A novel way of determining the structure of artonin I, an optically active Diels–Alder type adduct, with the aid of an enzyme system of Morus alba cell cultures

Hano, Yoshio; Aida, Miwa; Nomura, Taro; Ueda, Shinichi

doi:10.1039/c39920001177

Cited by 27 publications

(16 citation statements)

References 9 publications

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“…[108] Since 235 is only a minor metabolite from the root bark of Artocarpus heterophyllus (0.7 mg), structure determination was difficult. The cooccurrence of artocarpesin (236) in the same plant led to the proposed biogenesis and structure shown in Scheme 46.…”

Section: Kuwanon J and Chalcomoracinmentioning

confidence: 99%

Chemistry and Biology of Biosynthetic Diels–Alder Reactions

2003

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Nature's repertoire of biosynthetic transformations has recently been recognized to include the Diels-Alder cycloaddition reaction. Evidence now exists that there are enzymes that mediate the Diels-Alder reaction in secondary metabolic biosynthetic pathways. 2002 marked the 100th anniversary of Alder's birth and 75 years since the discovery of the Diels-Alder reaction. It would appear that living systems discovered and made use of this ubiquitously useful ring-forming reaction eons ago for the construction of complex natural products. In this Review an overview is given of all of the known classes of natural products (polyketides, isoprenoids, phenylpropanoids, alkaloids) that have been speculated to arise by a biological Diels-Alder reaction.

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Section: Kuwanon J and Chalcomoracinmentioning

confidence: 99%

Chemistry and Biology of Biosynthetic Diels–Alder Reactions

2003

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“…However, compelling evidence from a few notable examples implicate DielsAlderase enzymes to be involved in secondary metabolite biosynthesis. Isolation of optically active Diels-Alder type adducts, such as kuwanon H and J, from mulberry (Morus alba) tree extracts [19] and from feeding experiments with M. alba cell cultures [27,28] suggests the presence of a Diels-Alderase enzyme since both the diene and dienophile are achiral (fig. 3).…”

Section: Protein Diels-alderases: From Natural Products Sourcesmentioning

confidence: 98%

The Diels-Alder reaction and biopolymer catalysis

Tarasow¹,

Eaton²

1999

CMLS, Cell. Mol. Life Sci.

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The Diels-Alder reaction provides a general site. The RNA Diels-Alderase activity was also shown to be absolutely dependent on the nature of the base and facile entry for the synthesis of six-membered modification and the presence of cupric ion. Together, cyclic structures. Consequently, it has been used extenthese results suggest that this RNA Diels-Alderase sively by organic chemists for the construction of complex compounds with pharmaceutical potential. Nature achieves a portion of its rate acceleration through also appears to have utilized this reaction in the Lewis acid catalysis, a different mechanistic mode than biosynthesis of several secondary metabolites. Given similar protein Diels-Alderases. The notion that RNA its utility, various catalysts have been discovered for can accelerate reactions through Lewis acid catalysis suggests that modified RNA may serve as a tunable the reaction ranging from simple Lewis acidic transition metals to complex catalytic antibodies. More re-catalytic platform for the creation of structurally diverse compounds using a variety of powerful chemical cently, modified RNA has also been shown to be an effective Diels-Alderase with a highly specific active transformations.

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“…This compound has been previously reported from the root barks of an Indonesian Moraceae plant, Artocarpus heterophyllus Lam. (Hano et al 1992).…”

Section: Antibiotics and Compoundmentioning

confidence: 99%