Ultraviolet Absorption of Steroids.

Dorfman, Louis

doi:10.1021/cr60164a002

Cited by 328 publications

(60 citation statements)

References 73 publications

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“…Moreover, when grown in the presence of ergosterol, the FKaux3O mutant strain accumulated amounts of ignosterol similar to those accumulated in nonsupplemented inhibited cultures (Table El E Effect of sterol addition on growth of the FKaux3O mutant strain blocked with fenpropimorph (0.6 ,uM) for 24 h. The inoculum was 10i cells per ml. Growth yield was measured after 18 h. Symbols: A, ergosterol, 0.1 ,ug/ml; A, ergosterol, 1 or 10 ,ug/ml; O, cholestanol, 4 ,ug/ml; U, tergitol.…”

Section: Resultsmentioning

confidence: 99%

In vivo effects of fenpropimorph on the yeast Saccharomyces cerevisiae and determination of the molecular basis of the antifungal property

Marcireau

Guilloton

Karst

1990

Antimicrob Agents Chemother

111

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The effects of fenpropimorph on sterol biosynthesis and growth of Saccharomyces cerevisiae were examined to pinpoint the mode of action of fungicides that inhibit ergosterol biosynthesis. Taking advantage of sterol auxotrophy and sterol permeability in mutant strains, we show that growth inhibition is strongly correlated with inhibition of sterol biosynthesis. We confirm that in vivo and at low concentrations, fenpropimorph inhibits A8-*A7-sterol isomerase, and in addition, when it is used at higher concentrations, it inhibits A14-sterol reductase. We show also that the fungistatic effect of fenpropimorph is not due to the accumulation of abnormal sterols in treated cells but is linked to the specific inhibition of ergosterol biosynthesis, leading to the arrest of cell proliferation in the unbudded G1 phase of the cell cycle.

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Section: Resultsmentioning

confidence: 99%

In vivo effects of fenpropimorph on the yeast Saccharomyces cerevisiae and determination of the molecular basis of the antifungal property

Marcireau

Guilloton

Karst

1990

Antimicrob Agents Chemother

111

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“…All known compounds (7-24) were identified by comparison of their chromatographic behavior, and their MS and 1 H-NMR data with those of the authentic samples (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22) 33 (3H, s, H 3 -18), 2.55 (1H, m, H-20), 2.84 (2H, m, H-1a, H-4a 3H, s, H 3 -18), 1.14 (3H, s, H 3 -29), 1.23 (3H, s, H 3 -19), 1.24 (1H, m, H-15a), 1.25 (3H, s, H 3 -28), 1.35 (3H, s, H 3 -30), 1.50 (3H, s, H 3 -27), 1.52 (1H, m, H-16b), 1.53 (3H, s, H 3 -26), 1.63 (3H, m, H 2 -6, H-20), 1.76 (1H, m, H-15b), 1.83 (1H, m, H-22a C-NMR (100 MHz, CD 3 OD): see Table 1.…”

Section: Nudamentioning

confidence: 99%

“…In a continuation of our investigation of the chemical constituents from mushrooms, we describe here the isolation and structural elucidation of three new sterols, 5a,9a-epidioxy-(22E)-ergosta-7,22-diene3b ,6a -diol (1), 5a ,9a -epidioxy-(22E)-ergosta-7,22-diene3b ,6b -diol (2) and 3b ,5a ,9a ,14b -tetrahydroxy-(22E)-ergosta-7,22-dien-6-one (3), and three new triterpenoids, sublateriols A-C (4-6), as well as eighteen known compounds, (22E)-ergosta-5,7,9(11),22-tetraen-3b-ol (7), 2c,5) ergosterol (8), 2f,6) (22E)-ergosta-5,8,22-trien-3b-ol (9), 2c,7) ergosta-5,7-dien-3b-ol (10), 2c,6) (22E)-ergosta-7,22-dien-3b-ol (11), 2c,8) ergost-7-en-3b-ol (12), 2c,6) 5a,8a-epidioxy-(22E)-ergosta-6,22-dien-3b-ol (13), 2a,9) 5a,6a:8a,9a-diepoxy-(22E)-ergost-22-ene-3b ,7a -diol (14), 2e) 5a ,9a -epidioxy-3b -hydroxy-(22E)-ergosta-7,22-dien-6-one (15), 2b) 3b,5a,9a,14a-tetrahydroxy-(22E)-ergosta-7,22-dien-6-one (16), 2b) 3b ,5a , 9a-trihydroxy-(22E)-ergosta-7,22-dien-6-one (17), 2a,10) 3b, 5a,9a-tetrahydroxyergost-7-en-6-one (18), 2b) (22E)-ergosta-7,22-diene-3b,5a,6b-triol (19), 2a,11) ergost-7-ene-3b,5a,6b-triol (20), 2b,12) (22E)-ergosta-7,22-diene-3b,5a,6a,9a-tetrol (21), 2b) (22E)-ergosta-7,22-diene-3b,5a,6b,9a-tetrol (22), 2a,10) fasciculol B (23) 13,14) and fasciculol C (24) 14,15) from four edible mushrooms, Panellus (P.) serotinus (PERS. : FR.)…”

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confidence: 99%

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New Sterols and Triterpenoids from Four Edible Mushrooms.

Yaoita

Matsuki

Iijima

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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Four edible mushrooms, Panellus serotinus, Lepista nuda, Tricholoma matsutake and Naematoloma sublateritium, have been investigated chemically. Two new sterols, 5a a,9a a-epidioxy-(22E)-ergosta-7,22-diene-3b b,6a a-diol (1) and 5a a,9a a-epidioxy-(22E)-ergosta-7,22-diene-3b b,6b b-diol (2), have been isolated from Panellus serotinus. Compound 2 was also isolated from Lepista nuda. A new sterol, 3b b,5a a,9a a,14b b-tetrahydroxy-(22E)-ergosta-7,22-dien-6-one (3), and compound 2 have been isolated from Tricholoma matsutake. Three new triterpenoids, sublateriols A-C (4-6), have been isolated from Naematoloma sublateritium. The structures of the new compounds were elucidated on the basis of their spectral data.

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“…The UV spectrum of 1 exhibited absorption maximum at 285.5 (log e 4.21) nm, implying the presence of a heteroannular triene system in the compound. 10 11) The stereochemistry at the C-24 position for 1 was determined as R by comparison with the chemical shift values of 3-8. 8,9,11) The remaining unassigned carbon at d 159.2 (s) was given the long-range correlation from the doublet proton at d 6.90, which was showing geminal coupling with H-3 at d 4.87 (m).…”

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confidence: 99%

Two New Steroidal Derivatives from the Fruit Body of Chlorophyllum molybdites.

Yoshikawa

Ikuta

Arihara

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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In the course of our research program aimed at the discovery of biologically active compounds from fungi, we have reported previously the isolation and structure elucidation of lanostane triterpenoids from the fruit bodies of Laetiporus versisporus (LLOYD) IMAZ. (Polyporaceae), 1,2) and benzofuran glycosides and a C 10 acetylenic acid from L. sulphureus (FR.) MURR. var. miniatus (JUNGH.) IMAZ., 3) and a eudesmane sesquiterpene from Lactarius laeticolorus (IMAI) IMAZ. (Russulaceae). 4) We have initiated the chemical study for Chlorophyllum molybdites (MEYER : FR.) Massee belonging to the family Agaricaceae. It is a poisonous mushroom growing on the lawn and grass ground and is distributed in tropical and subtropical regions and a restricted area in Japan.5,6) Chemical study on this fungus had led to the isolation of the pyrrolidine derivative alkaloids lepiotins A and B by Ohta et al. 7)The 70% EtOH extract of the fresh fruit bodies of the fungi was separated by successive chromatographic steps on a silica gel column followed by reversed-phase HPLC with 70-87% MeOH to afford two new steroidal compounds, 1 and 2, together with six known ones. The known compounds, (22E, 24R)-5a ,8a -epidioxyergosta-6,9,22-triene-3b -ol (3), (22E, 24R)-ergosta-8(14),22-diene-3b ,7a -diol (4), (22E,24R)-5a , 6a-epoxyergosta-8(14),22-diene-3b,7a-diol (5), (22E,24R)-ergosta-7,22-diene-3b ,5a ,6b -triol (6),9) have previously been isolated from fungi and marine sponges.Compound 1 was obtained as an amorphous powder, which showed an [MϩH] ϩ ion at m/z 437.3532 in the highresolution (HR)-FAB-MS. This corresponds to a molecular formula C 29 H 44 N 2 O, requiring nine unsaturation equivalents. The IR spectrum of 1 showed absorptions at 3450, 1655, and 1545 cm Ϫ1. The UV spectrum of 1 exhibited absorption maximum at 285.5 (log e 4.21) nm, implying the presence of a heteroannular triene system in the compound. H-detected heteronuclear multiple bond correlation spectrum (HMBC), and rotating frame nuclear Overhauser and exchange spectroscopy (ROESY) experiments enabled us to identify the (22E)-ergosta-4,6,8(14),22-tetraene nucleus.11) The stereochemistry at the C-24 position for 1 was determined as R by comparison with the chemical shift values of 3-8. 8,9,11) The remaining unassigned carbon at d 159.2 (s) was given the long-range correlation from the doublet proton at d 6.90, which was showing geminal coupling with H-3 at d 4.87 (m). These observations recognized the presence of the urea junction at C-3 position, in addition to taking its molecular formula into consideration. Next, the nuclear Overhauser effect (NOE) interactions were observed between H-3/H-2a, H-3/H-2b, H-3/NH, and H-3/H-4, in turn, NH/H-1a, suggesting a-orientation of the ureido group at C-3. Accordingly, these studies led to structure 1 as (22E,24R)-3a-ureido-ergosta-4,6,8(14),22-tetraene.Compound 2 was obtained as an amorphous powder, and the molecular formula was established as C 34 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. Received February 19, 2001 accept...

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Ultraviolet Absorption of Steroids.

Cited by 328 publications

References 73 publications

In vivo effects of fenpropimorph on the yeast Saccharomyces cerevisiae and determination of the molecular basis of the antifungal property

In vivo effects of fenpropimorph on the yeast Saccharomyces cerevisiae and determination of the molecular basis of the antifungal property

New Sterols and Triterpenoids from Four Edible Mushrooms.

Two New Steroidal Derivatives from the Fruit Body of Chlorophyllum molybdites.

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