红树来源青霉属真菌次级代谢产物与生物活性(2007~2020)

doi:10.6023/cjoc202103044

摘要/Abstract

红树植物生长于缺氧、酸性、含盐的热带和亚热带地区的潮间带, 生长环境的特殊性为红树来源真菌提供了特殊的宿主环境. 红树来源真菌独特的遗传背景和代谢途径使得其次级代谢产物具有结构新颖且类型多样、生物活性多样化等特点. 青霉属(Penicillium sp.)真菌分布广泛, 为红树来源真菌的一大类群, 能够代谢产生生物碱类、肽类、萜类及聚酮类等结构类型多样且新颖的代谢产物, 大多具有抗肿瘤、抗炎、抗菌和酶抑制剂等多种生物活性. 综述了2007~2020年, 从红树来源青霉属真菌中发现的276个新化合物, 介绍了其结构和生物活性, 以期为后续红树来源青霉属真菌新型天然药物的开发提供参考.

关键词: 红树, 青霉属真菌, 次级代谢产物, 生物活性

Mangrove plants grow in tropical and subtropical intertidal zones with acid, salt and oxygen deficit. The particularity of the growth environment provides a special host environment for mangrove fungi. The unique genetic background and metabolic pathway of mangrove-derived fungi make their secondary metabolites have novel structures and diverse biological activities. The genus of Penicillium is widely distributed, which is a large group of mangrove-derived fungi. It can produce metabolites with various structural types and novel structures such as alkaloids, peptides, terpenes, polyketones and other metabolites. Most of them have anti-tumor, anti-inflammatory, anti-bacterial, enzyme inhibitors and other bioactivities. The advances of the 276 natural products produced from mangrove-derived Penicillium in recent 14 years (from 2007 to 2020) are reviewed, in order to provide reference for the development of new natural drugs of mangrove Penicillium sp. fungi.

Key words: mangrove, Penicillium sp., secondary metabolite, bioactivity

引用此文

曾尾女, 黄国雷, 王斌, 蔡瑾, 郑彩娟. 红树来源青霉属真菌次级代谢产物与生物活性(2007~2020)[J]. 有机化学, 2021, 41(11): 4255-4278.

Weinü Zeng, Guolei Huang, Bin Wang, Jin Cai, Caijuan Zheng. Secondary Metabolites and Bioactivities of Penicillium sp. Sourced from Mangrove from 2007 to 2020[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4255-4278.

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Plant species	Isolated fungi	Site	Ref．
Rhizospheric soil of mangrove plants	Penicillium javanicum HK1-22 Penicillium sp. HK1-22 Penicillium janthinellum HK1-6 Penicillium sp. SYFz-1 Penicillium sp. SCSIO041218 Penicillium pinophilum SCAU037 Penicillium pinophilum H608 Penicillium camemberti OUCMDZ-1492 Penicillium herquei MA-370 Penicillium polonicum H175 Penicillium polonicum MCCC3A00951	海南东寨港自然保护区海南东寨港自然保护区海南海南三亚三亚中国特呈岛厦门海南文昌海南福建张江口福建张江口	[1] [3] [4-7] [8-9] [10, 11] [12] [13] [14-16] [17] [18] [19]
Kandelia candel	Penicillium commune QQF-3 Penicillium aculeatum No. 9EB Penicillium chermesinum ZH4-E2 Penicillium sp. sk5GW1L Penicillium sp. sk14JW2P Penicillium sp. (SBE-8) Penicillium citrinum QJF-22	广东广东阳江广东广西广西香港海南海口	[20] [21] [22] [23-24] [25] [26] [27]
Bruguiera sexangula var. rhynchopetala	Penicillium sp. TGM112 Penicillium citrinum HL-5126 Penicillium simplicissimum MA-332 Penicillium sp. (J41221)	海南东寨港自然保护区海南东寨港自然保护区海南海南东寨港自然保护区	[28-29] [30-33] [34-35] [36]
Bruguiear gymnorrhiza	Penicillium sp. GD6 Penicillium thomi Penicillium sp. MA-37	广州湛江广西海南	[37-39] [40] [41-42]
Avicennia marina	Penicillium brocae MA-231 Penicillium sp. FJ-1 Penicillium brocae MA-192 Penicillium sp. ZH16 Penicillium citrinum	海南福建海南海南东寨港自然保护区福建	[43-47] [48] [49-50] [51] [52]
Acanthus ilicifolius	Penicillium chrysogenum HND11-24 Penicillium dipodomyicola HN4-3A Penicillium sp. (ZZF 32#) Penicillium sp. 299# Penicillium sp. FJ-1	海南海南广东湛江海南海南	[53] [54] [55] [56] [57]
Rhizophora stylosa	Penicillium oxalicum EN-201 Penicillium solitum GWQ-143	海南 /	[58] [59]
Cerbera manghas	Penicillium sp. HN29-3B1	海南东寨港自然保护区	[60-61]
Plant species	Isolated fungi	Site	Ref．
Aegiceras corniculatum	Penicillium sp. JP-1 Penicillium sp. (strain HKI0459)	福建福建厦门	[62] [63]
Sonneratia caseolaris	Penicillium janthinellum HDN13-309	海南	[64-67]
Ceriouiopps tagal	Penicillium sp. J-54 Penicillium sp. JY246	海南东寨港自然保护区南海	[2,68] [69]
Lumnitzera racemosa	Penicillium sumatrense MA-92 Penicillium bilaiae MA-267	海南文昌海南	[70] [71-72]
Myoporum bontioides	Penicillium chrysogenum V11	中国雷州半岛	[73-75]
Laguncularia racemose	Penicillium coffeae MA-314	海南岛	[76]
Sonneratia apetala	Penicillium sp. ZJ-SY2	广东	[77]
Hibiscus tiliaceus	Penicillium aurantiogriseum 328^# Penicillium commune G2M	广东海南	[78] [79]
Heritiera littoralis	Penicillium chermesinum strain HLit-ROR2 Penicillium sp. YYSJ-3	泰国广东珠海	[80] [81]
Excoecaria agallocha	Penicillium expansum 091006 Penicillium sp. Y2-2-1	海南文昌广东广州	[82-83] [84]
Bruguiera sexangula	Penicillium sp. 091402	海南	[85]
	Penicillium sp. 303^#	广东湛江	[86]
	Penicillium variabile	福建	[87]

Plant species	Isolated fungi	Site	Ref．
Rhizospheric soil of mangrove plants	Penicillium javanicum HK1-22 Penicillium sp. HK1-22 Penicillium janthinellum HK1-6 Penicillium sp. SYFz-1 Penicillium sp. SCSIO041218 Penicillium pinophilum SCAU037 Penicillium pinophilum H608 Penicillium camemberti OUCMDZ-1492 Penicillium herquei MA-370 Penicillium polonicum H175 Penicillium polonicum MCCC3A00951	海南东寨港自然保护区海南东寨港自然保护区海南海南三亚三亚中国特呈岛厦门海南文昌海南福建张江口福建张江口	[1] [3] [4-7] [8-9] [10, 11] [12] [13] [14-16] [17] [18] [19]
Kandelia candel	Penicillium commune QQF-3 Penicillium aculeatum No. 9EB Penicillium chermesinum ZH4-E2 Penicillium sp. sk5GW1L Penicillium sp. sk14JW2P Penicillium sp. (SBE-8) Penicillium citrinum QJF-22	广东广东阳江广东广西广西香港海南海口	[20] [21] [22] [23-24] [25] [26] [27]
Bruguiera sexangula var. rhynchopetala	Penicillium sp. TGM112 Penicillium citrinum HL-5126 Penicillium simplicissimum MA-332 Penicillium sp. (J41221)	海南东寨港自然保护区海南东寨港自然保护区海南海南东寨港自然保护区	[28-29] [30-33] [34-35] [36]
Bruguiear gymnorrhiza	Penicillium sp. GD6 Penicillium thomi Penicillium sp. MA-37	广州湛江广西海南	[37-39] [40] [41-42]
Avicennia marina	Penicillium brocae MA-231 Penicillium sp. FJ-1 Penicillium brocae MA-192 Penicillium sp. ZH16 Penicillium citrinum	海南福建海南海南东寨港自然保护区福建	[43-47] [48] [49-50] [51] [52]
Acanthus ilicifolius	Penicillium chrysogenum HND11-24 Penicillium dipodomyicola HN4-3A Penicillium sp. (ZZF 32#) Penicillium sp. 299# Penicillium sp. FJ-1	海南海南广东湛江海南海南	[53] [54] [55] [56] [57]
Rhizophora stylosa	Penicillium oxalicum EN-201 Penicillium solitum GWQ-143	海南 /	[58] [59]
Cerbera manghas	Penicillium sp. HN29-3B1	海南东寨港自然保护区	[60-61]
Plant species	Isolated fungi	Site	Ref．
Aegiceras corniculatum	Penicillium sp. JP-1 Penicillium sp. (strain HKI0459)	福建福建厦门	[62] [63]
Sonneratia caseolaris	Penicillium janthinellum HDN13-309	海南	[64-67]
Ceriouiopps tagal	Penicillium sp. J-54 Penicillium sp. JY246	海南东寨港自然保护区南海	[2,68] [69]
Lumnitzera racemosa	Penicillium sumatrense MA-92 Penicillium bilaiae MA-267	海南文昌海南	[70] [71-72]
Myoporum bontioides	Penicillium chrysogenum V11	中国雷州半岛	[73-75]
Laguncularia racemose	Penicillium coffeae MA-314	海南岛	[76]
Sonneratia apetala	Penicillium sp. ZJ-SY2	广东	[77]
Hibiscus tiliaceus	Penicillium aurantiogriseum 328^# Penicillium commune G2M	广东海南	[78] [79]
Heritiera littoralis	Penicillium chermesinum strain HLit-ROR2 Penicillium sp. YYSJ-3	泰国广东珠海	[80] [81]
Excoecaria agallocha	Penicillium expansum 091006 Penicillium sp. Y2-2-1	海南文昌广东广州	[82-83] [84]
Bruguiera sexangula	Penicillium sp. 091402	海南	[85]
	Penicillium sp. 303^#	广东湛江	[86]
	Penicillium variabile	福建	[87]

Compound	Source	Bioactivity (MIC, LD₅₀, IC₅₀)	Region	Year
1~5	A. marina	S. aureus: 0.25~32.0 μg/mL (except 4); Gaeumannomyces graminis: 0.25~64.0 μg/mL (except 4) Micrococcus luteus: 0.25 μg/mL (3);	Hainan	2015^[44]
6~11	A. marina	DU145/HeLa/HepG2/MCF-7/NCI-H460/SGC-7901/ SW1990/SW480/U251: 0.89~9 μmol/L (except 8/9)	Hainan	2014^[45]
12~15	A. marina	E. coli/A. hydrophilia/V. harveyi/V. parahaemolyticus: 16.0~32.0 μg/mL (14/15)	Hainan	2017^[47]
16~18	A. marina	E. coli/A. hydrophilia/V. harveyi: 16.0~64.0 μg/mL (16); E. coli/A. hydrophilia/V. harveyi: 32 μg/mL (18)	Hainan	2016^[46]
19	A. marina	S. aureus: 0.25 μg/mL	Hainan	2016^[44]
20~27	Root of S. caseolaris	SOD2/HO-1: 10 μmol/L (22/23)	Hainan	2020^[67]
28~33	Root of S. caseolaris	HeLa: 0.3~3.9 μmol/L (28~30); HL-60: 0.1~1.6 μmol/L (28~30)	Hainan	2017^[65]
34~41	Stem of A. corniculatum	BK_Ca: (34, 35, 37)	Fujian	2007^[63]
42	Rhizospheric soil of mangrove plant	H1N1: 28.3 μmol/L	Hainan	2013^[14]
43	Rhizospheric soil of mangrove Plant	H1N1: 38.9 μmol/L	Hainan	2013^[14]
44	Rhizospheric soil of mangrove plant	H1N1: 32.2 μmol/L	Hainan	2013^[14]
45	Rhizospheric soil of mangrove plant	/	Hainan	2013^[14]
46	Rhizospheric soil of mangrove plant	H1N1: 73.3 μmol/L	Hainan	2013^[14]
47	Rhizospheric soil of mangrove plant	H1N1: 34.1 μmol/L	Hainan	2013^[14]
48	Rhizospheric soil of mangrove plant	/	Hainan	2018^[16]
49	Rhizospheric soil of mangrove plan	/	Hainan	2020^[5]
50~53	Rhizospheric soil of mangrove plant	/	Hainan	2017^[11]
54	Leaves of R. stylosa	A. salina: 5.6 μmol/L	Hainan	2015^[58]
55~57	Rhizospheric soil of mangrove plant	AchE: 58.0 μmol/L (57)	Hainan	2014^[13]
58, 59	A. marina	S. aureus: 0.125 μg/mL (58)	Hainan	2017^[43]
60~62	Leaves of A. marina	A. salina: 36.7 μmol/L	Hainan	2014^[49]
63	B．gymnorrhiza	/	Hainan	2014^[38]
64~66	M. bontioides	Rhizoctonia solani: 195.98 μmol/L (64, 66); MTA-MB435/A549: 7.32~16.13 μmol/L	Leizhou Peninsula	2017^[74]2016^[75]
67	A. ilicifolius	/	Hainan	2015^[56]
68	Leaves of R. stylosa	A. salina: 2.3 μmol/L	Hainan	2015^[58]
69	Branch of C. manghas	/	Hainan	2015^[60]

Compound	Source	Bioactivity (MIC, LD₅₀, IC₅₀)	Region	Year
1~5	A. marina	S. aureus: 0.25~32.0 μg/mL (except 4); Gaeumannomyces graminis: 0.25~64.0 μg/mL (except 4) Micrococcus luteus: 0.25 μg/mL (3);	Hainan	2015^[44]
6~11	A. marina	DU145/HeLa/HepG2/MCF-7/NCI-H460/SGC-7901/ SW1990/SW480/U251: 0.89~9 μmol/L (except 8/9)	Hainan	2014^[45]
12~15	A. marina	E. coli/A. hydrophilia/V. harveyi/V. parahaemolyticus: 16.0~32.0 μg/mL (14/15)	Hainan	2017^[47]
16~18	A. marina	E. coli/A. hydrophilia/V. harveyi: 16.0~64.0 μg/mL (16); E. coli/A. hydrophilia/V. harveyi: 32 μg/mL (18)	Hainan	2016^[46]
19	A. marina	S. aureus: 0.25 μg/mL	Hainan	2016^[44]
20~27	Root of S. caseolaris	SOD2/HO-1: 10 μmol/L (22/23)	Hainan	2020^[67]
28~33	Root of S. caseolaris	HeLa: 0.3~3.9 μmol/L (28~30); HL-60: 0.1~1.6 μmol/L (28~30)	Hainan	2017^[65]
34~41	Stem of A. corniculatum	BK_Ca: (34, 35, 37)	Fujian	2007^[63]
42	Rhizospheric soil of mangrove plant	H1N1: 28.3 μmol/L	Hainan	2013^[14]
43	Rhizospheric soil of mangrove Plant	H1N1: 38.9 μmol/L	Hainan	2013^[14]
44	Rhizospheric soil of mangrove plant	H1N1: 32.2 μmol/L	Hainan	2013^[14]
45	Rhizospheric soil of mangrove plant	/	Hainan	2013^[14]
46	Rhizospheric soil of mangrove plant	H1N1: 73.3 μmol/L	Hainan	2013^[14]
47	Rhizospheric soil of mangrove plant	H1N1: 34.1 μmol/L	Hainan	2013^[14]
48	Rhizospheric soil of mangrove plant	/	Hainan	2018^[16]
49	Rhizospheric soil of mangrove plan	/	Hainan	2020^[5]
50~53	Rhizospheric soil of mangrove plant	/	Hainan	2017^[11]
54	Leaves of R. stylosa	A. salina: 5.6 μmol/L	Hainan	2015^[58]
55~57	Rhizospheric soil of mangrove plant	AchE: 58.0 μmol/L (57)	Hainan	2014^[13]
58, 59	A. marina	S. aureus: 0.125 μg/mL (58)	Hainan	2017^[43]
60~62	Leaves of A. marina	A. salina: 36.7 μmol/L	Hainan	2014^[49]
63	B．gymnorrhiza	/	Hainan	2014^[38]
64~66	M. bontioides	Rhizoctonia solani: 195.98 μmol/L (64, 66); MTA-MB435/A549: 7.32~16.13 μmol/L	Leizhou Peninsula	2017^[74]2016^[75]
67	A. ilicifolius	/	Hainan	2015^[56]
68	Leaves of R. stylosa	A. salina: 2.3 μmol/L	Hainan	2015^[58]
69	Branch of C. manghas	/	Hainan	2015^[60]

Compound	Source	Bioactivity (MIC, LD₅₀, IC₅₀)	Region	Year
70	M. bontioides	/	Leizhou Peninsula	2018^[73]
71	M. bontioides	/	Leizhou Peninsula	2018^[73]
72	Stem of B. gymnorrhiza	/	Guangdong	2018^[37]
73~75	Root of S. caseolaris	/	Hainan	2017^[64]
76	Root of S. caseolaris	H₂O₂-induced oxidative damage	Hainan	2017^[66]
77	Rhizospheric soil of mangrove plant	/	Fujian	2020^[19]
78	Leaves of E. agallocha	Salmonell paratyphi/E. coli/Shigella/ V. parahaemolyticus: 50 mg/mL	Guangdong	2020^[84]
79, 80	Soil of R. stylosa	DPPH: 5.6 (79), 4.7 μmol/L (80)	/	2015^[59]