A comprehensive review of secondary metabolites from the genus Agrocybe: Biological activities and pharmacological implications

Figures & data

Figure 1. Biomorphology of some Agrocybe species. (a) A. cylindracea in the wild. (b) Cultivated A. cyclindraceae. (c) A. praecox in the wild.

Table 1. Molecular weight, monosaccharide composition, molar ratio, and activity of Agrocybe polysaccharides.

Species	Name	Materials	MW (kDa)	Monosaccharide composition	Molar ratios	Activities	Reference
A. cylindracea	AG-AL	Fruit body	560	a-D-glucan	-	-	Kiho et al. (1989)
	ACP	Fruit body	2,840.9	Glucose, galactose	4.77:1	Anticancer activity	Liu et al. (2023)
	ACAP	Fruit body	1.82	Glucose			Liu et al. (2023)
	SACP-80	Fruit body	156	Β-(1→6)-glucopyranosyl, α-(1→6)-galactopyranosyl, α-(1→2,6)-glucopyranosyl	3:1:1	Anticancer activity	Wang et al. (2021); Wang et al. (2023)
	AG-HNl	Fruit body	2,000	Glucose	-	Hypoglycaemic activity	Kiho et al. (1994)
	AG-HN2	Fruit body	55	Galactose, glucose, fucose, mannose	36: 27: 17: 14	Hypoglycaemic activity	Kiho et al. (1994)
	EPS	Fermentation broth	-	Rhamnose, glucose	2.8:1	Antioxidant activity; antiaging activity	Zhao et al. (2017)
	ACP’	Fruit body	670	Mannose, ribose, rhamnose, glucuronic acid, glucose, galactose, xylose	0.29:0.47:0.25:1.72:1.51:0.94:1	Antiobesity activity	Zhu et al. (2022a)
A. cylindracea SL-02	MSPS	Mycelium	-	Rhamnose, arabinose, mannose, glucose, galactose	29:3:1:18.8:2.7	Antioxidant activity	Liu et al. (2016)
A. aegerita	AAP	Fruit body	710	Glucose, fructose, galactose, mannose	-	Antitumour activity	Xu et al. (2005); Ji et al. (2013)
	AAPS	Fruit body	18.1	Rhamnose, fucose, Arabinose, xylose, mannose, glucose, galactose	2.90:10.25:0.78:0.77:3.70:38.27:0.26	Antioxidant activity; antiaging activity	Liu et al. (2020)
	FG-Aa	Fruit body	13.8	Fucose, galactose	1:2.27	Immunomodulatory activity	Motoshima et al. (2018)
A. aegerita (Brig.) Sing	Ac-MPS	Mycelium	-	Fucose, arabinose, mannose, galactose, glucose	1.5:1:4.7:5.7:117.2	Antioxidant activity; antiaging activity	Jing et al. (2018a)
	Al-MPS	Mycelium	-	Fucose, mannose, galactose, glucose	1:4:2.3:23.2	Antioxidant activity; antiaging activity	Jing et al. (2018a)
	MPS	Mycelium	-	Arabinose, mannose, galactose, glucose	1:1.5:17:58.8	Antioxidant activity; antiaging activity	Jing et al. (2018b)
	En-MPS	Mycelium	-	Arabinose, mannose, galactose, glucose	1:8.2:24.3:77	Antioxidant activity; antiaging activity	Jing et al. (2018b)

MW, molecular weight; -, no data in the references.

Figure 2. Schematic representation of the regulatory mechanism of lectin (AAL) in tumour tumour-bearing mice.

Figure 3. Sterol compounds from Agrocybe.

Figure 4. Volatile compounds from Agrocybe aegerita.

Figure 5. Sesquiterpenoids from Agrocybe.

Figure 6. Dimeric sesquiterpenes from Agrocybe.

Figure 7. Alkyne compounds from Agrocybe.

Figure 8. Other types of compounds from Agrocybe.

Figure 9. The typical sesquiterpene synthase phylogenetic tree in basidiomycetes, sesquiterpenoids produced by STSs (Agr1–Agr11) from Agrocybe aegerita.

Table 2. Biological activity of Agrocybe secondary metabolites and their producers.

Species	Bioactive metabolites	Biological activities	Materials	References
A. aegerita	5,8-epidioxy-ergosta-6,22-dien-3β-ol (1)	Anti-inflammatory activity; antioxidant agents	Fruit body	Zhang et al. (2003)
	Ergosterol (2)	Anti-inflammatory activity	Fruit body	Zhang et al. (2003)
	Ceramide (80)	Inhibition of COX enzyme activity Anti-cancer activity	Fruit body	Diyabalanage et al. (2008)
A. chaxingu	Chaxine A (3)	Prevention of osteoporosis (osteoclast differentiation assay)	Fruit body	Kawagishi et al. (2007)
	Chaxine B (4)	Prevention of osteoporosis (osteoclast differentiation assay)	Fruit body	Choi et al. (2009); Zhabinskii et al. (2022)
	Chaxine C (5)	Prevention of osteoporosis (osteoclast differentiation assay); cytotoxic activity	Fruit body	Choi et al. (2009); McCloskey et al. (2017)
	Chaxine D (6)	Prevention of osteoporosis (osteoclast differentiation assay)	Fruit body	Choi et al. (2009)
	Chaxine E (7)	Prevention of osteoporosis (osteoclast differentiation assay)	Fruit body	Choi et al. (2009)
	Demethylincisterol A3 (8)	Antibacterial activity; cytotoxic activity	Fruit body	Kawagishi et al. (2007); Chen et al. (2015); Zhou et al. (2018)
A. salicacola	Agrocybin A (31)	-	Liquid culture	Liu et al. (2011)
	Agrocybin B (32)	-	Liquid culture	Liu et al. (2011)
	Agrocybin C (33)	-	Liquid culture	Liu et al. (2011)
	Agrocybin D (34)	-	Liquid culture	Liu et al. (2011); Dai et al. (2020)
	Agrocybin E (35)	-	Liquid culture	Liu et al. (2011); Dai et al. (2020)
	Agrocybin F (36)	-	Liquid culture	Liu et al. (2011); Dai et al. (2020)
	Agrocybin G (37)	-	Liquid culture	Liu et al. (2011); Dai et al. (2020)
	(2R)-2,3-dihydro-7-hydroxy-2-(hydroxymethyl)-2,4,6-trimeth-yl-1 H-indene-5-ethanol (38)	-	Liquid culture	Liu et al. (2011)
	Illudin T (39)	-	Liquid culture	Liu et al. (2011); Wang et al. (2011)
	Illudin I (40)	Cytotoxic activity	Liquid culture	Reina et al. (2004); Wang et al. (2011)
	Agrocybin H (41)	Cytotoxic activity; inhibitory effect on nitric oxide	Liquid culture	Dai et al. (2020)
	Agrocybin I (42)	-	Liquid culture	Dai et al. (2020)
	(±)-agrocybin J (43)	-	Liquid culture	Dai et al. (2020)
	(±)-agrocybin K (44)	-	Liquid culture	Dai et al. (2020)
	Dihydrogranuloinden (45)	Anticancer activity	Liquid culture	Dai et al. (2020)
	Echinolactone D (46)	-	Liquid culture	Dai et al. (2020)
	(2S,3S,9R)-14-hydroxy-5-desoxy-illudosin (47)	Cytotoxic activity	Liquid culture	Dai et al. (2020)
	Sterostrein O (48)	Cytotoxic activity	Liquid culture	Dai et al. (2020)
	(2R)-2,3-dihydro-7- hydroxy-2-(hydroxymethyl)-2,4,6-trimethyl-1 H-indene-5-ethanol (49)	-	Liquid culture	Dai et al. (2020)
	(50)	-	Liquid culture	Zhu et al. (2010a)
	(51)	-	Liquid culture	Zhu et al. (2010a)
	(52)	-	Liquid culture	Zhu et al. (2010a)
	Agrocybin H (Fomannosane-type) (53)	-	Liquid culture	Liu et al. (2012)
	Agrocybin I (Fomannosane-type) (54)	-	Liquid culture	Liu et al. (2012)
	Illudosin (55)	Antibacterial activity	Liquid culture	Liu et al. (2012)
	Agrocybone (65)	Antiviral activity	Liquid culture	Zhu et al. (2010b)
Agrocybe sp.	1α,2β-dihydroxymarasmone (56)	-	Liquid culture	Zheng et al. (2012)
	2β,3α-dihydroxymarasmone (57)	-	Liquid culture	Zheng et al. (2012)
	14-hydroxyoreadone (58)	-	Liquid culture	Zheng et al. (2012)
	Agrocybolacton (59)	Antibacterial activity	Liquid culture	Berg et al. (2002); Zheng et al. (2012)
	Marasmene (60)	-	Liquid culture	Zheng et al. (2012)
	14-hydroxymarasmene (61)	-	Liquid culture	Zheng et al. (2012)
	8-Hydroxy-2,4,6-octatriynamide (Agrocybin) (74)	Inhibitory activities against rice pathogens	Liquid culture	Zheng et al. (2016)
A. cylindracea	6-hydroxy-1H-indole-3-carboxaldehyde (75)	Free radical scavenging activity	Fruit body	Kim et al. (1997)
	6-hydroxy-1H-indole-3-acetamide (76)	Free radical scavenging activity	Fruit body	Kim et al. (1997)
	Agrocybenine (77)	-	Fruit body	Koshino et al. (1996)
A. cylindracea Maire K3793	Pasteurestin A (62)	Antibacterial activity		Takeuchi et al. (2002)
	Pasteurestin B (63)	Antibacterial activity		Takeuchi et al. (2002)
C. aegerita	Pasteurestin C (64)	Antibacterial activity	Mycelium	Surup et al. (2019)
	Bovistol A (66)	Cytotoxic activity	Mycelium	Surup et al. (2019)
	Bovistol B (67)	Weak antimicrobial activity	Mycelium	Surup et al. (2019)
	Bovistol C (68)	-	Mycelium	Surup et al. (2019)
A. praecox	Agrocybyne A (69)	Inhibitory activity against plant growth	Liquid culture	Fushimi et al. (2012)
	Agrocybyne B (70)	Inhibitory activity against plant growth	Liquid culture	Fushimi et al. (2012)
	Agrocybyne C (71)	Inhibitory activity against plant growth	Liquid culture	Fushimi et al. (2012)
	Agrocybyne D (72)	Inhibitory activity against plant growth	Liquid culture	Fushimi et al. (2012)
	Agrocybyne E (73)	-	Liquid culture	Fushimi et al. (2012)
	2-formyl-3,5-dihydroxybenzyl acetate (78)	-	Liquid culture	Fushimi et al. (2012)
	O-orsellinaldehyde (79)	Cytotoxic activity	Liquid culture	Lin and Liu (2006); Fushimi et al. (2012)

- No obvious biological activities were reported in the references.

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