WO2018166159A1 - Souche pezicula sp. sc1337 et méthode de préparation de dérivés d'ester trisaccharide l'utilisant - Google Patents

Souche pezicula sp. sc1337 et méthode de préparation de dérivés d'ester trisaccharide l'utilisant Download PDF

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WO2018166159A1
WO2018166159A1 PCT/CN2017/102048 CN2017102048W WO2018166159A1 WO 2018166159 A1 WO2018166159 A1 WO 2018166159A1 CN 2017102048 W CN2017102048 W CN 2017102048W WO 2018166159 A1 WO2018166159 A1 WO 2018166159A1
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pezicula
extract
fermentation culture
compound
fraction
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徐良雄
魏孝义
薛璟花
吴萍
李翰祥
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中国科学院华南植物园
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Publication of WO2018166159A1 publication Critical patent/WO2018166159A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/645—Fungi ; Processes using fungi
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/14—Fungi; Culture media therefor
    • C12N1/145—Fungal isolates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C07H13/06—Fatty acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides

Definitions

  • the present invention belongs to the field of natural products, and in particular relates to a strain of Pezicula sp. SC1337 and a method for preparing a trisaccharide derivative using the same.
  • Oligosaccharides refer to oligosaccharides which are bonded by 2 to 9 monosaccharide units via glycosidic bonds. According to the number of monosaccharides combined, they can be divided into disaccharides, trisaccharides, tetrasaccharides and pentoses. Some of the oligosaccharides are not digested by humans and animals but have special physiological functions and are called functional oligosaccharides.
  • an oligosaccharide ester When an oligosaccharide is conjugated to a fatty acid, an oligosaccharide ester is formed, which is a typical type of nonionic biosurfactant due to the simultaneous oleophilic and hydrophilic groups in the oligosaccharide ester molecule.
  • sugar esters tend to have better biocompatibility, biodegradability and safety and are a class of environmentally friendly surfactants. At present, sugar esters have been widely used in food, medicine, fermentation, cosmetics, detergents, fertilizers and other fields.
  • a first object of the present invention is to provide a Pezicula sp. SC1337 which is capable of producing five compounds having significant inhibitory activity against common pathogenic fungi of 12 plants and having a preservative effect on fruits.
  • the Pezicula sp. SC1337 of the present invention was deposited on the Guangdong Provincial Microbial Culture Collection Center (referred to as GDMCC on February 15, 2017, Address: Building 59, No. 100, Xianlie Middle Road, Guangzhou, Guangdong) Provincial Institute of Microbiology, Zip Code 510070), deposit number is GDMCC No: 60144.
  • the five compounds having obvious inhibitory activity against common pathogenic fungi of 12 plants and having a fresh-keeping effect on fruits all of which are trisaccharide ester compounds, the glycosyl moiety of which is 6'-position of trehalose and trehalose.
  • ⁇ -L-mannose composition, the 2, 3, and 4 positions of trehalose are respectively linked to three C5 to C11 linear or branched fatty acids, specifically compounds 1, 2, 3, 4 and 5, the compound
  • the structural formula of 1 is as shown in Formula 1
  • the structural formula of Compound 2 is as shown in Formula 2
  • the structural formula of Compound 3 is shown in Formula 3
  • the structural formula of Compound 4 is shown in Formula 4
  • the structural formula of Compound 5 is shown in Formula 5
  • a second object of the present invention is to provide a process for the preparation of the above compounds 1 to 5, which comprises the steps of:
  • the compounds 1 to 5 were isolated from a fermentation culture of Pezicula sp. SC1337.
  • the fermentation culture is a solid
  • the fermentation culture is leached with ethanol
  • the extract is removed to remove ethanol
  • a suspension is prepared with water
  • the extract is concentrated to obtain ethyl acetate.
  • the extract or when the fermentation culture is a liquid, the fermentation culture is extracted with ethyl acetate to obtain an extract, and the extract is concentrated to obtain an ethyl acetate extract;
  • the ethyl acetate extract was applied to a silica gel column at a volume ratio of 90:10 to 70:30 in a chloroform-methanol mixed solvent, and the similar fractions were collected by thin layer chromatography to collect the thin layer plate.
  • Fraction B was subjected to silica gel column chromatography, eluting with a gradient of 65%-85% methanol aqueous solution, and collecting a volume fraction of 85% methanol aqueous solution. The fraction was concentrated and then subjected to high performance liquid chromatography with a volume fraction of 85% methanol aqueous solution. Compounds 1 to 4 were obtained by separation and purification of the mobile phase.
  • the fermentation culture for preparing S. sphaeroides SC1337 is to immobilize S. sphaeroides SC1337 in wheat On the body medium, static culture was carried out at 24 to 28 ° C in the dark to obtain a solid fermentation culture.
  • the wheat solid medium was mixed with wheat and water at a mass ratio of 1:1.5; or S. sphaeroides SC1337
  • the rice solid solid medium is statically cultured at 24 to 28 ° C for 10 to 30 days in the dark to obtain a solid fermentation culture, and the rice solid medium is mixed with rice and water having a mass ratio of 1:1; or The S.
  • the sphaeroides SC1337 was cultured on PDB liquid medium in a dark state at 24 to 28 ° C for 3 to 8 days to obtain a liquid fermentation culture.
  • the PDB medium contained 6 g of potato extract per liter, and 20 g of glucose.
  • the rest is water, pH 6.0 to 6.5.
  • a third object of the invention is to provide the use of S. sphaeroides SC1337 for the preparation of compounds 1, 2, 3, 4 or 5.
  • the present invention isolates S. sphaeroides SC1337 from endophytes of the cedar, which is capable of producing five compounds having significant inhibitory activity against common pathogenic fungi of 12 plants and having a fresh-keeping effect on fruits, and thus can be prepared therefrom. These five compounds have obvious inhibitory activity against common pathogenic fungi of 12 plants and have a fresh-keeping effect on fruits. They are used for the control of phytopathogenic fungi and the preservation of fruits, and have broad application prospects.
  • GDMCC Guangdong Provincial Museum of Microbial Cultures on February 15, 2017 (referred to as GDMCC, Address: Guangdong Institute of Microbiology, Building 59, No. 100, Xianlie Middle Road, Guangzhou, China) Zip code: 510070), the deposit number is GDMCC No: 60144.
  • Figure 1 shows the colony morphology of Pezicula sp. SC1337.
  • Figure 2 is a mycelium and spore morphology of Pezicula sp. SC1337.
  • Example 1 Identification of Pezicula sp. SC1337 and its strains
  • the Pezicula sp. SC1337 of the present invention is isolated from the endophytic fungus of the genus Pinus sylvestris in the South China Botanical Garden, and the separation method is: the sample of the collected cedar branches is sterilized by 75% ethanol for 30 s, and then The mass fraction was treated with 10% sodium hypochlorite for 3 minutes, washed with sterile water for 3 times, dried, inoculated onto PDA medium, placed in a 28 ° C incubator for 5 days, and picked up the target colony with a sterile toothpick. The PDA medium was obtained.
  • Each liter contains 6 g of potato extract, 20 g of glucose, 20 g of agar, and the rest is water, pH 6.0-6.5, thereby separating Pezicula sp. SC1337.
  • the strain grew slowly on PDA medium. After 10 days of culture, the average diameter of the colonies was less than 4 cm, the edges were neat, the aerial hyphae were vigorous and loose, and it was fluffy; the colony was grayish brown in the front and slightly dark green. The edges are grayish white; the center of the colony is dark brown in the center, and the edges are light gray with a dark green color; no exudate, lack of soluble pigment.
  • the hyphae are 2 ⁇ 3 ⁇ m wide, the color is slightly light brown, branched and separated.
  • the spores are long oval, light brown, smooth, and the size is 14 ⁇ 22 ⁇ 4 ⁇ 6 ⁇ m.
  • the colony morphology and the morphology of hyphae (spore-containing) As shown in Figure 1 and Figure 2.
  • the mycelium was extracted by classical CTAB method, and the primer was obtained by ITS4(5'-3'):TCC TCC GCT TAT TGATAT GC and ITS5(5'-3'):GGA AGT AAA AGT CGT AAC AAG G.
  • the sequencing results were searched and homologyd by Blast in the Genbank database.
  • the homology of the ITS sequence fragment (917 bp) was the highest homology with Pezicula cinnamomea, and the ITS similarity was 96%. Therefore, the bacterium was named as: Pezicula sp. SC1337, which was deposited on February 15, 2017 in the Guangdong Provincial Collection of Microbial Cultures (GDMCC, Address: No. 100, Xianlie Middle Road, Guangzhou, 59) Guangdong Institute of Microbiology, No. 510070, the deposit number is GDMCC No: 60144.
  • Pezicula sp. SC1337 was cultured on a wheat solid medium (mixed with wheat and water at a mass ratio of 1:1.5), and statically cultured at 28 ° C for 12 days in the dark to obtain a solid fermentation culture.
  • the solid fermentation culture (3.6L) was soaked three times with an equal volume of 95% ethanol aqueous solution for 48 hours, the soaking solution was combined and filtered, then concentrated under reduced pressure to remove ethanol, and the volume was adjusted to 1 L with water, and then used. The volume was extracted with ethyl acetate three times, and the obtained ethyl acetate extracts were combined and concentrated to give ethyl acetate extract 17.6 g.
  • the ethyl acetate extract was applied to a silica gel column (silica gel 100-200 mesh, 300 g), and eluted with a gradient of 90:10 to 70:30 in a chloroform-methanol mixed solvent, and detected by thin layer chromatography (silica gel). Combine the similar fractions and collect the fractions of the chloroform-methanol volume ratio of 85:15 on the thin layer, which is more than 0.3 ⁇ 0.4. The mixture was concentrated to obtain a fraction A 1.69 g, and a fraction having a specific shift of 0.2 to 0.3, and concentrated under reduced pressure to obtain a fraction B of 8.50 g;
  • Fraction A was subjected to reversed-phase silica gel column chromatography (Develosil ODS, 75 ⁇ m, 150 g, product of Fuji Chemical Co., Japan), and eluted with a volume fraction of 88% methanol aqueous solution to collect the fractions in the main point concentration, and after combining, High performance liquid chromatography (LC-6AD semi-preparative high performance liquid chromatography, RID-10A detector, manufactured by Shimadzu Corporation, Japan; Shim-pack PRC-ODS, 10 ⁇ 250 mm, 4.5 ⁇ m) with a volume fraction of 88
  • Compound 1 a white powder, having the formula C 41 H 72 O 19 , a positive ion HRESIMS m/z 891.4552 [M+Na] + (calcd for C 41 H 72 O 19 Na, 891.4560), a positive ion ESIMS m/z 891 [ M+Na] + , 907[M+K] + ; negative ion ESIMS m/z 867[M-H] - , 903[M+Cl] - .
  • Table 1 The data of 1 H NMR and 13 C NMR (solvent: deuterated methanol) are shown in Table 1.
  • Compound 1 was identified as 6-O- ⁇ -L-mannosyl-3-O-(2-methylbutyryl)-4-O-(8-methyldecanoyl) by the above spectral data and two-dimensional nuclear magnetic resonance method.
  • -2-O-(4-methylhexanoyl) trehalose having the structural formula shown in Formula 1.
  • compound 2 white powder, molecular formula is C 40 H 70 O 19 , positive ion HRESIMS m/z 877.4411 [M+Na] + (calcd for C 40 H 70 O 19 Na, 877.4404), positive ion ESIMS m/z 877 [M+Na] + ; Negative ion ESIMS m/z 853 [M-H] - , 889 [M+Cl] - .
  • Table 1 H NMR and 13 C NMR solvent: deuterated methanol
  • Compound 2 was identified as 4-O-decanoyl-6-O- ⁇ -L-mannosyl-3-O-(2-methylbutyryl)-2-O- by the above spectral data and two-dimensional nuclear magnetic resonance method. (4-Methylhexanoyl) trehalose having a structural formula shown in Formula 2.
  • compound 3 white powder, having the formula C 39 H 68 O 19 , cation HRESIMS m/z 863.4255 [M+Na] + (calcd for C 39 H 68 O 19 Na, 863.4247), positive ion ESIMS m/z 863 [M+Na] + ; Negative ion ESIMS m/z 839 [M-H] - , 875 [M+Cl] - .
  • Table 1 H NMR and 13 C NMR solvent: deuterated methanol
  • Compound 3 was identified as 6-O- ⁇ -L-mannosyl-3-O-(2-methylbutyryl)-2-O-(4-methylhexanoyl) by the above spectral data and two-dimensional nuclear magnetic resonance method.
  • Compound 4 was identified as 6-O- ⁇ -L-mannosyl-3-O-(2-methylbutyryl)-2-O-(4-methylhexanoyl) by the above spectral data and two-dimensional nuclear magnetic resonance method.
  • -4-O-octanoyl trehalose the structural formula of which is shown in Formula 4.
  • Example 3 In vitro inhibitory activity test of the trisaccharide esters (Compounds 1-5) obtained in Example 2 against 12 common pathogenic fungi of plants
  • test strains used include: 1) Alternaria solani tomato Phytophthora; 2) Botryospuaeria berengeriana apple ring rot; 3) Botrytis cinerea Botrytis cinerea; 4) Colletotrichum gloeosporioides mango anthracnose; 5) Curvularia lunata banana crescent Mildew; 6) Fusarium oxysporium banana, Fusarium oxysporum; 7) Geotrichum citri-aurantii Phytophthora sinensis; 8) Helminthosporium maydis Phytophthora sphaeroides; 9) Penicillium italicum citrus Penicillium; 10) Peronophythora litchii Phytophthora glabrata; 11) Rhizoctonia solani rice sheath blight; 12) Ustilaginoidea virens rice smut.
  • the antifungal activity of the compounds 1 to 5 was determined by a filter paper agar diffusion method: the activated test bacteria were separately inoculated into a petri dish containing a PDA solid medium, and uniformly coated with a T-type applicator; the sample to be tested was Methanol was dissolved and formulated into 50 mg/mL. 10 ⁇ L of the solution was added to a filter paper (6 mm in diameter) and dried on a clean bench. Each filter paper finally contained 500 ⁇ g of the sample, and then the filter paper was placed on the filter paper. In the above culture dish, the inhibition width (the inhibition width is the average diameter of the inhibition zone) was measured after incubation at 28 ° C for 72 or 96 hours, and a filter paper of an equal volume of methanol was added as a negative control.
  • the results showed that the trisaccharide extract and the compounds 1 to 5 all inhibited the growth of the above various plant fungi, and the results are shown in Table 3.
  • the inhibition zone width was 10 to 22 mm.
  • the above trisaccharide extract is a mixture containing compounds 1 to 4 in which the compound ratio of 1, 2, 3, and 4 is about 60:35:4:1.
  • Example 4 Preservation experiment of trisaccharide extract obtained in Example 2 on postharvest citrus storage
  • Test sample The trisaccharide extract obtained in Example 2 (containing compound 1, 2, 3, and 4 in a mass ratio of about 60:35:4:1, which is a mixture of these four compounds) was dissolved in a small amount of ethanol. Dilute with water to 200, 400, 600 mg / L as a treatment solution.
  • the citrus fruit was soaked in the treatment solution for 5 min, dried, and then placed in a plastic basket which was sterilized by drying on a 75% alcohol surface, sealed in a 0.02 mm polyethylene film bag, and stored at 25 ° C for 15 days. Observe and record the disease index.
  • Test fruit Sugar orange is collected from the orchard.
  • the experimental results are shown in Table 4.
  • the trisaccharide extract has a significant inhibitory effect on the development of fungi during postharvest citrus storage, and is superior to the commonly used chemical antifungal agent thiram, which is equivalent to Tekdo and has obvious antiseptic and fresh-keeping effects.
  • the antibacterial and fresh-keeping effect of the trisaccharide extract is slightly worse than that of the chemical antifungal agent, but Baco is banned from use in the EU since 2004 due to its high toxicity.

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Abstract

L'invention concerne une souche Pezicula sp. SC1337 et une méthode de préparation de dérivés d'ester trisaccharide l'utilisant. Le nombre de conservation de Pezicula sp. SC1337 est GDMCC No: 60144. Pezicula sp. SC1337 peut être obtenu par séparation d'endophytes dans des branches de Taxodium distichum et peut être utilisé pour générer cinq composés ayant une activité d'inhibition évidente sur 12 sortes de champignons pathogènes communs de plante et pour avoir un effet de préservation de fraîcheur sur les fruits. Par conséquent, Pezicula sp. SC1337 peut être utilisé pour préparer les cinq composés ayant une activité d'inhibition évidente sur 12 sortes de champignons pathogènes communs de plante et ayant un effet de préservation de fraîcheur sur des fruits pour la prévention et le traitement de champignons pathogènes de plante et la préservation de la fraîcheur de fruits.
PCT/CN2017/102048 2017-03-15 2017-09-18 Souche pezicula sp. sc1337 et méthode de préparation de dérivés d'ester trisaccharide l'utilisant WO2018166159A1 (fr)

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CN110038019A (zh) * 2019-05-27 2019-07-23 惠州学院 一种三糖酯类化合物在制备抗细胞增殖性紊乱或抗癌药物中的应用
CN114606134A (zh) * 2021-03-10 2022-06-10 宁波大学 一种海绵共附生真菌及其在制备氧杂蒽醌类化合物中的应用
CN115011487A (zh) * 2022-05-12 2022-09-06 宁波大学 一种海绵共附生真菌及其在制备杂萜类化合物中的应用
CN114606135B (zh) * 2022-01-24 2023-09-29 宁波大学 一种海绵共附生真菌及其在制备甾醇类化合物中的应用

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CN106946955B (zh) * 2017-03-15 2019-06-21 中国科学院华南植物园 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用
CN110511878B (zh) * 2019-07-31 2021-06-11 中国林业科学研究院亚热带林业研究所 具抑菌能力和木质纤维素降解活性的新孢无柄盘菌及用途
CN111187724B (zh) * 2020-03-02 2022-02-01 安庆师范大学 一种蓝莓根部深色有隔内生真菌及其应用

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CN110038019A (zh) * 2019-05-27 2019-07-23 惠州学院 一种三糖酯类化合物在制备抗细胞增殖性紊乱或抗癌药物中的应用
CN114606134A (zh) * 2021-03-10 2022-06-10 宁波大学 一种海绵共附生真菌及其在制备氧杂蒽醌类化合物中的应用
CN114606134B (zh) * 2021-03-10 2023-11-14 宁波大学 一种海绵共附生真菌及其在制备氧杂蒽醌类化合物中的应用
CN114606135B (zh) * 2022-01-24 2023-09-29 宁波大学 一种海绵共附生真菌及其在制备甾醇类化合物中的应用
CN115011487A (zh) * 2022-05-12 2022-09-06 宁波大学 一种海绵共附生真菌及其在制备杂萜类化合物中的应用
CN115011487B (zh) * 2022-05-12 2023-08-18 宁波大学 一种海绵共附生真菌及其在制备杂萜类化合物中的应用

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