The structure of cyclooctatin, a new inhibitor of lysophospholipase.

Aoyama, Takayuki; Naganawa, Hiroshi; Muraoka, Yasuhiko; Aoyagi, Takaaki; Takeuchi, Tomio

doi:10.7164/antibiotics.45.1703

Cited by 27 publications

(23 citation statements)

References 3 publications

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“…LZ35Áheng strain by conjugal transfer to afford the LZ35Áheng-cyc strain. Fermentation of LZ35Áheng-cyc led to the isolation of cyclooctatin (Kim et al, 2009;Aoyama et al, 1992). Moreover, the sequence of the cyc gene showed 97% identity to cotB2 (Kim et al, 2009).…”

Section: Resultsmentioning

confidence: 99%

Crystallization and preliminary X-ray diffraction analysis of the diterpene cyclooctatin synthase (CYC) fromStreptomycessp. LZ35

Zhang

Shang

et al. 2014

Acta Cryst Sect F

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Terpenoids are a large and highly diverse group of natural products, with the most chemically diverse pool of structures. Terpene synthase is the key enzyme in the process of terpenoid synthesis. In this paper, the first diterpene synthase (CYC) of bacterial origin was successfully crystallized. Native and SeMetderivative crystals diffracted to 1.75 and 2.6 Å resolution, respectively. The native crystal belonged to space group P2 1 2 1 2 1 , with unit-cell parameters a = 59.10, b = 101.73, c = 108.93 Å , and contained two molecules per asymmetric unit. The SeMet-derivative crystal belonged to space group P2 1 , with unit-cell parameters a = 58.64, b = 109.47, c = 58.73 Å , = 119.35 , and had two molecules per asymmetric unit.

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Section: Resultsmentioning

confidence: 99%

Crystallization and preliminary X-ray diffraction analysis of the diterpene cyclooctatin synthase (CYC) fromStreptomycessp. LZ35

Zhang

Shang

et al. 2014

Acta Cryst Sect F

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“…Fusicoccane diterpenoids usually possessing a tricyclic (5-8-5) ring system (such as brassicicenes, cyclooctatins, fusicoccins, and periconicins) are biogenetically generated from geranylgeranyl diphosphate (GGDP) 18 , which are found from various natural sources, including bacteria 19 20 , fungi 21 22 23 24 , liverworts 25 26 , algas 27 , and higher plants 28 29 . Fusicoccane diterpenoids exhibit diverse biological activities, such as plant growth regulating activity (fusicoccins) 30 , lysophospholipase inhibitory activity (cyclooctatin) 31 , antimicrobial activity (periconicins) 32 33 , nitrification inhibitory activity (brachialactone) 34 , cytotoxicity against tumor cells (cotylenins) 35 , inhibiting insulin-stimulated GLUT4 fusion activity (fusicoccins) 35 , and so on.…”

Section: Discussionmentioning

confidence: 99%

Pericolactines A–C, a New Class of Diterpenoid Alkaloids with Unusual Tetracyclic Skeleton

Chen

et al. 2015

Sci Rep

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Fusicoccane diterpenoids usually possess a fused 5-8-5 tricyclic ring system, which are biogenetically generated from geranylgeranyl diphosphate (GGDP). In our report, three novel diterpenoid alkaloids with fusicoccane skeleton, pericolactines A–C (1–3), were isolated from Periconia sp.. Their structures with absolute configurations were determined by spectroscopic analyses and quantum chemical ECD calculation. Pericolactines A–C (1–3) are a new class of diterpenoid alkaloids with an unusual fused 5-5-8-5 tetracyclic ring system, which derive from a geranylgeranyl diphosphate (GGDP) and serine conjugated biosynthesis. They belong to the atypical diterpenoid alkaloids.

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“…Cyclooctat-9-en-7-ol ( 52 ), a member of the fusicoccane family of diterpenoids, is the biosynthetic precursor of cyclooctatin ( 45 ) [ 63 ], a potent inhibitor of lysophospholipase, which was isolated from Streptomyces melanosporofaciens [ 64 ]. The cyclization of geranylgeranyl diphosphate (GGPP, 44 ) to 52 features an unexpected carbon backbone rearrangement, which was shown recently by Kuzuyama and co-workers using isotopically labeled glucose in vivo and labeled GGPP in vitro [ 65 ].…”

Section: Reviewmentioning

confidence: 99%

Recent highlights in biosynthesis research using stable isotopes

Rinkel¹,

Dickschat²

2015

Beilstein J. Org. Chem.

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SummaryThe long and successful history of isotopic labeling experiments within natural products research has both changed and deepened our understanding of biosynthesis. As demonstrated in this article, the usage of isotopes is not at all old-fashioned, but continues to give important insights into biosynthetic pathways of secondary metabolites. This review with 85 cited references is structured by separate discussions of compounds from different classes including polyketides, non-ribosomal peptides, their hybrids, terpenoids, and aromatic compounds formed via the shikimate pathway. The text does not aim at a comprehensive overview, but instead a selection of recent important examples of isotope usage within biosynthetic studies is presented, with a special emphasis on mechanistic surprises.

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The structure of cyclooctatin, a new inhibitor of lysophospholipase.

Cited by 27 publications

References 3 publications

Crystallization and preliminary X-ray diffraction analysis of the diterpene cyclooctatin synthase (CYC) fromStreptomycessp. LZ35

Crystallization and preliminary X-ray diffraction analysis of the diterpene cyclooctatin synthase (CYC) fromStreptomycessp. LZ35

Pericolactines A–C, a New Class of Diterpenoid Alkaloids with Unusual Tetracyclic Skeleton

Recent highlights in biosynthesis research using stable isotopes

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