Manzamenones A-F from the Okinawan marine sponges Plakortis Sp.: novel dimeric fatty acid derivatives possessing a bicyclo[4.3.0]nonane skeleton

Tsukamoto, Sachiko; Takeuchi, Shigeru; Ishibashi, Masami; Kobayashi, Jun’ichi

doi:10.1021/jo00045a048

Cited by 50 publications

(21 citation statements)

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“…Recently, the real producer of keramamide D was revealed to be an unculturable symbiotic bacterium of Theonella sp. 15) Manzamenone A, a dimeric fatty acid derivative isolated from a marine sponge Plakortis sp., exhibited inhibitory activity against DNA polymerases 16,17) (Fig. 6).…”

Section: )mentioning

confidence: 97%

Search for New Bioactive Marine Natural Products and Application to Drug Development

Kobayashi

2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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Natural products are well recognized as an important source of lead compounds in drug development. During the past >30 years, we have discovered >1000 novel bioactive natural products from Okinawan marine organisms (sponges, tunicates, cone shells, etc.) and microorganisms (fungi, bacteria, dinoflagellates, etc.). Some of them are used as bioprobes useful for basic studies of life sciences, while others are expected to be candidates of drug leads.

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Section: )mentioning

confidence: 97%

Search for New Bioactive Marine Natural Products and Application to Drug Development

Kobayashi

2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…This compound showed inhibition of PTP1B with an IC 50 value of 2.11±0.66 μmol/L [35] . Research on an extract of the Okinawan sponge Plakortis (unknown species) led to the isolation of manzamenones B 304 and E 305, which are fatty acid derivatives possessing a bicycle [4,3,0]nonane skeketon [217] . Both manzamenones exhibited inhibitory activity with IC 50 values of 10.8 and 13.5 μmol/L, respectively [218] (Figure 18).…”

Section: Wwwchinapharcom Jiang Cs Et Almentioning

confidence: 99%

Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

2012

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This article provides an overview of approximately 300 secondary metabolites with inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), which were isolated from various natural sources or derived from synthetic process in the last decades. The structure-activity relationship and the selectivity of some compounds against other protein phosphatases were also discussed. Potential pharmaceutical applications of several PTP1B inhibitors were presented.

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“…Plakevulin A (20) Saito et al, in press) (Figure 12) is an oxylipin metabolite possessing a cyclopentene ring isolated together with manzamenone A (21) (Tsukamoto et al, 1992) from an Okinawan marine sponge Plakortis sp. The structure was elucidated on the basis of spectroscopic data, and the absolute configurations at three chiral centers were assigned by spectroscopic data of the reductive product of 20 and application of the modified Mosher's method.…”

Section: Bioactive Products From Tunicate and Spongementioning

confidence: 99%

Bioactive products from Okinawan marine micro- and macroorganisms

Kobayashi

Tsuda

2004

Phytochem Rev

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New bioactive natural products have been recently isolated from marine dinoflagellates, marine-derived fungi, marine sponges, and tunicates. Amphidinolides G (1), H (2), X (3), and Y (4) are cytotoxic macrocyclic metabolites separated from marine dinoflagellates Amphidinium sp. Speradine A (5), modiolides A (7) and B (8), sculezonones A (9) and B (10), seragakinone A (11), dictyonamides A (12) and B (13), and sporiolides A (14) and B (15) are secondary metabolites obtained from marine-derived fungi. The absolute stereochemistry of iejimalide B (17), a cytotoxic macrolide isolated from a marine tunicate, has been determined, while plakevulin A (20), an oxylipin metabolite, has been isolated from an Okinawan marine sponge Plakortis sp. In this review the isolation, structure elucidation, and bioactivities of these marine natural products are described.

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Manzamenones A-F from the Okinawan marine sponges Plakortis Sp.: novel dimeric fatty acid derivatives possessing a bicyclo[4.3.0]nonane skeleton

Cited by 50 publications

References 1 publication

Search for New Bioactive Marine Natural Products and Application to Drug Development

Search for New Bioactive Marine Natural Products and Application to Drug Development

Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

Bioactive products from Okinawan marine micro- and macroorganisms

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