Botrylactone Synthesis and Structure Revision: A Convergent Approach from D-Glucose

Bruns, W.; Horns, Stefan; Redlich, Hartmut

doi:10.1055/s-1995-3904

Cited by 14 publications

(22 citation statements)

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“…Application of the Mosher rule 12 showed a 7R configuration for esterificated products 11a and hence for (þ)-botrylactone (11). The stereochemistry of the rest of the chiral carbons was confirmed on the basis of NOE data ( Fig.…”

Section: Ddmentioning

confidence: 82%

Botrylactone: new interest in an old molecule—review of its absolute configuration and related compounds

Moraga¹,

Pinedo²,

Durán-Patrón³

et al. 2011

Tetrahedron

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a b s t r a c tThe absolute configuration of botrylactone, a unique compound with an interesting polyketide lactone skeleton with two oxirane bridges previously isolated from Botrytis cinerea and described as a powerful antibiotic, has been reviewed on the basis of sign of the optical rotation, NOE experiments and NMR method. The isolation of 7-deoxybotrylactone and 5-hydroxy-7-(4-hydroxydec-2(3)-enoyl) botrylactone enables us to characterize an intriguing new family of compounds with this interesting polyketide skeleton. A common biosynthetic origin with botcinin derivatives is proposed.

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Section: Ddmentioning

confidence: 82%

Botrylactone: new interest in an old molecule—review of its absolute configuration and related compounds

Moraga¹,

Pinedo²,

Durán-Patrón³

et al. 2011

Tetrahedron

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“…The isolation of botrylactone together with botcinins (Reino et al ., 2006), and the similarity of their spectroscopic data, suggest that these two compounds have a common biosynthetic origin. In addition, a recent structural and biosynthetic study (I. G. Collado, unpublished results) has shown that the stereochemistry of botrylactone is different from that described previously (Bruns et al ., 1995; Welmar et al ., 1979) and identical to that proposed for botcinin. The isolation of botrylactone from bcpks9 Δ and the absence of this metabolite in extracts from the bcpks6 Δ mutants are consistent with a common biosynthetic pathway.…”

Section: Resultsmentioning

confidence: 99%

The Botrytis cinerea phytotoxin botcinic acid requires two polyketide synthases for production and has a redundant role in virulence with botrydial

Dalmais¹,

Schumacher²,

Moraga³

et al. 2011

Molecular Plant Pathology

170

193

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The grey mould fungus Botrytis cinerea produces two major phytotoxins, the sesquiterpene botrydial, for which the biosynthesis gene cluster has been characterized previously, and the polyketide botcinic acid. We have identified two polyketide synthase (PKS) encoding genes, BcPKS6 and BcPKS9, that are up-regulated during tomato leaf infection. Gene inactivation and analysis of the secondary metabolite spectra of several independent mutants demonstrated that both BcPKS6 and BcPKS9 are key enzymes for botcinic acid biosynthesis. We showed that BcPKS6 and BcPKS9 genes, renamed BcBOA6 and BcBO9 (for B. cinerea botcinic acid biosynthesis), are located at different genomic loci, each being adjacent to other putative botcinic acid biosynthetic genes, named BcBOA1 to BcBOA17. Putative orthologues of BcBOA genes are present in the closely related fungus Sclerotinia sclerotiorum, but the cluster organization is not conserved between the two species. As for the botrydial biosynthesis genes, the expression of BcBOA genes is co-regulated by the Gα subunit BCG1 during both in vitro and in planta growth. The loss of botcinic acid production does not affect virulence on bean and tomato leaves. However, double mutants that do not produce botcinic acid or botrydial (bcpks6Δbcbot2Δ) exhibit markedly reduced virulence. Hence, a redundant role of botrydial and botcinic acid in the virulence of B. cinerea has been demonstrated.

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“…½ 25 D À31 (c 0.26, EtOH). UV max (EtOH) nm ("): 214 (12,700 1. FABMS m=z: 495 ðM þ NaÞ þ , 473 ðM þ HÞ þ .…”

Section: Methodsmentioning

confidence: 99%

“…Botrytis cinerea is a phytopathogen causing serious gray mold disease in many kinds of cultivated plants. The fungus produces many structurally diverse metabolites [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] and is particularly well known as a producer of abscisic acid, a plant hormone. 13) We have recently reported the isolation of new metabolites, botcinins A (1), B (2), C (3), D, E, and F, and the known metabolite, botcinolide, from an ethyl acetate extract of a strain of B. cinerea (AEM211) and their antifungal activity against Magnaporthe grisea, a pathogen of rice blast disease.…”

mentioning

confidence: 99%

2-epi-Botcinin A and 3-O-Acetylbotcineric Acid fromBotrytis cinerea

Sakuno

Tani

Nakajima

2007

Bioscience, Biotechnology, and Biochemistry

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Two metabolites, 2-epi-botcinin A and 3-O-acetylbotcineric acid, were isolated from Botrytis cinerea (AEM211). The former compound was new, and the latter was known but structurally revised by us. In a test for antifungal activity against Magnaporthe grisea, a pathogen of rice blast disease, 2-epi-botcinin A was 8 times less active than botcinin A (MIC 100 microM), and the MIC value for 3-O-acetylbotcineric acid being 100 microM.

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Botrylactone Synthesis and Structure Revision: A Convergent Approach from D-Glucose

Cited by 14 publications

References 0 publications

Botrylactone: new interest in an old molecule—review of its absolute configuration and related compounds

Botrylactone: new interest in an old molecule—review of its absolute configuration and related compounds

The Botrytis cinerea phytotoxin botcinic acid requires two polyketide synthases for production and has a redundant role in virulence with botrydial

2-epi-Botcinin A and 3-O-Acetylbotcineric Acid fromBotrytis cinerea

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