Isolation, X-ray structure and biological activity of deacetyldihydrobotrydial produced by Botrytis squamosa.

KIMURA, Yasuo; Fujioka, Hiroaki; Nakajima, Hiromitsu; Hamasaki, Takashi; IRIE, Miwako; Fukuyama, Keiichi; Isogai, Akira

doi:10.1271/bbb1961.50.2123

Cited by 12 publications

(16 citation statements)

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“…The absolute configurations for C-16, C-26, and C-24 were deduced by comparison of the experimental CD spectrum of 4 with the simulated ECD spectra for the 16S,24S,26R (4Aa) and 16R,24R,26S (4Ab) enantiomers of the simplified structure 4A (Figures 5 and S41). 4,6,7,8,9,12 59.0, CH 1.75,d (10.9) 1,3,4,6,7,8,9,12 58.8,CH 1.82,d (10.5) 1,4,6,7,8,9,12 6 46 . 5,6,8,12,13,14,15 49.9,CH 2 2.19,d (11.2) 5,6,8,12,13,14,15 7b 1.15,d (11.6) 5,6,8,9,13,14 1.07,d (10.3) 5, 6, 8, 9, 13, 14 1...…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…9,18,19 This class of metabolites was biosynthesized from a key intermediate, presilphiperfolan-8β-ol, which was derived from cyclization of the universal precursor farnesyl diphosphate. 12,20 In the current work, six new heterodimeric botryane ethers, named hypocriols A−F (1−6), were isolated from an extended investigation of the insect-associated Hypocrea sp.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Full-scan spectra were acquired over a scan range of m/z 100−1000 at 1.03 spectra/s. HPLC separations were performed on an 1.40,dd (11.1,2.9) 2,8,9,10,11 2 34.7,CH 1.77,m 1,3,4,10,11 3a 40.8, CH 2 1.83,ddd (12.2,3.4,3.4) 1,2,4,5,11 3b 1.12,dd (12.2,10.7) 1,2,4,5,11 4 73.4,CH 5.12,ddd (11.0,10.7,3.4) 2,3,5,6,31 5 58.8,CH 1.80,d (11.0) 3,4,6,7,8,9,12,13 6 46.6, qC 7a 50.4, CH 2 2.30, d (11.5) 6, 8, 12, 13, 14, 15 7b 1.24, d (11.5) 5, 6, 8, 9, 13, 14, 15 8 58 . The isolate was identified based on morphology and sequence (GenBank accession no. KF724627) analysis of the ITS region of the rDNA.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…The fraction (5.6 g) eluted with 100:1 CH 2 Cl 2 −MeOH was separated by silica gel CC using petroleum ether−EtOAc gradient Table 3. NMR Data for 5 and 6 (Acetone-d 6 ) 5 6 CH 1.59,d (12.5) 2,3,8,9,10,11 56.1,CH 1.61,d (12.4) 2,3,8,9,10,11 2 29.9, CH 1. 2, 4, 5, 11 4 73.0, CH 5.07, ddd (11.1,11.0,4.8) 5,6,31 73.0,CH 5.07,ddd (11.1,11.0,4.7) 5,6,31 5 60.5,CH 1.84,d (10.9) 3,4,6,7,8,9,12 61.0,CH 1.86,d (11.0) 4,6,8,9,12,13 6 39.4,qC 39.4,qC 7a 51.0, CH 2 1.80, d (11.5) 5, 6, 8, 12, 13, 14, 15 51.0, CH …”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…2, 4, 5, 11 4 73.0, CH 5.07, ddd (11.1,11.0,4.8) 5,6,31 73.0,CH 5.07,ddd (11.1,11.0,4.7) 5,6,31 5 60.5,CH 1.84,d (10.9) 3,4,6,7,8,9,12 61.0,CH 1.86,d (11.0) 4,6,8,9,12,13 6 39.4,qC 39.4,qC 7a 51.0, CH 2 1.80, d (11.5) 5, 6, 8, 12, 13, 14, 15 51.0, CH 2 1.85, d (11.6) 6, 8, 9, 12, 13, 14, 15 7b 1.07, d (11.5) 5, 6, 8, 9, 13, 14 1.11, d (11.6) 5, 6, 8, 9, 12, 13, 14 8 46 . 3. 12, d (12.2) 8, 9, 10, 14 3.28, d (10.2) 8, 9, 10, 14 16a 58 . 21, 22, 24, 25, 26, 28, 29, 30 23b 1.82, d (13.2) 21, 22, 24, 25, 26, 28, 29, 30 1.71, d (13.1) 21, 22, 24, 25, 26, 29, 30 24 49 . 1,4,5,9 3.79,s 1,5,…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Hypocriols A–F, Heterodimeric Botryane Ethers from Hypocrea sp., an Insect-Associated Fungus

Ren¹,

Zhu²,

Wang³

et al. 2016

J. Nat. Prod.

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The new heterodimeric botryane ethers hypocriols A-F (1-6) and the known compounds 4β-acetoxy-9β,10β,15α-trihydroxyprobotrydial (7), dihydrobotrydial (8), 10-oxodehydrodihydrobotrydial (9), and dehydrobotrydienol (10) were isolated from the solid cultures of an insect-associated fungus Hypocrea sp. The structures of 1-6 were elucidated primarily by NMR experiments. The absolute configuration of 1 was assigned using the modified Mosher method and electronic circular dichroism (ECD) calculations, whereas those for 3-5, and 2 and 6 were deduced via ECD calculations and circular dichroism data, respectively. Compounds 1-6 appear to be the first heterodimeric botryane ethers and showed antiproliferative effects against a small panel of four human tumor cell lines.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

See 3 more Smart Citations

Hypocriols A–F, Heterodimeric Botryane Ethers from Hypocrea sp., an Insect-Associated Fungus

Ren¹,

Zhu²,

Wang³

et al. 2016

J. Nat. Prod.

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Sesquiterpenoids

Connolly¹,

Hill²

1991

Dictionary of Terpenoids

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Synthesis and antifungal activity of analogues of naturally occurring botrydial precursors

et al. 1994

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Analog compounds of the proposed intermediates of the biogenetic pathway to botrydial have been synthesized. These compounds were tested for their potential antifungal activity against the phytopathogenBotrytis cinerea. Our results showed a fungistatic effect of some compounds on mycelium growth. The most significant effect was exerted by 2-α-hydroxy-2,3-dihydro-1-epiprobotrydial, which inhibited growth ofB. cinerea. Some aspects of structure-activity relationships are discussed.

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Isolation, X-ray structure and biological activity of deacetyldihydrobotrydial produced by Botrytis squamosa.

Cited by 12 publications

References 1 publication

Hypocriols A–F, Heterodimeric Botryane Ethers from Hypocrea sp., an Insect-Associated Fungus

Hypocriols A–F, Heterodimeric Botryane Ethers from Hypocrea sp., an Insect-Associated Fungus

Sesquiterpenoids

Synthesis and antifungal activity of analogues of naturally occurring botrydial precursors

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