Spiroxins, DNA cleaving antitumor antibiotics from a marine-derived fungus

McDonald, Leonard A.; Abbanat, Darren R.; Barbieri, Laurel R.; Bernan, Valerie S.; Discafani, Carolyn; Greenstein, Michael; Janota, Katarzyna; Korshalla, Joseph D.; Lassota, Peter; Tischler, Mark; Carter, Guy T.

doi:10.1016/s0040-4039(99)00242-7

Cited by 77 publications

(67 citation statements)

References 7 publications

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“…and in continuation of previously isolated similar coupling products named nodulisporins A-C. [11] The structure of 1 in which a chroman ring system is coupled to a naphthalene moiety, is unique and has previously not been encountered in natural products. Nodulisporin D is a further extension of the ever-growing group in which two bicyclic fragments are coupled by C-C and/or C-O bonds as found in the spiroxines, [12] palmarumycins, [13,14] or preussomerins [15,16] (see review article in ref. [17] ).…”

Section: Resultsmentioning

confidence: 99%

New Naphthalene‐Chroman Coupling Products from the Endophytic Fungus, Nodulisporium sp. from Erica arborea

et al. 2009

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Six novel metabolites, nodulisporins D-F (1-3), (3S,4S,5R)-2,4,6-trimethyloct-6-ene-3,5-diol (4), 5-hydroxy-2-hydroxymethyl-4H-chromen-4-one (5) and 3-(2,3-dihydroxyphenoxy)-butanoic acid (6) were isolated together with seven known compounds (7-13) from the culture extract of the endophytic fungus Nodulisporium sp. The relative configurations of these new compounds were determined by means of spectro-

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Section: Resultsmentioning

confidence: 99%

New Naphthalene‐Chroman Coupling Products from the Endophytic Fungus, Nodulisporium sp. from Erica arborea

et al. 2009

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“…We concluded that in the presence of HP20 cercosporamide was efficiently sequestered by the resin, thereby mitigating its self-toxic effect during the course of the fermentation. Adsorbent resins have been in use for some time to mitigate self-toxicity of metabolites produced by many soil bacteria (Table 1), and this technique is also known to increase stability of products during fermentations [2][3][4][5][6][7][8][9][10][11][12][13], but this approach has rarely been used for fungal fermentations [14][15][16].…”

Section: Pdb + 3% Hp20mentioning

confidence: 99%

“…Fermentations are generally performed in media containing an adsorbent resin to mitigate the self-toxicity of the product to the producer and to increase stability of the products excreted during fermentation. Many of the soil streptomyces producing highly toxic secondary metabolites have been fermented in media containing various adsorbent resins [2][3][4][5][6][7][8][9][10][11][12][13], but this approach has rarely been applied to improve secondary metabolite production in fungal fermentations [14][15][16]. Adsorbent resins are widely used for solid-phase extraction, isolation and purification of a wide variety of pharmaceutical products [17,18].…”

Section: Introductionmentioning

confidence: 99%

Fermentative production of self-toxic fungal secondary metabolites

Singh

Leighton

Barbieri

et al. 2009

J Ind Microbiol Biotechnol

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Fungi are well known for their vast diversity of secondary metabolites that include many life-saving drugs and highly toxic mycotoxins. In general, fungal cultures producing such metabolites are immune to their toxic effects. However, some are known to produce self-toxic compounds that can pose production optimization challenges if the metabolites are needed in large amounts for chemical modification. One such culture, LV-2841, was identified as the lead for one of our exploratory projects. This culture was found to be a slow grower that produced trace amounts of a known metabolite, cercosporamide, under the standard flask fermentation conditions, and extensive medium optimization studies failed to yield higher titers. Poor growth of the culture in liquid media was attributed to the self-toxicity of cercosporamide to the producing organism, and the minimum inhibitory concentration (MIC) of cercosporamide was estimated to be in the range of 8-16 microg/ml. Fermentations carried out in media containing Diaion HP20 resin afforded significantly higher titers of the desired compound. While several examples of resin-based fermentations of soil streptomyces have been published, this approach has rarely been used for fungal fermentations. Over a 100-fold increase in the production titer of cercosporamide, a self-toxic secondary metabolite, was achieved by supplementing the production medium with a commercially available neutral adsorbent resin.

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“…Marine fungal metabolite 1386A, a newly identified small molecular compound extracted from the mangrove fungus 1386A in the South China Sea showed cytotoxity to cancer cells. A class of DNA-cleaving antitumor antibiotics, spiroxins A-E, have been isolated from an unidentified fungus (LL-37H248) associated with an unidentified soft coral [57]. Spiroxin A showed potent cytotoxicity (IC 50 = 0.09 μg ml −1 ) against a panel of 25 diverse cell lines.…”

Section: Apoptosis Inducing Metabolitesmentioning

confidence: 99%

Natural Products with Anticancer Activity from Marine Fungi

Karuppiah

Zhang

2014

Handbook of Anticancer Drugs From Marine Origin

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Cancer is one of the major diseases, which require the improved drugs with fewer side effects. Until now, several marine natural products have been accessed for the anticancer property and few of them are in clinical trials too. Marine fungi are taxonomically diverse, largely productive, biologically active, and chemically unique offering a great scope for discovery of new anticancer drugs. The natural products isolated from the marine fungi are possibly inhibiting the processes such as inflammation, cell differentiation and survival, and metastasis of various signal transduction pathways and their by reducing the risk of cancer. In this chapter, we have discussed about the anticancer, anti-inflammatory and cytotoxic activities of marine derived fungi.

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Spiroxins, DNA cleaving antitumor antibiotics from a marine-derived fungus

Cited by 77 publications

References 7 publications

New Naphthalene‐Chroman Coupling Products from the Endophytic Fungus, Nodulisporium sp. from Erica arborea

New Naphthalene‐Chroman Coupling Products from the Endophytic Fungus, Nodulisporium sp. from Erica arborea

Fermentative production of self-toxic fungal secondary metabolites

Natural Products with Anticancer Activity from Marine Fungi

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