Bioactive Metabolites from a Hydrothermal Vent Fungus Aspergillus sp. YQ-13

Abstract

To study fermentation from strain Aspergillus sp. YQ-13, dwelling in sediment Kueishantao hydrothermal vents off Taiwan. Compounds were separated and purified by silica gel column, preparative HPLC techniques. Their structures were identified by the physicochemical properties and spectral analysis. The isolates were identified as 3-hydroxy-2-(2-hydroxy-6-methoxy-4-methylbenzoyl)-5-methoxy-benzoic acid methyl ester (1), myristic acid (2), orcinol (3), 1,2-seco-trypacidin (4), leporin A (5), chaetominine (6), 5-hydroxy-2-hydroxymethyl-4H-pyran-4one (7) and N-methyl-2-pyrolidinone (8). Compound 1 was identified as a new natural product belonging to diphenyl ketone family. Known compounds 5 and 6 exhibited antibiotic activity with MIC value of around 1 to 25 μg mL⁻¹ against Bacillus subtilis, Klebsiella pneumoniae, methicillin resistant Staphylococcus aureus (MRSA), Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli and Acinetobacter Bauman. Compounds 1, 4, 5 and 6 were tested by the methods of DPPH and FRAP assay, showing moderate antioxidant activities.

Keywords

Hydrothermal vent Marine fungi Natural products Antibiotic Antioxidant

References

Saleema

, Ali

M.S.

, Hussain

, Jabbar

, Ashraf

, Lee

Y.S.

(2007) Marine natural products of fungal origin. Natural Product Reports, 24, 1142–1152.

Cragg

G.M.

, Newman

D.J.

(2009) Nature: a vital source of leads for anticancer drug development. Phytochemistry Reviews, 8, 313–331.

Mittal

, Shrivastava

, Govil

, Kumar

, Bisen

P.S.

(2016) A novel anticandidal compound containing sulfur from endophytic fungus Emericella sp. Journal of Natural Products, 6, 188–193.

Rangnekar

S.S.

, Khan

(2015) Novel anti-inflammatory drugs from marine microbes. The Natural Products Journal, 5, 206–218.

Pettit

R.K.

(2011) Culturability and secondary metabolite diversity of extreme microbes: expanding contribution of deep sea and deep-sea vent microbes to natural product discovery. Marine Biotechnology, 13, 1–11.

Homann

V.V.

, Sandy

, Tincu

J.A.

, Templeton

A.S.

, Butler

(2009) Loihichelins A–F, a suite of amphiphilic siderophores produced by the marine Bacterium Halomonas LOB-5. Journal of Natural Products, 72, 884–888.

Andrianasolo

E.H.

, Haramaty

, Rosario-Passapera

, Bidle

, White

, Vetriani

, Falkowski

, Lutz

(2009) Ammonificins A and B, hydroxyethylamine chroman derivatives from a cultured marine hydrothermal vent bacterium, Thermovibrio ammonificans. Journal of Natural Products, 72, 1216–1219.

Jiang

, Ye

, Chen

C.T.

, Wang

, Liu

, He

, Wu

, Gan

, Ye

, Wu

(2013) Two novel hepatocellular carcinoma cycle inhibitory cyclodepsipeptides from a hydrothermal vent crab-associated fungus Aspergillus clavatus C2WU. Marine Drugs, 11, 4761–4772.

Pan

C.Q.

, Shi

Y.T.

, Auckloo

B.N.

, Chen

X.G.

, Chen

C.T.A.

, Tao

X.Y.

, Wu

(2016) An unusual conformational isomer of verrucosidin backbone from ahydrothermal vent fungus, Penicillium sp. Y-50–10. Marine Drugs, 14, 156.

10.

Mensor

L.L.

, Menezes

F.S.

, Leitao

G.G.

, Reis

A.S.

, Santos

T.C.

, Coube

C.S.

, Leitao

S.G.

(2001) Screening of Brazilian plant extracts for antioxidant activity by the use of DPPH free radical method. Phytotherapy Research, 15, 127–130.

11.

Benzie

I.F.

, Strain

J.J.

(1996) The ferric reducing ability of plasma (FRAP) as a measure of 'antioxidant power': the FRAP assay. Analytical Biochemistry, 239, 70–76.

12.

C.H.

, Huang

Y.J.

, Shen

Y.M.

(2005) Secondary metabolites of Aspergillus fumigatus. var. fumigatus. Chinese Journal of Natural Medicines, 3, 269–271.

13.

Liu

, Zhu

W.M.

, Zhang

Y.P.

, Zhu

T.J.

, Liu

H.B.

, Fang

Y.C.

, Gu

Q.Q.

(2006) A new diphenyl ether from marine-derived fungus Aspergillus sp. B-F-2. Journal of Antibiotics, 59, 362–365.

14.

Oohashi

, Ishikawa

, Nakao

(1996) Preparation of benzophenone carboxylic acid derivatives as inhibitors of function of eosinophils. J P. Patent 08,092,082.

15.

Shi

G.F.

, Sun

H.R.

, Zhao

Y.F.

, Chen

X.F.

(2008) Chemical constituents from the defatted seeds of Linum usitatissimum L. Natural Product Research & Development, 20, 60–62.

16.

Monde

, Satoh

, Nakamura

, Tamura

, Takasugi

(1998) Organochlorine compounds from a terrestrial higher plant: structures and origin of chlorinated orcinol derivatives from diseased bulbs of Lilium maximowiczii. Journal of Natural Products, 61, 913–921.

17.

Tepaske

M.R.

, Gloer

J.B.

, Wicklow

D.T.

, Dowd

P.F.

(1991) Leporin A: an antiinsectan N-alkoxypyridone from the sclerotia of Aspergillus leporis. Tetrahedron Letters, 32, 5687–5690.

18.

Dowd

P.F.

, Wicklow

D.T.

, Gloer

J.B.

, TePaske

M.R.

(1994) Leporin A, an antiinsectan fungal metabolite. U.S. Patent 5,281,609.

19.

Jiao

R.H.

, Xu

, Liu

J.Y.

, Ge

H.M.

, Ding

, Xu

, Zhu

H.L.

, Tan

R.X.

(2006) Chaetominine, a cytotoxic alkaloid produced by endophytic Chaetomium sp. IFB-E015. Organic Letters, 8, 5709–5712.

20.

Lin

, Lu

X.M.

, Fang

Y.C.

, Zhu

T.J.

, Gu

Q.Q.

, Zhu

W.M.

(2008) Two new 5-hydroxy-2-pyrone derivatives isolated from a marine-derived fungus Aspergillus flavus. Journal of Antibiotics, 61, 245–249.

21.

Latip

, Hartley

T.G.

, Waterman

P.G.

(1999) Lignans and coumarins metabolites from Melicophayesii. Phytochemistry, 51, 107–110.

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