Preparative Separation of Spirobisnaphthalenes from Endophytic Fungus Berkleasmium sp. Dzf12 by  High-Speed Counter-Current Chromatography

Shan, Tijiang; Lu, Shiqiong; Luo, Chen; Luo, Ruiya; Mou, Yan; Wang, Mingan; Peng, You-Liang; Zhou, Ligang

doi:10.3390/molecules181012896

Cited by 6 publications

(5 citation statements)

References 37 publications

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“…This technique has been successfully applied to the separation of a number of drugs, toxins and natural products [23][24][25][26]. Concurrently, the use of HPCCC in combination with gel permeation chromatography (GPC) on Sephadex LH-20 has been advantageously used for the isolation and purification of structurally diverse bioactive compounds from complex matrices derived from plants and cyanobacteria [27][28][29]. HPCCC is considered orthogonal to GPC [23], because the retention of the solutes in both techniques is caused by different mechanisms.…”

Section: Introductionmentioning

confidence: 99%

Dimeric cyanobacterial cyclopent-4-ene-1,3-dione as selective inhibitor of Gram-positive bacteria growth: Bio-production approach and preparative isolation by HPCCC

et al. 2016

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a b s t r a c tThe need for new antimicrobial agents is greater than ever because of the emergence of multidrug resistance in common pathogens and incidence of new infections. Cyclopent-4-ene-1,3-diones (CPDs) have been reported as a new class of compounds with promising antimicrobial and antifungal properties. Herein we report the selective antibiotic properties of nostotrebin 6, a phenolic CPD produced biotechnologically by the culture of cyanobacterium Nostoc sp. str. Lukešová 27/97. High performance countercurrent chromatography (HPCCC) combined with gel permeation chromatography (GPC) was used for the isolation of nostotrebin 6 with a relatively high 0.53 ± 0.1% yield (calculated from dried biomass) and final purity higher than 96%. Nostotrebin 6 was tested for its antimicrobial and antifungal activities by using standard micro-dilution method, and the results were expressed as minimal inhibitory concentrations (MICs). Nostotrebin 6 unequivocally inhibited the growth of Gram-positive reference (Enterococcus faecalis CCM 4224, Staphylococcus aureus CCM 4223 and Staphylococcus aureus CCM 3953) and multidrug-resistant (Staphylococcus haemolyticus A/16568, Staphylococcus aureus MRSA 4591 and Enterococcus faecium VanA 419/ana) strains. Its strongest effect was exerted against the Gram-positive bacteria with MICs ranging between 6.25 and 15.6 μg/mL. There was no effect on Gram-negative strains tested and yeasts. Our results suggest that nostotrebin 6 could serve as basic nucleus for further design of novel antibiotic agents and demonstrate that the bio-production approach based on HPCCC/GPC isolation endpoint is an efficient methodology for obtaining nostotrebin 6 in multi-gram scale. Furthermore, the presented isolation method can be easily up-scaled to process kilograms of the cyanobacterial biomass.

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Section: Introductionmentioning

confidence: 99%

Dimeric cyanobacterial cyclopent-4-ene-1,3-dione as selective inhibitor of Gram-positive bacteria growth: Bio-production approach and preparative isolation by HPCCC

et al. 2016

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“…Berkleasmium sp. Dzf12 was also found to be a high producer of palmarumycins C 12 and C 13 [7,8,9,10,11]. As part of our ongoing program to search for other palmarumycins from Berkleasmium sp.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial and Antioxidant Activities and Effect of 1-Hexadecene Addition on Palmarumycin C2 and C3 Yields in Liquid Culture of Endophytic Fungus Berkleasmium sp. Dzf12

Mou

Meng

et al. 2013

Molecules

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Two spirobisnaphthalenes, namely palmarumycins C 2 and C 3 , were isolated from cultures of the endophytic fungus Berkleasmium sp. Dzf12 after treatment with 1-hexadecene. After addition of 1-hexadecene at 10% to the medium on day 6 of culture, the maximal yields of palmarumycins C 2 and C 3 were obtained as 0.40 g/L and 1.19 g/L, which were 40.00 fold and 59.50 fold higher, respectively, in comparison with those of the control (0.01 g/L and 0.02 g/L). The results indicated that addition of 1-hexadecene can be an effective strategy for enhancing the production of palmarumycins C 2 and C 3 in liquid culture of endophytic fungus Berkleasmium sp. Dzf12. Palmarumycin C 3 exhibited stronger antimicrobial and antioxidant activities than palmarumycin C 2 .Keywords: spirobisnaphthalenes; palmarumycin C 2 ; palmarumycin C 3 ; endophytic fungus; Berkleasmium sp. Dzf12; 1-hexadecene; biological activityThe image canno t be display ed. Yo ur co mputer may no t hav e eno ugh memo ry to o pen the image, o r the image may hav e been co rrupted. Restart y o ur co mp uter, and then o p en the file ag ain. If the red x still ap p ears, y o u may hav e to d elete the imag e and then inser t it again.

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“…The two-phase solvent systems were screened according to the partition coefficients ( K values) of the target compounds [ 23 ]. The K values were determined by HPLC analysis as follows.…”

Section: Methodsmentioning

confidence: 99%

“…It overcomes the irreversible adsorptive loss of samples onto the solid support matrix and also has the unique features of high recovery, high efficiency and ease of scaling [ 18 ]. This method has been successfully applied to separate and purify a number of natural products from a variety of plant and microbial materials [ 19 , 20 , 21 , 22 , 23 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

Preparative Separation of Main Ustilaginoidins from Rice False Smut Balls by High-Speed Counter-Current Chromatography

Sun

Dong

et al. 2016

Toxins

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Ustilaginoidins are bis-naphtho-γ-pyrone mycotoxins isolated from the rice false smut balls (FSBs) infected by the pathogen Villosiclava virens in rice spikelets on panicles. In order to obtain large amounts of pure ustilaginoidins to further evaluate their biological activities and functions, phytotoxicity on rice, security to human and animals as well as to accelerate their applications as pharmaceuticals, preparative high-speed counter-current chromatography (HSCCC) was successfully applied to the isolation and purification of seven bis-naphtho-γ-pyrone mycotoxins, namely ustilaginoidins A (1), G (2), B (3), H (4), I (5), C (6), and J (7) from the ethyl acetate crude extract of rice FSBs. Both 1 and 2 were prepared by HSCCC from the low-polarity fraction of the crude extract using the two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water at the volume ratio of 6.5:3.5:5.0:5.0. Similarly, 3, 4 and 5 were prepared from the medium-polarity fraction using the system at the volume ratio of 4.0:5.0:5.0:6.0, and 6 and 7 were prepared from the higher-polarity fraction using the system at volume ratio of 3.0:5.0:4.0:6.7. A total of 6.2 mg of 1, 5.1 mg of 2, 3.9 mg of 3, 1.2 mg of 4, 5.7 mg of 5, 3.5 mg of 6, and 6.1 mg of 7 with purities of 88%, 82%, 91%, 80%, 92%, 81% and 83%, respectively, were yielded from total 62 mg fraction samples in three independent HSCCC runs. The structures of the purified ustilaginoidins were characterized by means of physicochemical and spectrometric analysis.

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Preparative Separation of Spirobisnaphthalenes from Endophytic Fungus Berkleasmium sp. Dzf12 by High-Speed Counter-Current Chromatography

Cited by 6 publications

References 37 publications

Dimeric cyanobacterial cyclopent-4-ene-1,3-dione as selective inhibitor of Gram-positive bacteria growth: Bio-production approach and preparative isolation by HPCCC

Dimeric cyanobacterial cyclopent-4-ene-1,3-dione as selective inhibitor of Gram-positive bacteria growth: Bio-production approach and preparative isolation by HPCCC

Antimicrobial and Antioxidant Activities and Effect of 1-Hexadecene Addition on Palmarumycin C2 and C3 Yields in Liquid Culture of Endophytic Fungus Berkleasmium sp. Dzf12

Preparative Separation of Main Ustilaginoidins from Rice False Smut Balls by High-Speed Counter-Current Chromatography

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