海绵共附生真菌Penicillium crustosum SCSIO 41442活性代谢产物研究

doi:10.11978/2025025

Abstract

Abstract:

A new alkaloid, diacedolinate (1), along with fourteen known compounds (2-15) was isolated from the sponge associated fungus Penicillium crustosum SCSIO 41442. The structures of these compounds were determined by spectrum analysis and ECD. All compounds were evaluated for their antioxidant and antimicrobial activities. The results showed that compound 1 exhibited weak antioxidant activity with an IC₅₀ value of (71.00±0.14) μg·mL^-1, while compound 2, in contrast, displayed broad antioxidant activity with an IC₅₀ value of (1.25±0.10) μg·mL^-1, compared with the positive control, vitamin C. In addition, compounds 9, 10, 11, and 15 demonstrated broad-spectrum antimicrobial activity against a variety of pathogens, including MRSA, Colletotrichum asianum HNM 408, Colletotrichum acutatum HNM RC178, and Alternaria alternate, with MIC values ranging from 2.5 to 160 μg·mL^-1. The bioactivities of these compounds are reported here for the first time.

Key words: sponge-derived fungi, Penicillium crustosum, secondary metabolites, antioxidant, antimicrobial

CLC Number:

Q936

LIANG Jiaqi, CHEN Xinqi, CHEN Yi, CONG Mengjing, CAO Qinlin, HUANG Xiaowen, LIU Yonghong, JAYASINGHE Lalith, CHEN Chunmei, ZHOU Xuefeng. Bioactive metabolites from the sponge-derived fungus Penicillium crustosum SCSIO 41442[J].Journal of Tropical Oceanography, 2025, 44(6): 188-195.

Figures/Tables 6

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References 20

[1]	BUGNI T S, CONCEPCIÓN G P, MANGALINDAN G C, et al, 2002. P-Sulfooxyphenylpyruvic acid from the red macro Alga Ceratodictyon spongiosum and its sponge symbiont Haliclona cymaeformis[J]. Phytochemistry, 60(4): 361-363. doi: 10.1016/S0031-9422(02)00098-5
[2]	CAMMI R, TOMASI J, 1995. Remarks on the use of the apparent surface charges (ASC) methods in solvation problems: Iterative versus matrix-inversion procedures and the renormalization of the apparent charges[J]. Journal of Computational Chemistry, 16(12): 1449-1458. doi: 10.1002/jcc.v16:12
[3]	CARROLL A R, COPP B R, DAVIS R A, et al, 2020. Marine natural products[J]. Natural Product Reports, 37(2): 175-223. doi: 10.1039/c9np00069k pmid: 32025684
[4]	DAI JINRUI, KARDONO L B S, TSAURI S, et al, 1991. Phenylacetic acid derivatives and a thioamide glycoside from Entada phaseoloides[J]. Phytochemistry, 30(11): 3749-3752. doi: 10.1016/0031-9422(91)80102-7
[5]	DU XIPING, ZHAO BAOBING, ZHENG ZHONGHUI, et al, 2011. Study on the isolation identification and antitumor activity of a phenol derivative from mangrove fungus BYY-1[J]. Journal of Jimei University (Natural Science, 16(6): 424-428.
	杜希萍, 赵保兵, 郑忠辉, 等, 2011. 红树内生真菌BYY-1中一个酚类化合物的分离鉴定与抗肿瘤活性[J]. 集美大学学报(自然科学版 ), 16(6): 424-428 (in Chinese with English abstract).
[6]	INDRANINGRAT A A G, SMIDT H, SIPKEMA D, 2016. Bioprospecting sponge-associated microbes for antimicrobial compounds[J]. Marine Drugs, 14(5): 87. doi: 10.3390/md14050087
[7]	KOZLOVSKII A G, ZHELIFONOVA V P, ANTIPOVA T V, 2013. Fungi of the genus Penicillium as producers of physiologically active compounds (Review)[J]. Applied Biochemistry and Microbiology, 49: 1-10. doi: 10.1134/S0003683813010092
[8]	LI HUAXUAN, CUI SHUJUN, XIAO CHAOJIANG, et al, 2019. Phenolic constituents from Ternstroemia gymnanthera and their analgesic activities[J]. Chinese Traditional Patent Medicine, 41(7): 1582-1586.
	李骅轩, 崔淑君, 肖朝江, 等, 2019. 厚皮香酚性成分及其镇痛活性[J]. 中成药, 41(7): 1582-1586 (in Chinese with English abstract).
[9]	LIU JUNLIANG, LOU YINGKAI, HU ZHIYU, et al, 2012. Purifications and structure elucidations of cyclopenol and cyclopenin[J]. Journal of Xiamen University (Natural Science, 51(3): 386-390.
	刘军亮, 楼盈凯, 胡志钰, 等, 2012. 圆弧菌醇和圆弧菌素的分离纯化及结构解析[J]. 厦门大学学报(自然科学版 ), 51(3): 386-390 (in Chinese with English abstract).
[10]	LIU BILI, QIU YINGKUN, YAN ZHIWEN, et al, 2021a. Studies on marine secondary metabolites of fungus Penicillium polonicum H92[J]. Chinese Journal of Marine Drugs, 40(4): 27-32.
	刘碧丽, 丘鹰昆, 颜志文, 等, 2021a. 海洋来源青霉菌Penicillium polonicum H92次级代谢产物的研究[J]. 中国海洋药物, 40(4): 27-32 (in Chinese with English abstract).
[11]	LIU SHUNZHI, HE FENGMING, et al, 2021b. Bioactive compounds derived from the marine-derived fungus MCCC3A00951 and their influenza neuraminidase inhibition activity in vitro and in silico[J]. Natural Product Research, 35(24): 5621-5628. doi: 10.1080/14786419.2020.1817015
[12]	MAO NING, XU WEIFENG, SHAO CHANGLUN, et al, 2021. Research on the alkaloids from the Gorgonian coral-derived fungus Penicillium chrysogenum[J]. Chinese Journal of Marine Drugs, 40(2): 17-20.
	毛宁, 徐伟锋, 邵长伦, 等, 2021. 1株柳珊瑚来源真菌Penicillium chrysogenum中生物碱化合物研究[J]. 中国海洋药物, 40(2): 17-20 (in Chinese with English abstract).
[13]	NEWAZ A W, YONG KUO, YI WENWEN, et al, 2023. Antimicrobial metabolites from the Indonesian mangrove sediment-derived fungus Penicillium chrysogenum sp. ZZ1151[J]. Natural Product Research, 37(10): 1702-1708. doi: 10.1080/14786419.2022.2103813
[14]	SHAALA L A, YOUSSEF D T A, 2021. Hemimycalins C-E; cytotoxic and antimicrobial alkaloids with hydantoin and 2-iminoimidazolidin-4-one backbones from the red sea marine sponge Hemimycale sp.[J]. Marine Drugs, 19(12): 691. doi: 10.3390/md19120691
[15]	SHARMA O P, BHAT T K, 2009. DPPH antioxidant assay revisited[J]. Food Chemistry, 113(4): 1202-1205. doi: 10.1016/j.foodchem.2008.08.008
[16]	SLABY B M, HACKL T, HORN H, et al, 2017. Metagenomic binning of a marine sponge microbiome reveals unity in defense but metabolic specialization[J]. The ISME Journal, 11(11): 2465-2478. doi: 10.1038/ismej.2017.101
[17]	SULISTYOWATY M I, UYEN N H, SUGANUMA K, et al, 2021. Six new phenylpropanoid derivatives from chemically converted extract of Alpinia galanga (L.) and their antiparasitic activities[J]. Molecules, 26(6): 1756. doi: 10.3390/molecules26061756
[18]	SUZUKI T, ETO K, KUBOTA Y, et al, 2016. Antioxidative catechol lignans/neolignans isolated from defatted kernel of Jatropha curcas[J]. Journal of Wood Science, 62(4): 339-348. doi: 10.1007/s10086-016-1563-6
[19]	WANG SANLANG, LI H T, ZHANG LIJIE, et al, 2016. Conversion of squid pen to homogentisic acid via Paenibacillus sp. TKU036 and the antioxidant and anti-inflammatory activities of homogentisic acid[J]. Marine Drugs, 14(10): 183. doi: 10.3390/md14100183
[20]	YANG GUOHUA, NENKEP V N, SIWE X N, et al, 2009. An acetophenone derivative, clavatol, and a benzodiazepine alkaloid, circumdatin A, from the marine-derived fungus Cladosporium[J]. Natural Product Sciences, 15(3): 130-133.

Position	δ_H, mult (J in Hz)	δ_C, type
2		174.75, C
3	4.17, s	75.35, CH
3a		133.42, C
4	6.89, d (2.2)	113.05, CH
5		154.52, C
6	6.67, dd (8.3, 2.2)	116.67, CH
7	6.71, d (8.7)	111.76, CH
7a		135.39, C
8		175.73, C
9	2.56, s	30.07, CH₃

Compound	IC₅₀/( μg·mL^-1)
1	71.00±0.14
2	1.25±0.10
Vitamin C ^a	5.90±0.05

Compound	MRSA	C. acutatum HNM RC178	C. asianum HNM 408	A. alternate
9	>160	2.5	>160	>160
10	>160	>160	5.0	>160
11	2.5	>160	80.0	>160
15	>160	>160	>160	160.0
Ampicillin ^a	0.625	-	-	-
Nystatin ^b	-	0.625	2.5	5.0

Bioactive metabolites from the sponge-derived fungus Penicillium crustosum SCSIO 41442

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