(−)-Complanine, an inflammatory substance of marine fireworm: a synthetic study

Nakamura, Kazuhiko; Tachikawa, Yu; Uemura, Daisuke

doi:10.3762/bjoc.5.12

Cited by 11 publications

(15 citation statements)

References 10 publications

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“…The isolated, synthetic complanine was identical in all its spectral data to the previously reported natural material [3], with an optical rotation in reasonable agreement ([α] D 22 −12.1 ( c 0.85, H 2 O), lit. −9.9 ( c 0.12, H 2 O)).…”

Section: Resultssupporting

confidence: 72%

“…Subsequent copper-mediated N–O bond cleavage gave chiral diol 8 in 97% ee (determined by HPLC analysis using a chiral stationary phase). Diol 8 had identical spectroscopic properties compared to those reported by Nakamura and Uemura and intercepted their synthesis of ( R )-(−)-complanine [3]. Thus, the conversion of 8 to the corresponding amino alcohol was readily effected by azide formation and subsequent reduction.…”

Section: Resultsmentioning

confidence: 56%

“…1), showing it to be related to other natural products that possess the vicinal amino alcohol moiety. Using a chiral-synthon approach, ( R )-(−)-complanine was synthesized in a sequence of nine linear steps, beginning with ( R )-malic acid [3]. …”

Section: Introductionmentioning

confidence: 99%

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Enantioselective total synthesis of (R)-(−)-complanine

Kamanos¹,

Withey²

2012

Beilstein J. Org. Chem.

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Section: Resultssupporting

confidence: 72%

Section: Resultsmentioning

confidence: 56%

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Enantioselective total synthesis of (R)-(−)-complanine

Kamanos¹,

Withey²

2012

Beilstein J. Org. Chem.

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“…Complanine is a non-peptidic carbon-based compound, and was shown to activate protein kinase C (PKC) in the presence of Ca 2+ and TPA (12- O- tetradecanoylphorbol 13-acetate) [ 177 ]. This activation leads to a signal transduction cascade resulting in the activation of an inflammatory mediator TNF-α (“Tumor Necrosis factor”) and its downstream signaling molecules [ 185 ]. In 2008, Nakamura et al hypothesized that complanine binds to the phospholipid binding site of PKC, and later confirmed this to be true [ 186 ].…”

Section: Lophotrochozoa (=Spiralia)mentioning

confidence: 99%

Quo Vadis Venomics? A Roadmap to Neglected Venomous Invertebrates

Reumont

Campbell

Jenner

2014

Toxins

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Venomics research is being revolutionized by the increased use of sensitive -omics techniques to identify venom toxins and their transcripts in both well studied and neglected venomous taxa. The study of neglected venomous taxa is necessary both for understanding the full diversity of venom systems that have evolved in the animal kingdom, and to robustly answer fundamental questions about the biology and evolution of venoms without the distorting effect that can result from the current bias introduced by some heavily studied taxa. In this review we draw the outlines of a roadmap into the diversity of poorly studied and understood venomous and putatively venomous invertebrates, which together represent tens of thousands of unique venoms. The main groups we discuss are crustaceans, flies, centipedes, non-spider and non-scorpion arachnids, annelids, molluscs, platyhelminths, nemerteans, and echinoderms. We review what is known about the morphology of the venom systems in these groups, the composition of their venoms, and the bioactivities of the venoms to provide researchers with an entry into a large and scattered literature. We conclude with a short discussion of some important methodological aspects that have come to light with the recent use of new -omics techniques in the study of venoms.

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“…Finally, we obtained new compounds, complanine (4) and neocomplanines A (5) and B (6) (Fig. 6) [43,44].…”

Section: Marine Firewormmentioning

confidence: 99%

Recent insights into natural venoms

Uemura

Han

Hanif

et al. 2012

Pure and Applied Chemistry

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Toxic substances that occur in nature have various structures and functions. In fact, the very novelty of their structures and functions sometimes extends far beyond the realm of human imagination, and the capabilities of these compounds are still largely untapped despite the major advances of modern science. In this report we focus on the most recent developments in this field, with a particular emphasis on natural venoms, marine sunscreen, and marine huge molecules.Finally, the U.S. Food and Drug Administration approved Halaven ® (eribulin mesylate) for the treatment of metastatic breast cancer on 16 November 2010. Overall, 25 years had elapsed from the discovery of halichondrin B (2) until it was developed into a drug.Let us consider the significance of the development of Halaven. First, the use of a 62-step chemical synthetic process to produce a molecule with 19 stereocenters as a pharmaceutical product is already quite an accomplishment. This demonstrates the rapid development of modern organic chemistry and the powerful impetus for making new drugs. Moreover, the rapid development of process chemistry that enables the supply of several kilograms a year is also apparent. An understanding of scientific facts and principles at an astonishingly high level is indispensable for drug discovery, and such processes should not be regarded simply as business endeavors [36].Eribulin (3) is a microtubule dynamics inhibitor, and its mode of action differs from taxanes and vinblastine, which inhibit both the growth and the shortening of microtubules [37,38]. Interestingly, eribulin causes the nonproductive aggregation of tubulin. NATURAL VENOMSWe will now focus on the most recent developments in the field of natural venoms. The toxic constituents produced by relatively lower animals have been well studied. Meanwhile, venomous mammals are extremely rare: only a few members of shrew and platypus have been demonstrated to produce toxic venom. However, owing to their instability as well as the difficulty of collecting fresh saliva and salivary gland specimens in sufficiently large amounts, their unique venoms have not been well investigated. The recent development of platypus and shrew venoms in this issue has been described by Dr. Masaki Kita [2,[39][40][41]. Spider wasp venomThe female solitary spider wasp, a member of the spider wasp family Pompilidae, hunts spiders and lays her eggs on them, just as described in the classic Souvenirs Entomologiques (Book of Insects in English) by Jean-Henri Fabre (Fig. 4). The spiders are paralyzed by an anesthetic, and they remain alive without decomposing to become food for larvae that hatch in the nest. Fabre describes the spider wasp as an expert anesthesiologist. However, is this really a case of inserting the stinger into a nerve and administering an anesthetic? To answer this question, we have started research by collecting spider wasps [42].D. UEMURA et al.

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(−)-Complanine, an inflammatory substance of marine fireworm: a synthetic study

Abstract: SummaryThe synthesis of (−)-complanine, an inflammatory substance of Eurythoe complanata, was accomplished by a “chiral synthon” approach. The absolute configuration of this molecule was determined to be R.

Cited by 11 publications

References 10 publications

Enantioselective total synthesis of (R)-(−)-complanine

Enantioselective total synthesis of (R)-(−)-complanine

Quo Vadis Venomics? A Roadmap to Neglected Venomous Invertebrates

Recent insights into natural venoms

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