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Review

Recent Advances in Chemistry and Bioactivities of Secondary Metabolites from the Genus Acremonium

by
Yuning Qin
†,
Humu Lu
†,
Xin Qi
,
Miaoping Lin
,
Chenghai Gao
,
Yonghong Liu
* and
Xiaowei Luo
*
Guangxi Key Laboratory of Marine Drugs, Institute of Marine Drugs, Guangxi University of Chinese Medicine, Nanning 530200, China
*
Authors to whom correspondence should be addressed.
†
These authors contributed equally to this work.
J. Fungi 2024, 10(1), 37; https://doi.org/10.3390/jof10010037
Submission received: 28 November 2023 / Revised: 26 December 2023 / Accepted: 26 December 2023 / Published: 3 January 2024
(This article belongs to the Special Issue Diversity of Marine Fungi and Their Secondary Metabolites)
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Abstract

:
Acremonium fungi is one of the greatest and most complex genera in Hyphomycetes, comprising 130 species of marine and terrestrial sources. The past decades have witnessed substantial chemical and biological investigations on the diverse secondary metabolites from the Acremonium species. To date, over 600 compounds with abundant chemical types as well as a wide range of bioactivities have been obtained from this genus, attracting considerable attention from chemists and pharmacologists. This review mainly summarizes the sources, chemical structures, and biological activities of 115 recently reported new compounds from the genus Acremonium from December 2016 to September 2023. They are structurally classified into terpenoids (42%), peptides (29%), polyketides (20%), and others (9%), among which marine sources are predominant (68%). Notably, these compounds were primarily screened with cytotoxic, antibacterial, and anti-inflammatory activities. This paper provides insights into the exploration and utilization of bioactive compounds in this genus, both within the scientific field and pharmaceutical industry.

1. Introduction

Natural products and their structural analogues have historically played a vital role in the drug discovery and development process, especially for cancer and infectious diseases [1,2]. Fungi are a hyper-diverse kingdom of life, with millions of species estimated to be present worldwide, and less than 10% of which have been described taxonomically. Of all the described and undescribed fungi, only 7% have been investigated for the chemistry of secondary metabolites [3]. Meanwhile, the secondary metabolites of filamentous fungi are largely untapped, owing to the magnitude of biosynthetic gene clusters combined with the historic number of sequenced genomes [4].
The Acremonium fungi, belonging to the Hypocreataceae family, is one of the greatest and most complicated genera in Hyphomycetes [5]. It is also a common and widely distributed fungus with about 130 species. According to the ecological habits and nutritional methods of the fungus, it is mainly divided into saprophytic, plant-parasitic, and authigenic types, and it can also survive in terrestrial or marine environments [6], but also live in close association with soil [7], plants [8], sponge [9], coral [10], algae [11], and holothurian [12], etc. Phylogenetic studies showed that the sources of Acremonium were related to at least three kinds of ascomycete fungi, Hypocreaceae, Ergotaceae, and Chaetomium [13].
As of July 2016, 356 compounds, including steroids, terpenoids, meroterpenoids, polyketides, alkaloids, peptides, and miscellaneous types, have been isolated from the genus Acremonium [14]. These compounds displayed a wide range of biological activities comprising antimicrobial, antitumor, immunosuppressive, antioxidant, and anti-inflammatory activities [14]. Notably, a series of ascochlorin derivatives isolated from A. sclerotigenum in our recent study were characterized as novel potent hDHODH inhibitors for the further development of anticancer agents [10]. The diverse and bioactive secondary metabolites from Acremonium have continued to attract great attention from chemists and pharmacologists.
The Acremonium fungi are producers of structurally diverse and pharmacologically active compounds. In this review, a total of 271 secondary metabolites (Known ones were summarized in Table S1), including 115 new compounds, were recently obtained from the genus Acremonium from December 2016 to September 2023. Structurally, they were classified into terpenoids (124 compounds), polyketides (66 compounds), peptides (45 compounds), steroids (18 compounds), alkaloids (9 compounds), and amides (9 compounds). Among them, 101 compounds displayed a wide range of biological activities, including antimicrobial, cytotoxic, anti-inflammatory, insecticidal, and enzyme inhibition activities. This review summarizes the sources, chemical structures, and biological activities of 115 new compounds reported in the genus Acremonium from December 2016 to September 2023.

2. Secondary Metabolites

2.1. Terpenoids

A total of 124 terpenoids have been reported in Acremonium fungi within the period 2016–2023, consisting of 31 sesquiterpenoids, 15 diterpenoids, 5 triterpenoids, and 78 meroterpenoids and miscellaneous types, while 99 compounds were found to have bioactivities. Remarkably, there are 20 new sesquiterpenoids, 11 new diterpenoids, 18 new meroterpenoids, and miscellaneous types.

2.1.1. Sesquiterpenoids

Several mophilane-type sesquiterpenoids, acremeremophilanes A–O (1–15), along with seven known analogues, were isolated from the deep-sea sediments derived from Acremonium sp. TVG-S004-0211 (Figure 1). Compounds 2–5 and 14 exhibited inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 macrophages with IC50 values ranging from 8 to 45 μM [15].
One new sesquiterpenoid, marinobazzanan (16), was isolated from marine sediment-derived Acremonium sp. CNQ-049, which showed an inhibition of cancer cell migration and invasion at non-toxic concentrations of 1, 2.5, and 5 μM by down-regulating transcription factors of Snail, Slug, and Twist. In addition, marinobazzananan reduced cell motility by down-regulating the expression level of KITENIN and by up-regulating the expression level of KAI 1, and it further reduced the number of metastatic nodules in the intraperitoneal xenograft mouse model [16]. Moreover, one new acorane-type sesquiterpene glycoside, isocordycepoloside A (17), was isolated from the fungus Acremonium sp. SF-7394 [17].
Meanwhile, three new trichothecenes, including two trichothecenes, 7-dehydro-8-dehydroxytrichothecinol B (18) and 8-deoxy-16-hydroxytrichothecinol B (19), along with one trichothecene analogue, 4-((Z)-but-2-enoyloxy)-8-chloro-12-hydroxy-7,13-epoxytrichothec-9-ene (20), and four known analogues, were isolated from the fungus A. crotocinigenum BCC 20012. Among them, the known compound trichothecin exerted the strongest antimalarial activity against Plasmodium falciparum K1 with an IC50 value of 0.05 mg/mL, and possessed cytotoxic activity against Vero cells with an IC50 value of 0.13 mg/mL [18].

2.1.2. Diterpenes

A chemical investigation of the marine-derived fungus A. striatisporum KMM 4401 resulted in the isolation of ten new diterpene glycosides, virescenosides Z9–Z18 (21–30), together with four known analogues [12] (Figure 2). One new diterpene, acrepseudoterin (31), was isolated from the fungus Acremonium sp. SF-7394. Acrepseudoterin inhibited the enzyme activity in a dose-dependent manner with an IC50 value of 22.8 ± 1.1 μM, which was identified as a competitive inhibitor of PTP1B [17].

2.1.3. Meroterpenoids

Twenty-five ascochlorin derivatives, biosynthesized through the farnesylation of orsellinic acid [19], were obtained from the coral-derived A. sclerotigenum GXIMD 02501, including 13 new compounds, acremochlorins A–M (32–44) (Figure 3). Compounds 32 and 44, two novel potent human dihydroorotate dehydrogenase (hDHODH) inhibitors, induced the apoptosis of triple-negative breast cancer (TNBC) cells by up-regulating the levels of cleaved-PARP1 and cleaved-caspase7, and further effectively inhibited tumor growth in a patient-derived TNBC xenograft model without significant weight loss or obvious toxicity in mice, showing higher safety than that of brequinar [10].
Meanwhile, ascofuranone and ascochlorin, two representative ascochlorin derivatives, were also reported as potential lead candidates for drug development targeting the hDHODH of cancer cells living under a tumor microenvironment [20]. Moreover, two known potential anti-tumor ascochlorins, 3-bromoascochlorin (BAS) and ilicicolin A (Ili-A), were also obtained from the coral-derived fungus A. sclerotigenum GXIMD 02501. BAS could induce the apoptosis, invasion, and migration of H446 and H69AR cells, and it further suppressed the tumor growth of a small cell lung cancer xenograft mouse model by inhibiting the mitogen-activated protein kinase (MAPK)/extracellular signal-regulated kinase (ERK) pathway [21]. Moreover, Ili-A showed efficacious activity against prostate cancer cells by abrogating EZH2/AR-mediated processes and demonstrated a synergistic anti-prostate cancer effect combined with enzalutamide in vivo, revealing a novel EZH2 inhibitor for the treatment of castration-resistant prostate cancer [22].
Ascofuranone and its derivatives, obtained from A. egyptiacum, were found as the first dual inhibitors of fumarate and oxygen respiration in Echinococcus multilocularis by targeting mitochondrial complexes II and III, suggesting potential lead compounds in the development of anthelminthic drugs [23]. One new ascochlorin, acremochlorin N (45), and a pair of new natural enantiomers, 3-phenylcyclopentane-1,2-diol (±-46) (Figure 4), together with nine known analogues were isolated from marine sediment-derived A. furcatum CS-280. All the isolates showed significant anti-Vibrio activities, especially against Vibrio harveyi and V. alginolyticus. Moreover, the presence of chlorine atoms in the ascochlorins could significantly enhance their antibacterial activity [24].
Meanwhile, four known ascochlorins, including ascochlorin, 10′-deoxy10′α-hydroxyascochlorin, 4′,5′-dihydro-4′-hydroxyascochlorin, and ascofuranone, were obtained from the sponge-derived Acremonium sp. IMB18-086. Ascochlorin and ascofuranone showed significant antibacterial activity against Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), Bacillus subtilis, and Candida albicans. Moreover, they showed significant cytotoxicity against A549 and/or HepG2 cell lines with IC50 values of 0.9–5.8 μM [25].
Acremine S (47) was isolated from the sponge Mycale sp. derived fungus A. persicinum KUFA 1007 and showed inhibitory activity against butyrylcholine esterase, which was three folds higher than that of galantamine [26]. Hexahydroacremonintriol (48), along with an analogue, acremonin A glucoside, were obtained from a tropical sinkhole derived from A. masseei CICY026. Both displayed insecticidal activity against Myzus persicae and/or Rhopalosiphum padi with settling inhibition ranging from 48% to 67% [27]. One new fusidic acid derivative, acremonidiol A (49), and three known analogs were obtained from the endophytic fungus A. pilosum F47. Among these, fusidic acid displayed a strong inhibitory effect on Gram-positive bacterium S. aureus, and the acetylation of the hydroxyl group at C-16 was crucial for antibacterial activity [28].

2.2. Peptides

A total of 45 peptides have been reported from Acremonium fungi during the period 2016–2023, including 33 new compounds, while 19 bioactive compounds were found.

2.2.1. Linear Peptides

One new linear peptide, acremopeptin (50), and a known one, adenopeptin, were obtained from the soil-derived fungus Acremonium sp. PF1450 [29]. Moreover, four new peptaibiotics, acremotins A–D (51–54) (Figure 5), along with a known peptaibiotic XR586 were isolated from the soil-derived fungus A. persicinum SC0105. Acremotins A–D showed strong inhibitory activity against Gram-positive bacteria, while the MIC values of acremotin D against S. aureus and MRSA were 12.5 and 6.25 μg/mL, respectively. Moreover, acremotins A–D and XR586 also showed cytotoxicity against three human cancer cell lines (A549, HeLa, and HepG2), with IC50 values ranging from 1.2 to 21.6 μM [30].
Six new 16-residue peptaibols, acremopeptaibols A–F (55–60), along with PF1171A, were isolated from the cultures of the sponge-associated fungus Acremonium sp. IMB18-086. Compounds 55 and 59 showed significant antibacterial activity against S. aureus, MRSA, B. subtilis, and C. albicans, with MIC values ranging from 16 to 64 μM [25]
Six new linear pentadecapeptides, emerimicins V–X (61–66) (Figure 6), were obtained from the soil-derived fungus A. tubakii MT053262. Emerimicins V (61) and VI (62) displayed strong toxicity toward Zebrafish embryos. In addition, emerimicin V showed certain activity against Enterococcus faecalis, MRSA, and vancomycin-resistant Enterococcus faecium with MIC values of 64, 32, and 64 μg/mL, respectively [31].
Four new peptides, acrepeptins A–D (67–70), and three known analogs, destruxin B, guangomide A, and guangomide B, were obtained from a marine algicolous fungus Acremonium sp. NTU492. Acrepeptins A (67) and B (68) exhibited significant inhibitory activity on NO production in LPS-activated microglia BV-2 cells, with IC50 values of 12.0 ± 2.3 and 10.6 ± 4.0 mM, respectively [32].

2.2.2. Cyclic Peptides

Four new hydroxamate-containing cyclopeptides, acremonpeptides A–D (71–74), together with a known one, Al (III)-acremonpeptide D, were obtained from the marine fungus A. persicinum SCSIO 115. Compounds 71, 72, and Al (III)-acremonpeptide D exhibited moderate antiviral activity against HSV-1 with EC50 values of 16, 8.7, and 14 μM, respectively [33] (Figure 7). Meanwhile, a new cyclic depsipeptide, acremonamide (75), was isolated from a marine-derived fungus Acremonium sp. strain CNQ-049 [34].
Six new hydroxamate siderophore cyclohexapeptides, Al (III)-acremonpeptide E (76), acremonpeptide E (77), Fe (III)-acremonpeptide E (78), acremonpeptide F (79), Al (III)-acremonpeptide F (80), and Fe (III)-acremonpeptide F (81), and one new cyclic pentapeptolide, aselacin D (82), together with a known compound, aselacin C, were isolated from the sponge-derived fungus A. persicinum F10. Compounds 76 and 80 showed pronounced antifungal activity against Aspergillus fumigatus and A. niger with a shared MIC value of 1 μg/mL, and both showed no cytotoxicity against human embryonic lung fibroblasts (MRC-5) at a concentration of 30 μM [35].
Two known cyclopeptides, (–)-ternatin and [D-Leu]-ternatin, were isolated from the EtOAc extract of the fungal strain Acremonium sp. SF-7394. [D-Leu]-esculetin inhibited the enzyme activity in a dose-dependent manner, with an IC50 value of 14.8 ± 0.3 μM [17].

2.3. Polyketides

A total of 60 polyketides have been reported from the genus Acremonium within the period, including 23 new compounds and 18 bioactive compounds.
One new dibenzoquinone, 2,7-dihydroxy-3,6,9-trimethyl-9H-xanthene-1,4,5,8-tetraone (83) (Figure 8), and a known analog, 3,3′,6,6′-tetrahydroxy-4,4′-dimethyl-1,1′-bi-p-benzoquinon, were obtained from the fungus A. cavaraeanum CA022 [36]. Meanwhile, a chemical examination of marine sponge Mycale sp. derived fungus A. persicinum KUFA 1007 led to the isolation of one new compound, acremine T (84) [26].
A chemical investigation on the endophytic fungus A. citrinum SS-g13 yielded a new γ-pyrone derivative, acrepyrone A (85), and three known sorbicillinoids, trichodimerol, dihydrotrichodimerol, and tetrahydrotrichodimerol [8]. A chemical investigation of the endophytic fungus A. citrinum MMF4 derived from the root of the mangrove plant Kandelia obovate resulted in the isolation of one new compound, triacremoniate (86), along with a known compound, acrepyrone A. Compound 86 had significant inhibitory effects on the proliferation of HeLa cells, with an IC50 value of 30.5 ± 1.99 μM [37].
Three new zinniol analogues, pleoniols A–C (87–89), along with a known compound were isolated from a mixed fermentation of two endophytic fungi, Pleosporales sp. F46 and A. pilosum F47, both of which originated from the pedicel of the medicinal plant Mahonia fortune [38]. Four dimethylated anthraquinone derivatives, including one new compound, 6,8-di-O-methylbipolarin (90), and three known compounds, aversin, 6,8-di-O-methylaverufin, and 6,8-di-O-methylnidurufin, were obtained from the marine-derived fungus A. vitellinum MH726097. Compound 90 showed the strongest insecticidal activity against the third instar larvae of Helicoverpa armigera, with a LC50 value of 0.72 mg/mL [39].
Three new chlorinated orsellinic aldehyde derivatives, orsaldechlorins A–C (91–93), and one new natural brominated orsellinic acid, 5-bromo-2,4-dihydroxy-6-methylbenzoic acid (94), along with ten known biosynthetically related derivatives were further characterized from the Beibu Gulf coral-associated fungus A. sclerotigenum GXIMD 02501. Most of them inhibited LPS-induced NF-κB activation in RAW 264.7 cells at a concentration of 20 μM. Notably, compounds 91 and 92 showed inhibitions of RANKL-induced osteoclast differentiation in bone marrow macrophages without cytotoxicity [40].
One new compound, fusidione (95), along with a known one, microperfuranone, were isolated from the sea-water-derived fungus A. fusidioides RZ01. Fusidione displayed inhibitory activity against HL-60 cells with an IC50 value of 44.9 μM [41].
A new benzoyl compound, 1-(2′-benzoyl-3,4-dihydroxy-1′-methoxycyclobut-2′-enyl)-3,4,5-trihydroxy-2-methylnona-2,6-dien-1-one (96) (Figure 9), was obtained from the endophytic fungus Acremonium sp. of Garcinia griffithii [42]. One new polyketide, acrefurcatone A (97), was isolated from the deep-sea cold-seep sediment-derived fungus A. furcatum CS-280, which showed strong activity against Pseudomonas aeruginosa with an MIC value of 8 μg/mL [24].
A chemical investigation of marine sediment-derived fungus Acremonium sp. resulted in the isolation of two new compounds, 3(S)-hydroxy-1-(2,4,5-trihydroxy-3,6dimethylphenyl)-hex-4E-en-1-one (98) and acremonilactone (99), along with eight known compounds. Among them, (2E,4E)-1-(2,6dihydroxy-3,5-dimethyl-phenyl) hexa-2,4-dien-1-one, sorbicillin, and tetrahydrotrichodimerol showed inhibitory activity against S. aureus, with a shared MIC value of 128 μg/mL. In addition, compounds 98 and trichodimerol showed 2,2-diphenyl-1-trinitrophenylhydrazine (DPPH) free radical scavenging activity with inhibition rates of 96.50% and 84.95% at a concentration of 0.5 mg/mL, respectively [43].
A chemical investigation of the terrestrial plant Fructus mori derived A. citrinum SS-g13 produced three new sorbicillinoids, trisorbicillinone E (100), acremosorbicillinoids A and B (101 and 102), and one new natural product, 2S,3S-acetyl-β-methyltryptophan, along with eight known sorbicillinoids. Among them, dihydrobisvertinolone showed significant cholesterol efflux-enhancing activity [44].
Moreover, three new sorbicillinoid derivatives, acresorbicillinols A–C (103–105), along with five known compounds were obtained from the marine-derived fungus A. chrysogenum C10. Compounds 104 and 105 displayed moderate activity against S. aureus and Cryptococcus neoformans with IC50 values of 86.93 ± 1.72 and 69.06 ± 10.50 μM, respectively. Moreover, compound 105 demonstrated strong DPPH free radical scavenging activity, with the IC50 value ranging from 11.53 ± 1.53 to 60.29 ± 6.28 μM in 24 h [45]. A chemical investigation of the deep-sea-derived A. alternatum provided two known bisorbicillinoids, tetrahydrotrichodimerol and dihydrotrichodimerol [46].

2.4. Steroids, Amides, or Alkaloids

2.4.1. Steroids

A total of eighteen steroids have been discovered from the genus Acremonium during the period 2016–2023, including four new compounds as well as five bioactive compounds.
A new steroid acremocholone (106) (Figure 10) and three known analogs, (22E)5α,8α-epidioxyergosta-6,22-dien-3β-ol, (22E, 24R)3β,5α,9α,14α-tetrahydroxyergosta-7,22-dien-6-one, and (22E, 24R)-3β-hydroxy-5,9-epoxyergosta-7,22-dien6-one, were obtained from the marine mesophotic zone ciocalypta sponge-associated fungus Acremonium sp. NBUF150. Particularly, compound 106 showed antibacterial activity against Vibrio scophthalmi, V. shilonii, and V. brasiliensis with a shared MIC value of 8 μg/mL. (22E)5α,8α-epidioxyergosta-6,22-dien-3β-ol inhibited the growth of V. shilonii and V. brasiliensis at 8 μg/mL and 32 μg/mL, respectively. Moreover, (22E,24R)-3β-hydroxy-5,9-epoxyergosta-7,22-dien6-one inhibited the growth of V. brasiliensis at 16 μg/mL [47].
A new compound, (22E)-25-carboxy-8β,14β-epoxy-4α,5α-dihydroxyergosta-2,22-dien-7-one (107), along with a known compound, 5α,8α-epidioxy ergosta-6,22-diene-3β-ol, were isolated from the fermentation products of the marine-sourced fungus A. fusidioides RZ01. Compound 107 showed inhibitory activity against HL-60 cells with an IC50 value of 16.6 μM [41].
Two new heterodimers, acremonidiols B and C (108 and 109), and four biosynthetically related known compounds were isolated from A. pilosum F47 [48]. Meanwhile, four known steroids, (22E,24R)-ergosta-5,7,22-trien-3β-ol, ergosterol endoperoxide, 11-O-acetyl-NGA0187, and NGA0187, were obtained from A. alternatum [46]. Ergosterol and ergosterol 5,8-endoperoxide were isolated from the culture of sponge-associated fungus A. persicum KUF1007 [26].
The sterol 3β,5α,6β,7α-tetrahydroxyergosta-8(14),22-diene was isolated from the liquid culture of A. persicum. Its antiproliferative potential was found to be comparable to or even stronger than that of commonly used anticancer drugs in breast cancer and colon cancer cell lines T-47 D and WiDr [49].

2.4.2. Amides

A total of nine amides have been discovered from the genus Acremonium during the period 2016–2023, including four new compounds and three bioactive compounds.
Three chloramphenicol derivatives, including one new natural product, 4R-(1R-hydroxy-(4-nitrophenyl)-methyl)-1,3-oxazolidin-2-one (110) (Figure 11), were isolated from a marine alga-derived fungus A. vitellinum MH726097. Compound 110 indicated insecticidal activity against Helicoverpa armigera with an LC50 value of 0.56 ± 0.03 mg/mL, while chloramphenicol and corynecin-I exhibited weak activity with LC50 values of 0.93 ± 0.05 and 0.91 ± 0.06 mg/mL, respectively [50].
A new compound, dietziamide C (111), was obtained from the mangrove-derived fungus A. citrinum MMF4 [37]. Meanwhile, one new deoxysphingoid derivative, named hypoculoside (112), along with a new aglycone derivative, hypoculine (113), were isolated from the fungus Acremonium sp. F2434. Compound 112 completely inhibited the growth of C. albicans with an IC50 value of 7.6 μM. Hypoculoside inhibited the growth of Saccharomyces cerevisiae cells with an IC50 value of 7.2 μM and also inhibited the growth of Gram-positive bacteria S. aureus with an IC50 value of 11.7 μM. Meanwhile, hypoculoside showed cytotoxicity against human lung and pancreatic cancer cell lines (IC50 = 9–14 μM) [51].
A known metabolite pseurotin A was isolated from the EtOAc extract of the fungal strain Acremonium sp. SF7394 [17]. Moreover, two ceramides, lactariamide B and (2S,2′R,3R,4E,8E,3′E)-2-(2′-hydroxy-3′-octadecenoylamino)-9-methyl-4,8-octadecadiene-l,3-diol, were obtained from A. alternatum [46].

2.4.3. Alkaloids

A total of nine alkaloids have been reported from the genus Acremonium during the period 2016–2023, including two new compounds and three bioactive compounds.
Two new alkaloids, acremokaloid A (114) and 2S, 3S-acetyl-β-methyltryptophan (115), were isolated from an endophytic fungus A. citrinum SS-g13 [44] (Figure 12). Moreover, a known compound, β-Adenosine, was obtained from the mangrove-derived fungus A. citrinum MMF4 [37].
Three rare 4-hydroxy-2-pyridone alkaloids, campyridones A and D, ilicicolin H, and one phenazine alkaloid, phenazine-1-carboxylic acid, were isolated from the coral-associated fungus A. sclerotigenum GXIMD 02501. Campyridone A and ilicicolin H showed cytotoxicity against two prostate cancer cell lines, with IC50 values of 17.6 ± 1.3 and 5.5 ± 1.2 μM for PC-3, and 25.4 ± 1.7 and 11.9 ± 1.3 μM for 22Rv1, respectively. In addition, phenazine-1-carboxylic acid showed anti-Vibrio activity, including V. parahemolyticus, V. alginolyticus, V. owensii, and V. coralliilyticus, with MIC values ranging from 0.047 to 0.067 mg/mL, and showed inhibition of LPS-induced NF-κB activation at 10 μM [52]. A chemical investigation of marine sediment-derived Acremonium sp. resulted in the isolation of one known compound, N-(2-hydroxyphenyl)-acetamide [43].

3. Comprehensive Overview and Conclusions

In this review, the sources, structural diversity, and biological activity of secondary metabolites from Acremonium fungi are summarized covering a period of time comprising the period between Dec 2016 and Sep 2023. A total of 271 compounds were obtained from the genus Acremonium. Among them, 115 were characterized as new compounds (42%) (Table 1). Notably, 169 compounds were predominantly marine-sourced and 77 ones were characterized as new compounds, accounting for nearly 67% of all new compounds. Most of the reviewed Acremonium fungi were isolated from marine habitats or terrestrial sources. Remarkably, the top three marine sources of these reviewed Acremonium fungi were sediments (22%), corals (16%), and sponges (12%) (Figure 13).
The chemical structures of the 115 recently reported secondary metabolites from Acremonium fungi can mainly be classified into four types, including terpenoids (46%), polyketides (24%), peptides (17%), and others (13%) consisting of steroids, amides, and alkaloids (Figure 14). However, among these 115 new compounds, terpenoids predominantly accounted for 42%, while polyketides, peptides, and other types accounted for 20%, 29%, and 9%, respectively. Moreover, it is worth noting that nearly 37.3% (101 compounds) showed broad-spectrum biological activities, including insecticidal, antibacterial, cytotoxic, enzyme inhibition, antiviral, anti-inflammatory, antioxidant, and antimalarial activities. Notably, antibacterial (35.6%), cytotoxic (35.6%), and anti-inflammatory (10.9%) represent the top three bioactivities.
In summary, widely distributed Acremonium fungi have hitherto been proven to be vital sources of novel and diverse secondary metabolites with a broad range of biological activities, revealing their great untapped potential in medicinal, agrochemical, and industrial applications. However, for most of these isolated compounds, the lack of deep pharmacological mechanisms as well as comprehensive pharmacokinetic evaluation limit their applications. Overall, this review will shed light on the further pharmacological investigation and medicinal utilization of these valuable secondary metabolites from this genus and will continuously arouse high interest in natural product chemistry, synthetic chemistry, pharmacology, and medicinal chemistry.

Supplementary Materials

The following supporting information can be downloaded at https://www.mdpi.com/article/10.3390/jof10010037/s1, Table S1: Recently reported known compounds from the genus Acremonium, along with their structures.

Author Contributions

Conceptualization, X.L. and Y.L.; methodology, Y.Q. and H.L.; validation, X.Q., M.L. and C.G.; data curation, Y.Q. and H.L.; writing—original draft preparation, Y.Q. and H.L.; writing—review and editing, X.L.; supervision, X.L.; funding acquisition, X.L. and Y.L. All authors have read and agreed to the published version of the manuscript.

Funding

This research was supported by the Natural Science Foundation of Guangxi (2023JJG140008, 2020GXNSFGA297002, 2023JJB140055), the National Natural Science Foundation of China (U20A20101, 82260692), the Special Fund for Bagui Scholars of Guangxi (Yonghong Liu), Guangxi Young and Middle-aged University Teachers’ Scientific Research Ability Enhancement Project (2023KY0296), and the Scientific Research Foundation of Guangxi University of Chinese Medicine (2022C038, 2023QN004).

Conflicts of Interest

The authors declare no conflicts of interest.

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Figure 1. Chemical structures of sesquiterpenoids (1–20).
Figure 1. Chemical structures of sesquiterpenoids (1–20).
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Figure 2. Chemical structures of sesquiterpenoids (21–31).
Figure 2. Chemical structures of sesquiterpenoids (21–31).
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Figure 3. Chemical structures of meroterpenoids (32–45).
Figure 3. Chemical structures of meroterpenoids (32–45).
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Figure 4. Chemical structures of miscellaneous terpenoids (46–49).
Figure 4. Chemical structures of miscellaneous terpenoids (46–49).
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Figure 5. Chemical structures of linear peptides (50–60).
Figure 5. Chemical structures of linear peptides (50–60).
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Figure 6. Chemical structures of linear peptides (61–70).
Figure 6. Chemical structures of linear peptides (61–70).
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Figure 7. Chemical structures of cyclic peptides (71–82).
Figure 7. Chemical structures of cyclic peptides (71–82).
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Figure 8. Chemical structures of polyketides (83–95).
Figure 8. Chemical structures of polyketides (83–95).
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Figure 9. Chemical structures of polyketides (96–105).
Figure 9. Chemical structures of polyketides (96–105).
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Figure 10. Chemical structures of steroids (106–109).
Figure 10. Chemical structures of steroids (106–109).
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Figure 11. Chemical structures of amides (110–113).
Figure 11. Chemical structures of amides (110–113).
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Figure 12. Chemical structures of alkaloids (114 and 115).
Figure 12. Chemical structures of alkaloids (114 and 115).
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Figure 13. The habitat distribution of these reviewed Acremonium fungi from December 2016 to September 2023.
Figure 13. The habitat distribution of these reviewed Acremonium fungi from December 2016 to September 2023.
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Figure 14. The structural diversity (left) and bioactivities (right) of secondary metabolites in Acremonium fungi from December 2016 to September 2023.
Figure 14. The structural diversity (left) and bioactivities (right) of secondary metabolites in Acremonium fungi from December 2016 to September 2023.
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Table 1. Recently reported new compounds from the genus Acremonium (December 2016 to September 2023).
Table 1. Recently reported new compounds from the genus Acremonium (December 2016 to September 2023).
CompoundsProducing StrainsSourcesBiological ActivitiesRef.
acremeremophilanes A–O (1–15)Acremonium sp. TVG-S004-0211deep-sea sediments2–5, 14:
LPS-induced NO production
(IC50: 8–45 μM)		[15]
marinobazzanan (16)Acremonium sp. CNQ-049marine sedimentsanti-tumor[16]
isocordycepoloside A (17)Acremonium sp. SF-7394an unidentified lichen-[17]
4-((Z)-but-2-enoyloxy)-12, 13-epoxytrichotheca-7, 9-diene (18)
4-((Z)-but-2-enoyloxy)-12, 13-epoxy-16-hydroxytrichothec-9ene (19)
4-((Z)-but-2-enoyloxy)-8-chloro-12-hydroxy-7, 13epoxytrichothec-9-ene (20)		A. crotocinigenum BCC 20012the petiole of the brackish water
palm		-[18]
virescenosides Z9–Z18 (21–30)A. striatisporum KMM 4401holothurian-[12]
acrepseudoterin (31)Acremonium sp. SF-7394an unidentified lichenPTP1B inhibitor
(IC50: 22.8 ± 1.1 μM)		[17]
acremochlorins A–M (32–44)A. sclerotigenum GXIMD 02501coral Pocillopora damicornis32, 36–38, 42–44: Cytotoxic (MDA-MB-231 and MDA-MB-468) (IC50: 0.48–45 μM)[10]
acremochlorin N (45)
3-phenylcyclopentane-1,2-diol (±-46)		A. furcatum
CS-280		marine
sediments		45–46: anti-Vibrio[24]
acremine S (47)A. persicinum KUFA 1007marine sponge Mycale sp.butyrylcholine esterase inhibiton[26]
hexahydroacremonintriol (48)A. masseei CICY026plant litterinsecticidal activity
(settling inhibition: 48–67%)		[27]
acremonidiol A (49)A. pilosum F47the pedicel of the Chinese medicinal plant Mahonia fortunei-[28]
acremopeptin (50)Acremonium sp. PF1450sediments-[29]
acremotins A–D (51–54)A. persicinum SC0105sediments54: antibacterial
(MIC: S. aureus 12.5 μg/mL, MRSA 6.25 μg/mL), anti-tumor (A549, HeLa, HepG2; IC50: 1.2–21.6 μM)		[30]
acremopeptaibols A–F (55–60)Acremonium sp. IMB18-086the sponge
Haliclona sp.		55, 59: antibacterial (S. aureus, MRSA, B. subtilis, C. albicans; MIC: 16–64 μM)[25]
emerimicins V–X (61–66)A. tubakii MT053262sediments61–62: toxic to zebrafish embryos.
61: antibacterial
(MIC: E. faecalis 64 μg/mL, MRSA 32 μg/mL, vancomycin-resistant E. faecium 64 μg/mL)		[31]
acrepeptins A–D (67–70)Acremonium sp. NTU492marine alga Mastophora rosea67 and 68:
LPS-induced NO production (IC50: 12.0 ± 2.3, 10.6 ± 4.0 mM)		[32]
acremonpeptides A–D (71–74)A. persicinum SCSIO 115marine sediments71 and 72: antiviral activity (HSV-1,
EC50: 16, 8.7 μM)		[33]
acremonamide (75)Acremonium sp. strain CNQ-049marine sediments-[34]
Al (III)-acremonpeptide E (76)
Acremonpeptide E (77)
Fe (III)-acremonpeptide E (78)
acremonpeptide F (79)
Al (III)-acremonpeptide F (80)
Fe (III)-acremonpeptide F (81)
aselacin D (82)		A. persicinum F10marine sponge Phakellia fuscaantifungal
76 (A. fumigatus MIC: 1 μg/mL)
80 (A. niger MIC: 1 μg/mL)		[35]
2,7-dihydroxy-3,6,9-trimethyl-9H-xanthene-1,4,5,8-tetraone (83)A. cavaraeanum CA022fruiting bodies of Shiraia bambusicola-[36]
acremine T (84)A. persicinum KUFA 1007marine sponge Mycale sp.-[26]
acrepyrone A (85)A. citrinum SS-g13the root of the plant Fructus mori-[8]
triacremoniate (86)A. citrinum. MMF4the root of
mangrove plant Kandelia obovata		86: anti-tumor
(HeLa;
IC50: 30.46 ± 1.99 μM)		[37]
pleoniols A–C (87–89)Pleosporales sp. F46 and A. pilosum F47the pedicel of the medicinal plant Mahonia fortunei-[38]
6,8-di-O-methylbipolarin (90)A. vitellinum MH726097the fresh inner tissue of an unidentified marine red alga90: insecticidal
(H. armigera;
LC50: 0.72 mg/mL)		[39]
orsaldechlorins A–C (91–93)
5-bromo-2,4-dihydroxy-6-methylbenzoic acid (94)		A. sclerotigenum GXIMD 02501coral Pocillopora damicornis91–92: inhibit osteoclast differentiation[40]
fusidione (95)A. fusidioides RZ01sea water95: anti-tumor
(HL-60;
IC50: 44.9 μM)		[41]
1-(2′-benzoyl-3,4-dihydroxy-
1′-methoxycyclobut-2′-enyl)-3,4,5-trihydroxy-2-methyl-nona-2,6-dien-1-one (96)		Acremonium spthe twigs of
Garcinia griffithii		-[42]
acrefurcatone A (97)A. furcatum CS-280marine sediments97: antibacterial
(P. aeruginosa;
MIC: 8 μg/mL)		[24]
3(S)-hydroxy-1-(2,4,5-trihydroxy-3,6dimethylphenyl)-hex-4E-en-1-one (98)
acremonilactone (99)		Acremonium sp. AN-13marine sediments98: DPPH free radical scavenging
(inhibition rates: 96.50%) 		[43]
trisorbicillinone E (100)
acremosorbicillinoids A and B (101 and 102)		A. citrinum SS-g13the root of the terrestrial plant Fructus mori-[44]
acresorbicillinols A–C (103–105)A. chrysogenum C10unknown104–105: antibacterial (S. aureus, C. neoformans;
IC50: 86.93 ± 1.72, 69.06 ± 10.50 μM)
105: antioxidant activity
(IC50:11.53 ± 1.53–60.29 ± 6.28 μM)		[45]
acremocholone (106)Acremonium sp. NBUF150the sponge Ciocalypta sp.106: antibacterial
(V. scophthalmi, V. shilonii, V. brasiliensis; MIC: 8, 8, 8 μg/mL)		[47]
(22E)-25-carboxy-8β,14β-epoxy-4α,5α-dihydroxyergosta-2,22-dien-7-one (107)A. fusidioides RZ01sea water107: anti-tumor
(HL-60; IC50: 16.6 μM)		[41]
acremonidiols B and C (108 and 109)A. pilosum F47the pedicel of the Chinese medicinal plant Mahonia fortune-[46]
4R-(1R-Hydroxy-(4-nitrophenyl)-methyl)-1,3-oxazolidin-2-one (110)A. vitellinum MH726097fresh inner tissue of an unidentified
marine red alga		110: insecticidal activity
(H. armigera; LC50: 0.56 ± 0.03 mg/mL)		[50]
dietziamide C (111)A. citrinum. MMF4the root of
mangrove plant Kandelia obovata		-[37]
hypoculoside (112)
hypoculine (113)		Acremonium sp. F2434sediments112: antibacterial
(C. albicans, S. aureus, S. cerevisiae;
IC50: 11.7, 7.6, 7.2 μM)
113: anti-tumor (LUNG, PAAD;
IC50: 9–14 μM)		[51]
acremokaloid A (114)
2S,3S-acetyl-β-methyltryptophan (115)		A. citrinum SS-g13terrestrial plant Fructus mori-[44]
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Qin, Y.; Lu, H.; Qi, X.; Lin, M.; Gao, C.; Liu, Y.; Luo, X. Recent Advances in Chemistry and Bioactivities of Secondary Metabolites from the Genus Acremonium. J. Fungi 2024, 10, 37. https://doi.org/10.3390/jof10010037

AMA Style

Qin Y, Lu H, Qi X, Lin M, Gao C, Liu Y, Luo X. Recent Advances in Chemistry and Bioactivities of Secondary Metabolites from the Genus Acremonium. Journal of Fungi. 2024; 10(1):37. https://doi.org/10.3390/jof10010037

Chicago/Turabian Style

Qin, Yuning, Humu Lu, Xin Qi, Miaoping Lin, Chenghai Gao, Yonghong Liu, and Xiaowei Luo. 2024. "Recent Advances in Chemistry and Bioactivities of Secondary Metabolites from the Genus Acremonium" Journal of Fungi 10, no. 1: 37. https://doi.org/10.3390/jof10010037

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