Biotechnology Bulletin ›› 2023, Vol. 39 ›› Issue (5): 63-76.doi: 10.13560/j.cnki.biotech.bull.1985.2022-1006
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MA Fang-fang(), LIU Guan-wen, PANG Bing, JIANG Chun-mei, SHI Jun-ling()
Received:
2022-08-19
Online:
2023-05-26
Published:
2023-06-08
MA Fang-fang, LIU Guan-wen, PANG Bing, JIANG Chun-mei, SHI Jun-ling. Strategies of Increasing Flavonoid Production in Engineered Bacteria by Intensifying the Efflux of Flavonoid in Cells[J]. Biotechnology Bulletin, 2023, 39(5): 63-76.
基因 Gene | 转运蛋白Transporter | 位置/转运方向 Location/Transport direction | 类黄酮 Flavonoid | 基因来源 Source of gene | 工程菌 Engineering bacterium | 参考文献 Reference |
---|---|---|---|---|---|---|
Abcc1 (NC_000082) | MRP | 小肠基底外侧膜/到血液 | 柚皮素Naringin 橙皮素Hesperidin (葡萄糖醛酸化和甲基化Glucuronidation and methylation) | 小家鼠 Mus musculus(House mouse) | 大肠杆菌Escherichia coli 金黄色葡萄糖球菌Staphylococcus aureus | [ |
Abcc2 (NC_000085) | MRP | 小肠细胞顶点/到小肠 | 柚皮素Naringin 橙皮素Hesperidin (葡萄糖醛酸化和甲基化Glucuronidation and methylation) | 小家鼠 Mus musculus(House mouse) | 苏云金芽孢杆菌Bacillus thuringiensis | [ |
Abcc3 (NC_000077) | MRP | 小肠基底外侧膜/到血液 | 柚皮素Naringin (葡萄糖醛酸化和甲基化Glucuronidation and methylation) | 小家鼠 Mus musculus(House mouse) | 大肠杆菌Escherichia coli 金黄色葡萄糖球菌Staphylococcus aureus | [ |
MRP2 (NC_000017) | MRP | 小肠基底外侧膜/到血液 | 表没食子儿茶素没食子酸酯Epigallocatechin gallate(硫酸化和甲基化Sulfation and methylation) | 人类 Homo sapiens(Human) | 酿酒酵母Saccharomyces cerevisiae | [ |
ABCB1 (NC_000007) | P-gp | 肠道管腔细胞/参与外排 | 4'-羟-6-甲基黄酮 4'-hydroxy-6- Methylflavone 4'-羟-6-甲氧基黄酮 4'-hydroxy-6-methoxyflavone 4'-羟-β-萘基黄酮 4'-hydroxy-β- Naphthoflavone | 人类 Homo sapiens(Human) | 金黄色葡萄糖球菌Staphylococcus aureus MRSA6 | [ |
ABCG2 (NC_000072) | BCRP | 肠道管腔细胞/参与外排 | 染料木素Genistein (硫酸化和葡萄糖醛酸化Sulfation and glucuronidation) | 小家鼠 Mus musculus(House mouse) | 大肠杆菌Escherichia coli | [ |
Table 1 Animal flavonoid transport genes successfully expressed in genetically engineered bacteria
基因 Gene | 转运蛋白Transporter | 位置/转运方向 Location/Transport direction | 类黄酮 Flavonoid | 基因来源 Source of gene | 工程菌 Engineering bacterium | 参考文献 Reference |
---|---|---|---|---|---|---|
Abcc1 (NC_000082) | MRP | 小肠基底外侧膜/到血液 | 柚皮素Naringin 橙皮素Hesperidin (葡萄糖醛酸化和甲基化Glucuronidation and methylation) | 小家鼠 Mus musculus(House mouse) | 大肠杆菌Escherichia coli 金黄色葡萄糖球菌Staphylococcus aureus | [ |
Abcc2 (NC_000085) | MRP | 小肠细胞顶点/到小肠 | 柚皮素Naringin 橙皮素Hesperidin (葡萄糖醛酸化和甲基化Glucuronidation and methylation) | 小家鼠 Mus musculus(House mouse) | 苏云金芽孢杆菌Bacillus thuringiensis | [ |
Abcc3 (NC_000077) | MRP | 小肠基底外侧膜/到血液 | 柚皮素Naringin (葡萄糖醛酸化和甲基化Glucuronidation and methylation) | 小家鼠 Mus musculus(House mouse) | 大肠杆菌Escherichia coli 金黄色葡萄糖球菌Staphylococcus aureus | [ |
MRP2 (NC_000017) | MRP | 小肠基底外侧膜/到血液 | 表没食子儿茶素没食子酸酯Epigallocatechin gallate(硫酸化和甲基化Sulfation and methylation) | 人类 Homo sapiens(Human) | 酿酒酵母Saccharomyces cerevisiae | [ |
ABCB1 (NC_000007) | P-gp | 肠道管腔细胞/参与外排 | 4'-羟-6-甲基黄酮 4'-hydroxy-6- Methylflavone 4'-羟-6-甲氧基黄酮 4'-hydroxy-6-methoxyflavone 4'-羟-β-萘基黄酮 4'-hydroxy-β- Naphthoflavone | 人类 Homo sapiens(Human) | 金黄色葡萄糖球菌Staphylococcus aureus MRSA6 | [ |
ABCG2 (NC_000072) | BCRP | 肠道管腔细胞/参与外排 | 染料木素Genistein (硫酸化和葡萄糖醛酸化Sulfation and glucuronidation) | 小家鼠 Mus musculus(House mouse) | 大肠杆菌Escherichia coli | [ |
Fig. 1 Vesicle-mediated flavonoid transport in plants a:Tapetal corpuscles transport flavonoids by means of cytoplasmic vesicles; b:vesicle fusion transport is mediated by vacuolar sorting receptors(VSR)and SNARE in general plants; c:arabidopsis uses the protein storage vacuole to enter the central vacuole; d:anthocyanins enter the central large vacuole by means of cargo protein fusion anterior chamber
基因 Gene | 转运蛋白 Transporter | 转运底物 Substrate | 分布位置 Location | 基因来源 Gene source | 工程菌Engineering microorganism | 参考文献 Reference |
---|---|---|---|---|---|---|
TRANSPARENT TESTA12(tt12) (AJ294464) | MATE | 花青素-3-葡萄糖Cyanidin-3-O-glucoside | 花青素苷液泡Anthocyanin vacuole | 拟南芥Arabidopsis thaliana | 大肠杆菌Escherichia coli酿酒酵母Saccharomyces cerevisiae | [ |
花青素-3-葡萄糖转移酶 Cyanidin 3-O-Glucosyltransferase(3GT) (NC_003076) | UDP-d-葡萄糖转运蛋白 UDP-d-glucose transporter proteins GLF | 花青素-3-葡萄糖Cyanidin-3-O-glucoside | 细胞质Cytoplasm | 拟南芥Arabidopsis thaliana | 大肠杆菌Escherichia coli BL21 | [ |
花青素-3-葡萄糖转移酶 Cyanidin 3-O-Glucosyltransferase(3GT) (NC_003076) | UDP-d-葡萄糖转运蛋白 UDP-d-glucose transporter proteins GALU1 | 花青素-3-葡萄糖Cyanidin-3-O-glucoside | 细胞质Cytoplasm | 拟南芥Arabidopsis thaliana | 谷氨酸棒状杆菌Corynebacterium glutamicum | [ |
ZmMrp3 (AY609318) | MRP | 花青素-3-葡萄糖Cyanidin-3-O-glucoside | 花青素苷液泡Anthocyanin vacuole | 玉米 Zea mays | 大肠杆菌Escherichia coli | [ |
Bronze-2(Bz2) (NC_050096) | GST | 花青素-3-葡萄糖Cyanidin-3-O-glucoside | 细胞质Cytoplasm | 玉米 Zea mays | 大肠杆菌Escherichia coli | [ |
葡萄原花青素O-甲基转移酶Vitis vinifera Anthocyanin O-methyltransferase(VvAOMT) (NC_012007) | 花色素苷O-甲基转移酶Anthocyanin O-methyltransferase(AOMT) | 花青素-3-葡萄糖Cyanidin 3-O-glucoside, 甲基花青素3-O-葡萄糖 Peonidin 3-O- glucoside | 细胞质Cytoplasm | 葡萄 Vitis vinifera | 大肠杆菌Escherichia coli DH5α and BL21 | [ |
Table 2 Plant flavonoid transporters successfully expressed in genetically engineered bacteria
基因 Gene | 转运蛋白 Transporter | 转运底物 Substrate | 分布位置 Location | 基因来源 Gene source | 工程菌Engineering microorganism | 参考文献 Reference |
---|---|---|---|---|---|---|
TRANSPARENT TESTA12(tt12) (AJ294464) | MATE | 花青素-3-葡萄糖Cyanidin-3-O-glucoside | 花青素苷液泡Anthocyanin vacuole | 拟南芥Arabidopsis thaliana | 大肠杆菌Escherichia coli酿酒酵母Saccharomyces cerevisiae | [ |
花青素-3-葡萄糖转移酶 Cyanidin 3-O-Glucosyltransferase(3GT) (NC_003076) | UDP-d-葡萄糖转运蛋白 UDP-d-glucose transporter proteins GLF | 花青素-3-葡萄糖Cyanidin-3-O-glucoside | 细胞质Cytoplasm | 拟南芥Arabidopsis thaliana | 大肠杆菌Escherichia coli BL21 | [ |
花青素-3-葡萄糖转移酶 Cyanidin 3-O-Glucosyltransferase(3GT) (NC_003076) | UDP-d-葡萄糖转运蛋白 UDP-d-glucose transporter proteins GALU1 | 花青素-3-葡萄糖Cyanidin-3-O-glucoside | 细胞质Cytoplasm | 拟南芥Arabidopsis thaliana | 谷氨酸棒状杆菌Corynebacterium glutamicum | [ |
ZmMrp3 (AY609318) | MRP | 花青素-3-葡萄糖Cyanidin-3-O-glucoside | 花青素苷液泡Anthocyanin vacuole | 玉米 Zea mays | 大肠杆菌Escherichia coli | [ |
Bronze-2(Bz2) (NC_050096) | GST | 花青素-3-葡萄糖Cyanidin-3-O-glucoside | 细胞质Cytoplasm | 玉米 Zea mays | 大肠杆菌Escherichia coli | [ |
葡萄原花青素O-甲基转移酶Vitis vinifera Anthocyanin O-methyltransferase(VvAOMT) (NC_012007) | 花色素苷O-甲基转移酶Anthocyanin O-methyltransferase(AOMT) | 花青素-3-葡萄糖Cyanidin 3-O-glucoside, 甲基花青素3-O-葡萄糖 Peonidin 3-O- glucoside | 细胞质Cytoplasm | 葡萄 Vitis vinifera | 大肠杆菌Escherichia coli DH5α and BL21 | [ |
类黄酮 Flavonoid | 外排基因 Efflux gene | 微生物 Microorganism | 转运蛋白家族 Transporter protein | 参考文献 Reference |
---|---|---|---|---|
查尔酮Chalcone (2E)-1-(4'-氨苯基)-3-(4-甲氧苯基)- 2丙-烯-1-酮 (2E)-1-(4'-aminophenyl)-3-(4-methoxyphenyl)-prop-2-en-1-one | MepA (NC_016941) | 金黄色葡萄球菌Staphylococcus aureus | ABC转运蛋白 ABC transporters | [ |
木犀草素Luteolin 芹菜素Apigenin 山奈酚Kaempferol 鼠李素Rhamnetin | NorA (NC_007795) | 金黄色葡萄球菌Staphylococcus aureus NCTC 8325 | ABC转运蛋白 ABC transporters | [ |
染料木素Genistein 芹菜素Apigenin 表儿茶素没食子酸酯Epicatechin gallate | NorA、TetK、MsrA(NC_007795) | 金黄色葡萄球菌Staphylococcus aureus NCTC 8325 | ABC转运蛋白 ABC transporters | [ |
二氢黄酮Flavonone | LmrA (NZ_CP059048) | 乳酸乳球菌 Lactococcus lactis | ABC转运蛋白 ABC transporters | [ |
类黄酮Flavonoid | YvcC (AGE65090) | 枯草芽孢杆菌 Bacillus subtilis | ABC转运蛋白 ABC transporters | [ |
类黄酮Flavonoid | DrrAB (AAC43341) | 波赛链霉菌 Streptomyces peucetius | ABC转运蛋白 ABC transporters | [ |
原儿茶酸Protocatechuic-acid 龙胆酸Gentisic-acid 毛花甙丙Lanatoside-C 大豆甙元Diadzein | MexB (NC_002516) | 铜绿假单胞菌Pseudomonas aeruginosa PAO1 | RND转运蛋白 RND transporters | [ |
龙胆酸Gentisic-acid 毛花甙丙Lanatoside-C 大豆甙元Diadzein | AcrB (NC_000913) | 大肠杆菌 Escherichia coli str. K-12 substr. MG1655 | RND转运蛋白 RND transporters | [ |
表没食子儿茶素没食子酸酯Epigallocatechin gallate | CmeABC、CmeDEF (NC_002163) | 空肠弯曲菌Campylobacter jejuni NCTC 11168 | RND转运蛋白 RND transporters | [ |
槲皮素Quercetin | AcrAB-TolC (NC_000913) | 大肠杆菌 Escherichia coli str. K-12 substr. MG1655 | RND转运蛋白 RND transporters | [ |
硫酸原黄素Proflavine | Acel (QWB10945) | 鲍曼不动杆菌Acinetobacter baumannii | PACE转运蛋白 PACE transporters | [ |
Table 3 Microbial transporters involved in flavonoid efflux
类黄酮 Flavonoid | 外排基因 Efflux gene | 微生物 Microorganism | 转运蛋白家族 Transporter protein | 参考文献 Reference |
---|---|---|---|---|
查尔酮Chalcone (2E)-1-(4'-氨苯基)-3-(4-甲氧苯基)- 2丙-烯-1-酮 (2E)-1-(4'-aminophenyl)-3-(4-methoxyphenyl)-prop-2-en-1-one | MepA (NC_016941) | 金黄色葡萄球菌Staphylococcus aureus | ABC转运蛋白 ABC transporters | [ |
木犀草素Luteolin 芹菜素Apigenin 山奈酚Kaempferol 鼠李素Rhamnetin | NorA (NC_007795) | 金黄色葡萄球菌Staphylococcus aureus NCTC 8325 | ABC转运蛋白 ABC transporters | [ |
染料木素Genistein 芹菜素Apigenin 表儿茶素没食子酸酯Epicatechin gallate | NorA、TetK、MsrA(NC_007795) | 金黄色葡萄球菌Staphylococcus aureus NCTC 8325 | ABC转运蛋白 ABC transporters | [ |
二氢黄酮Flavonone | LmrA (NZ_CP059048) | 乳酸乳球菌 Lactococcus lactis | ABC转运蛋白 ABC transporters | [ |
类黄酮Flavonoid | YvcC (AGE65090) | 枯草芽孢杆菌 Bacillus subtilis | ABC转运蛋白 ABC transporters | [ |
类黄酮Flavonoid | DrrAB (AAC43341) | 波赛链霉菌 Streptomyces peucetius | ABC转运蛋白 ABC transporters | [ |
原儿茶酸Protocatechuic-acid 龙胆酸Gentisic-acid 毛花甙丙Lanatoside-C 大豆甙元Diadzein | MexB (NC_002516) | 铜绿假单胞菌Pseudomonas aeruginosa PAO1 | RND转运蛋白 RND transporters | [ |
龙胆酸Gentisic-acid 毛花甙丙Lanatoside-C 大豆甙元Diadzein | AcrB (NC_000913) | 大肠杆菌 Escherichia coli str. K-12 substr. MG1655 | RND转运蛋白 RND transporters | [ |
表没食子儿茶素没食子酸酯Epigallocatechin gallate | CmeABC、CmeDEF (NC_002163) | 空肠弯曲菌Campylobacter jejuni NCTC 11168 | RND转运蛋白 RND transporters | [ |
槲皮素Quercetin | AcrAB-TolC (NC_000913) | 大肠杆菌 Escherichia coli str. K-12 substr. MG1655 | RND转运蛋白 RND transporters | [ |
硫酸原黄素Proflavine | Acel (QWB10945) | 鲍曼不动杆菌Acinetobacter baumannii | PACE转运蛋白 PACE transporters | [ |
微生物 Microorganism | 修饰 Modification | 酶类 Enzyme | 修饰位点 Modification site | 参考文献Reference |
---|---|---|---|---|
乳酸菌Lactobacillus 乳球菌Lactococcus 双歧杆菌Bifidobacteria 肠球菌Enterococcus 链霉菌Streptomyces 黑曲霉Aspergillus niger | 糖基化Glycosylation | 糖基转移酶 Glycosyltransferase 糖苷酶Glycosidase 淀粉蔗糖酶Starch sucrase α-淀粉酶α -amylase | 主要为B环C-3'羟基,然后依次为B环C-4'羟基> A环C-7> A环C-5> A环C-8 | [ |
南极假丝酵母 Candida antarctica | 乙酰基化Acetoxylation | 脂肪酶Lipase 蛋白酶Protease | 主要为伯羟基,酰基化程度取决于酰基供体脂肪酸、芳香酸和乙烯基酯的链长 | [ |
灰色链霉菌Streptomyces griseus 球孢白僵菌Beauveria bassiana 枯草芽孢杆菌Bacillus subtilis | 羟基化Hydroxylation | 酪氨酸酶Tyrosinase | 主要为B环C-3'羟基 | [ |
球孢白僵菌Beauveria bassiana 大肠杆菌Escherichia coli 链霉菌KCTC 0041BP Streptomyces sp. KCTC 0041BP 灰色链霉菌Streptomyces griseus | 甲基化Methylation | 甲基转移酶 Methyltransferase | 主要为B环C-3'和C-4'羟基,然后依次为A环C-7 >A环C-5 >C环 C-3 | [ |
Table 4 Enzymes that catalyze flavonoid derivatives in microorganisms
微生物 Microorganism | 修饰 Modification | 酶类 Enzyme | 修饰位点 Modification site | 参考文献Reference |
---|---|---|---|---|
乳酸菌Lactobacillus 乳球菌Lactococcus 双歧杆菌Bifidobacteria 肠球菌Enterococcus 链霉菌Streptomyces 黑曲霉Aspergillus niger | 糖基化Glycosylation | 糖基转移酶 Glycosyltransferase 糖苷酶Glycosidase 淀粉蔗糖酶Starch sucrase α-淀粉酶α -amylase | 主要为B环C-3'羟基,然后依次为B环C-4'羟基> A环C-7> A环C-5> A环C-8 | [ |
南极假丝酵母 Candida antarctica | 乙酰基化Acetoxylation | 脂肪酶Lipase 蛋白酶Protease | 主要为伯羟基,酰基化程度取决于酰基供体脂肪酸、芳香酸和乙烯基酯的链长 | [ |
灰色链霉菌Streptomyces griseus 球孢白僵菌Beauveria bassiana 枯草芽孢杆菌Bacillus subtilis | 羟基化Hydroxylation | 酪氨酸酶Tyrosinase | 主要为B环C-3'羟基 | [ |
球孢白僵菌Beauveria bassiana 大肠杆菌Escherichia coli 链霉菌KCTC 0041BP Streptomyces sp. KCTC 0041BP 灰色链霉菌Streptomyces griseus | 甲基化Methylation | 甲基转移酶 Methyltransferase | 主要为B环C-3'和C-4'羟基,然后依次为A环C-7 >A环C-5 >C环 C-3 | [ |
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