合成生物学助力萜类香精香料可持续生产

doi:10.12211/2096-8280.2024-057

合成生物学 ›› 2025, Vol. 6 ›› Issue (2): 334-356.DOI: 10.12211/2096-8280.2024-057

合成生物学助力萜类香精香料可持续生产

张梦瑶¹^,²^,³, 蔡鹏¹^,², 周雍进¹^,²

^1.中国科学院大连化学物理研究所生物技术研究部，辽宁大连 116023
^2.大连市能源生物技术重点实验室，辽宁大连 116023
^3.中国科学院大学，北京 100049

收稿日期:2024-07-31 修回日期:2024-09-18 出版日期:2025-04-30 发布日期:2025-05-20
通讯作者: 周雍进
作者简介:张梦瑶（1999—），女，博士研究生。研究方向为天然产物的生物合成。E-mail：myzhang@dicp.ac.cn
周雍进（1984—），男，博士，研究员。研究方向为基于甲醇生物转化与天然产物生物合成。E-mail：zhouyongjin@dicp.ac.cn
基金资助:
国家重点研发计划(2022YFC2105900);中国科学院特别研究助理资助项目

Synthetic biology drives the sustainable production of terpenoid fragrances and flavors

ZHANG Mengyao¹^,²^,³, CAI Peng¹^,², ZHOU Yongjin¹^,²

^1.Division of Biotechnology，Dalian Institute of Chemical Physics，Chinese Academy of Sciences，Dalian 116023，Liaoning，China
^2.Dalian Key Laboratory of Energy Biotechnology，Dalian 116023，Liaoning，China
^3.University of Chinese Academy of Sciences，Beijing 100049，China

Received:2024-07-31 Revised:2024-09-18 Online:2025-04-30 Published:2025-05-20
Contact: ZHOU Yongjin

摘要/Abstract

摘要：

香精香料是个人护理产品中的重要成分，其中，萜类化合物及其衍生物在天然香料市场中有着重要的地位。近年来，合成生物学的蓬勃发展为解决萜类香料产能瓶颈及开发更多元化的新型香料化合物带来了新机遇。本文探讨了合成生物学在萜类香料可持续生产中的应用和发展，介绍了数据驱动的合成生物学和生物技术创新如何赋能萜类香料生产，讨论比较了萜类合成的经典合成途径和替代合成途径，并探讨了萜类合酶挖掘与改造进展。在此基础上，着重介绍了单萜类、倍半萜类和降异戊二烯类香料的细胞工厂合成现状，包括元件改造、途径优化和萜类解毒等关键技术策略。最后，对当前专利布局和产业化竞争格局进行了总结分析，并对未来发展的挑战和机遇进行了展望，包括生物合成技术的挑战、新产物的发掘与设计，以及市场监管与安全性问题。

关键词: 合成生物学, 萜类化合物, 香精香料, 细胞工厂, 知识产权

Abstract:

The demand for personal care products has been increasing steadily. Consumers are now seeking for products that offer enhanced functionality, natural ingredients, and superior feeling experiences. Fragrances and flavors are key components in personal care formulations. Terpenes and their derivatives dominate natural fragrances due to their diverse structures and scents, widespread availability from plants and animals, stable function, and high safety profile. The terpene fragrance market is projected to grow at an annual growth rate of 6.4%, reaching $1.01 billion by 2028, indicating a high market revenue and promising future. Currently, the acquisition of natural terpene fragrances is constrained by the long growth cycle of plants, low terpene content, and high extraction cost. Thus, there is an urgent need for developing new technology, such as synthetic biology, to achieve large-scale production of diverse fragrance compounds at an environment-friendly manner. This review explores the application and development of synthetic biology in the sustainable production of terpene fragrances, highlighting how data-driven synthetic biology and biotechnological innovations empower terpene fragrance production. It also compares classical and alternative terpenoid biosynthesis pathways, elucidating their differences and advantages, which can offer comprehensive insights for chassis design toward terpenoid efficient biosynthesis. Additionally, this review explores recent advances in terpene synthase discovery and engineering as well as cell factory construction. Furthermore, we comprehensively summarizes challenges encountered in the construction of three major types of terpene fragrance cell factories: monoterpenes, sesquiterpenes, and nor-isoprenoids, and discusses metabolic engineering strategies that can be employed to address these issues, including enzyme optimization, pathway reconstruction, and cellular detoxification. At the end, we comment the current landscape of patents and industrial competition, offering insights into future challenges and opportunities, including the hurdles of biosynthesis technology, the discovery and design of new products, as well as the market regulation and safety concerns.

Key words: synthetic biology, terpenoid, fragrances and flavors, cell factory, intellectual property

中图分类号:

Q816

张梦瑶, 蔡鹏, 周雍进. 合成生物学助力萜类香精香料可持续生产[J]. 合成生物学, 2025, 6(2): 334-356.

ZHANG Mengyao, CAI Peng, ZHOU Yongjin. Synthetic biology drives the sustainable production of terpenoid fragrances and flavors[J]. Synthetic Biology Journal, 2025, 6(2): 334-356.

图/表 9

图1 合成生物学中数据及生物技术驱动的“设计-构建-测试-学习”循环

Fig. 1 Data- and biotechnology-driven ‘Design-Build-Test-Learn’ cycle in synthetic biology

图2 经典的萜类合成途径与常见替代合成途径（G3P—D-甘油醛-3-磷酸； PYR—丙酮酸； DXP—1-脱氧-D- 木酮糖-5-磷酸酯； MEP—2-C-甲基-D-赤藓糖醇-4-磷酸； CDP-ME—4-焦磷酸胞苷-2-C-甲基-D-赤藓糖醇； CDP-MEP—4-焦磷酸胞苷-2-C-甲基-D-赤藓糖醇-2-磷酸； MEcPP—2-C-甲基-D-赤藓糖醇-2，4-环焦磷酸； HMBPP—4-羟基-3-甲基-2-丁烯基焦磷酸； DMAPP—二甲基烯丙基焦磷酸； GPP—香叶基焦磷酸； FPP—法尼基焦磷酸； GGPP—香叶基香叶基焦磷酸； MG-CoA—3-甲基戊烯二酰辅酶A； MB-CoA—3-甲基-2-丁烯酰辅酶A； MB—3-甲基-2-丁烯醛； DMAP—二甲基烯丙基磷酸； M3P—甲羟戊酸-3-磷酸； M3P5P—甲羟戊酸-3，5-焦磷酸； IP—异戊烯基磷酸； AcCoA—乙酰辅酶A； AcAcCoA—乙酰乙酰辅酶A； HMG-CoA—3-羟基-3-甲基戊二酰辅酶A； MVA—甲羟戊酸； M5P—甲羟戊酸-5-磷酸； MVAPP—甲羟戊酸焦磷酸； IPP—异戊烯基焦磷酸； NPP—橙花基焦磷酸； Z，Z-FPP—Z，Z-法尼基焦磷酸； NNPP—橙花橙花基焦磷酸； DXS—DXP合酶； DXR—DXP还原异构酶； MCT—MEP胞苷酰转移酶； CMK—CDP-ME激酶； MDS—ME-CPP合酶； HDS—HMB-PP合酶； HDR—HMB-PP还原酶； ERG10—乙酰辅酶A硫解酶； ERG13—3-羟基-3-甲基戊二酰-CoA合酶； HMGR—3-羟基-3-甲基戊二酰辅酶A还原酶； ERG12/MK—甲羟戊酸激酶； ERG8/PMVK—磷酸甲羟戊酸激酶； ERG19/MVD—甲羟戊酸焦磷酸脱羧酶； LiuC—烯酰辅酶A水合酶； AibAB—戊烯二酰辅酶A脱羧酶； cbjALD—酰基辅酶A还原酶； YahK—醇脱氢酶； ThiM—羟乙基噻唑激酶； IPK—异戊烯基磷酸激酶； IDI—异戊烯基焦磷酸异构酶； GPPS—香叶基焦磷酸合酶； FPPS—法尼基焦磷酸合酶； GGPPS—香叶基香叶基焦磷酸合酶； NPPS—橙花基焦磷酸合酶； zFPPS—Z，Z-法尼基焦磷酸合酶； NNPPS—橙花橙花基焦磷酸合酶； M3K—甲羟戊酸-3-激酶； M3P5K—甲羟戊酸-3-磷酸-5-激酶； BMD—甲羟戊酸焦磷酸脱羧酶； IPK—异戊烯基磷酸激酶；PMD—甲羟戊酸-5-磷酸脱羧酶）

Fig. 2 Classical terpene biosynthetic pathways and alternative chemical synthetic routes(G3P—D-glyceraldehyde 3-phosphate; PYR—pyruvate; DXP—1-deoxy-D-xylulose 5-phosphate; MEP—2-C-methyl-D-erythritol 4-phosphate; CDP-ME—4-diphophocytidyl-2-C-methyl-D-erythrito; CDP-MEP—4-diphophocytidyl-2-C-methyl-D-erythritol 2phosphate; MEcPP—2-C-methyl-D-erythritol 2,4-cyclodiphosphate; HMBPP—4-hydroxy-3-methyl-butenyl diphosphate; DMAPP—dimethylallyl diphosphate; GPP—geranyl diphosphate; FPP—farnesyl diphosphate; GGPP—geranylgeranyl diphosphate; MG-CoA—3-methylglutaconyl-CoA; MB-CoA—3-methyl-2-butenoyl-CoA; MB—3-methyl-2-butenal; DMAP—dimethylallyl phosphate; M3P—mevalonate 3-phosphate; M3P5P—mevalonate 3,5-biphosphate; IP—isopentenyl phosphate; AcCoA—acetyl-CoA; AcAcCoA—acetoacetyl-CoA; HMGCoA—3-hydroxy-3-methylglutaryl-CoA; MVA—mevalonate; M5P—mevalonate 5-phosphate; MVAPP—mevalonate diphosphate; IPP—isopentenyl diphosphate; NPP—neryl diphosphate; Z,Z-FPP—Z,Z-farnesyl diphosphate; NNPP—nerylneryl diphosphate; DXS—DXP synthase; DXR—DXP reductoisomerase; MCT—MEP cytidylyltransferase; CMK—CDP-ME kinase; MDS—ME-CPP synthase; HDS—HMB-PP synthase; HDR—HMB-PP reductase; ERG10—ACCT acetyl-CoA C-acetyl transferase; ERG13—HMGS HMG-CoA synthase; HMGR—HMG-CoA reductase; ERG12—MK MVA kinase; ERG8—PMVK phosphomevalonate kinase; ERG19—MVD diphosphomevalonate decarboxylase; LiuC—enoyl-CoA hydratase; AibAB—glutaconyl-CoA decarboxylase; cbjALD—acyl-CoA reductase; YahK—alcohol dehydrogenase; ThiM—hydroxyethylthiazole kinase; IPK—isopentenyl phosphate kinase; IDI—isopentenyl-diphosphate isomerase; GPPS—geranyl pyrophosphate synthase; FPPS—farnesyl pyrophosphate synthase; GGPPS—geranylgeranyl diphosphate synthase; NPPS—nerol pyrophosphate synthase; zFPPS—Z,Z-Farnesyl diphosphate synthase; NNPPS—nerylneryl diphosphate synthase; M3K—mevalonate 3-kinase; M3P5K—mevalonate 3-phosphate 5-kinase; BMD—mevalonate biphosphate decarboxylase; IPK—isopentenyl phosphate kinase; PMD—mevalonate 5-phosphate decarboxylase.)

图3 萜类合酶的挖掘与改造

Fig. 3 Mining and engineering terpene synthases

表1 经典的萜类香料细胞工厂汇总

Table 1 Summary of cell factories for producing terpene fragrances

结构	化合物	气味特征	底盘菌株	培养条件	产量/(g/L)	参考文献
链状单萜	香叶醇 Geraniol	温和、甜香、花果香气	大肠杆菌	摇瓶发酵	2.1	[73]
	香叶醇 Geraniol	温和、甜香、花果香气	巴斯德毕赤酵母	24孔板发酵	1.2	[74]
	月桂烯 Myrcene	甜香脂香气	大肠杆菌	摇瓶发酵	1.2	[75]
	香茅醇 Citronellol	甜润玫瑰花香	酿酒酵母	5 L生物反应器	8.3	[76]
	芳樟醇 Linalool	铃兰清香	菠萝潘托氏菌	5 mL试管	S型5.6 R型3.7	[77]
单环单萜	柠檬烯 Limonene	柠檬香气	大肠杆菌	3 L生物反应器	3.6	[78]
	α-松油醇 α-Terpineol	丁香花气味	酿酒酵母	5 L生物反应器	21.8	[79]
	左旋香芹酮 (-)-Carvone	兰花香气、类清新薄荷气味	大肠杆菌	摇瓶发酵柠檬烯为底物	44.3	[80]
双环单萜	龙脑 Borneol	极强的樟脑和松木香气	酿酒酵母	摇瓶补料	0.75	[81]
	α-蒎烯 α-Pinene	松木芳香，清新草本气味	大肠杆菌	摇瓶发酵	0.17	[82]
	香桧烯 Sabinene	湿泥土气味与木质香气	酿酒酵母	摇瓶发酵	0.15	[83]
链状倍半萜	橙花叔醇 Nerolidol	清新柔和的木质香及花果香	酿酒酵母	摇瓶发酵	3.5	[84]
	β-法尼烯 β-Farnesol	青草与柑橘混合的清新香气	酿酒酵母	200 t生物反应器	130	[85]
	法尼醇 Farnesol	温和的花香调	大肠杆菌	试管	0.53	[86]
单环倍半萜	红没药烯 Bisabolene	果香与香脂香	酿酒酵母	5 L生物反应器	9.8	[87]
	α-葎草烯 α-Humulene	丁香香型	热带念珠菌	30 L生物反应器	4.1	[88]
	右旋大根香叶烯D (-)-Germacrene D	辛辣的胡椒香气	酿酒酵母	5 L生物反应器	7.9	[89]
双环倍半萜	右旋瓦伦烯 (+)-Valencene	愉悦的柑橘香	酿酒酵母	15 L生物反应器	16.6	[70]
	右旋诺卡酮 (+)-Nootkatone	葡萄柚的香气	酿酒酵母	5 L生物反应器	0.80	[90]
	檀香醇 Santalol	柔和温暖的木质香型	酿酒酵母	5 L生物反应器	1.3	[91]
三环倍半萜	α-檀香烯 α-Santalene	温暖细腻的檀香木香气	巴斯德毕赤酵母	1 L生物反应器	21.5	[92]
	长叶烯 Longifolene	鸢尾花与木质香	大肠杆菌	5 L生物反应器	0.38	[93]
	广藿香醇 Patchoulol	广藿芳香	酿酒酵母	5 L生物反应器	1.6	[94]
单环降异戊二烯	α-紫罗酮 α-Ionone	强烈的紫罗兰花与鸢尾根香	酿酒酵母	摇瓶补料	0.48	[95]
	β-紫罗酮 β-Ionone	紫罗兰与玫瑰香，含木质香	解脂耶氏酵母	3 L生物反应器	0.98	[96]

表1 经典的萜类香料细胞工厂汇总

Table 1 Summary of cell factories for producing terpene fragrances

结构	化合物	气味特征	底盘菌株	培养条件	产量/(g/L)	参考文献
链状单萜	香叶醇 Geraniol	温和、甜香、花果香气	大肠杆菌	摇瓶发酵	2.1	[73]
	香叶醇 Geraniol	温和、甜香、花果香气	巴斯德毕赤酵母	24孔板发酵	1.2	[74]
	月桂烯 Myrcene	甜香脂香气	大肠杆菌	摇瓶发酵	1.2	[75]
	香茅醇 Citronellol	甜润玫瑰花香	酿酒酵母	5 L生物反应器	8.3	[76]
	芳樟醇 Linalool	铃兰清香	菠萝潘托氏菌	5 mL试管	S型5.6 R型3.7	[77]
单环单萜	柠檬烯 Limonene	柠檬香气	大肠杆菌	3 L生物反应器	3.6	[78]
	α-松油醇 α-Terpineol	丁香花气味	酿酒酵母	5 L生物反应器	21.8	[79]
	左旋香芹酮 (-)-Carvone	兰花香气、类清新薄荷气味	大肠杆菌	摇瓶发酵柠檬烯为底物	44.3	[80]
双环单萜	龙脑 Borneol	极强的樟脑和松木香气	酿酒酵母	摇瓶补料	0.75	[81]
	α-蒎烯 α-Pinene	松木芳香，清新草本气味	大肠杆菌	摇瓶发酵	0.17	[82]
	香桧烯 Sabinene	湿泥土气味与木质香气	酿酒酵母	摇瓶发酵	0.15	[83]
链状倍半萜	橙花叔醇 Nerolidol	清新柔和的木质香及花果香	酿酒酵母	摇瓶发酵	3.5	[84]
	β-法尼烯 β-Farnesol	青草与柑橘混合的清新香气	酿酒酵母	200 t生物反应器	130	[85]
	法尼醇 Farnesol	温和的花香调	大肠杆菌	试管	0.53	[86]
单环倍半萜	红没药烯 Bisabolene	果香与香脂香	酿酒酵母	5 L生物反应器	9.8	[87]
	α-葎草烯 α-Humulene	丁香香型	热带念珠菌	30 L生物反应器	4.1	[88]
	右旋大根香叶烯D (-)-Germacrene D	辛辣的胡椒香气	酿酒酵母	5 L生物反应器	7.9	[89]
双环倍半萜	右旋瓦伦烯 (+)-Valencene	愉悦的柑橘香	酿酒酵母	15 L生物反应器	16.6	[70]
	右旋诺卡酮 (+)-Nootkatone	葡萄柚的香气	酿酒酵母	5 L生物反应器	0.80	[90]
	檀香醇 Santalol	柔和温暖的木质香型	酿酒酵母	5 L生物反应器	1.3	[91]
三环倍半萜	α-檀香烯 α-Santalene	温暖细腻的檀香木香气	巴斯德毕赤酵母	1 L生物反应器	21.5	[92]
	长叶烯 Longifolene	鸢尾花与木质香	大肠杆菌	5 L生物反应器	0.38	[93]
	广藿香醇 Patchoulol	广藿芳香	酿酒酵母	5 L生物反应器	1.6	[94]
单环降异戊二烯	α-紫罗酮 α-Ionone	强烈的紫罗兰花与鸢尾根香	酿酒酵母	摇瓶补料	0.48	[95]
	β-紫罗酮 β-Ionone	紫罗兰与玫瑰香，含木质香	解脂耶氏酵母	3 L生物反应器	0.98	[96]

图4 单萜类香料细胞工厂常见的工程化改造策略

Fig. 4 Engineering strategies for monoterpene fragrance cell factories

图5 提升倍半萜合酶对FPP可得性的常见策略

Fig. 5 Strategies for enhancing FPP availability to sesquiterpene synthases.

图6 α/β-紫罗兰酮生物合成途径

Fig. 6 Schematic diagram of biosynthetic pathway of α,β-ionone

图7 全球十年内萜类香料生物合成相关文献与专利分布(The data were from Google Patents and Google Scholar using “terpene fragrances” and “synthetic biology” as the keywords, July 17th, 2024.)

Fig. 7 Global literatures and patents related to terpene fragrance biosynthesis that were publicized within the last decade

图8 当前合成生物技术公司与传统香料产业的格局

Fig. 8 Current landscape of synthetic biology companies and traditional fragrance industries

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合成生物学助力萜类香精香料可持续生产

Synthetic biology drives the sustainable production of terpenoid fragrances and flavors

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