Strongylodiols A, B and C, new cytotoxic acetylenic alcohols isolated from the Okinawan marine sponge of the genus Strongylophora as each enantiomeric mixture with a different ratio

Watanabe, Kinzo; Tsuda, Yuichiro; Yamane, Yoshihisa; Takahashi, Haruko; Iguchi, Kazuo; Naoki, Hideo; Fujita, Tsuyoshi; Soest, R.W.M. van

doi:10.1016/s0040-4039(00)01692-0

Cited by 53 publications

(50 citation statements)

References 10 publications

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“…Hydroxylation at the 6-position in a compound related to 34A may yield the strongylodiols A-J (34C-L), which were isolated from an Okinawan Petrosia (Strongylophora) sp. as enantiomeric (6R:6S) mixtures ranging from 97:3 to 69:31 for 34L and 34G, respectively [361,362]. It is uncommon to isolate natural products as enantiomeric mixtures; in this case, it is not yet known whether the mixture is an isolation artifact or reflective of the enzymatic activities.…”

Section: Marine Fatty Acids Andmentioning

confidence: 99%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

291

228

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Polyacetylenic natural products are a substantial class of often unstable compounds containing a unique carbon-carbon triple bond functionality, that are intriguing for their wide variety of biochemical and ecological functions, economic potential, and surprising mode of biosynthesis. Isotopic tracer experiments between 1960 and 1990 demonstrated that the majority of these compounds are derived from fatty acid and polyketide precursors. During the past decade, research into the metabolism of polyacetylenes has swiftly advanced, driven by the cloning of the first genes responsible for polyacetylene biosynthesis in plants, moss, fungi, and actinomycetes, and the initial characterization of the gene products.The current state of knowledge of the biochemistry and molecular genetics of polyacetylenic secondary metabolic pathways will be presented together with an up-to-date survey of new terrestrial and marine natural products, their known biological activities, and a discussion of their likely metabolic origins.

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Section: Marine Fatty Acids Andmentioning

confidence: 99%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

291

228

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“…Acetylenic alcohols, a group of sponge metabolites, exhibit great structural variations in chain length and functional groups [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. Most of these compounds have shown various interesting bioactivities such as brine shrimp lethality [1], cytotoxicity [2][3][4][5][6][9][10][11][12][13][14], a-glucosidase inhibition [15] and HIV-1 integrase inhibition [16].…”

Section: Introductionmentioning

confidence: 99%

“…Most of these compounds have shown various interesting bioactivities such as brine shrimp lethality [1], cytotoxicity [2][3][4][5][6][9][10][11][12][13][14], a-glucosidase inhibition [15] and HIV-1 integrase inhibition [16].…”

Section: Introductionmentioning

confidence: 99%

Identification of Novel Acetylenic Alcohols and a New Dihydrothiopyranone from the Tropical Sponge Reniochalina sp.

Lee

Won

et al. 2008

Lipids

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Two new acetylenic alcohols (1-2) and a new dihydrothiopyranone (3) were isolated from the tropical sponge Reniochalina sp. Their structures were determined by spectroscopic and chemical methods to be (3R)-hydroxyoctatriacont-(4E)-en-1-yne (1), 5-hydroxyheptatriacont-(3Z)-en-1-yne (2) and 2-hexadecyl-2,3-dihydrothiopyran-4-one (3). The acetylenic alcohol (1) exhibited significant growth inhibitory effect against human tumor cell lines.

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“…Yang et al have synthesized the falcarinol and panaxjapyne A by the asymmetric addition of alkynylzinc reagents to acrolein and propionaldehyde catalyzed by a 1,1'-bi-2-naphthol (BINOL)/Ti(O i Pr)4 complex and a classic Cadiot-Chodkiewicz cross-coupling reaction with high enantioselectivity (>99% ee) [16]. Zheng et al have successfully synthesized (S)-strongylodiol A and (S)-strongylodiol B, which were extracted from an Okinawan marine sponge of the genus Strongylophora and exhibited cytotoxic activities against tumor cells, by using a zinc-amino alcohol complex catalyzed 1,3-diynes addition to aldehydes with respective ee values of 55% and 58% [17,18]. However, in these reports, the chiral diynols with two or more chiral centers, such as falcarindiol or panaxytriol, were not investigated.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes

et al. 2016

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An enantioselective total synthesis of chiral falcarindiol analogues from buta-1,3-diyn-1-yltriisopropylsilane is reported. The key step in this synthesis is BINOL-promoted asymmetric diacetylene addition to aldehydes. The two chiral centers of the falcarindiol analogues can be produced by using the same kind of catalyst with high selectivity, and the final product can be obtained in only six steps.

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Strongylodiols A, B and C, new cytotoxic acetylenic alcohols isolated from the Okinawan marine sponge of the genus Strongylophora as each enantiomeric mixture with a different ratio

Cited by 53 publications

References 10 publications

Biosynthesis and function of polyacetylenes and allied natural products

Biosynthesis and function of polyacetylenes and allied natural products

Identification of Novel Acetylenic Alcohols and a New Dihydrothiopyranone from the Tropical Sponge Reniochalina sp.

Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes

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