Alkaloids from an algicolous strain of Talaromyces sp.

Haibin Yang; Fang Li; Naiyun Ji

doi:10.1007/s00343-015-4316-2

Your Location：

Home >

Browse articles >

Alkaloids from an algicolous strain of Talaromyces sp.

OriginalPaper | Updated：2023-05-16

- Alkaloids from an algicolous strain of Talaromyces sp.
- Alkaloids from an algicolous strain of Talaromyces sp.
- 海洋湖沼学报（英文） 2016年34卷第2期页码：367-371
- Affiliations：
  
  1. College of Chemistry and Molecular Engineering Qingdao University of Science & Technology
  2. Key Laboratory of Coastal Biology and Bioresource Utilization Yantai Institute of Coastal Zone Research Chinese Academy of Sciences
- Author bio：
- Funds：
  
  Supported by the National Key Technology Research and Development Program for Agriculture (No. 2012BAD32B09), the National Natural Science Foundation of China (Nos. 41106137, 41106136), the Taishan Scholar Program of Shandong Province, and the Chinese Academy of Sciences for Key Topics in Innovation Engineering (No. KZCX2-YW-QN209)
- DOI：10.1007/s00343-015-4316-2
  中图分类号：
- 网络首发：2015-09-29，
  
  纸质出版：2016
- Accepted：
Scan QR Code
Alkaloids from an algicolous strain of Talaromyces sp.[J]. 海洋湖沼学报（英文）, 2016,34(2):367-371.

Yang, H., Li, F. & Ji, N. Alkaloids from an algicolous strain of Talaromyces sp.., Chin. J. Ocean. Limnol. 34, 367–371 (2016). https://doi.org/10.1007/s00343-015-4316-2
Alkaloids from an algicolous strain of Talaromyces sp.[J]. 海洋湖沼学报（英文）, 2016,34(2):367-371. DOI： 10.1007/s00343-015-4316-2.

Yang, H., Li, F. & Ji, N. Alkaloids from an algicolous strain of Talaromyces sp.., Chin. J. Ocean. Limnol. 34, 367–371 (2016). https://doi.org/10.1007/s00343-015-4316-2 DOI：

摘要

Abstract

Compounds isolated and identified in a culture of the alga-endophytic fungus Talaromyces sp. cf-16 included two naturally occurring alkaloids

2-[(S)-hydroxy(phenyl)methyl]-3-methylquinazolin-4(3H)-one (1a) and 2-[(R)-hydroxy(phenyl)methyl]-3-methylquinazolin-4(3H)-one (1b)

that were identified for the first time. In addition

seven known compounds (2–8) were obtained from the culture. Following chiral column chromatography

compounds 1a and 1b were identified as enantiomers by spectroscopic analyses and quantum chemical calculations. Bioassay results showed that 5 was more toxic to brine shrimp than the other compounds

and that 3–6 could inhibit Staphylococcus aureus.

关键词

Keywords

references

Batishta J M, Batista A N L, Rinaldo D, Vilegas W, Ambrósio D L, Cicarelli R M B, Bolzani V S, Kato M J, Nafie L A, López S N, Furlan M. 2011. Absolute configuration and selective trypanocidal activity of gaudichaudianic acid enantiomers. J. Nat. Prod., 74 (5): 1154–1160.

Bruhn T, Schaumlöffel A, Hemberger Y, Bringmann G. 2013. SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra, Version 1.62. Chirality, 25: 243–249, http://www-organik. chemie.uni-wuerzburg.de/lehrstuehlearbeitskreise/bringmann/specdis. Accessed on 2013-10-05.

Catir M, Cakici M, Karabuga S, Ulukanli S, Sahin E, Kilic H. 2009. Synthesis of 4, 4’-biquinazoline alcohols as chiral catalysts in enantioselective alkynylation of aldehydes with phenyl acetylene. Tetrahedron: Asymmetry, 20 (24): 2845–2853.

Fan Y Q, Wang Y, Liu P P, Fu P, Zhu T H, Wang W, Zhu W M. 2013. Indole-diterpenoids with anti-H1N1 activity from the aciduric fungus Penicillium camemberti OUCMDZ-1492. J. Nat. Prod., 76 (7): 1328–1336.

Fremlin L J, Piggott A M, Lacey E, Capon R J. 2009. Cottoquinazoline A and cotteslosins A and B, metabolites from an Australian marine-derived strain of Aspergillus versicolor. J. Nat. Prod., 72 (4): 666–670.

Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Scalmani G, Barone V, Mennucci B, Petersson G A, et al. 2010. Gaussian 09, Revision C. 01. http://www.gaussian.com/g_prod/g09.htm. Accessed on 2014-02-23.

Itabashi T, Hosoe T, Wakana D, Fukushima K, Takizawa K, Yaguchi T, Okada K, De Campos Takaki G M, Kawai K. 2009. A new indoloditerpene derivative, penijanthine A, isolated from Penicillium janthinellum. J. Nat. Med., 63 (1): 96–99.

Ji N Y, Liang X R, Sun R R, Miao F P. 2014. A rule to distinguish diastereomeric bianthrones by 1 H NMR. RSC Adv., 4 (15): 7710–7715.

Ji N Y, Liu X H, Miao F P, Qiao M F. 2013. Aspeverin, a new alkaloid from an algicolous strain of Aspergillus versicolor. Org. Lett., 15 (10): 2327–2329.

Li X D, Miao F P, Liang X R, Wang B G, Ji N Y. 2013. Two halosesquiterpenes from Laurencia composita. RSC Adv., 3 (6): 1953–1956.

MarvinSketch with calculator plugins for structure property prediction and calculation. 2014. ChemAxon, Marvin 6.2.2. http://www.chemaxon.com. Accessed on 2014-04-19.

Mazzeo G, Santoro E, Andolfi A, Cimmino A, Troselj P, Petrovic A G, Superchi S, Evidente A, Berova N. 2013. Absolute configurations of fungal and plant metabolites by chiroptical methods. ORD, ECD, and VCD studies on phyllostin, scytolide, and oxysporone. J. Nat. Prod., 76 (4): 588–599.

Miao F P, Liang X R, Liu X H, Ji N Y. 2014. Aspewentins A-C, norditerpenes from a cryptic pathway in an algicolous strain of Aspergillus wentii. J. Nat. Prod., 77 (2): 429–432.

Miao F P, Liang X R, Yin X L, Wang G, Ji N Y. 2012. Absolute configurations of unique harziane diterpenes from Trichoderma species. Org. Lett., 14 (15): 3815–3817.

Musuku A, Selala M I, De Bruyne T, Claeys M, Schepens P J C, Tsatsakis A, Shtilman M I. 1994. Isolation and structure determination of a new roquefortine-related mycotoxin from Penicillium v errucosum var. cyclopium isolated from cassava. J. Nat. Prod., 57 (7): 983–987.

Nozawa K, Nakajima S, Kawai K, Udaqawa S. 1988. Isolation and structures of indoloditerpenes, possible biosynthetic intermediates to the tremorgenic mycotoxin, paxilline, from Emericella s t riata. J. Chem. Soc., Perkin Trans., 1 (9): 2607–2610.

Rufino A T, Ribeiro M, Judas F, Salgueiro L, Lopes M C, Cavaleiro C, Mendes A F. 2014. Anti-inflammatory and chondroprotective activity of (+)-a-pinene: structural and enantiomeric selectivity. J. Nat. Prod., 77 (2): 264–269.

Rundberget T, Wilkins A L. 2002. Thomitrems A and E, two indole-alkaloid isoprenoids from Penicillium crustosum Thom. Phytochemistry, 61 (8): 979–985.

Santoro S, Superchi S, Messina F, Santoro E, Rosati O, Santi C, Marcotullio M C. 2013. Agarsenone, a cadinane sesquiterpenoid from Commiphora erythraea. J. Nat. Prod., 76 (7): 1254–1259.

Scott P M, Polonsky J, Merrien M A. 1979. Configuration of the 3, 12 double bond of roquefortine. J. Agric. Food Chem., 27 (1): 201–202.

Stephens P J, Pan J J, Devlin F J, Cheeseman J R. 2008a. Determination of the absolute configurations of natural products using TDDFT optical rotation calculations: the iridoid oruwacin. J. Nat. Prod., 71 (2): 285–288.

Stephens P J, Pan J J, Devlin F J, Urbanová M, Julínek O, Hájícek J. 2008b. Determination of the absolute configurations of natural products via density functional theory calculations of vibrational circular dichroism, electronic circular dichroism, and optical rotation: the isoschizozygane alkaloids isoschizogaline and isoschizogamine. Chirality, 20 (3-4): 454–470.

Tennant G. 1966. The chemistry of polyazaheterocyclic compounds. Part 1. The structure and reactivity of the 1, 2, 3-triazolo[1, 5-a ]quinazoline ring system. J. Chem. Soc. (C), 2 290–2 295.

Wu R B, Cheng Z B, Han Q H, Lin T T, Zhou J W, Tang G H, Yin S. 2014. Determination of the absolute stereochemistry of two new aristophyllene sesquiterpenes: a combined theoretical and experimental investigation. Chirality, 26 (4): 189–193.

浏览量

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Quinosumycin, a novel anti-MRSA thioether-linked quinolinone-quinazolinone heterodimer from a marine actinomycete Streptomyces diastaticus NBU2966

Phylogenetic diversity and bioactivity of culturable deepsea-derived fungi from Okinawa Trough

Extracts of the seaweed Bifurcaria bifurcata display antifungal activity against human dermatophyte fungi

Preparation by enzymolysis and bioactivity of iron complex of fish protein hydrolysate (Fe-FPH) from low value fish

含缺陷轮盘失效概率分析流程与数值模拟