The structure of bostrycin

Noda, Toshiharu; Take, Teruo; Watanabe, Tetsuo; Abe, Jinnosuke

doi:10.1016/s0040-4020(01)93004-2

Cited by 36 publications

(23 citation statements)

References 10 publications

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“…Compound 4 was identified as abscisic acid, the plant hormone, from its spectroscopic data. Bostrycin (3) was first isolated from Bostryconema alpestre [4,5] and then from Nigrospora oryzae [8], Arthrinium phaeospermum [9], and Alternaria eichhorniae [10]. Antibacterial and phytotoxic activities have been described in these papers.…”

Section: Resultsmentioning

confidence: 99%

“…methoxy-1,2,4,4a,9a,10-hexahydroanthracen-9-one (named as 1-deoxytetrahydrobostrycin, 2), from Aspergillus sp. collected in Manado, Indonesia, together with a red pigment bostrycin (3) [4ϳ10], and the plant hormone abscisic acid (4). We describe herein the isolation, structure elucidation, and biological activity of two new compounds 1 and 2.…”

Section: Introductionmentioning

confidence: 99%

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Tetrahydrobostrycin and 1-Deoxytetrahydrobostrycin, Two New Hexahydroanthrone Derivatives, from a Marine-derived Fungus Aspergillus sp.

Nakazawa

Ukai

et al. 2008

J Antibiot

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Two new hexahydroanthrones, tetrahydrobostrycin (1) and 1-deoxytetrahydrobostrycin (2), were isolated from a marine-derived fungus Aspergillus sp. strain 05F16 collected at the coral reef of Manado, Indonesia, together with bostrycin and abscisic acid. The structures of new compounds were determined on the basis of their spectral data. Compound 1 showed weak antibacterial activity against Staphylococcus aureus and Escherichia coli and 2 against S. aureus.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Tetrahydrobostrycin and 1-Deoxytetrahydrobostrycin, Two New Hexahydroanthrone Derivatives, from a Marine-derived Fungus Aspergillus sp.

Nakazawa

Ukai

et al. 2008

J Antibiot

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“…So far, there have been only three fungi which produced compounds of bostrycin type. 10,[15][16][17] Apart from their antitumor activity, 15) this is the first report on their antimalarial and antimycobacterial activities.…”

Section: Resultsmentioning

confidence: 99%

“…In the course of our ongoing search for bioactive metabolites from the endophytic fungi, the crude extract of the unidentified fungus PSU-N24, isolated from Garcinia nigrolineata, showed interesting antimicrobial, 1) antimalarial 2) and antimycobacterial 2) activities. Further investigation of this extract led to the isolation and structural elucidation of three new hydronaphthalenone derivatives (1-3) and one new dihydroramulosin derivative (4) together with eight known compounds; (R)-mellein (5), 5) cis-4-hydroxymellein (6), 6) 8-dihydroramulosin (7), 7) 6-hydroxyramulosin (8), 7) griseofulvin (9), 8) 3-(2-hydroxypropyl)benzene-1,2-diol (10), 9) desoxybostrycin (11) 10) and austrocortinin (12). 11) Their isolation, structure determination and biological activities including antibacterial, antifungal, antimalarial and antimycobacterial activities are described in this paper.…”

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Hydronaphthalenones and a Dihydroramulosin from the Endophytic Fungus PSU-N24

et al. 2008

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Three new hydronaphthalenone derivatives (1-3) and one new dihydroramulosin derivative (4), were isolated from the endophytic fungus PSU-N24 together with eight known compounds. Their structures were elucidated by spectroscopic methods. Griseofulvin (9) displayed strong antifungal activity against Microsporum gypseum SH-MU-4 with a minimum inhibitory concentration (MIC) value of 2 m mg/ml while all metabolites exhibited very weak antibacterial activity (MIC valueՆ128 m mg/ml) against Staphylococcus aureus, both standard and methicillin-resistant strains. 3-(2-Hydroxypropyl)benzene-1,2-diol (10) showed moderate antimalarial activity against Plasmodiun falciparum with an IC 50 value of 6.68 m mg/ml. For antimycobacterial activity against Mycobacterium tuberculosis, compound 3 gave the best activity with the MIC value of 12.50 m mg/ml.

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“…To confirm the assigned structures and to obtain information bearing on the probable conformations of these materials, a complete analysis of the proton spectrum of acetonide 2 was undertaken. In the interim Noda et al (2) reported the results of their structural study of bostrycin (3), a closely related tetrahydroanthraquinone pigment. These authors found that treatment of hydrogenation products of 3 with p-bromobenzoyl chloride in pyridine yielded a crystalline ester which was subsequently hydrolyzed in these laboratories to give altersolanol B as judged by t.1.c.…”

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Stereochemistry of some Altersolanol B Derivatives and their Correlation with Bostrycin

Gordon¹,

Stoessl²,

Stothers³

1972

Can. J. Chem.

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The results of a complete analysis of the proton spectra of altersolanol B acetonide indicate that this compound exists preferentially in the half-chair conformation corresponding to that favored by the parent pigment in the solid state, as shown by previous X-ray studies. In contrast, the triacetate derivative apparently adopts the alternative half-chair conformation.Les rtsultats d'une analyse compltte r.m.n. de l'altersolanol B acttonide indique que ce compost existe prtftrentiellement sous la forme demi-chaise correspondant a celle favoriste par le pigment de base dans I'ttat solide, comme l'ont montr6 de prictdentes etudes rayons-X. En revanche, le dtrivt triacttate adopte apparemment la conformation demi-chaise alternative.Canadian Journal of Chemistry, 50, 122 (1972) In an earlier paper on some metabolites of Alternaria solani (I), structures were proposed for altersolanol B (1, R = R' = H), its triacetate (1, R = R' = Ac) and isopropylidene (2) derivatives. To confirm the assigned structures and to obtain information bearing on the probable conformations of these materials, a complete analysis of the proton spectrum of acetonide 2 was undertaken. In the interim Noda et al. (2) reported the results of their structural study of bostrycin (3), a closely related tetrahydroanthraquinone pigment. These authors found that treatment of hydrogenation products of 3 with p-bromobenzoyl chloride in pyridine yielded a crystalline ester which was subsequently hydrolyzed in these laboratories to give altersolanol B as judged by t.1.c. and U.V. spectra. X-Ray diffraction results for the p-bromobenzoate 1 (R = H, R' = p-BrC,H,CO) were presented by Takenaka et al. (3). As a further check on the correspondence between the two pigments a sample of acetonide 2 was treated with p-bromobenzoic anhydride in tetrahydrofuran containing some y-dimethylaminopyridine to yield an acetonide ester. Upon removal of the isopropylidene group, the resulting p-bromobenzoate was compared to an authentic sample of the degradation product obtained by Noda et al. mixture m.p., i.r. and U.V. spectra and specific rotation. Consequently, the structures originally proposed are undoubtedly correct but the question of preferred conformation remained.In addition to the methyl proton absorptions, the high field region of the proton spectrum of 2 consists of two overlapping AB patterns one of which is part of an ABX system; since the two AB patterns are long-range coupled a better description of the spin system may be ABMNX. To Can. J. Chem. Downloaded from www.nrcresearchpress.com by 34.214.212.150 on 05/11/18For personal use only.

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The structure of bostrycin

Cited by 36 publications

References 10 publications

Tetrahydrobostrycin and 1-Deoxytetrahydrobostrycin, Two New Hexahydroanthrone Derivatives, from a Marine-derived Fungus Aspergillus sp.

Tetrahydrobostrycin and 1-Deoxytetrahydrobostrycin, Two New Hexahydroanthrone Derivatives, from a Marine-derived Fungus Aspergillus sp.

Hydronaphthalenones and a Dihydroramulosin from the Endophytic Fungus PSU-N24

Stereochemistry of some Altersolanol B Derivatives and their Correlation with Bostrycin

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