Bioactive marine metabolites.  Part 13.  Kabiramide C, a novel antifungal macrolide from nudibranch eggmasses

Matsunaga, Shigeki; Fusetani, Nobuhiro; Hashimoto, Kanehisa; Koseki, Koshi; Noma, Masana

doi:10.1021/ja00264a053

Cited by 135 publications

(70 citation statements)

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“…Three trisoxazole macrolides possessing a 30-R, 毬 -enone moiety, including the known kabiramide G (1) and the new kabiramides J (2) and K (3), were isolated from the sponge Pachastrissa nux, along with the previously reported Kabiramides B (4), C (5), and D (6). To date, the enone moiety has been found to associate solely with the trisoxazole macrolides from Pachastrissa nux.…”

Section: Kabiramide Cmentioning

confidence: 91%

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RETRACTED: Antimicrobial secondary metabolites from marine gastropod egg capsules and egg masses

Kaviarasan

Siva

Yogamoorthi

2012

Asian Pacific Journal of Tropical Biomedicine

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Section: Kabiramide Cmentioning

confidence: 91%

“…Antitumour and antifungal macrocolides have been isolated from the egg ribbon of nudibranch Hexabranchus sanguineus [5] . The gelatinous egg masses of the sea hare Aplysia Juliana have been shown to lose antimicrobial activity during embryonic development [6] .…”

Section: Kabiramide Cmentioning

confidence: 99%

RETRACTED: Antimicrobial secondary metabolites from marine gastropod egg capsules and egg masses

Kaviarasan

Siva

Yogamoorthi

2012

Asian Pacific Journal of Tropical Biomedicine

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“…RedA and C, and SphB, G, and F were isolated from the sponge Reidispongia coerulea collected south of New Caledonia and extracted according to published protocols (6,7). Kabiramide C (KabC) and halichondramide (Hal) were provided as a generous gift by Junichi Tanaka (University of Ryukyus, Okinawa, Japan) (13,14,16). Ulapualide A (UlaA) was provided as a generous gift by the late Paul Scheuer (University of Hawaii, Honolulu) (11).…”

Section: Methodsmentioning

confidence: 99%

“…All of these compounds, which include the aplyronins, mycalolides (9, 10) ulapualides (11), halichondramides (12,13), and kabiramides (12,14) (Fig. 1B) share the characteristic of a macrocyclic ring and tail, where the primary region of variability within and between different families of macrolides is associated with the macrocyclic component.…”

mentioning

confidence: 99%

Structures of microfilament destabilizing toxins bound to actin provide insight into toxin design and activity

Allingham

Zampella

D’Auria

et al. 2005

Proc. Natl. Acad. Sci. U.S.A.

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Marine macrolides that disrupt the actin cytoskeleton are promising candidates for cancer treatment. Here, we present the actinbound x-ray crystal structures of reidispongiolide A and C and sphinxolide B, three marine macrolides found among a recently discovered family of cytotoxic compounds. Their structures allow unequivocal assignment of the absolute configuration for each compound. A comparison of their actin-binding site to macrolides found in the trisoxazole family, as well as the divalent macrolide, swinholide A, reveals the existence of a common binding surface for a defined segment of their macrocyclic ring. This surface is located on a hydrophobic patch adjacent to the cleft separating domains 1 and 3 at the barbed-end of actin. The large area surrounding this surface accommodates a wide variety of conformations and designs observed in the macrocyclic component of barbed-end-targeting macrolides. Conversely, the binding pocket for the macrolide tail, located within the cleft itself, shows very limited variation. Functional characterization of these macrolides by using in vitro actin filament severing and polymerization assays demonstrate the necessity of the N-methyl-vinylformamide moiety at the terminus of the macrolide tail for toxin potency. These analyses also show the importance of stable interactions between the macrocyclic ring and the hydrophobic patch on actin for modifying filament structure and how this stability can be compromised by subtle changes in macrolactone ring composition. By identifying the essential components of these complex natural products that underlie their high actin affinity, we have established a framework for designing new therapeutic agents.cytoskeleton ͉ cytotoxins ͉ macrolides ͉ marine natural products

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“…When disturbed, both gastropterids discharge a mucus secretion that include 2, which suggests BDEs contribute to predator deterrence. Also, S. nigropunctatum transfers 2 to egg masses, where it could help prevent predation or fouling by bacteria, fungi, or other benthic organisms (Matsunaga et al, 1986). BDEs have a variety of biological activities (Sharma and Vig, 1972;Fu et al, 1995;Handayani et al, 1997) including defense against predators (Duffy and Paul, 1992;Pennings et al, 1994).…”

Section: Discussionmentioning

confidence: 99%

Chemical Defenses of Cryptic and Aposematic Gastropterid Molluscs Feeding on their Host Sponge Dysidea granulosa

2006

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Numerous opisthobranchs are known to sequester chemical defenses from their prey and use them for their own defense. Information on feeding biology is critical for understanding the ecology and evolution of molluscs, yet information on feeding biology is still scarce for many groups. Gastropterid molluscs are often found on sponges, but there is controversy as to whether they are true sponge feeders. On Guam, we found the gastropterids Sagaminopteron nigropunctatum and S. psychedelicum on the sponge Dysidea granulosa. They seem to rely on contrasting defense strategies as S. psychedelicum has vivid colors, consistent with the warning coloration found in many chemically defended opisthobranchs, whereas S. nigropunctatum is highly cryptic on the sponge. S. nigropunctatum is avoided by the pufferfish Canthigaster solandri in aquarium assays. We analyzed the secondary metabolites of the two species and found that both share polybrominated diphenyl ethers (BDEs) with their host sponge D. granulosa. S. psychedelicum and S. nigropunctatum sequester the major BDE in the sponge and accumulate it in the mantle at approximately the same concentration as in the sponge (4.03 and 2.37%, respectively), and concentrate it in their parapodia at over twice the sponge concentration (7.97 and 10.10%, respectively). We also detected trace amounts in the mucus secretion of S. psychedelicum, and quantified significant amounts in the mucus (1.84%) and egg masses (2.22%) of S. nigropunctatum. Despite contrasting color patterns displayed by the two gastropterid species, they seem to share a similar

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Bioactive marine metabolites. Part 13. Kabiramide C, a novel antifungal macrolide from nudibranch eggmasses

Cited by 135 publications

References 0 publications

RETRACTED: Antimicrobial secondary metabolites from marine gastropod egg capsules and egg masses

RETRACTED: Antimicrobial secondary metabolites from marine gastropod egg capsules and egg masses

Structures of microfilament destabilizing toxins bound to actin provide insight into toxin design and activity

Chemical Defenses of Cryptic and Aposematic Gastropterid Molluscs Feeding on their Host Sponge Dysidea granulosa

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