Advances in biosynthesis of quercetin glycoside derivatives

doi:10.11949/0438-1157.20200070

Abstract

Abstract:

Natural products of glycosides are the main forms of secondary metabolites in plants and have important biological activities. Glycosylation modification can change its water solubility and stability, and produce special biological activities and functions. Therefore, glycoside products are suitable for commercialization and have important medicinal and industrial values. Especially it is widely applied to anti-cancer drugs and daily chemical products, thus glycoside compounds have been concerned and studied. In recent years, the biosynthesis of glycoside products had made great progress. In this paper, the important glycoside compound quercetin is illustrated to introduce the biosynthesis of glycoside compounds, and the engineering strategy of high-yield glycoside compounds is described from the perspective of glycosyltransferase and precursor supply. It provides technological support for researchers to obtain the high-yield strains of plant glycosides by utilizing synthetic biology techniques.

Key words: plant glycosides, quercetin, UDP-sugars, metabolism, molecular biology, enzyme

摘要：

糖苷类天然产物是植物中次级代谢产物的主要存在形式，具有重要的生物活性。通过糖基化修饰可以改变其水溶性、稳定性，产生特殊的生物活性和功能，因此易于商品化应用，具有重要的药用价值和工业价值，尤其在抗癌药物和日化用品中有着广泛应用。近年来糖苷类产物的生物合成也取得了重大的进展。以重要的糖苷化合物槲皮素为例介绍了糖苷化合物的生物合成，从糖基转移酶和前体供应等角度阐述了生物高产糖苷类化合物的工程策略,为利用合成生物学技术获得植物糖苷的高产菌株提供了技术参考。

关键词: 植物糖苷, 槲皮素, UDP-糖, 代谢, 分子生物学, 酶

CLC Number:

Q 74

Yueyang FENG, Ying WANG, Mingdong YAO, Wenhai XIAO, Mingzhu DING. Advances in biosynthesis of quercetin glycoside derivatives[J]. CIESC Journal, 2020, 71(7): 2945-2955.

封悦洋, 王颖, 姚明东, 肖文海, 丁明珠. 生物合成槲皮素糖苷类衍生物的研究进展[J]. 化工学报, 2020, 71(7): 2945-2955.

Figures/Tables 7

References 76

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糖苷	糖供体	糖基转移酶	UDP-sugars生物合成相关基因	产量/(mg/L)	文献
quercetin-4'-O-glucoside	UDPG	AtUGT74F1	—	0.19	[44]
quercetin-3'-O-glucoside	UDPG	AtUGT71C1	—	8	[44]
quercetin-3-O-glucoside	UDPG	AtUGT73B3	—	99.3	[44]
quercetin-3-O-glucoside	UDPG	AtUGT73B3	Δpgi	3900	[45]
quercetin-7-O-glucoside	UDPG	AtUGT76E12	—	4.74	[44]
quercetin-7-O-glucoside	UDPG	AtUGT84B1	Δpgi	95	[45]
quercetin-3-O-rhamnoside	UDP-Rha	AtUGT78D1	RHM2	150	[46]
quercetin-3-O-rhamnoside	UDP-Rha	AtGT	BaSP, MUM4, Δpgm, ΔushA, Δagp, ΔgalETKM	1120	[47]
quercetin-3-O-galactoside	UDP-Gal	PhF3GT	BaSP, galE, Δpgm, ΔushA, Δagp, ΔgalETKM	940	[47]
quercetin-3-O-galactoside	UDP-Gal	PhUGT	GmSUS-galE	2134	[48]
quercetin-3-O-xyloside	UDP-Xyl	AtGT3	naf44530-galU, calS8, calS9, Δpgi, Δzwf, ΔushA	23.78	[49]
quercetin-3-O-xyloside	UDP-Xyl	AtUGT78D3(E380Q)	ecugd, AtUXS, ΔarnA	150	[50]
quercetin-3-O-arabinoside	UDP-Ara	AtUGT78D3	ecugd, AtUXS, OsUXE, ΔarnA	158	[50]
quercetin-3-O-glucuronide	UDP-GlcA	VvUGT	ecugd, ΔarnA	687	[51]
quercetin-3-O-N-acetylglucosamine	UDP-GlcNAc	AtUGT78D2	galU	380	[52]
quercetin-3,7-di-O-glucoside	UDPG	AtUGT76E12	—	0.71	[44]
quercetin-7,3'-di-O-glucoside	UDPG	AtUGT71C1	—	10.9	[44]
quercetin-3-O-glucoside-7-O-rhamnoside	UDPG UDP-Rha	AtUGT78D2 AtUGT89C1	—	67	[53]
quercetin-3-O-glucosyl(1→2)xyloside	UDPG UDP-Xyl	AtUGT78D2 AtUGT79B1	ecugd, AtUXS	65	[54]
quercetin-3-O-glucosyl(1→6)rhamnoside	UDPG UDP-Rha	BcUGT1 GmFg2	AtRHM2	119.8	[54]
quercetin-3-O-glucuronic acid-7-O-rhamnoside	UDP-GlcA UDP-Rha	VvUGT AtUGT89C1	ecugd, AtRHM2	44.8	[55]
quercetin-3-O-arabinosE-7-O- rhamnoside	UDP-Ara UDP-Rha	AtUGT78D3 AtUGT89C1	OsUXE, AtUXS, ecugd, AtRHM	45.1	[55]

糖苷	糖供体	糖基转移酶	UDP-sugars生物合成相关基因	产量/(mg/L)	文献
quercetin-4'-O-glucoside	UDPG	AtUGT74F1	—	0.19	[44]
quercetin-3'-O-glucoside	UDPG	AtUGT71C1	—	8	[44]
quercetin-3-O-glucoside	UDPG	AtUGT73B3	—	99.3	[44]
quercetin-3-O-glucoside	UDPG	AtUGT73B3	Δpgi	3900	[45]
quercetin-7-O-glucoside	UDPG	AtUGT76E12	—	4.74	[44]
quercetin-7-O-glucoside	UDPG	AtUGT84B1	Δpgi	95	[45]
quercetin-3-O-rhamnoside	UDP-Rha	AtUGT78D1	RHM2	150	[46]
quercetin-3-O-rhamnoside	UDP-Rha	AtGT	BaSP, MUM4, Δpgm, ΔushA, Δagp, ΔgalETKM	1120	[47]
quercetin-3-O-galactoside	UDP-Gal	PhF3GT	BaSP, galE, Δpgm, ΔushA, Δagp, ΔgalETKM	940	[47]
quercetin-3-O-galactoside	UDP-Gal	PhUGT	GmSUS-galE	2134	[48]
quercetin-3-O-xyloside	UDP-Xyl	AtGT3	naf44530-galU, calS8, calS9, Δpgi, Δzwf, ΔushA	23.78	[49]
quercetin-3-O-xyloside	UDP-Xyl	AtUGT78D3(E380Q)	ecugd, AtUXS, ΔarnA	150	[50]
quercetin-3-O-arabinoside	UDP-Ara	AtUGT78D3	ecugd, AtUXS, OsUXE, ΔarnA	158	[50]
quercetin-3-O-glucuronide	UDP-GlcA	VvUGT	ecugd, ΔarnA	687	[51]
quercetin-3-O-N-acetylglucosamine	UDP-GlcNAc	AtUGT78D2	galU	380	[52]
quercetin-3,7-di-O-glucoside	UDPG	AtUGT76E12	—	0.71	[44]
quercetin-7,3'-di-O-glucoside	UDPG	AtUGT71C1	—	10.9	[44]
quercetin-3-O-glucoside-7-O-rhamnoside	UDPG UDP-Rha	AtUGT78D2 AtUGT89C1	—	67	[53]
quercetin-3-O-glucosyl(1→2)xyloside	UDPG UDP-Xyl	AtUGT78D2 AtUGT79B1	ecugd, AtUXS	65	[54]
quercetin-3-O-glucosyl(1→6)rhamnoside	UDPG UDP-Rha	BcUGT1 GmFg2	AtRHM2	119.8	[54]
quercetin-3-O-glucuronic acid-7-O-rhamnoside	UDP-GlcA UDP-Rha	VvUGT AtUGT89C1	ecugd, AtRHM2	44.8	[55]
quercetin-3-O-arabinosE-7-O- rhamnoside	UDP-Ara UDP-Rha	AtUGT78D3 AtUGT89C1	OsUXE, AtUXS, ecugd, AtRHM	45.1	[55]

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