07H239-A, a New Cytotoxic Eremophilane Sesquiterpene from the Marine-Derived Xylariaceous Fungus LL-07H239

McDonald, Leonard A.; Barbieri, Laurel R.; Bernan, Valerie S.; Janso, Jeffrey E.; Lassota, Peter; Carter, Guy T.

doi:10.1021/np049924g

Cited by 56 publications

(53 citation statements)

References 8 publications

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“…This class of compound is reported as fungal metabolite and presents a branched unsaturated fatty acid chain bonded at C1 or C3. [18][19][20][21] The placement of the unsaturated fatty acid chain, deduced by previous discussion, at C-3 was readily established from the HMBC experiment. Thus, the HMBC spectrum of 3 exhibited correlation peaks among the acylated oxymethine hydrogen at H 5.48 (H-3) with the carbons at C 38.5 (C-4), 131.9 (C-2), 11.7 (C-12), 41.3 (C-5), 130.0 (C-1) and the carbonyl carbon C 167.9 (C-1 ' ).…”

Section: Resultsmentioning

confidence: 82%

A new eremophilane-type sesquiterpene from the phytopatogen fungus Lasiodiplodia theobromae (Sphaeropsidaceae)

Nunes¹,

Oliveira²,

Arriaga³

et al. 2008

J. Braz. Chem. Soc.

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O fungo fitopatogênico Lasiodiplodia theobromae, isolado de goiaba, foi cultivado em arroz por 32 dias à temperatura ambiente. Extração com CH 2 Cl 2 :MeOH (3:7), seguido de fracionamento cromatográfico do extrato forneceu o esteróide ergosterol. Da cultura fúngica em meio de Czapeck por 40 dias à temperatura ambiente, foram isolados a isocumarina cis-4-hidroximeleína e um sesquiterpeno do tipo eremofilano. O sesquiterpeno eremofilano está sendo descrito pela primeira vez na literatura. Este é o primeiro relato do isolamento de um sesquiterpeno eremofilano para o gênero Lasiodiplodia.The phytopatogenic fungus Lasiodiplodia theobromae, isolated from guava, was cultivated in rice for 32 days at room temperature. Extraction with CH 2 Cl 2 :MeOH (3:7), followed by chromatography fractionation of the extract provided ergosterol. From the fungus culture in Czapeck medium for 40 days at room temperature, were isolated isocoumarin cis-4-hydroxymeleine and an eremophilane-type sesquiterpene. The latter compound is being reported for the first time in the literature. Also, this is the first time that an eremophilane sesquiterpene is described for Lasiodiplodia genus.

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Section: Resultsmentioning

confidence: 82%

A new eremophilane-type sesquiterpene from the phytopatogen fungus Lasiodiplodia theobromae (Sphaeropsidaceae)

Nunes¹,

Oliveira²,

Arriaga³

et al. 2008

J. Braz. Chem. Soc.

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“…SS080624SCf1. Although eremophilane analogs are known to be isolated from many fungal metabolites, [11][12][13][14][15] this paper is the first report that a tunicatederived Penicillium sp. produces terpenoid compounds.…”

Section: Structure Elucidationmentioning

confidence: 88%

New sesquiterpenes, JBIR-27 and -28, isolated from a tunicate-derived fungus, Penicillium sp. SS080624SCf1

et al. 2009

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In the course of our screening program for novel metabolites from tunicate-derived fungi, novel sesquiterpenoids, named JBIR-27 (1) and -28 (2), together with known sporogen-AO1 and phomenone, were isolated from the culture broth of Penicillium sp. SS080624SCf1. The structures of 1 and 2 were determined to be eremophilane analogs on the basis of extensive NMR and MS analyses. Sporogen-AO1, phomenone and 2 showed cytotoxicity against human cervical carcinoma cell line HeLa at IC 50 values of 8.3, 19 and 92 mM, respectively, whereas 1 was inactive at a concentration of 80 mM. Keywords: cytotoxicity; JBIR-27; JBIR-28; Penicillium sp.; terpenoid; tunicate INTRODUCTION Many bioactive substances have been isolated from marine organisms, such as marine microorganisms, phytoplankton, algae, sponges and tunicates. Moreover, marine microorganisms have been studied as the important resources for new biologically active metabolites. 1 Especially, marine-derived fungi are emerging as an attractive source for discovering new bioactive compounds. 2 Indeed, cytotoxic metabolites, such as diketopiperazine alkaloids, 3 trichodermatides 4 and carbonarones, 5 have been isolated from metabolites of marine-derived fungi. Tunicates are a rich source of unique and biologically active metabolites. 1 However, there have been few reports of compounds isolated from tunicate-derived fungi. 6,7 Therefore, we attempted to isolate fungi from a tunicate, Didemnum molle, and obtain secondary metabolites from the fungal culture broths.In the course of chemical screening for novel compounds from the metabolites of tunicate-derived fungi, we isolated two novel sesquiterpenoid compounds, designated as JBIR-27 (1) and -28 (2), from the culture broth of Penicillium sp. SS080624SCf1 (Figure 1). In addition, we also isolated known derivatives, sporogen-AO1 8 and phomenone 9 (Figure 1). This paper describes the fermentation, isolation and brief biological activity of 1, 2, sporogen-AO1 and phomenone, in addition to the taxonomy of the producing microorganism. The structure elucidation of 1 and 2 is also reported.

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“…Besides these morphologic characteristics, Xylaria species are producers of secondary metabolites, including isocoumarin, 3,4 cytochalasins, [4][5][6] xanthones, 7 xyloketals, [8][9][10] sesquiterpenes, 11 that contribute to their classification in this genus. In our study we detected isocoumarins and cytochalasins in the fungus extracts using mass spectrometry, which reinforce the hypothesis of its classification as a Xylareaceous fungus.…”

Section: Introductionmentioning

confidence: 99%

Two novel eremophilane sesquiterpenes from an endophytic Xylariaceous fungus isolated from leaves of Cupressus lusitanica

Amaral¹,

Rodrigues‐Filho²

2010

J. Braz. Chem. Soc.

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Dois novos sesquiterpenos eremofilanos, cupressolideo A e cupressolideo B, além de dois outros conhecidos, foram isolados a partir do extrato AcOEt do meio de cultura de uma espécie de Xylaria, isolada como fungo endofítico dos tecidos sadios das folhas de Cupressus lusitanica. Estudos espectroscópicos, usando EM e RMN, levaram às estruturas dos dois sesquiterpenos de esqueleto eremofilanos, novos na literatura.Two new eremophilane sesquiterpenes, cupressolide A and cupressolide B, along with two known sesquiterpenes, has been characterized from the EtOAc extract of a liquid medium where a Xylariaceous fungus, isolated as an endophytic fungus from health tissues of Cupressus lusitanica leaves, was cultivated. The structures of the isolated compounds were determined by analyses of their MS and NMR spectroscopic data.

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07H239-A, a New Cytotoxic Eremophilane Sesquiterpene from the Marine-Derived Xylariaceous Fungus LL-07H239

Abstract: 07H239-A (1), a new eremophilane sesquiterpene from a marine-derived xylariaceous fungus, was isolated, characterized, and shown to be cytotoxic toward a variety of cancer cell lines, with some selectivity for a CCRFCEM leukemia line (IC(50) = 0.9 microg/mL).

Cited by 56 publications

References 8 publications

A new eremophilane-type sesquiterpene from the phytopatogen fungus Lasiodiplodia theobromae (Sphaeropsidaceae)

A new eremophilane-type sesquiterpene from the phytopatogen fungus Lasiodiplodia theobromae (Sphaeropsidaceae)

New sesquiterpenes, JBIR-27 and -28, isolated from a tunicate-derived fungus, Penicillium sp. SS080624SCf1

Two novel eremophilane sesquiterpenes from an endophytic Xylariaceous fungus isolated from leaves of Cupressus lusitanica

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