Penicilloitins A and B, new antimicrobial fatty acid esters from a marine endophytic Penicillium species
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Samar S.A. Mourshid
Abstract
Two new antimicrobial fatty acid esters, penicilloitins A and B (1 and 2), along with α-cyclopiazonic acid (3), tryptamine (4) and indole-3-carbaldehyde (5), were isolated from mycelial extracts and the culture broth of a marine endophytic Penicillium species and their structures established by spectroscopic techniques including 1D (1H NMR and 13C NMR) and 2D NMR (COSY, multiplicity-edited HSQC, and HMBC) as well as HRESIMS. Of these compounds, 1, 3 and 4 displayed modest antimicrobial activity.
Acknowledgement
This project was supported by the NSTIP strategic technologies program in the Kingdom of Saudi Arabia, project no. 11-BIO1556-03. The authors also gratefully acknowledge the Science and Technology Unit, King Abdulaziz University, for technical support.
References
1. Pelaez F. The historical delivery of antibiotics from microbial natural products – Can history repeat? Biochem Pharmacol 2006;71:981–90.10.1016/j.bcp.2005.10.010Suche in Google Scholar
2. Proksch P, Putz A, Ortlepp S, Kjer J, Bayer M. Bioactive natural products from marine sponges and fungal endophytes. Phytochem Rev 2010;9:475–89.10.1007/s11101-010-9178-9Suche in Google Scholar
3. Rateb ME, Ebel R. Secondary metabolites of fungi from marine habitats. Nat Prod Rep 2011;28:290–344.10.1039/c0np00061bSuche in Google Scholar
4. Abo-Kadoum MA, Abo-Dahab NF, Awad MF, Abdel-Hadi AM. Marine-derived fungus, Penicillium aurantiogriseum AUMC 9757: a producer of bioactive secondary metabolites. J Basic Appl Mycol 2013;4:77–83.Suche in Google Scholar
5. Subramani R, Kumar R, Prasad P, Aalbersberg W. Cytotoxic and antibacterial substances against multi-drug resistant pathogens from marine sponge symbiont: Citrinin, a secondary metabolite of Penicillium sp. Asian Pac J Trop Biomed 2013;3:291–6.10.1016/S2221-1691(13)60065-9Suche in Google Scholar
6. Shaala LA, Youssef DTA. Identification and bioactivity of compounds from the fungus Penicillium sp. CYE-87 isolated from a marine tunicate. Mar Drugs 2015;13:1698–709.10.3390/md13041698Suche in Google Scholar PubMed PubMed Central
7. Li Q, Wang G. Diversity of fungal isolates from three Hawaiian marine sponges. Microbiol Res 2009;164:233–41.10.1016/j.micres.2007.07.002Suche in Google Scholar PubMed
8. White TJ, Bruns T, Lee S, Taylor J. Amplification and direct sequencing of fungal ribosomal RNA genes for phylogenetics. Chapter 38. In: Innis M, Gelfand D, Sninsky J, White T, editors. PCR Protocols: a guide to methods and applications. Orlando, FL: Academic Press, 1990:315–22.10.1016/B978-0-12-372180-8.50042-1Suche in Google Scholar
9. Valgas C, de Souza SM, Smània EFA, Smânia J. Screening methods to determine antibacterial activity of natural products. Brazil J Microbiol 2007;38:369–80.10.1590/S1517-83822007000200034Suche in Google Scholar
10. Singh RP, Jain DA. Anticandidal potential of Crinum asiaticum leaves extract against selected oral and vaginal Candida pathogens. Asian J Biochem Pharm Res 2011;1:283–91.Suche in Google Scholar
11. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990;82:107–12.10.1093/jnci/82.13.1107Suche in Google Scholar PubMed
12. Boyd MR, Paull KD. Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen. Drug Dev Res 1995;34:91–109.10.1002/ddr.430340203Suche in Google Scholar
13. Yoshikawa M, Shimada H, Matsuda H, Yamahara J, Murakami N. Bioactive constituents of Chinese natural medicines. J Chem Pharm Bull 1996;44:1656–62.10.1248/cpb.44.1656Suche in Google Scholar PubMed
14. Wang YN, Tian L, Hua HM, Lu X, Sun S, Wu HH, et al. Two new compounds from the broth of the marine fungus Penicillium griseofulvum Y19-07. J Asian Nat Prod Res 2009;11:912–7.10.1080/10286020903219923Suche in Google Scholar PubMed
15. Lin AQ, Du L, Fang YC, Wang FZ, Zhu TJ, Gu QQ, et al. Iso-α-Cyclopiazonic acid, a new natural product isolated from the marine-derived fungus Aspergillus flavus CF-3. Chem Nat Compd 2009;45:677–680.10.1007/s10600-009-9433-8Suche in Google Scholar
16. McKay MJ, Carroll AR, Quinn RJ, Hooper JNA. 1,2-bis(1H-indol-3-yl)ethane-1,2-dione, an indole alkaloid from the marine sponge Smenospongia sp. J Nat Prod 2002;65:595–7.10.1021/np010347vSuche in Google Scholar PubMed
17. Ashour MA, Elkhayat ES, Ebel R, Edrada RA, Proksch P. Indole alkaloid from the Red Sea sponge Hyrtios erectus. Arkivoc 2007;xv:225–231.10.3998/ark.5550190.0008.f22Suche in Google Scholar
©2016 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- Research Articles
- Seasonal variation of gastroprotective terpenoids in Maytenus robusta (Celastraceae) quantified by gas chromatography-flame ionization detection (GC-FID)
- Plicosepalin A, a new antioxidant catechin–gallic acid derivative of inositol from the mistletoe Plicosepalus curviflorus
- New lupan-type triterpenoids
- Penicilloitins A and B, new antimicrobial fatty acid esters from a marine endophytic Penicillium species
- Anti-acetylcholinesterase activity of essential oils and their major constituents from four Ocimum species
- The chemical composition, antimicrobial, and antioxidant activities of Pycnocycla spinosa and Pycnocyla flabellifolia essential oils
- Biological evaluation and docking studies of some benzoxazole derivatives as inhibitors of acetylcholinesterase and butyrylcholinesterase
- LC/ESI-MS/MS profiling of Ulmus parvifolia extracts and evaluation of its anti-inflammatory, cytotoxic, and antioxidant activities
- Antiproliferative effect of synthetic cyclic imides (methylphtalimides, carboxylic acid phtalimides and itaconimides) against human cancer cell lines
- Anti-inflammatory activity of highly oxygenated terpenoids from Achillea biebersteinii Afan
- Annual Reviewer Acknowledgement
- Reviewer acknowledgement Biosciences – Zeitschrift für Naturforschung C, volume 71 (2016)
Artikel in diesem Heft
- Frontmatter
- Research Articles
- Seasonal variation of gastroprotective terpenoids in Maytenus robusta (Celastraceae) quantified by gas chromatography-flame ionization detection (GC-FID)
- Plicosepalin A, a new antioxidant catechin–gallic acid derivative of inositol from the mistletoe Plicosepalus curviflorus
- New lupan-type triterpenoids
- Penicilloitins A and B, new antimicrobial fatty acid esters from a marine endophytic Penicillium species
- Anti-acetylcholinesterase activity of essential oils and their major constituents from four Ocimum species
- The chemical composition, antimicrobial, and antioxidant activities of Pycnocycla spinosa and Pycnocyla flabellifolia essential oils
- Biological evaluation and docking studies of some benzoxazole derivatives as inhibitors of acetylcholinesterase and butyrylcholinesterase
- LC/ESI-MS/MS profiling of Ulmus parvifolia extracts and evaluation of its anti-inflammatory, cytotoxic, and antioxidant activities
- Antiproliferative effect of synthetic cyclic imides (methylphtalimides, carboxylic acid phtalimides and itaconimides) against human cancer cell lines
- Anti-inflammatory activity of highly oxygenated terpenoids from Achillea biebersteinii Afan
- Annual Reviewer Acknowledgement
- Reviewer acknowledgement Biosciences – Zeitschrift für Naturforschung C, volume 71 (2016)
