A Novel Indole-diterpenoid, JBIR-03 with Anti-MRSA Activity from Dichotomomyces cejpii var. cejpii NBRC 103559

Ogata, Masahiro; Ueda, Jun-ichi; Hoshi, Midori; Hashimoto, Junko; Nakashima, Takuji; Anzai, Kozue; Takagi, Motoki; Shin‐ya, Kazuo

doi:10.1038/ja.2007.83

Cited by 49 publications

(46 citation statements)

References 7 publications

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“…The presence of 4-hydroxy-4-methylpent-2-enyl moiety in 3 was deduced to be necessary for the antibacterial activity against E. coli. These preliminary results, together with a previous Letter, 6 implied that endophytic fungus A. oryzae might play an important role to defend marine herbivores and bacteria for the red alga H. japonica. Indoloditerpenes are known as potent tremorgenic mycotoxins, which arouse tremor in animals by affecting neurotransmission.…”

Section: Introductionmentioning

confidence: 83%

“…[1][2][3]7 In our screening program for biologically active natural products from marine algae and their associated fungi, we have investigated an isolate of the fungus Aspergillus oryzae obtained from the marine red alga Heterosiphonia japonica. Two new indoloditerpene derivatives designated asporyzin A (1) and asporyzin B (2), one new indoloditerpene named asporyzin C (3), and three known indoloditerpenes JBIR-03 (4), 6 emindole SB (5), 5 and emeniveol (6) 4 were isolated and identified from the fungus (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

“…Two new indoloditerpene derivatives asporyzin A (1) and asporyzin B (2), one new indoloditerpene asporyzin C (3), and three known related indoloditerpenes JBIR-03 (4), emindole SB (5), and emeniveol (6) were isolated from an endophytic fungus Aspergillus oryzae, isolated from the marine red alga Heterosiphonia japonica. Their structures were unambiguously established by spectroscopic techniques.…”

Section: Introductionmentioning

confidence: 99%

“…[4][5][6] Identification of these compounds was accomplished by analysis of 1D and 2D NMR data and comparison with literature values. [4][5][6] In order to determine the chemical defensive function of this endophytic fungus A. oryzae for the marine red alga H. japonica, compounds 1-6 were examined for insecticidal and antimicrobial activities. Compound 4 was more active in the assay for insecticidal activity against brine shrimp (Artemia salina), 11 which was probably due to the presence of indole and tetrahydrofuran units by comparison with the other compounds ( Table 2).…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Indoloditerpenes from an algicolous isolate of Aspergillus oryzae

Qiao¹,

Ji²,

Liu³

et al. 2010

Bioorganic & Medicinal Chemistry Letters

124

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Section: Introductionmentioning

confidence: 83%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Indoloditerpenes from an algicolous isolate of Aspergillus oryzae

Qiao¹,

Ji²,

Liu³

et al. 2010

Bioorganic & Medicinal Chemistry Letters

124

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“…From this fungus recently several indoloditerpenes with activity against methicillin-resistant Staphylococcus aureus [10] and at GPR18 and cannabinoid receptors have been isolated [11]. 16-O-desmethylasporyergosterol-ß-Dmannoside (2) and xanthocillin X dimethyl ether (4) reduced Aβ-42 production in Aftin-5 treated cells.…”

Section: Introductionmentioning

confidence: 99%

Aβ-42 lowering agents from the marine-derived fungus Dichotomomyces cejpii

et al. 2015

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Sequential Transformations to Access Polycyclic Chemotypes: Asymmetric Crotylation and Metal Carbenoid Reactions

Becerril

Lian

et al. 2011

Angewandte Chemie

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The development of sequential, asymmetric transformations can provide rapid access to novel molecules with a high degree of skeletal and stereochemical diversity.[1] However, efficient control of the regio-and stereoselectivity during each step remains a significant challenge. [2] In this regard, stereochemically well-defined building blocks obtained from our organosilane-based enantioselective crotylation methodology [3] have been successfully employed for the preparation of libraries of complex molecules. [4] We anticipated that the sequential use of the organosilane methodology with the rhodium(II)-catalyzed asymmetric cyclopropanation [5] would produce stereochemically well-defined cyclopentene compounds with unprecedented structural complexity. In the context of diversity-oriented synthesis (DOS), [6,7] these materials would in turn retain additional reaction sites for "functional-group pairing" [8] to enable further enhancement in the complexity of the polycyclic frameworks (Scheme 1).The decomposition of unbranched vinyl diazoesters in the presence of a rhodium catalyst and an appropriate olefin donor has been extensively explored.[9] However, reports of the use of more complex diazoesters that have branching at the positions a and b to the vinyl group are less common.[4c] In this context, we envisioned that organosilane-based crotylation products would be ideally suited for the synthesis of complex diazoesters, and could thus potentially expand the scope of asymmetric transformations that utilize vinyl diazoester intermediates. Accordingly, our study was initiated with a three-component enantioselective crotylation [3] using silanes (R)-1 and (S)-1, and a subsequent diazotization to afford complex a-diazoesters 2 in high stereoselectivity. Both bromoaryl (2 a, 2 b; Scheme 2 ) and allyl ether functionalities (2 c, 2 d), both of which are necessary for further ring construction at a later stage, were readily introduced using this methodology.With the complex vinyl diazoester building blocks 2 available in useful amounts, the asymmetric synthesis of vinyl cyclopropanes was conducted using the cyclic vinyl ethers 2,3-dihydrofuran and 2,3-dihydropyran (Table 1). The reactions generally proceeded in good yields, and the diastereoselectivity was dependent on the structure of the carbenoid and the configuration of the metal catalyst. Unsurprisingly, the cyclopropanations exhibited varying levels of selectivity, which resulted from the combination of the chiral rhodium catalyst and diastereomeric a-diazoester. For instance, vinyl diazoester 2 a, which is derived from silane (R)-1, exhibited good diastereoselectivity with [Rh 2 {(S)-dosp} 4 ], but low selectivity with [Rh 2 {(R)-dosp} 4 ] ( Table 1, entries 1 and 3). In contrast, Scheme 1. Skeletal and stereochemical variation by sequential asymmetric transformations. L.A. = Lewis acid.

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A Novel Indole-diterpenoid, JBIR-03 with Anti-MRSA Activity from Dichotomomyces cejpii var. cejpii NBRC 103559

Cited by 49 publications

References 7 publications

Indoloditerpenes from an algicolous isolate of Aspergillus oryzae

Indoloditerpenes from an algicolous isolate of Aspergillus oryzae

Aβ-42 lowering agents from the marine-derived fungus Dichotomomyces cejpii

Sequential Transformations to Access Polycyclic Chemotypes: Asymmetric Crotylation and Metal Carbenoid Reactions

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