Cytotoxic eremophilane sesquiterpenoids from the saprobic fungus Berkleasmium nigroapicale BCC 8220

Isaka, Masahiko; Srisanoh, Urarat; Veeranondha, Sukitaya; Choowong, Wilunda; Lumyong, Saisamorn

doi:10.1016/j.tet.2009.08.077

Cited by 35 publications

(35 citation statements)

References 12 publications

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“…C-NMR (DEPT) revealed 32 C-atom signals including those of seven Me, nine CH 2 , seven CH (involving two olefinic and two O-bearing C-atoms), and nine quaternary Catoms (including four olefinic, three CO, one O-bearing, and one sp 3 quaternary Catoms). The NMR data of 2 ( Table 2) very closely resembled to those of berkleasmin C except for one additional AcO group [20]. The AcO group was assigned to C(15') through ester bond, since HMBCs from HÀC(15') to C(1''), and from HÀC(2'') to C(1'') were observed.…”

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confidence: 62%

“…Comparison of the physicochemical properties with reported data allowed identification of the compound 3 as berkleasmin C [20], recently reported from the saprobic fungus B. nigroapicale and shown to possess cytotoxicity against cancer cell lines (NCI-H187, MCF-7, and KB) and antimalarial activities.…”

Section: Pestalotiopin C (2) Showed An Hr-esi-ms Pseudo-molecular-ionmentioning

confidence: 95%

“…As a continuation of this work, two new eremophilane-type sesquiterpenoids, named pestalotiopins B and C (1 and 2, resp. ), and one known compound, berkleasmin C (3) [20], were obtained (Fig. 1).…”

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confidence: 99%

“…Details of the isolation and structure elucidation of these compounds are reported herein. C-NMR Data for 1 (at 600 and 150 MHz, resp., in CDCl 3 ) [20], and this suggested that 1 is composed of a tricyclic sesquiterpene core attached to a long-chain acid through an ester linkage. Further interpretation of HMBC spectrum showed the following long-range correlations ( Fig.…”

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confidence: 99%

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Eremophilane‐Type Sesquiterpenoids from the Fermentation Broth of Plant Endophytic Fungus Pestalotiopsis photiniae Isolated from the Chinese Podocarpaceae Plant Podocarpus macrophyllus

Yang

Zhang

Zhu

et al. 2011

Helvetica Chimica Acta

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Two new sesquiterpenoid esters, pestalotiopins B and C (1 and 2, resp.) related to the eremophilane class, together with one known compound, berkleasmin C (3), were isolated from the fermentation broth of the plant endophytic fungus Pestalotiopsis photiniae. Their structures and relative configurations were elucidated by extensive spectroscopic analysis including 1D-and 2D-NMR (HSQC, HMBC, and NOESY), and MS experiments. Compound 1 has an interesting lactam structure, and this type of sesquiterpenoid with a lactam structure is reported for the first time.

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confidence: 62%

Section: Pestalotiopin C (2) Showed An Hr-esi-ms Pseudo-molecular-ionmentioning

confidence: 95%

mentioning

confidence: 99%

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confidence: 99%

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Eremophilane‐Type Sesquiterpenoids from the Fermentation Broth of Plant Endophytic Fungus Pestalotiopsis photiniae Isolated from the Chinese Podocarpaceae Plant Podocarpus macrophyllus

Yang

Zhang

Zhu

et al. 2011

Helvetica Chimica Acta

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“…TR-022, together with a known compound, berkleasmin A (3) (Figure 1). 10 In this paper, the taxonomy of the producing strain, isolation, physicochemical properties and structure elucidation of 1 and 2, as well as circumvention activities of ABK resistance of the isolated compounds, are described.…”

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confidence: 99%

Paraphaeosphaeride D and berkleasmin F, new circumventors of arbekacin resistance in MRSA, produced by Paraphaeosphaeria sp. TR-022

et al. 2016

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Two new compounds, designated paraphaeosphaeride D (1) and berkleasmin F (2) together with a previously known compound, berkleasmin A (3), isolated from a culture broth of the fungus Paraphaeosphaeria sp. TR-022, proved to be new circumventors of arbekacin (ABK) resistance in methicillin-resistant Staphylococcus aureus (MRSA). The structures of 1 and 2 were elucidated by spectroscopic analyses, including various NMR experiments. All compounds showed 10-100 times ABK circumvention activities using the paper disc method and reduced the MIC values of ABK against MRSA from 16 μg ml(-1) to 4 μg ml(-1) (fourfold) using the agar dilution method. These new compounds might be promising lead compounds for developing circumventors of ABK resistance in MRSA.

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Enantioselective Multicomponent Synthesis of Fused 6–5 Bicyclic 2‐Butenolides by a Cascade Heterobicyclisation Process

Suero¹,

Campa²,

Torre-Fernández³

et al. 2012

Chemistry A European J

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The successive coupling of an alkoxy(aryl/heteroaryl)carbene complex of chromium with either a ketone or an imide lithium enolate and then a 3-substituted (H, TMS, PhCH(2), PhCH(2)CH(2), Me) propargylic organomagnesium reagent has afforded novel hydroxy-substituted bicyclic [4.3.0]-γ-alkylidene-2-butenolides with three modular points that has allowed the efficient introduction of molecular complexity, including a homopropargylic alcohol core. The selective formation of these five- or six-component heterobicyclisation products is the result of the regioselective integration of the Grignard reagent as a propargyl fragment followed by a cascade CO/alkyne/CO insertion, ketene trapping and elimination sequence. By using lithium enolates of chiral N-acetyl-2-oxazolidinones and the corresponding propargylic organocerium reagents, both enantiomers of these bicyclic heterocycles were efficiently prepared with very high enantiomeric purity. Architecturally, these fused bicyclic butenolides are characterised by a highly unsaturated and oxygenated core and they exhibit strong blue fluorescence in solution.

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Cytotoxic eremophilane sesquiterpenoids from the saprobic fungus Berkleasmium nigroapicale BCC 8220

Cited by 35 publications

References 12 publications

Eremophilane‐Type Sesquiterpenoids from the Fermentation Broth of Plant Endophytic Fungus Pestalotiopsis photiniae Isolated from the Chinese Podocarpaceae Plant Podocarpus macrophyllus

Eremophilane‐Type Sesquiterpenoids from the Fermentation Broth of Plant Endophytic Fungus Pestalotiopsis photiniae Isolated from the Chinese Podocarpaceae Plant Podocarpus macrophyllus

Paraphaeosphaeride D and berkleasmin F, new circumventors of arbekacin resistance in MRSA, produced by Paraphaeosphaeria sp. TR-022

Enantioselective Multicomponent Synthesis of Fused 6–5 Bicyclic 2‐Butenolides by a Cascade Heterobicyclisation Process

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