北部湾软珊瑚共附生真菌Scopulariopsis sp. SCSIO 41229次级代谢产物研究

doi:10.11978/2024184

Abstract

Abstract:

In this study, we aimed to investigate the secondary metabolites from the coral-derived fungus Scopulariopsis sp. SCSIO 41229, collected from the Beibu Gulf. The fungal extract was isolated using silica gel column chromatography, reverse-phase silica gel column chromatography, thin-layer chromatography (TLC), and high-performance liquid chromatography (HPLC). The structures of the isolated compounds were elucidated through nuclear magnetic resonance (NMR), mass spectrometry (MS), and literature comparison. Nine known compounds were identified, including neocyclocitrinols A-D (1-4), penicillenol A₂ (5), cyclo-(D-Phe-L-Ile) (6), cyclo-(L-tryptophyl-L-phenylalanyl) (7), (+)-penicilactam A (8), and (8E, 10E)-7-oxo-8, 10-heptadecadienoic acid (9). Notably, these compounds were reported from Scopulariopsis sp. for the first time. Bioassays indicated that compounds 2 and 4 exhibited weak antioxidant activity, while compounds 2, 4, and 8 showed weak acetylcholinesterase inhibitory activity.

Key words: coral-derived fungus, secondary metabolites, Scopulariopsis sp., C25 steroids

CLC Number:

O629

HE Yanchun, XU Shuna, LIU Yonghong, YANG Bin. Study on the secondary metabolites of the soft coral-derived fungus Scopulariopsis sp. SCSIO 41229 from the Beibu Gulf[J].Journal of Tropical Oceanography, 2025, 44(4): 170-176.

Figures/Tables 3

Fig. 1

Fig. 2

Tab. 1

1H NMR and 13C NMR chemical shifts (δ) of compounds 1-4 in DMSO-d6"

No.	1		2		3		4
No.	δ_H, mult, J/Hz	δ_C, mult	δ_H, mult, J/Hz	δ_C, mult	δ_H, mult, J/Hz	δ_C, mult	δ_H, mult, J/Hz	δ_C, mult
1	5.55, dd, 8.4, 6.2	122.1, CH	5.55, dd, 8.4, 6.2	122.1, CH	5.55, dd, 8.3, 6.2	122.1, CH	5.55, dd, 8.4, 6.2	122.1, CH
2a	2.07, ddt, 13.0, 9.0, 2.2	36.0, CH₂	2.07, ddt, 13.0, 8.3, 2.2	36.0, CH₂	2.07, ddt, 13.0, 8.4, 2.2	36.0, CH₂	2.07, ddt, 13.1, 8.4, 2.2	36.0, CH₂
2b	2.34, ddd, 13.2, 11.1, 6.2	36.0, CH₂	2.34, ddd, 13.3, 11.1, 6.3	36.0, CH₂	2.34, ddd, 13.3, 11.1, 6.3	36.0, CH₂	2.39~2.30, m	36.0, CH₂
3	3.15~3.08, m	63.1, CH	3.15~3.09, m	63.1, CH	3.14~3.09, m	63.1, CH	3.16~3.07, m	63.1, CH
4a	2.60, m	41.4, CH₂	2.66~2.59, m	41.4, CH₂	2.65~2.60, m	41.4, CH₂	2.65~2.60, m	41.4, CH₂
4b	1.53~1.49, m	41.4, CH₂	1.57~1.51, m	41.4, CH₂	1.55~1.53, m	41.4, CH₂	1.54~1.51, m	41.4, CH₂
5	2.71~2.66, m	48.1, CH	2.70~2.66, m	48.1, CH	2.70~2.67, m	48.1, CH	2.68, m	48.1, CH
6		204.1, C		204.2, C		204.2, C		204.2, C
7	5.43~5.41, s	124.3, CH	5.42, s	124.3, CH	5.43~5.41, s	124.3, CH	5.42, s	124.3, CH
8		157.0, C		157.0, C		157.1, C		157.0, C
9	2.84, dd, 11.9, 5.8	53.3, CH	2.85, dd, 12.0, 5.7	53.2, CH	2.85, dd, 11.8, 5.7	53.3, CH	2.85, dd, 11.8, 5.7	53.3, CH
10		145.6, C		145.6, C		145.6, C		145.6, C
11a	1.56, dt, 15.9, 6.3	27.4, CH₂	1.57~1.51, m	27.5, CH₂	1.59~1.55, m	27.4, CH₂	1.59~1.53, m	27.5, CH₂
11b	1.86~1.78, m	27.4, CH₂	1.86~1.79, m	27.5, CH₂	1.86~1.78, m	27.4, CH₂	1.86~1.78, m	27.5, CH₂
12a	1.43, td, 13.6, 13.2, 4.8	36.9, CH₂	1.51~1.47, m	37.3, CH₂	1.53~1.49, m	36.9, CH₂	1.51~1.46, m	37.3, CH₂
12b	1.75, ddd, 12.4, 8.6, 3.9	36.9, CH₂	1.75, td, 12.8, 4.3	37.3, CH₂	1.77, m	36.9, CH₂	1.76, dd, 12.7, 4.3	37.3, CH₂
13		47.0, C		46.7, C		46.9, C		46.6, C
14	2.27, t, 9.7	54.3, CH	2.25, q, 9.5, 8.9	54.5, CH	2.26, t, 9.8	54.3, CH	2.28~2.20, m	54.5, CH
15	1.56, dt, 15.9, 6.3	22.4, CH₂	1.57~1.51, m	22.3, CH₂	1.59~1.55, m	22.4, CH₂	1.59~1.53, m	22.3, CH₂
15	1.56, dt, 15.9, 6.3	22.4, CH₂	1.57~1.51, m	22.3, CH₂	1.59~1.55, m	22.4, CH₂	1.54~1.51, m	22.3, CH₂
16a	1.75, ddd, 12.4, 8.6, 3.9	23.7, CH₂	1.81, ddd, 10.7, 4.3, 2.4	23.8, CH₂	1.86~1.78, m	23.7, CH₂	1.86~1.78, m	23.8, CH₂
16b	1.70~1.67, m	23.7, CH₂	1.70~1.65, m	23.8, CH₂	1.70~1.65, m	23.7, CH₂	1.59~1.53, m	23.8, CH₂
17	2.22, td, 9.3, 8.7, 2.0	59.0, CH	2.25, q, 9.5, 8.9	58.6, CH	2.22, td, 9.3, 8.6, 2.0	58.9, CH	2.28~2.20, m	58.6, CH
18	2.47, d, 5.9	27.2, CH₂	2.47, d, 5.8	27.2, CH₂	2.47, d, 5.8	27.2, CH₂	2.47, d, 4.1	27.2, CH₂
19	0.53, s	13.5, CH₃	0.49, s	13.3, CH₃	0.53, s	13.4, CH₃	0.49, s	13.3, CH₃
20		135.8, C		135.8, C		135.0, C		135.0, C
21	1.66, d, 1.3	17.4, CH₃	1.68, d, 1.2	18.9, CH₃	1.63, d, 1.3	17.3, CH₃	1.65, s	18.8, CH₃
22	5.15, dt, 8.8, 1.2	128.2, CH	5.16, dt, 8.8, 1.3	127.1, CH	5.21, dt, 8.4, 1.3	128.3, CH	5.22, d, 8.3	127.3, CH
23	3.95, t, 7.8	72.0, CH	3.97~3.93, m	72.2, CH	4.05, dd, 8.4, 4.1	71.5, CH	4.08, d, 7.9	71.7, CH
24	3.40, d, 6.6	70.3, CH	3.39, d, 6.5	70.4, CH	3.50, s	69.8, CH	3.4, d, 5.0	69.8, CH
25	0.96, d, 6.3	18.9, CH₃	0.94, d, 6.3	19.1, CH₃	0.97, d, 6.3	18.6, CH₃	0.96, d, 6.3	18.3, CH₃
3-OH	4.62, d, 4.3		4.62, d, 4.3		4.63, d, 4.3		4.62, d, 4.4
23-OH	4.48, s		4.50, d, 4.2		4.39, s		4.42~4.36, m
24-OH	4.38, s		4.36, s		4.32~4.29, m		4.28, s

Tab. 1

References 27

[1]	黄玉玲, 马丽英, 荣先国, 等, 2017. 佩特曲霉菌次生代谢产物的研究[J]. 中成药, 39(7): 1415-1419.
	HUANG YULING, MA LIYING, RONG XIANGUO, et al, 2017. Secondary metabolites from Aspergillus petrakii[J]. Chinese Traditional Patent Medicine, 39(7): 1415-1419 (in Chinese with English abstract).
[2]	刘炳新, 韦霞, 肖细姬, 等, 2021. 南海软珊瑚共附生真菌Aspergillus sp. EGF15-0-3苯甲醛类化合物研究[J]. 热带海洋学报, 40(4): 63-69.
	LIU BINGXIN, WEI XIA, XIAO XIJI, et al, 2021. Research on benzaldehydes from the soft coral-associated symbiotic fungus Aspergillus sp. EGF15-0-3[J]. Journal of Tropical Oceanography, 40(4): 63-69 (in Chinese with English abstract).
[3]	陆春菊, 陆玫霖, 刘昕明, 等, 2021. 广西涠洲岛柳珊瑚共附生真菌多样性及其抑菌活性[J]. 热带海洋学报, 40(5): 45-52.
	LU CHUNJU, LU MEILIN, LIU XINMING, et al, 2021. Diversity and anti-bacteria activity of the Gorgonian derived fungi from Weizhou Island of Guangxi Zhuang Autonomous Region[J]. Journal of Tropical Oceanography, 40(5): 45-52 (in Chinese with English abstract)
[4]	朱俊衡, 宋蒙蒙, 胡怡伟, 等, 2022. 深海橘青霉Penicillium citrinum SCSIO41305化学成分及其乙酰胆碱酯酶抑制活性研究[J]. 中国海洋药物, 41(5): 27-31.
	ZHU JUNHENG, SONG MENGMENG, HU YIWEI, et al, 2022. Chemical constituents of a deep-sea derived Penicillium citrinum SCSIO41305 and their acetylcholinesterase inhibitory activities evaluation[J]. Chinese Journal of Marine Drugs, 41(5): 27-31 (in Chinese with English abstract).
[5]	AINSWORTH T D, THURBER R V, GATES R D, 2010. The future of coral reefs: a microbial perspective[J]. Trends in Ecology & Evolution, 25(4): 233-240.
[6]	AMAGATA T, AMAGATA A, TENNEY K, et al, 2003. Unusual C25 steroids produced by a sponge-derived Penicillium citrinum[J]. Organic Letters, 5(23): 4393-4396.
[7]	CASTILLO M A, MOYA P, CANTÍN A, et al, 1999. Insecticidal, anti-juvenile hormone, and fungicidal activities of organic extracts from different Penicillium species and their isolated active components[J]. Journal of Agricultural and Food Chemistry, 47(5): 2120-2124.
[8]	CHEN YING, PANG XIAOYAN, HE YANCHUN, et al, 2022. Secondary metabolites from coral-associated fungi: source, chemistry and bioactivities[J]. Journal of Fungi, 8(10): 1043.
[9]	DOU ZHENDE, HE XIAOPING, XU PENG, et al, 2022. Rapid separation and purification of two C25 steroids with bicyclic [4. 4. 1] A/B rings from the marine fungus Aspergillus sp. LS116 by high-speed counter-current chromatography in stepwise elution mode[J]. Natural Product Research, 36(14): 3770-3774.
[10]	DU LIN, ZHU TIANJIAO, FANG YUCHUN, et al, 2008. Unusual C25 steroid isomers with bicyclo [4. 4. 1] A/B rings from a volcano ash-derived fungus Penicillium citrinum[J]. Journal of Natural Products, 71(8): 1343-1351.
[11]	ELNAGGAR M S, EBADA S S, ASHOUR M L, et al, 2016. Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp[J]. Tetrahedron, 72(19): 2411-2419.
[12]	FAN HAO, SHAO XUEHUA, WU PINGPING, et al, 2024. Exploring brominated aromatic butenolides from Aspergillus terreus EGF7-0-1 with their antifungal activities[J]. Journal of Agricultural and Food Chemistry, 72(36): 19869-19882.
[13]	HE ZHIHUI, XIE CHUNLAN, WU TAIZONG, et al, 2023. Tetracyclic steroids bearing a bicyclo [4. 4. 1] ring system as potent antiosteoporosis agents from the deep-sea-derived fungus Rhizopus sp. W23[J]. Journal of Natural Products, 86(1): 157-165.
[14]	HOANG T P T, ROULLIER C, GENTA-JOUVE G, et al, 2019. C25 steroids from the marine mussel-derived fungus Penicillium ubiquetum MMS330[J]. Phytochemistry Letters, 34: 18-24.
[15]	KIMURA Y, TANI K, KOJIMA A, et al, 1996. Cyclo-(l-tryptophyl-l-phenylalanyl), a plant growth regulator produced by the fungus Penicillium sp[J]. Phytochemistry, 41(3): 665-669.
[16]	KRAMER A, LABES A, IMHOFF J F, 2016. Phylogenetic relationship and secondary metabolite production of marine fungi producing the cyclodepsipeptides scopularide A and B[J]. Marine Biotechnology, 18(4): 466-474.
[17]	LAI DAOWAN, BRÖTZ-OESTERHELT H, MÜLLER W E G, et al, 2013. Bioactive polyketides and alkaloids from Penicillium citrinum, a fungal endophyte isolated from Ocimum tenuiflorum[J]. Fitoterapia, 91: 100-106.
[18]	LIN SHENG, CHEN K Y, FU PENG, et al, 2015. Structure determination of two unusual C25 steroids with bicyclo [4. 4. 1] A/B rings from Penicillium decumbens by NMR spectroscopy[J]. Magnetic Resonance in Chemistry, 53(3): 223-226.
[19]	LIU JUNYANG, WU JIANLEI, FAN JIANHONG, et al, 2018. Asymmetric total synthesis of cyclocitrinol[J]. Journal of the American Chemical Society, 140(16): 5365-5369.
[20]	MOU XIAOFENG, LIU XIN, XU RUFANG, et al, 2018. Scopuquinolone B, a new monoterpenoid dihydroquinolin-2(1H)-one isolated from the coral-derived Scopulariopsis sp. fungus[J]. Natural Product Research, 32(7): 773-776.
[21]	SHAO CHANGLUN, XU RUFANG, WANG CHANGYUN, et al, 2015. Potent antifouling marine dihydroquinolin-2(1H)-one-containing alkaloids from the Gorgonian coral-derived fungus Scopulariopsis sp[J]. Marine Biotechnology, 17(4): 408-415.
[22]	WANG JIE, YAO QIFENG, AMIN M, et al, 2017. Penicillenols from a deep-sea fungus Aspergillus restrictus inhibit Candida albicans biofilm formation and hyphal growth[J]. Journal of Antibiotics, 70(6): 763-770.
[23]	XIA MINGWEN, CUI CHENGBIN, LI CHANGWEI, et al, 2014. Three new and eleven known unusual C25 steroids: activated production of silent metabolites in a marine-derived fungus by chemical mutagenesis strategy using diethyl sulphate[J]. Marine Drugs, 12(3): 1545-1568.
[24]	YANG JIANKUN, ZHANG BIN, GAO TONG, et al, 2018. A pair of enantiomeric 5-oxabicyclic [4. 3. 0] lactam derivatives and one new polyketide from the marine-derived fungus Penicillium griseofulvum[J]. Natural Product Research, 32(19): 2366-2369.
[25]	YANG ZHI, DI YINGTONG, ZHANG YU, et al, 2020. Four new compounds from Neoboletus magnificus[J]. Natural Product Research, 34(8): 1152-1157.
[26]	YING YOUMIN, ZHENG ZHENZHEN, ZHANG LIWEN, et al, 2014. Rare C25 steroids produced by Penicillium chrysogenum P1X, a fungal endophyte of Huperzia serrata[J]. Helvetica Chimica Acta, 97(1): 95-101.
[27]	YU FEIXUE, LI ZHE, CHEN YAO, et al, 2017. Four new steroids from the endophytic fungus Chaetomium sp. M453 derived of Chinese herbal medicine Huperzia serrata[J]. Fitoterapia, 117: 41-46.

Study on the secondary metabolites of the soft coral-derived fungus Scopulariopsis sp. SCSIO 41229 from the Beibu Gulf

RichHTML

PDF (PC)

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 3

References 27

Related Articles 15

Metrics

Comments

Recommended 0

[1]	HE Mingfeng, HUANG Jiaxiang, TIAN Yongqi. Research on the antioxidant and antibacterial activities of secondary metabolites from Gelidium-derived fungus Aspergillus fumigatus 9-1 [J]. Journal of Tropical Oceanography, 2025, 44(3): 157-166.
[2]	YANG Jie, YAO Feihua, LI Xiaoyan, SHI Jieyu, YI Xiangxi, GAO Chenghai. Secondary metabolites from the fungal-bacterial symbiont Aspergillus spelaeus GXIMD 04541 / Sphingomonas echinoides GXIMD 04532 derived from Mauritia arabica [J]. Journal of Tropical Oceanography, 2025, 44(2): 56-63.
[3]	KONG Weiqi, JIN Xin, LIU Yonghong, GAO Chenghai, CHEN Xianqiang. Studies on secondary metabolites of Sargassum fusiforme derived fungus Aspergillus sp. GXIMD 02045 [J]. Journal of Tropical Oceanography, 2025, 44(1): 154-161.
[4]	YUAN Yuan, ZHANG Yuanyuan, XU Fuquan, LIU Qingchao, WANG Junfeng. Secondary metabolites from the sponge-derived fungus Aspergillus sp. SCSIO 41018 and their free radical scavenging activity [J]. Journal of Tropical Oceanography, 2024, 43(6): 196-200.
[5]	XIAO Yang, YAN Jing, YANG Shuyu, ZHANG Tangjie, WENG Jie, LI Qilin, LIU Hongcun, MENG Juan, YANG Lifang. Study on the secondary metabolites and hypoglycemic and lipid lowering activities of actinomyces Streptomyces olivaceuss 10127 from the Guangxi mangrove sediments [J]. Journal of Tropical Oceanography, 2024, 43(6): 181-189.
[6]	AN Fan, JIANG Yue, WANG Yu, CAO Guangping, GAO Chenghai, LIU Yonghong, YI Xiangxi, BAI Meng. Studies on secondary metabolites of endophytic fungus Aspergillus terreus GXIMD 03158 isolated from mangroves Acanthus ilicifolius L. [J]. Journal of Tropical Oceanography, 2024, 43(5): 41-48.
[7]	LIN Yingting, SUN Ying, HU Jiangnan, DONG Shuai. Study on secondary metabolites of the endophytic fungus Talaromyces sp. XXH006 Isolated from Conus literatus [J]. Journal of Tropical Oceanography, 2024, 43(4): 181-188.
[8]	WANG Jiaxi, LU Humu, QI Xin, GAO Chenghai, LIU Yonghong, LUO Xiaowei. Study on the secondary metabolites from the Weizhou Island coral Acropora austera associated fungus Arachniotus ruber GXIMD 02510 and their antibacterial activity [J]. Journal of Tropical Oceanography, 2024, 43(4): 174-180.
[9]	QUAN Miaomiao, MA Qingyun, YANG Li, XIE Qingyi, DAI Haofu, HAO Yu’e, ZHAO Youxing. Study on the secondary metabolites of marine fungus Phaeospheriopsis sp. ZYX-Z-811 [J]. Journal of Tropical Oceanography, 2024, 43(2): 121-127.
[10]	LIU Ying, XIAO Yang, ZHU Zhenxin, LIU Hongcun, JIANG Mingguo, ZHU Yuzhang, LIN Kun, WU Jincheng, LU Xiaomei, HUANG Xiaoning, LIANG Haina, LU Wensen, YANG Lifang. Study on the Secondary Metabolites of Marine Streptomyces Sporoverrucosus 33510 [J]. Journal of Tropical Oceanography, 2024, 43(2): 128-134.
[11]	FENG Guangfu, HE Jeyi, BAI Meng, YI Xiangxi, LIU Xinming, LUO Lianxiang, GAO Chenghai. Secondary Metabolites from Hydaranth of Coral Goniopora columna in the Beibu Gulf [J]. Journal of Tropical Oceanography, 2024, 43(2): 135-139.
[12]	XING Nannan, REN Runxin, TANG Zhenzhou, LUO Zhihong, XIA Chenxi, LIU Yonghong, PENG Liang, CHEN Xianqiang. Study on the secondary metabolites of fungus Aspergillus sp. GXIMD02003 derived from marine sediment in the Weizhou island [J]. Journal of Tropical Oceanography, 2023, 42(5): 154-160.
[13]	LIANG Hanqiao, CHEN Wenfeng, FAN Yikai, ZHU Zidong, MA Guoxu, CHEN Deli, TIAN Jing. Research progress on the secondary metabolites and activities of endophytic fungi of genus Aspergillus and Trichoderma from mangroves [J]. Journal of Tropical Oceanography, 2023, 42(4): 12-24.
[14]	YE Yuxiu, LUO Xiaowei, YANG Bin, LIN Xiuping, LIU Yonghong, ZHOU Xuefeng. Study on the secondary metabolites of reef habitat algae-derived fungus Pestalotiopsis neglecta SCSIO41403 from the South China Sea [J]. Journal of Tropical Oceanography, 2022, 41(3): 186-190.
[15]	ZHANG Han, TAN Yanhong, YANG Bin, LIU Yonghong, LI Yunqiu. Study on the secondary metabolites from the South China Sea soft coral-derived fungus Acremonium sp. SCSIO41216 [J]. Journal of Tropical Oceanography, 2021, 40(6): 135-139.