TRPV1, TRPV2, and TRPV3 channels, but are inactive against the TRPA1 receptor. Monanchomycalin B is the most active among all published marine alkaloids (EC 50 6.02, 2.84, and 3.25 µM for TRPV1, TRPV2, and TRPV3, correspondingly). Moreover, monanchomycalin B and urupocidin A are the first samples of marine alkaloids affecting the TRPV2 receptor. Two semi-synthetic urupocidin A derivatives were also obtained and tested against TRP (Transient Receptor Potential) receptors that allowed us to collect some data concerning the structure-activity relationship in this series of compounds. We showed that the removal of one of three side chains or double bonds in the other side chains in urupocidin A led to a decrease of the inhibitory activities. New ligands specific to the TRPV subfamily may be useful for the design of medicines as in the study of TRP channels biology.

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“…It was shown that this sponge contained a new cytotoxic polycyclic guanidine alkaloid that we called monanchocidin [8]. We investigated the sterol fraction from this sponge collected near the shores of Urup Is.…”

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Sterols from the toxin-containing far-east sponge Monanchora pulchra

2012

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It was shown earlier that toxin-containing marine invertebrates, in particular sponges (phylum Porifera) and sea cucumbers (phylum Echinodermata, class Holothurioidea), often contain unusual sterols instead of cholesterol and other ' 5 -sterols, in contrast with other animals [1]. They differ from cholesterol either by the position of the double bond in the steroid core (sometimes its absence) [2][3][4] or by the presence of highly alkylated side chains [5,6]. According to a hypothesis proposed by us, the unusual sterols protect the biomembranes of toxin-producing marine invertebrates from the lytic action of their own toxins as a result of sterol-toxin biochemical coordination occurring in such instances [7].In continuation of the search for new sources of biologically active compounds among invertebrates of Far-East seas, we recently found that EtOH extracts of the sponge Monanchora pulchra exhibited high cytotoxic activity. It was shown that this sponge contained a new cytotoxic polycyclic guanidine alkaloid that we called monanchocidin [8]. We investigated the sterol fraction from this sponge collected near the shores of Urup Is. (Kuril Islands, 46°07.0 N, 150°02 E) in August 2008 in order to test further this hypothesis.The sponge for chemical investigation was stored at -20°C. Thawed ground biological material (18.9 g dry wt.) was extracted (3u) with EtOH. The combined extracts were concentrated to dryness in vacuo and distributed between H 2 O and BuOH. The evaporated BuOH layer (2.14 g) was dissolved in EtOH (90%) and extracted (3u) with hexane. The combined hexane layers were concentrated to afford total nonpolar substances (0.69 g). A part (0.215 g) of this total was chromatographed over a column of silica gel (KSK, 50-160 Pm) using a hexaneoEtOAc gradient (4:1) to afford the total sterol fraction (57 mg, 0.92% of dry wt) that was separated using HPLC into three subfractions consisting of ' 5 -(1.3 mg) and ' 7 -sterols (24.3 mg), and stanols (21 mg). These were analyzed using PMR as described before [2,3,9,10].The structures of the free sterols as the acetylated derivatives were identified using GC and comparison with the relative retention times (RRT) of standard sterols and using GC-MS as before [2,3,9,10]. Table 1 presents the results. Table 1 shows that the sterol fraction from the studied sponge contained 29 previously known C 26 , C 27 , C 28 , C 29 , and C 30 compounds that had double bonds in the ' 7 , ' 7,22 , ' 7,24(28) , ' 0 , ' 22 , ' 5 , ' 5,22 , and ' 5,24(28) positions. Sterols of the ' 7 series were basic and made up 52.1% of the total sterol fraction. The stanol content was 45.1% whereas ' 5 -sterols were a minor fraction with a content of 2.8%. The principal components of the fraction were identified as 5-D-cholestan-3E-ol and 5D-cholest-7-en-3E-ol. Thus, yet another instance of toxin-(unusual sterols) biochemical coordination was found.

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Monanchocidin: A New Apoptosis-Inducing Polycyclic Guanidine Alkaloid from the Marine Sponge Monanchora pulchra

Cited by 83 publications

References 18 publications

Introduction to Anticancer Drugs from Marine Origin

Introduction to Anticancer Drugs from Marine Origin

Marine Cyclic Guanidine Alkaloids Monanchomycalin B and Urupocidin A Act as Inhibitors of TRPV1, TRPV2 and TRPV3, but not TRPA1 Receptors

Sterols from the toxin-containing far-east sponge Monanchora pulchra

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