New fungal lactone, LL-P880.beta., and a new pyrone, LL-880.gamma., from a Penicillium species

McGahren, William J.; Ellestad, George A.; Morton, George O.; Kunstmann, M. P.; Mullen, Patricia

doi:10.1021/jo00960a023

Cited by 53 publications

(28 citation statements)

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“…Compound 2 was isolated as an optically active white powder with ½a 21:8 D 2 98.7 (c 0.6, MeOH). The molecular (Table 1), the signals at d H 5.49 (1H, d, J ¼ 2.5 Hz) and 6.09 (1H, d, J ¼ 2.5 Hz) due to olefinic protons, and at d H 3.77 (3H, s) due to ZOCH 3 , along with IR absorption bands at 1738, 1654, 1576, 1235 cm 21 and a UV maximum at 282 nm, revealed the presence of a 4-methoxy-6-substituted a-pyrone moiety in 2 [12]. The cross-peaks between H-7 and H-8/H-9/H-10/H-11 were observed in the 1 H, 1 H COSY spectrum (Figure 2), which allowed us to establish one spin system from C-7 to C-11.…”

Section: Resultsmentioning

confidence: 99%

Two new compounds from the plant endophytic fungus Pestalotiopsis versicolor

Yang

Huang

et al. 2014

Journal of Asian Natural Products Research

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A new coumarin, 4,6-dihydroxy-7-formyl-3-methylcoumarin (1), and an α-pyrone derivative, 6-[(7S,8R)-8-propyloxiran-1-yl]-4-methoxy-pyran-2-one (2), together with four known α-pyrone derivatives (3-6), were isolated from the broth extract of the plant endophytic fungus Pestalotiopsis versicolor. Their structures were elucidated by extensive spectroscopic analysis and by comparison of the chemical shift values with those of related known compounds.

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Section: Resultsmentioning

confidence: 99%

Two new compounds from the plant endophytic fungus Pestalotiopsis versicolor

Yang

Huang

et al. 2014

Journal of Asian Natural Products Research

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“…The work was carried out in connection with an antiprotozoal program, but no data were presented to either confirm or deny these properties for these isolates. 43 In 1986, the physical, chemical, and biological properties of LL-P88O7, extracted from Penicillium citreo-viride, were detailed. Using a dwarf seedling rice bioassay (Oryzae sativa L. cv.…”

Section: R2 H Ohmentioning

confidence: 99%

Unusual plant‐growth regulators from microorganisms

Cutler¹,

Wells

1988

Critical Reviews in Plant Sciences

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For at least 35 years, five major plant-growth regulators have predominated the field of plant growth and development. One of the reasons for the preoccupation with indole-3-acetic acid, the gibberellins (especially GA 3 ), abscisic acid, the cytokinins, and ethylene has been the relatively large quantities with which these metabolites can be obtained from either natural sources or by synthesis. The bulk of the literature attests to the availability of these compounds. For example, the literature concerning gibberellins had already amounted to 632 abstracts and articles by 1957 66 when gibberellin, specifically GA 3 , was a relatively newly discovered compound compared to indole-3-acetic acid and ethylene.It is significant that the five major plant-growth regulators have, at last, all been found in microorganisms. Indole-3-acetic acid was discovered in Rhkopus suinis n early in the developmental history of plant-growth regulators and was called rhizopin. Gibberellins were isolated from Gibberella fujikuori (Fusarium moniliforme). 5 Ethylene has been found emanating from numerous fungi. 30 Abscisic acid and its metabolites have been recent topics of discussion relative to their identification and large titer in Cercospora cruenta.' 9 "-54 This organism produces mostly 2-cis-( + )-abscisic acid, which is the active isomer, as opposed to 2-trans-{ -)-abscisic acid which is inactive. The last well-known metabolites to be isolated from microorganisms, the cytokinins, have only recently been reported. These include transzeatin, franj-zeatin riboside, and the novel cytokinin 6-(4-hydroxy-l,3-dimethyIbut-frarc.y-2-enyIamino)-9-B-D-ribofuranosylpurine 6lf from Pseudomonas syringae pv. savastanoi, the causal organism of olive knot, which includes stem galls in ash, oleander, privet, and jasmine. Initial studies with crude ethyl acetate extracts of the culture filtrate showed that olive and tobacco callus cultures were stimulated and this indicated the probable presence of a cytokinin. Thus, all of the "major" classes of plant-growth regulators have been accounted for in microorganisms. Furthermore, it appears that the genetic influence governing the production of these important compounds has not been deleted during the evolutionary process. Until recently, it was believed that these compounds were almost totally responsible for events taking place in the differentiation and development of plants including, in certain cases, the etiology of plant diseases.Any discussion of plant-growth regulators that includes compounds other than these five often raises a hue and cry among certain circles of scientists. But the evidence supports the facts to show that there are fungal and bacterial metabolites that promote plant growth and others that inhibit it. Earlier, we reviewed the literature on (+ )-hexylitaconic acid, from Aspergillus niger K-88, that promoted lettuce root growth by approximately 250%, relative

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“…Methylation of 21 with dimethyl sulfate in acetone gave an epimeric mixture of 22a and 22b (2: 1) The CD curve of 2a showed a negative Cotton effect (,1E= -12) at 245 nm, indicating that the asymmetric center of C 6 in the lactone ring had the same S configuration as that in 2c, which exhibited ,1E = -12.5 at 246 nm. 1 ) On the other hand, a positive Cotton effect (,1E= + 12.3) at 245 nm in the CD spectrum of 2b determined the stereochemistry at C 6 as R. 5 ) Acetylation of 2a and subsequent bromination of 23 with N-bromosuccinimide (NBS) under a tungsten lamp gave 24, which was immediately treated with diazabicyclo- In summary, we devised an efficient synthetic route to produce stereoisomers of LL-P880f3 and LL-P880y after starting from a carbohydrate derivative. The synthetic method described here could be adapted for the preparation of other isomers and congeners of pestalotin.…”

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confidence: 99%