Structures and Phytotoxicity of Metabolites from<i>Valsa ceratosperma</i>

Okuno, Toshikatsu; Oikawa, Satoru; Goto, Takanobu; Sawai, Ko; Shirahama, Haruhisa; Matsumoto, Takeshi

doi:10.1080/00021369.1986.10867484

Cited by 11 publications

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“…PSU-F100 exhibited antibacterial activity against the standard Staphylococcus aureus ATCC 25923 (SA). We report herein the isolation and structure determination of one new [11]cytochalasin derivative, xylarisin (1), together with six known metabolites: three mellein derivatives: (R)-(Ϫ)-mellein methyl ether (2), 4) (R)-(Ϫ)-5-carboxymellein (3) 5) and (R)-(Ϫ)-5-hydroxymethylmellein (4), 5) one pyrone derivative: 6-[(1R)-1-hydroxypentyl]-4-methoxy-2H-pyran-2-one (5) 6) and two carboxylic acids: (2E,4S)-2,4-dimethyloct-2-enoic acid (6) 7) and piliformic acid (7). 8,9) Compound 6 was isolated from a natural source for the first time.…”

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An [11]Cytochalasin Derivative from the Marine-Derived Fungus Xylaria sp. PSU-F100

Rukachaisirikul

Khamthong

Sukpondma

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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A new [11]cytochalasin derivative, xylarisin (1), was isolated from the marine-derived fungus Xylaria sp. PSU-F100 along with six known metabolites: three mellein derivatives (2-4), one pyrone derivative (5) and two carboxylic acids (6,7). The structure and stereochemistry of 1 were determined by NMR and X-ray diffraction analyses. All isolated compounds showed mild antibacterial activity against standard Staphylococcus aureus ATCC 25923 and methicillin-resistant strain.

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confidence: 99%

An [11]Cytochalasin Derivative from the Marine-Derived Fungus Xylaria sp. PSU-F100

Rukachaisirikul

Khamthong

Sukpondma

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Fraction V was submitted to repeated column chromatography on RP-18 silica gel with MeOH-H 2 O gradient (1:1, 6:4) and silica gel with CHCl 3 -MeOH gradient (9:1, 8:2) to afford 4 (32 mg), 5 (8 mg). Fraction VI was repeatedly subjected to column chromatography on Sephadex LH-20 with MeOH and RP-18 silica gel with MeOH-H 2 O gradient (3:7, 6:4) to give compounds 7 (24 mg), 8 (46 mg), and 10 (35 mg).The compounds were identified using NMR and mass spectrometry by comparison with reported spectroscopic data in the literature and determined as 5-hydroxymellein (1) [6], 5-methylmellein (2) [7], 5-carboxymellein (3) [7,8], hymatoxin C (4) [9], hymatoxin D (5) [9], halorosellinic acid (6) [8], cerebroside C (7) [10], (2S,3S,4R,2cR)-2-(2c-hydroxytetracosanoylamino)octadecane-1,3,4-triol (8) [11], cerevisterol (9) [12], adenosine (10) [13], and succinic acid (11) [14]. Compounds 2-9 were isolated from the fungal genus Xylaria for the first time.…”

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confidence: 99%

“…The compounds were identified using NMR and mass spectrometry by comparison with reported spectroscopic data in the literature and determined as 5-hydroxymellein (1) [6], 5-methylmellein (2) [7], 5-carboxymellein (3) [7,8], hymatoxin C (4) [9], hymatoxin D (5) [9], halorosellinic acid (6) [8], cerebroside C (7) [10], (2S,3S,4R,2cR)-2-(2c-hydroxytetracosanoylamino)octadecane-1,3,4-triol (8) [11], cerevisterol (9) [12], adenosine (10) [13], and succinic acid (11) [14]. Compounds 2-9 were isolated from the fungal genus Xylaria for the first time.…”

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Secondary metabolites of endophytic fungus Xylaria sp. YC-10 of Azadirachta indica

Chen

Miao

2011

Chem Nat Compd

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Endophytic fungi grow within their plant host without causing apparent disease symptoms. In their symbiotic association, the host plant protects and feeds the endophyte, which in return produces bioactive metabolites to enhance the growth and competitiveness of the host and to protect it from herbivores and plant pathogens [1]. They are recognized as producers of a vast array of secondary metabolites, many of them with promising bioactivities [1][2][3]. Azadirachta indica A. Juss (Meliaceae), commonly known as "neem," is of considerable economic importance. Our previous investigation of endophytic fungi from A. indica resulted in some new bioactive compounds [4,5]. In continuous work, we have studied the secondary metabolites of Xylaria sp. YC-10 from A. indica and obtained 11 compounds.The fungal strain Xylaria sp. YC-10 was isolated from the stem of A. indica collected in Yuanjiang County, Yunnan Province, P. R. China. It was classified as a Xylaria species by its morphological characteristics and its rDNA sequence analysis. The strain was deposited in Yunnan Institute of Microbiology, Kunming, P. R. China.The fungus was cultured in 500 mL Erlenmeyer flasks (u 200) containing 100 mL of PDB medium at 200 rpm at 28qC for 6 days on a rotary shaker. The culture broth was filtered to remove mycelia. The filtrate was concentrated under reduced pressure to 5 L and then exhaustively extracted with EtOAc (3 u 5 L). After removal of the solvent in vacuum, the resulting residue (30.6 g) was subjected to column chromatography on silica gel eluting with petroleum-acetone (5:1-1:1) to afford seven fractions (I-VII). Fraction I was repeatedly subjected to column chromatography on silica gel with petroleum-acetone (20:1) to give compound 2 (18 mg). Repeated chromatography of fraction II on RP-18 silica gel with MeOH-H 2 O (8:2) and petroleum-EtOAc (7:3) afforded compound 1 (30 mg). Fraction III was submitted to column chromatography on RP-18 silica gel with MeOH-H 2 O gradient (6:4, 8:2) to afford compounds 3 (50 mg) and 9 (26 mg). Fraction IV was repeatedly chromatographed on Sephadex LH-20 with MeOH and RP-18 silica gel with MeOH-H 2 O gradient (1:1, 6:4, 7:3) to yield compounds 6 (25 mg) and 11 (93 mg). Fraction V was submitted to repeated column chromatography on RP-18 silica gel with MeOH-H 2 O gradient (1:1, 6:4) and silica gel with CHCl 3 -MeOH gradient (9:1, 8:2) to afford 4 (32 mg), 5 (8 mg). Fraction VI was repeatedly subjected to column chromatography on Sephadex LH-20 with MeOH and RP-18 silica gel with MeOH-H 2 O gradient (3:7, 6:4) to give compounds 7 (24 mg), 8 (46 mg), and 10 (35 mg).The compounds were identified using NMR and mass spectrometry by comparison with reported spectroscopic data in the literature and determined as 5-hydroxymellein (1) [6], 5-methylmellein (2) [7], 5-carboxymellein (3) [7,8], hymatoxin C (4) [9], hymatoxin D (5) [9], halorosellinic acid (6) [8], cerebroside C (7) [10], (2S,3S,4R,2cR)-2-(2c-hydroxytetracosanoylamino)octadecane-1,3,4-triol (8) [11], cerevisterol (9) [12], adenosine (10...

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“…Therefore, the structure of 1 was established as (3R,4aR,5S,6R)-6-hy-(3R,4aR,5S,6R)-6-Hydroxy-5-methylramulosin: a New Ramulosin Derivative from a Marine-Derived Sterile Mycelium droxy-5-methylramulosin. Metabolites belonging to a family of ramulosin (5) 9-13) isolated so far contain commonly 3R,4aR configuration, and also mellein (6) 7,14) derivatives bear 3R configuration. Among them, 6-hydroxyramulosin, which was isolated from several fungi, 9-11) possesses a boriented hydroxy group at C-6, while the hydroxy group at C-6 in 1 was found to be a-oriented.…”

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confidence: 99%

“…[1][2][3] In the course of our search for new biologically active compounds from marine-derived organisms, [4][5][6] we report here the isolation and structure elucidation of (3R,4aR,5S,6R)-6-hydroxy-5-methylramulosin (1), along with three known compounds, (Ϫ)-5-methylmellein (2), (Ϫ)-5-hydroxymethylmellein (3), and (Ϫ)-(3R,4R)-cis-4-hydroxy-5-methylmellein (4), which were isolated from Valsa ceratosperma, the pathogenic fungus of apple canker. 7) The marine-derived fungus was isolated from the green alga, Codium fragile (SURINGAR) HARIOT, collected in Toyama Bay in the Japan Sea. The fungus was grown on agar plates composed of 50% seawater with nutrients.…”

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(3R,4aR,5S,6R)‐6‐Hydroxy‐5‐methylramulosin: A New Ramulosin Derivative from a Marine‐Derived Sterile Mycelium.

et al. 2007

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Marine microorganisms have attracted considerable attention as important sources of structurally diverse secondary metabolites and as potential leads for drug discovery. [1][2][3] In the course of our search for new biologically active compounds from marine-derived organisms, [4][5][6] we report here the isolation and structure elucidation of (3R,4aR,5S,6R)-6-hydroxy-5-methylramulosin (1), along with three known compounds, (Ϫ)-5-methylmellein (2), (Ϫ)-5-hydroxymethylmellein (3), and (Ϫ)-(3R,4R)-cis-4-hydroxy-5-methylmellein (4), which were isolated from Valsa ceratosperma, the pathogenic fungus of apple canker. 7) The marine-derived fungus was isolated from the green alga, Codium fragile (SURINGAR) HARIOT, collected in Toyama Bay in the Japan Sea. The fungus was grown on agar plates composed of 50% seawater with nutrients. The culture plates were extracted with EtOH. The extract was partitioned between EtOAc and H 2 O. The EtOAc-soluble fraction (4.5 g) was subjected to ordinary and reverse-phase silica gel column chromatography and HPLC to furnish 1 (16.0 mg), 2 (12.0 mg), 3 (26.0 mg), and 4 (3.6 mg).Compound 1 has a molecular formula of C 11 H 16 O 4 as established by HR-FAB-MS, and the molecular formula requires four degrees of unsaturation. The 1 H-NMR spectrum in CDCl 3 (Table 1) (Fig. 1). The heteronuclear multiplebond correlation (HMBC) experiment of 1 showed the correlations between H 2 -7 and two quaternary carbons C-8 (d 173.1) and C-8a (d 93.1) and between three hydrogens H-4b, H-4a, and H-5 and C-8a (Fig. 1). HMBCs were observed from H-3 to a carbonyl carbon C-1 (d 171.7) and from the downfield hydroxy resonance 8-OH to C-8 and C-8a, which clarified the connectivity of the quaternary carbons C-1, C-8, and C-8a. Thus, the planar structure of 1 was shown (Fig. 1). The relative stereochemistry of 1 was elucidated by its NOE experiment. NOE correlations between H-4a and two signals H-3 and H-6 indicated that they were oriented on the same side ( Fig. 1) at axial positions; hence the 3-Me and 6-OH groups were in equatorial orientation. While the correlations between 5-Me and two hydrogens H-4a (d 1.90) and H-7a (d 2.31) revealed that they were the opposite side of H-3, H4a, and H-6 and that they were in axial orientaion. The absolute stereochemistry of 1 was substantiated by applying the lactone sector rule by CD measurement, in which the signs, used in the ketone octant rule, are reversed for lactone sectors. 8) The sector projection, in which 1 is viewed in the plane of the lactone group along the line of the carboxyl group and its attached carbon atom, is shown in Fig. 2. The CD spectrum of 1 showed the positive Cotton effect observed at 260 nm (D eϭϩ126) due to the lactone group with the exocyclic a,b-double bond and with the b-hydroxy group bearing hydrogen bonding to the oxygen at C-1. As shown in Fig. 2, the positive contribution was exhibited for 1. Therefore, the structure of 1 was established as (3R,4aR,5S,6R)-6-hy-

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Structures and Phytotoxicity of Metabolites fromValsa ceratosperma

Cited by 11 publications

References 0 publications

An [11]Cytochalasin Derivative from the Marine-Derived Fungus Xylaria sp. PSU-F100

An [11]Cytochalasin Derivative from the Marine-Derived Fungus Xylaria sp. PSU-F100

Secondary metabolites of endophytic fungus Xylaria sp. YC-10 of Azadirachta indica

(3R,4aR,5S,6R)‐6‐Hydroxy‐5‐methylramulosin: A New Ramulosin Derivative from a Marine‐Derived Sterile Mycelium.

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