深海、沙漠、火山、极地来源链霉菌新天然产物(2009~2020)

doi:10.6023/cjoc202010004

有机化学 ›› 2021, Vol. 41 ›› Issue (5): 1804-1820.DOI: 10.6023/cjoc202010004 上一篇下一篇

综述与进展

深海、沙漠、火山、极地来源链霉菌新天然产物(2009~2020)

江婷^a, 蒲洪^a, 段燕文^a^,^b^,^c, 颜晓晖^a^,^d, 黄勇^a^,^c^,^*()

a 中南大学湘雅国际转化医学联合研究院长沙 410013
b 组合生物合成与天然产物药物湖南省工程研究中心长沙 410011
c 新药组合生物合成国家地方联合工程研究中心长沙 410011
d 天津中医药大学中医药研究院天津 301617

收稿日期:2020-10-05 修回日期:2020-11-24 发布日期:2020-12-19
通讯作者: 黄勇
基金资助:
国家自然科学基金(81473124); 国家自然科学基金(81872779); 中南大学中央高校基本科研业务费专项资金(2019zzts774)

New Natural Products of Streptomyces Sourced from Deep-Sea, Desert, Volcanic, and Polar Regions from 2009 to 2020

Ting Jiang^a, Hong Pu^a, Yanwen Duan^a^,^b^,^c, Xiaohui Yan^a^,^d, Yong Huang^a^,^c^,^*()

a Xiangya International Academy of Translational Medicine, Central South University, Changsha 410013
b Hunan Engineering Research Center of Combinatorial Biosynthesis and Natural Product Drug Discovery, Changsha 410011
c National Engineering Research Center of Combinatorial Biosynthesis for Drug Discovery, Changsha 410011
d Institute of Traditional Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 301617

Received:2020-10-05 Revised:2020-11-24 Published:2020-12-19
Contact: Yong Huang
About author:
* Corresponding author. E-mail: jonghuang@csu.edu.cn
Supported by:
National Natural Science Foundation of China(81473124); National Natural Science Foundation of China(81872779); Fundamental Research Funds for the Central Universities of Central South University (CSU)(2019zzts774)

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摘要/Abstract

链霉菌是天然产物的重要来源, 但从土壤来源等普通生态环境筛选出的链霉菌中发现新化合物的比例有所降低. 深海、沙漠、火山或极地属于极端环境, 从中分离出的链霉菌因其特殊气候、地质或营养条件等的差异, 有可能产生较多新颖天然产物. 综述了2009年至2020年来从深海、沙漠、火山或极地链霉菌中发现的155个新天然产物, 介绍了它们的结构和生物活性.

关键词: 链霉菌, 深海, 火山, 沙漠, 天然产物, 生物活性

Streptomyces are important sources of natural products. However, it is more challenging to discover novel compounds from Streptomyces strains isolated from common environmental samples, such as typical soil samples. Due to the unique climates, varying geological and nutrition conditions, deep-sea, desert, volcanic and polar environments are extreme habitats for Streptomyces. These unique habitats are regarded as rare and under-explored niches of new Streptomyces strains and their natural products. The recent advancement of the structures and bioactivities of 155 natural products is reviewed, produced by various Streptomyces strains isolated from these extreme environments from 2009 to 2020.

Key words: Streptomyces, deep-sea, volcano sediments, desert, polar regions, natural products, biological activity

引用此文

江婷, 蒲洪, 段燕文, 颜晓晖, 黄勇. 深海、沙漠、火山、极地来源链霉菌新天然产物(2009~2020)[J]. 有机化学, 2021, 41(5): 1804-1820.

Ting Jiang, Hong Pu, Yanwen Duan, Xiaohui Yan, Yong Huang. New Natural Products of Streptomyces Sourced from Deep-Sea, Desert, Volcanic, and Polar Regions from 2009 to 2020[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1804-1820.

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Compd.	Source	Bioactivity (MIC or IC₅₀)	Depth/m	Region	Year
Caboxamycin (1)	NTK 937	B. subtilis/S. lentus: 8~20 μmol?L ^–1 AGS/ HepG2/MCF-7: 28.6~29.4 μmol?L ^–1	3814	Canary Basin	2009^[23]
Benzoxacystol (2)	NTK 935	Inhibitory activity against glycogen synthase kinase-3β	3814	Canary Basin	2011^[24]
3'-hydroxycaboxamycin (3)	NTK 937	—	3814	Canary Basin	2017^[28]
Ammosamides A/B (4/5)	CNR-698	HCT-116: 320 nmol?L^–1	1618	Bahamas	2009^[29]
Lobophorins E/F (6/7)	SCSIO 01127	S. aureus/E. faecalis: 8 μg/mL ( 6) SF-268/ MCF-7/H460: 2.93~6.82 μmol?L ^–1 (7)	135	South China Sea	2011^[76]
Lobophorins G (8)	MS100061	BCG: 1.56 μg/mL B. subtilis: 3.125 μg/mL M. tuberculosisH37Rv: 16 μg/mL	NA	South China Sea	2013^[32]
Lobophorins H/I (9/10)	12A35	B. subtilisCMCC 63501: 1.57 μg/mL (9) 50 μg/mL ( 10)	2134	South China Sea	2013^[34]
Lobophorins J (11)	12A35	—	2134	South China Sea	2015^[35]
Lobophorin K (12)	M-207	S. aureus: 40~80 μg/mL MiaPaca-2/ MCF-7/THLE-2: 6.3~34.0 μmol?L ^–1	180	Cantabrian Sea	2017^[36]
Lobophorin L/M (13/14)	4506	M. luteus/B. huringiensis: 4~8 μg/mL (13)	NA	South China Sea	2020^[37]
Spiroindimicins A~D (15~18)	SCSIO 03032	CCRF-CEM/B16/H460: 4~12 μg/mL (except 15)	3412	Indian Ocean	2012^[44]
Spiroindimicins G/H (19/20)	SCSIO 03032	SF-268/MCF-7/HepG2/A549: 10.28~ 33.02 μmol?L ^–1	3412	South China Sea	2019^[45]
Indinicins A~E (21~25)	SCSIO 03032	SF-268/MCF-7/H460/HepG2: 9.7~ 44.6 μmol?L ^–1	3412	Indian Ocean	2014^[46]
Indinicins F/G (26/27)	SCSIO 03032	—	3412	Indian Ocean	2019^[45]
Lynamicins F/G (28/29)	SCSIO 03032	SF-268/H460/HepG2/MCF-7: >100 μmol?L^–1	3412	Indian Ocean	2014^[46]
Heronamides D~F (30~32)	SCSIO 03032	—	3412	Indian Ocean	2014^[49]
Dionemycin (33)/34	SCSIO 11791	S. aureus ATCC 29213/MRSA:0.5~2 μg/mL H460/MDA-MB-231/HCT-116/ HepG2/MCF10A: 3.1~11.2 μmol?L ^–1	1765	South China Sea	2020^[22]
Grincamycins B~F (35~39)	SCSIO LR32	HepG2/SW-1990/HeLa/H460/MCF-7/ B16: 1.1~31 μmol?L ^–1 (except 39)	3370	South China Sea	2012^[50]
Grincamycins G/H (40/41)	SCSIO LR32	Jurkat T-cell: 3.0 μmol?L ^–1 (41)	3370	South China Sea	2012^[51]
Grincamycins I~K (42~44)	SCSIO LR32	MDA?MB?435/MDA?MB?231/H460/ HCT-116/HepG2/MCF10A: 2.43~ 25.87 μmol?L ^–1	3370	South China Sea	2018^[52]
Marfuraquinocins A~D (45~48)	SCSIO 3406	S. aureus ATCC 29213/MRSE: 8~64 μg/mL SF268/ MCF-7/H460/HepG2: 3.6~26.9 μmol?L ^–1	3536	South China Sea	2013^[54]
Phenaziterpenes A~B (49/50)	SCSIO 3406	A. hydrophila ATCC 7966: 64 μg/mL (49) SF268/MCF-7/HepG2: 9.3~54.5 μmol?L^–1	3536	South China Sea	2013^[54]
Sungsanpin (51)	SNJ013	Inhibitory activity against A549	138	Jeju Island	2013^[55]
Strepsesquitriol (52)	SCSIO 10355	Inhibitory activity against lipopoly saccharide induced TNFα production	3412	Indian Ocean	2013^[56]
Compd.	Source	Bioactivity (MIC or IC₅₀)	Depth/m	Region	Year
Tetroazolemycins A/B (53/54)	FXJ8.012	K. pneumoniae/Metal ion-binding activity	NA	Indian Ocean	2013^[57]
Mycemycins C~E (55~57)	FXJ8.012	Anti-HIV-1 reverse transcriptase activity	NA	Indian Ocean	2015^[67]
Champacyclin (58)	C42	Erwinia amylovora: 25 μmol?L ^–1	241	Baltic Sea	2013^[59]
Xiamenmycins C/D (59/60)	M1-94P	WI26: 15 μg/mL/30 μg/mL	2628	Pacific	2013^[60]
Desotamides B~D (61~63)	SCSIO ZJ46	S. pnuemoniae NCTC 7466/S. aureus ATCC 29213/MRSE Shhs-E1: 12.5~32.0 μg/mL	3536	South China Sea	2014^[64]
Bafilomycins B1/C1(64/65)	NA4	Inhibitory activities against Fusarium spp. and R. solani	1464	South China Sea	2015^[65]
Marformycins A~F (66~71)	SCSIO 10141	M. luteus: 0.06~4.0 μg/mL	1396	South China Sea	2014^[66]
Marangucyclines A/B (72/73)	SCSIO 11594	E. faecalisATCC29212: 64.0 μg/mL A594/CNE2/HepG2/MCF-7: 0.24~ 0.56 μmol?L ^–1 (73)	2403	South China Sea	2015^[67]
74/75	PKU-MA01297	—	3202	Indian Ocean	2019^[68]
76	SCSIO 04496	—	3536	South China Sea	2016^[77]
Tunicamycin E (77)	SCSIO S15077	B. thuringiensis/C. albicans CMCC (F) 98001/C. albicans ATCC 96901: 0.5~ 32 μg /mL	3536	South China Sea	2018^[69]
Atratumycin (78)	SCSIO ZH16	M. tuberculosis H37Ra/H37Rv: 3.8/ 14.6 μmol?L ^–1	3536	South China Sea	2019^[61]
79/80	OUCMBZ-4112	—	2206	South China Sea	2016^[62]
81	OUCMDZ-2167	—	2061	South China Sea	2016^[63]
Butenolids 1/2 (82/83)	TP-A0873	Peroxisome proliferator activated receptor- PPARα agonists	NA	Toyama Bay	2014^[78]
Ahpatinins Ac/Pr (84/85)	ACT232	Aspartic protease inhibitors: 0.01~0.05 μmol?L^–1	1174	Sagami Bay	2014^[64]
Fradiamines A/B (86/87)	MM456M-F7	Clostridium dif?cile: 8~32 μg/mL	806	Sagami Bay	2017^[71]
88~90	M-157	HepG2: 51.5 μmol?L ^–1	2000	Cantabrian Sea	2018^[72]
Anthracimycin B (91)	M-169	S. aureus MB5393/S. aureus ATCC29213/ E. faecium CL144754/E. faecalisCL144492 0.125~8.0 μmol?L ^–1	1500	Cantabrian Sea	2018^[74]
Flaviogeranins B~D (92~94)	B9173	S. aureus/M. smegmatis: 5.0~35.7 μg/mL A549/Hela: 0.4~50.2 μmol?L ^–1	NA	Pacific Ocean	2020^[75]

Compd.	Source	Bioactivity (MIC or IC₅₀)	Depth/m	Region	Year
Caboxamycin (1)	NTK 937	B. subtilis/S. lentus: 8~20 μmol?L ^–1 AGS/ HepG2/MCF-7: 28.6~29.4 μmol?L ^–1	3814	Canary Basin	2009^[23]
Benzoxacystol (2)	NTK 935	Inhibitory activity against glycogen synthase kinase-3β	3814	Canary Basin	2011^[24]
3'-hydroxycaboxamycin (3)	NTK 937	—	3814	Canary Basin	2017^[28]
Ammosamides A/B (4/5)	CNR-698	HCT-116: 320 nmol?L^–1	1618	Bahamas	2009^[29]
Lobophorins E/F (6/7)	SCSIO 01127	S. aureus/E. faecalis: 8 μg/mL ( 6) SF-268/ MCF-7/H460: 2.93~6.82 μmol?L ^–1 (7)	135	South China Sea	2011^[76]
Lobophorins G (8)	MS100061	BCG: 1.56 μg/mL B. subtilis: 3.125 μg/mL M. tuberculosisH37Rv: 16 μg/mL	NA	South China Sea	2013^[32]
Lobophorins H/I (9/10)	12A35	B. subtilisCMCC 63501: 1.57 μg/mL (9) 50 μg/mL ( 10)	2134	South China Sea	2013^[34]
Lobophorins J (11)	12A35	—	2134	South China Sea	2015^[35]
Lobophorin K (12)	M-207	S. aureus: 40~80 μg/mL MiaPaca-2/ MCF-7/THLE-2: 6.3~34.0 μmol?L ^–1	180	Cantabrian Sea	2017^[36]
Lobophorin L/M (13/14)	4506	M. luteus/B. huringiensis: 4~8 μg/mL (13)	NA	South China Sea	2020^[37]
Spiroindimicins A~D (15~18)	SCSIO 03032	CCRF-CEM/B16/H460: 4~12 μg/mL (except 15)	3412	Indian Ocean	2012^[44]
Spiroindimicins G/H (19/20)	SCSIO 03032	SF-268/MCF-7/HepG2/A549: 10.28~ 33.02 μmol?L ^–1	3412	South China Sea	2019^[45]
Indinicins A~E (21~25)	SCSIO 03032	SF-268/MCF-7/H460/HepG2: 9.7~ 44.6 μmol?L ^–1	3412	Indian Ocean	2014^[46]
Indinicins F/G (26/27)	SCSIO 03032	—	3412	Indian Ocean	2019^[45]
Lynamicins F/G (28/29)	SCSIO 03032	SF-268/H460/HepG2/MCF-7: >100 μmol?L^–1	3412	Indian Ocean	2014^[46]
Heronamides D~F (30~32)	SCSIO 03032	—	3412	Indian Ocean	2014^[49]
Dionemycin (33)/34	SCSIO 11791	S. aureus ATCC 29213/MRSA:0.5~2 μg/mL H460/MDA-MB-231/HCT-116/ HepG2/MCF10A: 3.1~11.2 μmol?L ^–1	1765	South China Sea	2020^[22]
Grincamycins B~F (35~39)	SCSIO LR32	HepG2/SW-1990/HeLa/H460/MCF-7/ B16: 1.1~31 μmol?L ^–1 (except 39)	3370	South China Sea	2012^[50]
Grincamycins G/H (40/41)	SCSIO LR32	Jurkat T-cell: 3.0 μmol?L ^–1 (41)	3370	South China Sea	2012^[51]
Grincamycins I~K (42~44)	SCSIO LR32	MDA?MB?435/MDA?MB?231/H460/ HCT-116/HepG2/MCF10A: 2.43~ 25.87 μmol?L ^–1	3370	South China Sea	2018^[52]
Marfuraquinocins A~D (45~48)	SCSIO 3406	S. aureus ATCC 29213/MRSE: 8~64 μg/mL SF268/ MCF-7/H460/HepG2: 3.6~26.9 μmol?L ^–1	3536	South China Sea	2013^[54]
Phenaziterpenes A~B (49/50)	SCSIO 3406	A. hydrophila ATCC 7966: 64 μg/mL (49) SF268/MCF-7/HepG2: 9.3~54.5 μmol?L^–1	3536	South China Sea	2013^[54]
Sungsanpin (51)	SNJ013	Inhibitory activity against A549	138	Jeju Island	2013^[55]
Strepsesquitriol (52)	SCSIO 10355	Inhibitory activity against lipopoly saccharide induced TNFα production	3412	Indian Ocean	2013^[56]
Compd.	Source	Bioactivity (MIC or IC₅₀)	Depth/m	Region	Year
Tetroazolemycins A/B (53/54)	FXJ8.012	K. pneumoniae/Metal ion-binding activity	NA	Indian Ocean	2013^[57]
Mycemycins C~E (55~57)	FXJ8.012	Anti-HIV-1 reverse transcriptase activity	NA	Indian Ocean	2015^[67]
Champacyclin (58)	C42	Erwinia amylovora: 25 μmol?L ^–1	241	Baltic Sea	2013^[59]
Xiamenmycins C/D (59/60)	M1-94P	WI26: 15 μg/mL/30 μg/mL	2628	Pacific	2013^[60]
Desotamides B~D (61~63)	SCSIO ZJ46	S. pnuemoniae NCTC 7466/S. aureus ATCC 29213/MRSE Shhs-E1: 12.5~32.0 μg/mL	3536	South China Sea	2014^[64]
Bafilomycins B1/C1(64/65)	NA4	Inhibitory activities against Fusarium spp. and R. solani	1464	South China Sea	2015^[65]
Marformycins A~F (66~71)	SCSIO 10141	M. luteus: 0.06~4.0 μg/mL	1396	South China Sea	2014^[66]
Marangucyclines A/B (72/73)	SCSIO 11594	E. faecalisATCC29212: 64.0 μg/mL A594/CNE2/HepG2/MCF-7: 0.24~ 0.56 μmol?L ^–1 (73)	2403	South China Sea	2015^[67]
74/75	PKU-MA01297	—	3202	Indian Ocean	2019^[68]
76	SCSIO 04496	—	3536	South China Sea	2016^[77]
Tunicamycin E (77)	SCSIO S15077	B. thuringiensis/C. albicans CMCC (F) 98001/C. albicans ATCC 96901: 0.5~ 32 μg /mL	3536	South China Sea	2018^[69]
Atratumycin (78)	SCSIO ZH16	M. tuberculosis H37Ra/H37Rv: 3.8/ 14.6 μmol?L ^–1	3536	South China Sea	2019^[61]
79/80	OUCMBZ-4112	—	2206	South China Sea	2016^[62]
81	OUCMDZ-2167	—	2061	South China Sea	2016^[63]
Butenolids 1/2 (82/83)	TP-A0873	Peroxisome proliferator activated receptor- PPARα agonists	NA	Toyama Bay	2014^[78]
Ahpatinins Ac/Pr (84/85)	ACT232	Aspartic protease inhibitors: 0.01~0.05 μmol?L^–1	1174	Sagami Bay	2014^[64]
Fradiamines A/B (86/87)	MM456M-F7	Clostridium dif?cile: 8~32 μg/mL	806	Sagami Bay	2017^[71]
88~90	M-157	HepG2: 51.5 μmol?L ^–1	2000	Cantabrian Sea	2018^[72]
Anthracimycin B (91)	M-169	S. aureus MB5393/S. aureus ATCC29213/ E. faecium CL144754/E. faecalisCL144492 0.125~8.0 μmol?L ^–1	1500	Cantabrian Sea	2018^[74]
Flaviogeranins B~D (92~94)	B9173	S. aureus/M. smegmatis: 5.0~35.7 μg/mL A549/Hela: 0.4~50.2 μmol?L ^–1	NA	Pacific Ocean	2020^[75]

Compd.	Source	Activity (MIC or IC₅₀)	Region	Time
Chaxalactins A~C (95~97)	C34	S. aureus: <1 μg/mL L. monocytogenes/ B. subtilis: 3~6 μg/mL	Atacama	2011^[79]
Chaxamycins A~D (98~101)	C34	S. aureusATCC 25923: 0.05 μg/mL ( 101) MRSA: <1 μg/mL ( 101)	Atacama	2011^[90]
Atacamycins A~C (102~104)	C38	R.solanacearum/PDE-4B2 Enzyme inhibitor: 1.30~4.07 μmol?L ^–1/antiproliferative	Atacama	2011^[91]
Abenquines A~D (105~109)	DB634	Enzyme inhibitor for phosphodiesterase type 4b	Atacama	2011^[89]
Luteoride D (110)/Pseurotin G (111)	C34+MR2012	—	Atacama	2017^[115]
Asenjonamides A~C (112~114)	KNN 42.f	S. aureus/B. subtilis/E. coli/E. faecalis/M. smegmatis: 1.8~17.3 μg/mL	Atacama	2018^[96]
Chaxapeptin (115)	C58	Inhibitory activity against A549	Atacama	2015^[100]
Leepeptin (116)	C34^T	—	Atacama	2019^[101]
Huascopeptin (117)	HST28^T	—	Atacama	2020^[102]
118	WAB9	Pseudomonas aeruginosa IPA1: 10 μg/mL	Saharan	2015^[103]
Pyridine-2,5-diacetamide (119)	DA3-7	E. coliATCC 10536/C.neoformansATCC 90113: 31.25 μg/mL	Saudi Arabian	2018^[104]
Grincamycins L~N (120~122)	XZHG99 T	A549/H157/MCF-7/MDA-MB-231/ HepG2: 1.92~9.12 μmol?L ^–1	Color desert	2018^[69]

Compd.	Source	Activity (MIC or IC₅₀)	Region	Time
Chaxalactins A~C (95~97)	C34	S. aureus: <1 μg/mL L. monocytogenes/ B. subtilis: 3~6 μg/mL	Atacama	2011^[79]
Chaxamycins A~D (98~101)	C34	S. aureusATCC 25923: 0.05 μg/mL ( 101) MRSA: <1 μg/mL ( 101)	Atacama	2011^[90]
Atacamycins A~C (102~104)	C38	R.solanacearum/PDE-4B2 Enzyme inhibitor: 1.30~4.07 μmol?L ^–1/antiproliferative	Atacama	2011^[91]
Abenquines A~D (105~109)	DB634	Enzyme inhibitor for phosphodiesterase type 4b	Atacama	2011^[89]
Luteoride D (110)/Pseurotin G (111)	C34+MR2012	—	Atacama	2017^[115]
Asenjonamides A~C (112~114)	KNN 42.f	S. aureus/B. subtilis/E. coli/E. faecalis/M. smegmatis: 1.8~17.3 μg/mL	Atacama	2018^[96]
Chaxapeptin (115)	C58	Inhibitory activity against A549	Atacama	2015^[100]
Leepeptin (116)	C34^T	—	Atacama	2019^[101]
Huascopeptin (117)	HST28^T	—	Atacama	2020^[102]
118	WAB9	Pseudomonas aeruginosa IPA1: 10 μg/mL	Saharan	2015^[103]
Pyridine-2,5-diacetamide (119)	DA3-7	E. coliATCC 10536/C.neoformansATCC 90113: 31.25 μg/mL	Saudi Arabian	2018^[104]
Grincamycins L~N (120~122)	XZHG99 T	A549/H157/MCF-7/MDA-MB-231/ HepG2: 1.92~9.12 μmol?L ^–1	Color desert	2018^[69]

Compd.	Streptomyces sp.	Activity (MIC or IC₅₀)	Region	Time
Ohmyungsamycins A/B (123/124)	SNJ042	M. tuberculosis H37Rv: 33.3/108.3 nmol?L^–1, HCT-116/A549/SNΜ-638/ MDA-MB-231: 359~816 nmol?L^–1 (123)	Korean volcanic	2013^[112]
Pontemazines A/B (125/126)	ΜT1123	Protective effect on HT-22 mouse hippocampal neuronal cells	Korean volcanic	2015^[111]
Ulleungdin (127)	KCB13F003	Inhibitory activity against A549	Korean volcanic	2018^[96]
Donghaesulfins A/B (128/129)	SΜD119	Induced quinone reductase activity/ antiangiogenesis	Korean volcanic	2019^[116]
Donghaecyclinones A~C (130~132)	SUD119	HCT116/MDA-MB231/SNU638/A549/ SK-HEP1: 6.0~28.9 μnmol?L ^–1	Korean volcanic	2020^[117]

深海、沙漠、火山、极地来源链霉菌新天然产物(2009~2020)

New Natural Products of Streptomyces Sourced from Deep-Sea, Desert, Volcanic, and Polar Regions from 2009 to 2020

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Compd.	Source	Activity (MIC or IC₅₀)	Region	Time
Nitrosporeusines A/B (133/134)	NitrosporeusCQT14-24	Inhibit H1N1 virus	Arctic	2013^[123]
135/136	CavourensisYY01-17	—	Antarctic	2013^[124]
Nitrosporeunols A~G (137~143)	nitrosporeus YBH10-5	—	Arctic	2014^[132]
Arcticoside (144) C-1027 chromophore-V (145)	ART5	MDA-MB231/HCT-116: 0.9~2.7 μmol?L ^–1 (94)	Arctic	2014^[126]
146~148	623F	—	Arctic	2015^[127]
149	NJES13	—	Antarctic	2015^[128]
Antartin (150)	SCO736	A549/H1299/U87	Antarctic	2018^[133]
Cyclamenols B~D (151~153)	OUCMDZ-4348	N87: 10.8 μmol?L ^–1 (151)	Antarctic	2019^[130]
Cyclamenols E~F (154~155)	OUCMDZ-4348	N87: 9.8 μmol?L ^–1 (154)	Antarctic	2020^[131]

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