Rubralactone, Rubralides A, B and C, and Rubramin Produced by<i>Penicillium rubrum</i>

Kimura, Yasuo; Yoshinari, Takashi; Koshino, Hiroyuki; Fujioka, Shozo; Okada, Katsuhide; Shimada, Atsumi

doi:10.1271/bbb.70112

Cited by 35 publications

(27 citation statements)

References 11 publications

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“…In addition to compounds 1 – 4 , six known secondary metabolites including N -methylphenyldehydroalanyl- l -prolin-anhydrid ( 5 ) [18,19], cyclo- trans -4-OH-( d )-Pro-( d )-Phe ( 6 ) [20], cyclo( d )-Pro-( d )-Val ( 7 ) [20], rubralide C ( 8 ) [21], 5′-epialtenuene ( 9 ) [22] and altenuene ( 10 ) [22] (Figure 1), were also isolated, and their structures were elucidated by comparing the NMR data with those of literature reports [18,19,20,21,22]. …”

Section: Resultsmentioning

confidence: 99%

Secondary Metabolites from Penicillium pinophilum SD-272, a Marine Sediment-Derived Fungus

Wang

et al. 2013

Marine Drugs

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Two new secondary metabolites, namely, pinodiketopiperazine A (1) and 6,7-dihydroxy-3-methoxy-3-methylphthalide (2), along with alternariol 2,4-dimethyl ether (3) and l-5-oxoproline methyl ester (4), which were isolated from a natural source for the first time but have been previously synthesized, were characterized from the marine sediment-derived fungus Penicillium pinophilum SD-272. In addition, six known metabolites (5–10) were also identified. Their structures were elucidated by analysis of the NMR and mass spectroscopic data. The absolute configuration of compound 1 was determined by experimental and calculated ECD spectra. Compound 2 displayed potent brine shrimp (Artemia salina) lethality with LD50 11.2 μM.

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Section: Resultsmentioning

confidence: 99%

Secondary Metabolites from Penicillium pinophilum SD-272, a Marine Sediment-Derived Fungus

Wang

et al. 2013

Marine Drugs

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“…A literature search revealed that just four natural phthalide derivatives have been reported from lichens: Buellolide and canesolide from Buellia canescens ; 5,7‐dihydroxy‐6‐methylphthalide from Anamylopsora pulcherrima ; and 7‐hydroxy‐5‐methoxy‐6‐methylphthalide from Usnea aciculifera . However, this type of compound was often found from fungi, such as rubralide C closely related to 5 , which has been isolated from the marine sediment‐derived fungus Penicillium pinophilum SD‐272 . The majority of secondary metabolites found in lichens are produced by the fungal partner.…”

Section: Discussionmentioning

confidence: 99%

New phenolic compounds from the lichen Parmotrema praesorediosum (Nyl.) Hale (Parmeliaceae)

Huynh

Takenaka

et al. 2015

Magnetic Reson in Chemistry

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“…). The rubralides A and C at a concentration of 100 mg L −1 , in tests with lettuce seeds, inhibited the hypocotyl elongation by 46% and 55%, respectively . The cryphonectric acid 5 (Fig.…”

Section: Introductionmentioning

confidence: 95%

Herbicidal activity of isobenzofuranones and in silico identification of their enzyme target

Teixeira

Alvarenga

Lopes

et al. 2019

Pest Management Science

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BACKGROUND Given the weed resistance to various herbicides with different mechanisms of action, the search for new compounds that are more effective and exhibit low levels of impact to other species in nature has been imperative in the field of the agriculture. For this purpose, 16 phthalides, and furan‐2(5H)‐one were synthetized and evaluated for their effectiveness as herbicides in seeds of Sorghum bicolor (sorghum), Cucumis sativus (cucumber), and Allium cepa (onion). Furthermore, a preliminary in silico study was carried out to identify the enzyme target of the most active compounds. RESULTS In the assays with S. bicolor, the mixture rac‐(3aR,4R,5S,6S,7S,7aS)‐5,6‐dibromohexahydro‐4,7‐methanoisobenzofuran‐1(3H)‐one + rac‐(3aR,4R,5R,6R,7S,7aS)‐5,6‐dibromohexahydro‐4,7‐methanoisobenzofuran‐1(3H)‐one (15a + 15b) showed comparable inhibitory activity to (S)‐metolachlor, which was used as control herbicide at concentrations ranging from 50 μm to 1000 μm. The developments of the seeds evaluated were altered by all 17 compounds, either stimulating or inhibiting. The best results were presented by compounds 15a, and 15b, either in their pure form or as a mixture. CONCLUSION The results presented by 15a, and 15b were superior to the activity of the commercial herbicide (S)‐metolachlor in the assays with C. sativus, and A. cepa. The in silico study provides strong evidence that the most active compounds bind to strigolactones esterases D14 through the same binding site of (5R)‐5‐hydroxy‐3‐methylfuran‐2(5H)‐one (H3M), which is one of the strigolactones (SLs) cleavage products. © 2019 Society of Chemical Industry

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Rubralactone, Rubralides A, B and C, and Rubramin Produced byPenicillium rubrum

Cited by 35 publications

References 11 publications

Secondary Metabolites from Penicillium pinophilum SD-272, a Marine Sediment-Derived Fungus

Secondary Metabolites from Penicillium pinophilum SD-272, a Marine Sediment-Derived Fungus

New phenolic compounds from the lichen Parmotrema praesorediosum (Nyl.) Hale (Parmeliaceae)

Herbicidal activity of isobenzofuranones and in silico identification of their enzyme target

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