Amphidinolide X (I), a Novel 16‐Membered Macrodiolide from Dinoflagellate Amphidinium sp.

Tsuda, Masashi; Izui, Naoko; Shimbo, Kazutaka; Sato, Masaaki; Fukushi, Eri; Kawabata, Jun; Katsumata, Kazuhito; Horiguchi, Takeo; Kobayashi, Jun’ichi

doi:10.1002/chin.200344196

Cited by 3 publications

(4 citation statements)

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“…3 and Fig. 5 ) (Kubota et al, 2000a;Shimbo et al, 2002;Tsuda et al, 1999Tsuda et al, ,2003a. While these structures are unique, some do share similarities with previously characterized amphidinolides.…”

Section: E From Amphidinium Spsupporting

confidence: 64%

“…Stable isotope incorporation experiments have been performed on amphidinolide B, C, H, J, T1, W, X, and Y (Fig. 5) (Kobayashi et al, 1995Kubota et al, 2001b;Sato et al, 2000;Tsuda et al, 2001Tsuda et al, ,2002Tsuda et al, ,2003a. These studies have revealed that all carbons of the amphidinolides, including pendent methyl groups, which are more typically derived from S-adenosylmethionine (SAM) or propionate incorporation, are derived from acetate.…”

Section: A Amphidinolidesmentioning

confidence: 99%

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The Biosynthesis of Polyketide Metabolites by Dinoflagellates

Rein

Snyder

2006

Advances in Applied Microbiology Volume 59

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Section: E From Amphidinium Spsupporting

confidence: 64%

Section: A Amphidinolidesmentioning

confidence: 99%

The Biosynthesis of Polyketide Metabolites by Dinoflagellates

Rein

Snyder

2006

Advances in Applied Microbiology Volume 59

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“…Amphidinolide X (23) [40] is a cytotoxic 16-membered macrolide consisting of polyketide-drived diacid and diol units. The absolute configurations at C-10 and C-17 were elucidated to be S and R, respectively, by application of a modified Mosher's method.…”

Section: -5 Amphidinolides X and Ymentioning

confidence: 99%

Amphidinolides and Its Related Macrolides from Marine Dinoflagellates

Kobayashi

2008

J Antibiot

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144

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This review covers the recent results described in our publications on several new cytotoxic macrolides isolated from dinoflagellates of the genus Amphidinium in addition to an overview of the isolation, structure elucidation, synthesis, biosynthesis, and bioactivity of a series of cytotoxic macrolides, named amphidinolides, reported so far. IntroductionMarine dinoflagellates, a diverse group of unicellular eukaryotes, have been recognized as real producers of marine toxins responsible to fish and algal poisoning, as well as biologically unique organisms due to their taxonomic position and unusual chromosome structure and composition. Marine dinoflagellates have also proved to be one of the most important source of bioactive natural products, which have been investigated worldwide. We have continuously studied structurally intriguing and biologically interesting bioactive macrolides and polyketides from dinoflagellates Amphidinium sp., which are symbionts of Okinawan marine flatworms Amphiscolops sp.Thirty Culture of Dinoflagellates Amphidinium sp.Large-scale cultures of the dinoflagellates of the genus Amphidinium have been performed using seawater medium enriched with Provasoli's Erd-Schriber (ES) supplement. Static incubation with illumination in a cycle of 16 hours of light and 8 hours of darkness was carried out for two weeks at 25°C. The cultures were harvested by removal of the supernatant through suction and then centrifugation to obtain algal cells. Harvested cells were extracted with MeOH -toluene, and the extracts were subjected to a systematic separation using several chromatographies to yield cytotoxic macrolides [15ϳ26]. Isolation of New Macrolides 3-1. Amphidinolactones A and BA new 13-membered macrolide, amphidinolactone A (38), C 20 H 30 O 4 , was isolated from a strain (Y-25) of a dinoflagellate Amphidinium sp. [15]. Detailed analyses of the 1 H-1 H COSY spectrum of 38 revealed connectivities of a long carbon chain from C-2 to C-20. 1 H and 13 C chemical shifts of CH 2 -2 and CH-12 suggested that C-12 was involved in an ester linkage with C-1. 1 H-1 H couplings of the two disubstituded double bonds at C-5 and C-9 indicated the Z and E geometries, respectively. Geometries of two disubstituted double bonds at C-14 and C-17 were assigned as both Z by NOESY correlations and the carbon chemical shift of C-16, which was a typical value for a methylene carbon between two Z double bonds. Thus, the gross structure of amphidinolactone A was elucidated to be 38. The relative configurations at C-8, C-11, and C-12 in 38 were deduced from NOESY correlations.A new 26-membered macrolide, amphidinolactone B (39), C 32 H 54 O 8 , has been isolated from the same dinoflagellate Amphidinium sp. (strain Y-25) as described above [16]. Detailed analyses of the 1 H-1 H COSY and TOCSY spectra as well as HMBC correlations indicated connectivities of a long carbon chain from C-2 to C-26. 1 H and 13 C chemical shifts of C-25 indicated that C-25 was involved in an ester linkage with C-1. The NOESY correlation for...

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“…Discodermolide has been shown to possess the identical tubulin polymer stabilizing properties as taxol, which certainly indicates that comprehensive preclinical studies should be undertaken [12] . Among recent discoveries of significance, Sebastianines A and B, two novel pyridoacridine alkaloids with fresh ring systems, have been isolated from the tunicate Cystodytes dellechiajai [13] , and a novel cytotoxic 16-membered macrodiolide, Amphidinolide X, has been isolated from a marine dinoflagellate Amphidinium sp [14] .…”

Section: Discussionmentioning

confidence: 99%

Potent bioactive compounds from the ocean: some interesting aspects and applications

Pandey¹

2012

Pharmacognosy Journal

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over seventy percent of the earth's surface is covered by oceans, and it is an established fact now, that life originated in the oceans. additionally, the oceans are also the source of matchless natural products that are mainly accumulated in living organisms. several bioactive compounds of therapeutic interest have been isolated from marine invertebrates, and some of them have been reported to be of microbial origin. Numerous of these compounds show pharmacological activities and are helpful for the invention and discovery of bioactive compounds, primarily for deadly diseases like cancer, acquired immuno-deficiency syndrome, etc., while others have also been shown to possess several valuable properties. the secondary metabolites of microorganisms, algae and invertebrates, possess lifesaving properties, and are deadly toxins as well, depending on the dosage. the useful applications of these compounds, as bio-markers is also being explored, to further enrich pharmacological information. recent developments have opened colossal areas of research for the isolation of biologically active compounds from marine flora and fauna.

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Amphidinolide X (I), a Novel 16‐Membered Macrodiolide from Dinoflagellate Amphidinium sp.

Cited by 3 publications

References 1 publication

The Biosynthesis of Polyketide Metabolites by Dinoflagellates

The Biosynthesis of Polyketide Metabolites by Dinoflagellates

Amphidinolides and Its Related Macrolides from Marine Dinoflagellates

Potent bioactive compounds from the ocean: some interesting aspects and applications

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