: Isolation and structure of halistatin 1 from the eastern Indian Ocean marine sponge Phakellia carteri

Pettit, George R.; Tan, Rui; Gao, Feng; Williams, M. D.; Doubek, Dennis L.; Boyd, Michael R.; Schmidt, Jean M.; Chapuis, Jean Charles; Hamel, Ernest; Bai, Ruoli; Hooper, John N. A.; Tackett, Larry P.

doi:10.1021/jo00061a030

Cited by 108 publications

(29 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The semisynthetic roflamycoin spiro-tetrahydropyran 11 is the only previous example of a polyene spiro- bis - tetrahydropyran macrolide, while the marinisporolides are the first spiroketal-polyenone-polyol macrolides class reported from natural sources. Spiroketals are commonly found in milbemycin 20 analogues and in polyether or polyol macrolide classes, such as spirastrellolides, 21 cytovaricins, 22 halistatin 1, 23 and halichondrin B, 24 inter alia .…”

Section: Resultsmentioning

confidence: 99%

Marinisporolides, Polyene-Polyol Macrolides from a Marine Actinomycete of the New Genus Marinispora

et al. 2008

View full text Add to dashboard Cite

Two new polyene macrolides, marinisporolides A and B (1, 2), were isolated from the saline culture of the marine actinomycete, strain CNQ-140, identified as a member of the new marine genus “Marinispora.” The marinisporolides are 34 membered macrolides composed of a conjugated pentaene and several pairs of 1,3-dihydroxyl functionalities. Marinisporolide A (1) contains a bicyclic spiro-bis-tetrahydropyran ketal functionality, while marinisporolide B (2) is the corresponding hemiketal. The structures of these new compounds were assigned by combined spectral and chemical methods including extensive 2D NMR experiments and correlations of 13C NMR data with Kishi’s Universal NMR Database. Chemical modifications, including methanolysis, acetonide formation, and application of the modified Mosher method, provided the full stereostructures of these molecules. Three additional macrolides, marinisporolides C–E (3–5), which are olefin geometric isomers of marinisporolide A (1), were also isolated and their structures defined. Under room light, marinisporolides A and B readily photoisomerize to C–E indicating that they are most likely produced by photochemical conversion during the cultivation or isolation procedures. Although polyenes, marinisporolides A (1) and B (2) showed weak to no antifungal activity against Candida albicans.

show abstract

Section: Resultsmentioning

confidence: 99%

Marinisporolides, Polyene-Polyol Macrolides from a Marine Actinomycete of the New Genus Marinispora

et al. 2008

View full text Add to dashboard Cite

show abstract

“…We describe here the isolation and structure Considerable research effort is currently being focused on determination of these two novel alkaloids as well as their sigdiscovery of new marine animal antineoplastic and (or) cytonificant cancer cell growth inhibitory activity. toxic constituents based on nitrogen, oxygen, and (or) sulfur heterocyclic systems (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15). Among the nitrogen heterocyclic compounds, dolastatins 10 (16) (1) and 15 (17) (2), ecteinascidin 729 (9) (3), and cephalostatin 1 (4) (18) are especially noteworthy.…”

Section: Introductionmentioning

confidence: 99%

Antineoplastic agents 285. Isolation and structures of cephalostatins 14 and 15

Pettit

Ichihara

et al. 1994

Can. J. Chem.

Self Cite

View full text Add to dashboard Cite

,2260 (1994).The tube-inhabiting marine worm, Cephalodiscus gilchristi has been found to produce a series of cytotoxic and antineoplastic disteroidal alkaloids. A substantial study concerned with discovery of new cell growth inhibitory constituents of this marine animal has led to isolation of cephalostatins 14 (50) and 15 (5b). The structures were determined by interpretation of spectral data, principally high-field (400 and 500 MHz) NMR and HRFABMS combined with NMR spectral relationships to cephalostatin 1 (4) where the structure was previously assigned by X-ray crystal structure analysis. The stereochemical assignments were established employing the ROESY NMR technique. Both new cephalostatins significantly inhibited growth of the P388 lymphocytic leukemia and a selection of human cancer cell lines. The two new cephalostatins further enhance knowledge of structure-activity parameters for these potentially important steroidal alkaloids. On a trouvC que le ver marin habitant un tube, Cephalodiscus gilchristi, produit une sCrie d'alcaloi'des distCroi'daux cytotoxiques et antinCoplastiques. Une Ctude importante relative B la dCcouverte de nouveaux constituants de cet animal marin inhibants la croissance de nouvelles cellules a conduit B I'isolement des cephalostatines 14 (50) et 15 (5b). On a dCtermini le structures par I'interprCtation des donnCes spectrales obtenues principalement par RMN A champ ClevC (400 et 500 MHz) et par HRFABMS combink avec des relations spectrales avec la ctphalostatine 1 (4) dont la structure a Cte attribuCe anterieurernent par diffraction des rayons X. Les attributions stCrkochimiques ont Ct C faites par la technique REOSY de la RMN. Les deux nouvelles cCphalostatines inhibent fortement la croissance de la leuctmie lymphocytaire P388 ainsi qu'une selection de cellules humaines can&reuses. Les deux nouvelles ~Cphalostatines augmentent nos connaissances sur les paramktres structure-activitC de ces alcaloi'des stCroi'daux potentiellement importants.[Traduit par la ridaction]

show abstract

“…A low amount of starting material is thus an undisputed way to miss out on the most active compounds as they are by definition not needed in the same amounts as other metabolites. The antimitotic macrolide halistatin-1 for example is only present at 8.8 parts per billion in the organism (Pettit et al 1993) illustrating that attention to the “small peaks” can be crucial. This has been obvious several times in the MabCent screening where seemingly empty HPLC fractions generate positive results in the screening assays.…”

Section: Discussionmentioning

confidence: 99%

MabCent: Arctic marine bioprospecting in Norway

Svenson

2012

Phytochem Rev

View full text Add to dashboard Cite

The deep waters surrounding the coastline of the northern parts of Norway represent an exciting biotope for marine exploration. Dark and cold Arctic water generates a hostile environment where the ability to adapt is crucial to survival. These waters are nonetheless bountiful and a diverse plethora of marine organisms thrive in these extreme conditions, many with the help of specialised chemical compounds. In comparison to warmer, perhaps more inviting shallower tropical waters, the Arctic region has not been as thoroughly investigated. MabCent is a Norwegian initiative based in Tromsø that aims to change this. Since 2007, scientists within MabCent have focussed their efforts on the study of marine organisms inhabiting the Arctic waters with the long term goal of novel drug discovery and development. The activities of MabCent are diverse and range from sampling the Arctic ice shelf to the chemical synthesis of promising secondary metabolites discovered during the screening process. The current review will present the MabCent pipeline from isolation to identification of new bioactive marine compounds via an extensive screening process. An overview of the main activities will be given with particular focus on isolation strategies, bioactivity screening and structure determination. Pitfalls, hard earned lessons and the results so far are also discussed.

show abstract

: Isolation and structure of halistatin 1 from the eastern Indian Ocean marine sponge Phakellia carteri

Cited by 108 publications

References 0 publications

Marinisporolides, Polyene-Polyol Macrolides from a Marine Actinomycete of the New Genus Marinispora

Marinisporolides, Polyene-Polyol Macrolides from a Marine Actinomycete of the New Genus Marinispora

Antineoplastic agents 285. Isolation and structures of cephalostatins 14 and 15

MabCent: Arctic marine bioprospecting in Norway

Contact Info

Product

Resources

About