Spiculisporic acid E, a new spiculisporic acid derivative and ergosterol derivatives from the marine-sponge associated fungus Talaromyces trachyspermus (KUFA 0021)

Natural Product Communications

Volumn 9, Issue 8, 2014, Pages 1147-1150

  Kumla, Decha ^a,b   Dethoup, Tida ^b   Buttachon, Suradet ^a,c   Singburaudom, Narong ^b   Silva, Artur M S ^d   Kijjoa, Anake ^a,c  

^a UNIVERSITY OF PORTO   (Portugal)

^b KASETSART UNIVERSITY   (Thailand)

^c UNIVERSITY OF PORTO   (Portugal)

^d UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

22 tetraen 3 one; 3 Acetyl ergosterol 5; 8 endoperoxide; Ergosta 4, 6, 8 (14); Glaucanic acid; Glauconic acid; Spiculisporic acid E; Talaromyces trachyspermus (KUFC 0021)

Indexed keywords

3 ACETYL ERGOSTEROL 5, 8 ENDOPEROXIDE; ERGOSTA 4, 6, 8 (14), 22 TETRAEN 3 ONE,GLAUCANIC ACID; ERGOSTA 4,6,8 (14), 22 TETRAEN 3 ONE,GLAUCONIC ACID; ERGOSTEROL; NATURAL PRODUCT; SPICULISPORIC ACID E; UNCLASSIFIED DRUG;

ARTICLE; BREAST ADENOCARCINOMA; CANDIDA ALBICANS; DRUG ISOLATION; FUNGUS CULTURE; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; GROWTH INHIBITION; HUMAN; IN VITRO STUDY; LUNG NON SMALL CELL CANCER; MCF 7 CELL LINE; MELANOMA; PROTEIN BINDING; TALAROMYCES; TALAROMYCES TRACHYSPERMUS;

4-BUTYROLACTONE; ANIMALS; ERGOSTEROL; MOLECULAR STRUCTURE; PORIFERA; TALAROMYCES;

EID: 84906715682     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1400900822     Document Type: Article

References (21)

1. Manoch L, Dethoup T, Yilmaz N, Houbraken J, Samson RA. (2013) Two new Talaromyces species from soil in Thailand. Mycoscience, 54, 335-342.
2. Pitt JI. (1980) The genus Penicillium and its telemorphic states Eupenicillium and Talaromyces. Academic Press, London, 1-148.
3. Nozawa K, Saito R, Udagawa SI, Nakajima S, Kawai KI. (1995) An azaphilone from Talaromyces tardifaciens. Phytochemistry, 39, 719-721.
4. Suzuki S, Hosoe T, Nozawa K, Kawai KI, Yaguchi T, Udagawa SI. (2000) Antifungal substances against pathogenic fungi, talaroconvolutins, from alaromyces convolutus. Journal of Natural Products, 63, 768-772. (Pubitemid 30452169)
5. Dong Y, Yang J, Zhang H, Lin J, Ren X, Liu M, Lu X, He J. (2006) Wortmannilactones A-D, 22-membered triene macrolides from Talaromyces wortmannii. Journal of Natural Products, 69, 128-130. (Pubitemid 43241769)
6. Kimura T, Nishida M, Kuramochi K, Sugawara F, Yoshida H, Mizushina Y. (2008) Novel azaphilones, kasanosins A and B, which are specific inhibitors of eukaryotic DNA polymerases β and κ from Talaromyces sp. Bioorganic & Medicinal Chemistry, 16, 4594-4599. (Pubitemid 351539024)
7. Li AQ, Yang YG, Zeng Y, Zou C, Zhao PJ. (2010) A new azaphilone, kasanosin C, from an endophytic Talaromyces sp. T1BF. Molecules, 15, 3993-3997.
8. Dethoup T, Manoch L, Kijjoa A, Nascimento MSJ, Paupairoj P, Silva AMS, Eaton G, Herz W. (2006) Bacillisporins D and E, new oxyphenalenone dimers from Talaromyces bacillisporus. Planta Medica, 72, 957-960. (Pubitemid 44378966)
9. Dethoup T, Manoch L, Kijjoa K, Pinto M, Gales L, Damas AM, Silva AMS, Eaton G, Herz W. (2007) Merodrimanes and other constituents from Talaromyces thailandiasis. Journal of Natural Products, 70, 1200-1202. (Pubitemid 47279916)
10. Shiozawa H, Takahashi M, Takatsu T, Kinoshita T, Tanzawa K, Hosoya T, Furuya K, Takahashi S. (1995) Trachyspic acid, a new metabolite produced by Talaromyces trachyspermus, that inhibits tumor cell heparanase. Taxonomy of the producing strain, fermentation, isolation, structural elucidation, and biological activity. The Journal of Antibiotics, 48, 357-362.
11. Frisvad JC, Filtenborg O, Samson RA, Stalk AC. (1990) Chemotaxonomy of the genus Talaromyces. Antonie van Leeuwenhoek, 57, 179-189. (Pubitemid 20268941)
12. Barton DHR, Bloomer JL, Jackman LM, Rodriguez-Hahn L, Sutherland, JK. (1962) The constituents of glauconic, glaucanic and byssochlamic acid. Experientia, XVIII, 345-388.
13. Kobayashi M, Krishna MM, Ishida K, Anjaneyulu V. (1992) Marine sterols. XXII. Occurrence of 3-oxo-4, 6, 8(14)-triunsaturated steroids in the sponge Dysidea herbacea. Chemical& Pharmaceutical Bulletin, 40, 72-74.
14. Kim DH, Jung SJ, Chung IS, Lee YH, Kim DK, Kim SH, Kwon BM, Jeong TS, Park MH, Seoung NS, Baek NI. (2005) Ergosterol peroxide from flowers of Erigeron annus L. as an anti-atherosclerosis agent. Archives of Pharmaceutical Research, 20, 541-545.
15. Cantrell CL, Franzblau SG, Fischer NH. (2001) Antimycobacterial plant terpenoids. Planta Medica, 67, 685-694. (Pubitemid 33044471)
16. Brown SP, Goodwin NC, MacMillan DWC. (2003) The first enantioselective organocatalytic Mukaiyama-Michael reaction: A direct method for the synthesis of enantioenriched γ-butenolide architechure. Journal of American Chemical Society, 125, 1192-1194. (Pubitemid 36159830)
17. Wang R, TM, Shen MH, Yang MQ, Feng QY, Tang XM, Li XM. (2012) Spiculisporic acids B-D, three new γ-butenolide derivatives from a sea urchin-derived fungus Aspergillus sp. HDf2. Molecules, 17, 13175-13182.
18. Goodwin NC. (2007) Application of iminium activation technologies to natural product synthesis: Total synthesis of spiculisporic acids, progress towards the total synthesis of cylindrocycophane F, and formal synthesis of cylindrocyclophane A. PhD thesis. California Institute of Technology, Pasadena, California, 48.
19. Eamvijarn A, Gomes NM, Dethoup T, Buaruang, J, Manoch L, Silva A, Pedro M, Marini I, Roussis V, Kijjoa A. (2013) Bioactive meroditerpenes and indole alkaloids from the soil fungus Neosartorya fischeri (KUFC 6344), and the marine-derived fungi Neosartorya laciniosa (KUFC 7896) and Neosartorya tsunodae (KUFC 9213). Tetrahedron, 69, 8583-8591.
20. Gomes NM, Bessa, LJ, Buttachon S, Costa PM, Buaruang J, Dethoup T, Silva AMS, Kijjoa A. (2014). Antibacterial and antibiofilm activities of tryptoquivalines and meroditerpenes isolated from the marine-derived fungi Neosartorya paulistensis, N. laciniosa, N. tsunodae, and the soil fungi N. fischeri and N. siamensis. Marine Drugs, 12, 822-839.
21. Stolk AC, Samson RA. (1972) Studies on Talaromyces and related genera II. The genus Talaromyces. Studies in Mycology, 2, 1-65.