Structure and chemistry of antibiotic LL-Z1271.alpha., an antifungal carbon-17 terpene

Ellestad, George A.; Evans, Ralph H.; Kunstmann, M. P.; Lancaster, John; Morton, George O.

doi:10.1021/ja00721a031

Cited by 44 publications

(31 citation statements)

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“…The absolute configuration of the compounds was determined by comparing CD curves with those previously reported for this class of compounds 17,19,25. Compounds 1–5 showed negative Cotton effects at 265–270 nm in CD curves indicating that the absolute configuration at common asymmetric centers was 4 S , 5 R , 6 S , 7 R , 8 R , 10 S as depicted.…”

Section: Resultsmentioning

confidence: 93%

Biologically Active Tetranorditerpenoids from the Fungus Sclerotinia homoeocarpa Causal Agent of Dollar Spot in Turfgrass

Herath

Carvalho

et al. 2009

J. Nat. Prod.

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Nine new tetranorditerpenoid dilactones (2-10), together with two previously reported norditerpenoids dilactones (1, 11), and two known putative biosynthetic intermediates oidiolactone-E (12) and 13 were isolated from an ethyl acetate extract of a culture medium of Sclerotinia homoeocarpa. Structures and absolute configuration of these compounds were determined by spectroscopic methods and confirmed by X-ray crystallographic analysis of representative compounds. Compounds were evaluated for herbicidal, antiplasmodial and cytotoxic activities. Compounds 1, 2, 6, 7, 11 were more active as growth inhibitors in a duckweed bioassay (I 50 values of 0.39 -0.95 µM) than more than half of 26 commercial herbicides previously evaluated using the same bioassay. Some of these compounds exhibited strong antiplasmodial activities as well, but they also had cytotoxic activity thus precluding them as potential antimalarial agents.Malaria continues to be a major cause of morbidity and mortality in many parts of the tropics and subtropics. Every year about 500 million people become ill with malaria and over a million people, most of them young children, die of this disease. 1 Wide-spread resistance to first-line antimalarial drugs has hampered the effective control of this disease. Many efforts are underway to develop new classes of antimalarials to counter this trend. 2 One of these involves searching for compounds to inhibit unique metabolic pathways in the apicoplast. 2,3 Plasmodium parasites, which cause malaria in humans, contain an organelle called the apicoplast. 4 The apicoplast is very similar to plastids (chloroplasts are one of several plastid forms) of plants and is believed to have been acquired by the engulfment of an ancestral alga and retention of the algal plastid. The apicoplast is essential for the survival of parasites, and it contains many plant-like metabolic pathways such as essential amino acid, heme, and type *To whom correspondence should be addressed. Tel.: 1-662-915-1019. Fax: 1-662-915-1006. dhammika@olemiss.edu . NIH Public AccessAuthor Manuscript J Nat Prod. Author manuscript; available in PMC 2010 December 1. NIH-PA Author ManuscriptNIH-PA Author Manuscript NIH-PA Author ManuscriptII fatty acid biosynthesis not present in the vertebrate hosts of malaria parasites. 4 Several studies have been initiated to evaluate antimalarial activity of herbicides and natural phytotoxins which are known to inhibit metabolic pathways of the plastid in plants. 5 -7 A number of plant pathogenic fungi are known to release phytotoxins that disrupt biological processes in plants. [8][9][10] Some of these have also been shown to inhibit metabolic pathways in the plastid; 11 thus, plant pathogens could be a potential source of antimalarial compounds.As part of a program to search for antimalarial compounds from natural sources, we initiated a project to screen phytopathogenic fungi for antimalarial activity. Sclerotinia homoeocarpa is the causal agent of "dollar spot," the most prevalent disease of turfgrass in...

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Section: Resultsmentioning

confidence: 93%

Biologically Active Tetranorditerpenoids from the Fungus Sclerotinia homoeocarpa Causal Agent of Dollar Spot in Turfgrass

Herath

Carvalho

et al. 2009

J. Nat. Prod.

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“…A real life example for the MDOC analysis with an apparent degree of exibility is oidiolactone B (4). The mould isolated compound 100,101 shows activity against human fungal infections and cancer cell lines. 102 The absolute conguration of its ve stereogenic centres has been established as 5S7R8R9S13S (Fig.…”

Section: Conformational Exibility: Oidolactone Bmentioning

confidence: 99%

Configuration determination by residual dipolar couplings: accessing the full conformational space by molecular dynamics with tensorial constraints

et al. 2019

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“…[92]). These molecules present a wide range of biological activity, including antitumoral, insecticidal, antifeedant, allelopathic, and fungicidal activities, special attention being paid to their the antifungal activity.…”

Section: Use Of Communic Acids As Starting Materials For the Synthmentioning

confidence: 99%

Communic Acids: Occurrence, Properties and Use as Chirons for the Synthesis of Bioactive Compounds

et al. 2012

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Communic acids are diterpenes with labdane skeletons found in many plant species, mainly conifers, predominating in the genus Juniperus (fam. Cupresaceae). In this review we briefly describe their distribution and different biological activities (anti- bacterial, antitumoral, hypolipidemic, relaxing smooth muscle, etc.). This paper also includes a detailed explanation of their use as chiral building blocks for the synthesis of bioactive natural products. Among other uses, communic acids have proven useful as chirons for the synthesis of quassinoids (formal), abietane antioxidants, ambrox and other perfume fixatives, podolactone herbicides, etc., featuring shorter and more efficient processes.

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Structure and chemistry of antibiotic LL-Z1271.alpha., an antifungal carbon-17 terpene

Abstract: The structure of a novel CnH20O5 terpenoid antifungal agent I, labeled LL-Z1271», is elucidated. In addition, the chemistry of some interesting base hydrolysis products of this mold metabolite is discussed.

Cited by 44 publications

References 1 publication

Biologically Active Tetranorditerpenoids from the Fungus Sclerotinia homoeocarpa Causal Agent of Dollar Spot in Turfgrass

Biologically Active Tetranorditerpenoids from the Fungus Sclerotinia homoeocarpa Causal Agent of Dollar Spot in Turfgrass

Configuration determination by residual dipolar couplings: accessing the full conformational space by molecular dynamics with tensorial constraints

Communic Acids: Occurrence, Properties and Use as Chirons for the Synthesis of Bioactive Compounds

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