Cytotoxic Alkaloids and Antibiotic Nordammarane Triterpenoids from the Marine-Derived Fungus <i>Aspergillus sydowi</i>

Zhang, Min; Wang, Wenliang; Fang, Yuchun; Zhu, Tianjiao; Gu, Qianqun; Zhu, Weiming

doi:10.1021/np700737g

Cited by 144 publications

(141 citation statements)

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“…1 Our group has reported the isolation of azaspiracid-22 2 and JBIR-44 3 from marine sponges. Marine microorganisms, especially fungi, 4 are an untapped resource of novel bioactive substances such as diketopiperazine alkaloids, 5 trichodermatides 6 and carbonarones. 7 We have also reported the discovery of new sesquiterpenes, JBIR-27 and JBIR-28; 8 a new aspochracin derivative, JBIR-15; 9 new glycosyl benzenediols, JBIR-37 and JBIR-38; 10 and a new sorbicillinoid, JBIR-59 11 from marine-derived fungi.…”

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“…Â50 mm, Waters); flow rate, 0.8 ml min À1 ; solvent, 30% CH 3 CN aqueous solution containing 0.1% formic acid; detection, 340 nm. The Rts of the standard FDAA derivatives were as follows: L-isoleucine, 2.71 min; D-isoleucine, 5.72 min; L-allo-isoleucine, 2.76 min and D-alloisoleucine, 5.90 min. The chromatograms of the hydrolysate derivatives of 1 showed a peak corresponding to D-allo-isoleucine (5.90 min).…”

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confidence: 99%

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Isolation of 2 new metabolites, JBIR-74 and JBIR-75, from the sponge-derived Aspergillus sp. fS14

2010

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The marine environment has become an attractive new source of chemical diversity for drug discovery, as new bioactive substances are isolated from marine organisms, including phytoplankton, algae, sponges, tunicates and mollusks. 1 Our group has reported the isolation of azaspiracid-22 2 and JBIR-44 3 from marine sponges. Marine microorganisms, especially fungi, 4 are an untapped resource of novel bioactive substances such as diketopiperazine alkaloids, 5 trichodermatides 6 and carbonarones. 7 We have also reported the discovery of new sesquiterpenes, JBIR-27 and JBIR-28; 8 a new aspochracin derivative, JBIR-15; 9 new glycosyl benzenediols, JBIR-37 and JBIR-38; 10 and a new sorbicillinoid, JBIR-59 11 from marine-derived fungi. The Calcarea class of sponges has been recognized as a reliable source of richly bioactive metabolites possessing a 2-aminoimidazole skeleton. [12][13][14] However, the isolation of fungi from calcareous marine sponges has not been reported. Therefore, we attempted to isolate marine fungi from an unidentified calcareous marine sponge and then searched for secondary metabolites in the cultures of the isolated strains. In this study, we report the isolation of Aspergillus sp. fS14 from this marine sponge, and the fermentation, isolation and structure elucidation of two new compounds, designated JBIR-74 (1) and JBIR-75 (2) ( Figure 1a).The producing fungus, Aspergillus sp. fS14, was isolated from the unidentified marine sponge (class, Calcarea) collected offshore of Taketomikita, Ishigaki Island, Okinawa Prefecture, Japan, according to the previously reported method using jewfish (Argyrosomus argentatus) extract agar. 15,16 The sponge was rinsed with sterilized seawater, finely minced with scissors and resuspended in sterilized seawater. A 100 ml aliquot of this suspension was spread on jewfish extract agar plates prepared in 50% (v/v) artificial seawater (Marine art SF-1; Tomita Pharmaceutical, Tokyo, Japan) and supplemented with 35 mg ml À1 of nalidixic acid and 50 mg ml À1 of cycloheximide. Cycloheximide-resistant fungal colonies grew on the agar plates and were transferred to potato dextrose agar slants, where individual strains were maintained. Strain fS14 was cultivated in a 50 ml test tube containing 15 ml of seed medium (2.4 g l À1 Potato Dextrose Broth; BD Biosciences, San Jose, CA, USA). The test tube was shaken on a reciprocal shaker (355 r.p.m.) at 27 1C for 3 days. A 5 ml aliquot of the seed culture was inoculated into a 500 ml Erlenmeyer flask containing 15 g brown rice (Hitomebore, Miyagi, Japan), 30 mg Bacto Yeast Extract (BD Biosciences), 15 mg sodium tartrate, 15 mg potassium hydrogen phosphate and 45 ml water, and incubated in static culture at 27 1C for 14 days.The culture (one flask) was extracted with 80% aq. Me 2 CO (100 ml) and concentrated in vacuo. The aqueous concentrate was extracted with EtOAc (50 mlÂ3). The organic layer was evaporated after drying over Na 2 SO 4 . The residue (0.31 g) was subjected to normal-phase medium-pressure liquid chromatography (Purif-Pac...

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Isolation of 2 new metabolites, JBIR-74 and JBIR-75, from the sponge-derived Aspergillus sp. fS14

2010

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“…24 Recently, a number of modified derivatives of 2-11 have been isolated from Aspergillus strains including A. fumigatus. 18,25 Some of them differ from 2-11 just in their stereochemistry at C12 and C13; that is, b-hydroxyl instead of a-hydroxyl groups. In some cases, the 13-hydroxyl was oxidized to keto group or methylated to methoxy group.…”

Section: Structures Of Fumitremorgin-type Alkaloids and Their Producementioning

confidence: 99%

“…Compounds with modifications at one or both prenyl moieties, such as hydroxylation, oxidation and peroxidation, have also been isolated. 18,25 …”

Section: Structures Of Fumitremorgin-type Alkaloids and Their Producementioning

confidence: 99%

“…7,18,25,38 Obviously, the nine genes of the clusters mentioned above could not account for the synthesis of all of these compounds. It should be questioned whether some of these compounds are enzymatic products in living organisms or results of chemical reactions; for example, oxidation by atmospheric oxygen.…”

Section: Molecular Biological and Biochemical Investigations On The Bmentioning

confidence: 99%

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Genome mining and biosynthesis of fumitremorgin-type alkaloids in ascomycetes

2010

J Antibiot

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Fungi

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: The Fungal Kingdom: The Concept of Marine Fungi Mastigomycetes and Eumycetes (True Fungi) Elements of Classification of Eumycetes Background Information on the Structure of Chitin Fatty Acids Sterols Membrane Peptides of Fungi: Peptaibols General Comments on Secondary Metabolites of Marine Fungi Substances Isolated from Fungi Collected from the Surface of the Sea Substances Isolated from Fungi from Sediments and other Inert Substrates Substances Isolated from Fungi Associated with Cyanobacteria Algicolous Fungi: General Remarks Substances Isolated from Fungi Associated with Green Algae and Marine Spermatophyta Substances Isolated from Fungi Associated with Red Algae Substances Isolated from Fungi Associated with Brown Algae Substances Isolated from Lignicolous Fungi Substances Isolated from Fungi Associated with Sponges Substances Isolated from Fungi Associated with Cnidarians Substances Isolated from Fungi Associated with Mollusks Substances Isolated from Fungi Associated with Bryozoans Substances Isolated from Fungi Associated with Echinoderms Substances Isolated from Fungi Associated with Crustaceans Substances Isolated from Fungi Associated with Tunicates (Ascidians) Substances Isolated from Fungi Associated with Fish Summary of Marine‐Derived Fungi

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Cytotoxic Alkaloids and Antibiotic Nordammarane Triterpenoids from the Marine-Derived Fungus Aspergillus sydowi

Cited by 144 publications

References 26 publications

Isolation of 2 new metabolites, JBIR-74 and JBIR-75, from the sponge-derived Aspergillus sp. fS14

Isolation of 2 new metabolites, JBIR-74 and JBIR-75, from the sponge-derived Aspergillus sp. fS14

Genome mining and biosynthesis of fumitremorgin-type alkaloids in ascomycetes

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