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Article ; Online: Large-scale screening of natural genetic resource in the hydrocarbon-producing microalga Botrycoccus braunii identified novel fast-growing strains

Koji Kawamura / Suzune Nishikawa / Kotaro Hirano / Ardianor Ardianor / Rudy Agung Nugroho / Shigeru Okada

Scientific Reports, Vol 11, Iss 1, Pp 1-

2021 Volume 13

Abstract: Abstract Algal biofuel research aims to make a renewable, carbon–neutral biofuel by using oil-producing microalgae. The freshwater microalga Botryococcus braunii has received much attention due to its ability to accumulate large amounts of petroleum-like ...

Abstract	Abstract Algal biofuel research aims to make a renewable, carbon–neutral biofuel by using oil-producing microalgae. The freshwater microalga Botryococcus braunii has received much attention due to its ability to accumulate large amounts of petroleum-like hydrocarbons but suffers from slow growth. We performed a large-scale screening of fast-growing strains with 180 strains isolated from 22 ponds located in a wide geographic range from the tropics to cool-temperate. A fast-growing strain, Showa, which recorded the highest productivities of algal hydrocarbons to date, was used as a benchmark. The initial screening was performed by monitoring optical densities in glass tubes and identified 9 wild strains with faster or equivalent growth rates to Showa. The biomass-based assessments showed that biomass and hydrocarbon productivities of these strains were 12–37% and 11–88% higher than that of Showa, respectively. One strain, OIT-678 established a new record of the fastest growth rate in the race B strains with a doubling time of 1.2 days. The OIT-678 had 36% higher biomass productivity, 34% higher hydrocarbon productivity, and 20% higher biomass density than Showa at the same cultivation conditions, suggesting the potential of the new strain to break the record for the highest productivities of hydrocarbons.
Keywords	Medicine ; R ; Science ; Q
Subject code	500
Language	English
Publishing date	2021-04-01T00:00:00Z
Publisher	Nature Portfolio
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article: Molecular cloning and functional characterization of NADPH-dependent cytochrome P450 reductase from the green microalga Botryococcus braunii, B race

Tsou, Chung-Yau / Shigeki Matsunaga / Shigeru Okada

The Society for Biotechnology, Japan Journal of bioscience and bioengineering. 2018 Jan., v. 125, no. 1

2018

Abstract: The green microalga Botryococcus braunii of the B race accumulates various lipophilic compounds containing a 10,11-oxidosqualene epoxide moiety in addition to large amounts of triterpene hydrocarbons. While 2,3-squalene epoxidases have already been ... ...

Abstract	The green microalga Botryococcus braunii of the B race accumulates various lipophilic compounds containing a 10,11-oxidosqualene epoxide moiety in addition to large amounts of triterpene hydrocarbons. While 2,3-squalene epoxidases have already been isolated and characterized from the alga, the enzyme that catalyzes the 10,11-epoxidation of squalene has remained elusive. In order to obtain a molecular tool to explore a 10,11-squalene epoxidase, cDNA cloning of an NADPH-dependent cytochrome P450 reductase (CPR) that is required by both squalene epoxidases and cytochrome P450 enzymes was carried out. The isolated cDNA contained an open reading frame (1998 bp) that encoded for a protein with 665 amino acid residues with a predicted molecular weight of 71.46 kDa and a theoretical pI of 5.49. Analysis of the deduced amino acid sequence revealed the presence of conserved motifs, including FMN, FAD, and NADPH binding domains, which are typical of other CPRs and necessary for enzyme activity. By truncation of the N-terminal transmembrane anchor and addition of a 6× His-tag, BbCPR was heterologously produced in Escherichia coli and purified by Ni-NTA affinity chromatography. The purified recombinant enzyme showed optimal reducing activity of cytochrome c at around a neutral pH at a temperature range of 30–37°C. For steady state kinetic parameters, the recombinant enzyme had a km for cytochrome c and NADPH of 11.7±1.6 and 9.4±1.4 μM, and a kcat for cytochrome c and NADPH of 2.78±0.09 and 3.66±0.11 μmol/min/mg protein, respectively. This is the first study to perform the functional characterization of a CPR from eukaryotic microalgae.
Keywords	affinity chromatography ; amino acid sequences ; amino acids ; Botryococcus braunii ; complementary DNA ; cytochrome c ; cytochrome P-450 ; enzyme activity ; enzymes ; Escherichia coli ; microalgae ; molecular cloning ; molecular weight ; NADP (coenzyme) ; open reading frames ; pH ; squalene ; temperature ; triterpenoids
Language	English
Dates of publication	2018-01
Size	p. 30-37.
Publishing place	Elsevier B.V.
Document type	Article
ZDB-ID	1465387-4
ISSN	1347-4421 ; 1389-1723
ISSN (online)	1347-4421
ISSN	1389-1723
DOI	10.1016/j.jbiosc.2017.07.010
Database	NAL-Catalogue (AGRICOLA)

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Article: 3D reconstruction of endoplasmic reticulum in a hydrocarbon-secreting green alga, Botryococcus braunii (Race B)

Suzuki, Reiko / Ichiro Nishii / Shigeru Okada / Tetsuko Noguchi

Planta. 2018 Mar., v. 247, no. 3

2018

Abstract: MAIN CONCLUSION: Based on 3D sections through cells of Botryococcus braunii, the structure of three domains of endoplasmic reticulum, and their spatial and functional relationships to other organelles are clarified. Oil production by photosynthetic ... ...

Abstract	MAIN CONCLUSION: Based on 3D sections through cells of Botryococcus braunii, the structure of three domains of endoplasmic reticulum, and their spatial and functional relationships to other organelles are clarified. Oil production by photosynthetic microalgae has attracted attention since these oils can be converted into renewable, carbon-neutral fuels. The green alga B. braunii accumulates large amounts of hydrocarbons, 30–50% of cell dry weight, in extracellular spaces rather than its cytoplasm. To advance the knowledge of hydrocarbon biosynthesis and transport pathways in this alga, we utilized transmission EM combined with rapid freezing and image reconstruction. We constructed detailed 3D maps distinguishing three ER domains: rdER with ribosomes on both sides, rsER with ribosomes on one side, and sER without ribosomes. The rsER and sER domains were especially prominent during the oil body formation and oil secretion stages. The ER contacted the chloroplasts, oil bodies, or plasma membrane via the rsER domains, oriented with the ribosome-free surface facing the organelles. We discuss the following transport pathway for hydrocarbons and their precursors in the cytoplasm: chloroplast → endoplasmic reticulum (ER) → oil bodies → ER → plasma membrane → secretion. This study represents the first 3D study of the three-domain classification (rdER, rsER and sER) of the ER network among eukaryotic cells. Finally, we propose the novel features of the ERs in plant cells that are distinct from the latest proposed model for the ERs in mammalian cells.
Keywords	Botryococcus braunii ; biosynthesis ; chloroplasts ; digital images ; endoplasmic reticulum ; eukaryotic cells ; freezing ; fuels ; hydrocarbons ; lipid bodies ; mammals ; microalgae ; models ; oils ; photosynthesis ; plasma membrane ; ribosomes ; secretion
Language	English
Dates of publication	2018-03
Size	p. 663-677.
Publishing place	Springer Berlin Heidelberg
Document type	Article
ZDB-ID	208909-9
ISSN	1432-2048 ; 0032-0935 ; 1866-2749
ISSN (online)	1432-2048
ISSN	0032-0935 ; 1866-2749
DOI	10.1007/s00425-017-2811-8
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Structure Elucidation of Calyxoside B, a Bipolar Sphingolipid from a Marine Sponge Cladocroce sp. through the Use of Beckmann Rearrangement

Kenji Sugawara / Hiroshi Watarai / Yuji Ise / Hisayoshi Yokose / Yasuhiro Morii / Nobuhiro Yamawaki / Shigeru Okada / Shigeki Matsunaga

Marine Drugs, Vol 19, Iss 287, p

2021 Volume 287

Abstract: Marine sponges are an excellent source of biologically active secondary metabolites. We focus on deep-sea sponges for our discovery study. A marine sponge Cladocroce sp. exhibited cytotoxic activity in the bioactivity screening. From this sponge a ... ...

Abstract	Marine sponges are an excellent source of biologically active secondary metabolites. We focus on deep-sea sponges for our discovery study. A marine sponge Cladocroce sp. exhibited cytotoxic activity in the bioactivity screening. From this sponge a previously unreported cytotoxic glycosphingolipid, calyxoside B, was isolated and the structure of this compound was elucidated by analyses of MS and NMR spectra and chemical derivatization. We converted the ketone in the middle of a long aliphatic chain into an oxime to which was applied Beckmann rearrangement to afford two positional isomers of amides. The products were subjected to acidic hydrolysis followed by LC-MS analysis, permitting us to assign unequivocally the position of the ketone. Calyxoside B shows cytotoxicity against HeLa cells with an IC 50 value of 31 µM and also weakly stimulated the production of cytokines in mice.
Keywords	marine natural products ; marine sponge ; glycosphingolipid ; structure elucidation ; Biology (General) ; QH301-705.5
Language	English
Publishing date	2021-05-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
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Article: Effects of 2-azahypoxanthine on extracellular terpene accumulations by the green microalga Botryococcus braunii, race B

Nakamura, Hiromasa / Hirokazu Kawagishi / Shigeki Matsunaga / Shigeru Okada

Algal research. 2016 Dec., v. 20

2016

Abstract: The B race of the green microalga Botryococcus braunii accumulates large amounts of triterpene hydrocarbons that are attractive as a source for biofuels. The alga, however, exhibits rather slow growth and this characteristic has hindered its practical ... ...

Abstract	The B race of the green microalga Botryococcus braunii accumulates large amounts of triterpene hydrocarbons that are attractive as a source for biofuels. The alga, however, exhibits rather slow growth and this characteristic has hindered its practical application for biofuel production. In order to test a phytohormone-like compound that may regulate the growth or hydrocarbon production of this alga, the effects of 2-azahypoxanthine (AHX) on algal biomass and terpene contents in the extracellular matrix (ECM) in the Showa strain of B. braunii were investigated. The biomass of the Showa strain increased with AHX supplementation under static culture conditions although such effects were not observed in cultures with aeration or agitation. AHX supplementation significantly induced the accumulation of secondary carotenoids, including species-specific tetramethylsqualene (TMS)-conjugated carotenoids, botryoxanthin A and braunixanthin 1. Conversely, the addition of AHX showed a tendency to slightly lower the triterpene hydrocarbon (botryococcenes) content in the ECM. These metabolic changes in tri- and tetraterpene accumulation could be caused by a reduction in nitrogen uptake from the culture medium due to AHX addition. Thus, there is a possibility that AHX could be used as a reagent to modulate terpene biosynthesis in the B race of B. braunii.
Keywords	aeration ; agitation ; biofuels ; biomass ; biosynthesis ; Botryococcus braunii ; carotenoids ; culture media ; extracellular matrix ; fuel production ; microalgae ; nitrogen ; triterpenoids
Language	English
Dates of publication	2016-12
Size	p. 267-275.
Publishing place	Elsevier B.V.
Document type	Article
ISSN	2211-9264
DOI	10.1016/j.algal.2016.10.023
Database	NAL-Catalogue (AGRICOLA)

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Article: Colony-wise Analysis of a Theonella swinhoei Marine Sponge with a Yellow Interior Permitted the Isolation of Theonellamide I

Fukuhara, Kazuya / Kentaro Takada / Ryuichi Watanabe / Toshiyuki Suzuki / Shigeru Okada / Shigeki Matsunaga

Journal of natural products. 2018 Oct. 22, v. 81, no. 11

2018

Abstract: There are several examples of marine organisms whose metabolic profiles differ among conspecifics inhabiting the same region. We have analyzed the metabolic profile of each colony of a Theonella swinhoei marine sponge with a yellow interior and noticed ... ...

Abstract	There are several examples of marine organisms whose metabolic profiles differ among conspecifics inhabiting the same region. We have analyzed the metabolic profile of each colony of a Theonella swinhoei marine sponge with a yellow interior and noticed the patchy distribution of one metabolite. This compound was isolated and its structure was studied by a combination of spectrometric analyses and chemical degradation, showing it to be a congener in the theonellamide class of bicyclic peptides. Theonellamides had previously been isolated by us only from T. swinhoei with a white interior and not from those with a yellow interior.
Keywords	Porifera ; aquatic organisms ; chemical degradation ; metabolites ; peptides
Language	English
Dates of publication	2018-1022
Size	p. 2595-2599.
Publishing place	American Chemical Society and American Society of Pharmacognosy
Document type	Article
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.8b00591
Database	NAL-Catalogue (AGRICOLA)

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Article: Miuramides A and B, Trisoxazole Macrolides from a Mycale sp. Marine Sponge That Induce a Protrusion Phenotype in Cultured Mammalian Cells

Suo, Rei / Hisanori Kohtsuka / Kentaro Takada / Shigeki Matsunaga / Shigeru Okada / Yuji Ise

Journal of natural products. 2018 Apr. 03, v. 81, no. 4

2018

Abstract: Morphology-guided cell-based screening of the extract of a Mycale sp. marine sponge led to the isolation of two trisoxazole macrolides, miuramides A (1) and B (2), which induced characteristic morphological changes in 3Y1 cells. The structure of 1 ... ...

Abstract	Morphology-guided cell-based screening of the extract of a Mycale sp. marine sponge led to the isolation of two trisoxazole macrolides, miuramides A (1) and B (2), which induced characteristic morphological changes in 3Y1 cells. The structure of 1 including absolute configuration was elucidated by a combination of the analysis of spectroscopic data, derivatization, and degradation. Both compounds exhibit potent cytotoxicity against 3Y1 cells.
Keywords	cytotoxicity ; derivatization ; macrolides ; mammals ; Mycale ; phenotype ; screening ; spectral analysis
Language	English
Dates of publication	2018-0403
Size	p. 1108-1112.
Publishing place	American Chemical Society and American Society of Pharmacognosy
Document type	Article
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.8b00101
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Article: Isolation and characterization of 4-hydroxy-3-methylbut-2-enyl diphosphate reductase gene from Botryococcus braunii, race B

Uchida, Hidenobu / Eiichi Mizohata / Ichiro Nishii / Koremitsu Sumimoto / Shigeki Matsunaga / Shigeru Okada / Tomoka Oki

Journal of plant research. 2018 Sept., v. 131, no. 5

2018

Abstract: The B race of a green microalga Botryococcus braunii Kützing produces triterpene hydrocarbons that is a promising source for biofuel. In this algal race, precursors of triterpene hydrocarbons are provided from the 2-C-methyl-D-erythritol 4-phosphate (MEP) ...

Abstract	The B race of a green microalga Botryococcus braunii Kützing produces triterpene hydrocarbons that is a promising source for biofuel. In this algal race, precursors of triterpene hydrocarbons are provided from the 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway. The terminal enzyme of this pathway, 4-hydroxy-3-methylbut-2-enyl diphosphate reductase (HDR) is regarded as one of the key enzymes that affect yields of products in terpene biosynthesis. In order to better understand the MEP pathway of the alga, cDNA and genomic clones of HDR were obtained from B. braunii Showa strain. B. braunii HDR (BbHDR) is encoded on a single copy gene including a 1509-bp open reading frame that was intervened by 6 introns. The exon–intron structure of BbHDR genes did not show clear relation to phylogeny, while its amino acid sequence reflected phyla and classes well. BbHDR sequence was distinctive from that of the HDR protein from Escherichia coli in the residues involved in hydrogen-bond network that surrounds substrate. Introduction of BbHDR cDNA into an E. coli HDR deficient mutant resulted in recovery of its auxotrophy. BbHDR expression level was upregulated from the onset of liquid culture to the 24th day after inoculation with a 2.5-fold increase and retained its level in the subsequent period.
Keywords	amino acid sequences ; biofuels ; biosynthesis ; Botryococcus braunii ; clones ; complementary DNA ; enzymes ; Escherichia coli ; genomics ; hydrogen bonding ; introns ; microalgae ; mutants ; open reading frames ; phylogeny ; triterpenoids
Language	English
Dates of publication	2018-09
Size	p. 839-848.
Publishing place	Springer Japan
Document type	Article
ZDB-ID	2077362-6
ISSN	1618-0860 ; 0918-9440
ISSN (online)	1618-0860
ISSN	0918-9440
DOI	10.1007/s10265-018-1039-4
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Article: Poecillastrin E, F, and G, cytotoxic chondropsin-type macrolides from a marine sponge Poecillastra sp

Irie, Raku / Kentaro Takada / Shigeki Matsunaga / Shigeru Okada / Yuji Ise / Yuki Hitora

Tetrahedron. 2018 Mar. 29, v. 74

2018

Abstract: Poecillastrin E (1), F (2), and G (3) were isolated from a marine sponge Poecillastra sp. as the cytotoxic constituents. Their planar structures were determined by analyzing the MS and NMR spectra. They are closely related to the known poecillastrin C (4) ...

Abstract	Poecillastrin E (1), F (2), and G (3) were isolated from a marine sponge Poecillastra sp. as the cytotoxic constituents. Their planar structures were determined by analyzing the MS and NMR spectra. They are closely related to the known poecillastrin C (4). The absolute configuration of the Î²-hydroxyaspartic acid (OHAsp) residue was determined to be D-threo by Marfey's analysis of the hydrolysate. The mode of lactone ring formation of OHAsp residue in 1â3 was determined by selective reduction of the ester linkage followed by acid hydrolysis.
Keywords	acid hydrolysis ; chemical structure ; cytotoxicity ; hydrolysates ; macrolides ; nuclear magnetic resonance spectroscopy ; Porifera
Language	English
Dates of publication	2018-0329
Size	p. 1430-1434.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	204285-x
ISSN	1464-5416 ; 0040-4020 ; 0563-2064
ISSN (online)	1464-5416
ISSN	0040-4020 ; 0563-2064
DOI	10.1016/j.tet.2018.01.037
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Article ; Online: Detection of the oil-producing microalga Botryococcus braunii in natural freshwater environments by targeting the hydrocarbon biosynthesis gene SSL-3

Kotaro Hirano / Takuya Hara / Ardianor / Rudy Agung Nugroho / Hendrik Segah / Naru Takayama / Gumiri Sulmin / Yukio Komai / Shigeru Okada / Koji Kawamura

Scientific Reports, Vol 9, Iss 1, Pp 1-

2019 Volume 11

Abstract: Abstract The green microalga Botryococcus braunii produces hydrocarbon oils at 25–75% of its dry weight and is a promising source of biofuel feedstock. Few studies have examined this species’ ecology in natural habitats, and few wild genetic resources ... ...

Abstract	Abstract The green microalga Botryococcus braunii produces hydrocarbon oils at 25–75% of its dry weight and is a promising source of biofuel feedstock. Few studies have examined this species’ ecology in natural habitats, and few wild genetic resources have been collected due to difficulties caused by its low abundance in nature. This study aimed to develop a real-time PCR assay for specific detection and quantification of this alga in natural environments and to quantify spatiotemporal variations of wild B. braunii populations in a tropical pond. We designed PCR primers toward the hydrocarbon biosynthesis gene SSL-3 and examined amplification specificity and PCR efficiency with 70 wild strains newly isolated from various environments. The results demonstrated that this PCR assay specifically amplified B. braunii DNA, especially that of B-race strains, and can be widely used to detect wild B. braunii strains in temperate and tropical habitats. Field-testing in a tropical pond suggested a diurnal change in the abundance of B. braunii in surface water and found B. braunii not only in surface water, but also at 1–1.5 m deep and in bottom sediments. This method can contribute to efficient genetic resource exploitations and may also help elucidate the unknown ecology of B. braunii.
Keywords	Medicine ; R ; Science ; Q
Subject code	580
Language	English
Publishing date	2019-11-01T00:00:00Z
Publisher	Nature Publishing Group
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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