TABLE 5.
Classes of endophytic fungal secondary metabolites (SMs) with biological potential activities.
| Classes of SMs | Sub classes of SMs | Compounds with references | Endophytic fungal sources | Chemical structures* | Potential biological properties |
| a. Alkaloids | Indole derivative alkaloids | Vinblastine, vincristine (Keglevich et al., 2012; Kumar et al., 2013) | F. oxysporum | 1, 2 | Antitumor drugs |
| Chaetoglobosin (Zhang Y. et al., 2012; Huang et al., 2016) | C. elatum | 3 | Antitumor activity against breast tumor and cholangiocarcinoma cell lines | ||
| Pyridines and pyrrolizidines | Asperfumoid (Zhang Y. et al., 2012; Li et al., 2015) | Penicillium sp. | 4 | Potent cytotoxic | |
| 7,8-dimethyl-isoalloxazine (Owen and West, 1971; Zhang Y. et al., 2012; Li et al., 2015) | Penicillium sp. | 5 | Cytotoxic agent | ||
| Lolines (Bush et al., 1997; Tan and Zou, 2001) | 6 | Allelopathic and insecticidal properties | |||
| Amines and amides | Peramine (Schardl and Phillips, 1997; Tan and Zou, 2001) | Neotyphodium sp., Epichloë sp. | 7 | Insecticidal- pyrrolopyrazine alkaloid | |
| Phomoenamide (Rukachaisirikul et al., 2008) | Phomopsis sp. | 8 | Antibacterial properties | ||
| Ergovaline (Flieger et al., 1997; Duringer et al., 2007; Rukachaisirikul et al., 2008; Zhang Y. et al., 2012) | Neotyphodium sp., Claviceps sp. | 9 | Neurotoxicity in livestock (feeding repellent) | ||
| Quinoline and isoquinoline | Camptothecin (Sriram et al., 2005; Shao et al., 2010; Zhang Y. et al., 2012; Wu et al., 2015) | Nothapodytes fortida | 10 | Potent cytotoxic drug, antiprotozoal, and anti-HIV properties | |
| Penicinoline and its derivatives (Shao et al., 2010; Zhang Y. et al., 2012; Bladt et al., 2013; Naveen et al., 2017) | Penicillium sp., Auxarthron reticulatum, and mangroves associated endophytic fungal species | 11 | Cytotoxic compound | ||
| b. Terpenoids | Sesquiterpenes | Chokols and its derivatives (A, C, D, F) (Hiroyuki et al., 1989) | E. typhina | 12, 13, 14, 15 | Fungicidal properties against C. phlei pathogen |
| Heptelidic acid and hydroheptelidic acid (Calhoun et al., 1992; Tan and Zou, 2001) | Phyllosticta sp. | 16, 17 | Toxic against C. fumiferana larvae | ||
| Diterpenes | Taxol (paclitaxel) (Nicolaou et al., 1994; Tan and Zou, 2001; Lin et al., 2014) | T. andreanae | 18 | Anticarcinogenic drug | |
| Subglutinol A and B (Nicolaou et al., 1994; Tan and Zou, 2001; Lin et al., 2014) | F. subglutinans | 19, 20 | Immunosuppressive property | ||
| c. Polyketides | 6-O-Methylalaternin (Mousa and Raizada, 2013) | Ampelomyces sp. | 21 | Biocontrol agent against parasitic fungi | |
| Altersolanol A (Mousa and Raizada, 2013) | A. solani | 22 | Antibiotic (antibacterial) properties | ||
| Palmarumycin CP17 (Martínez-Luis et al., 2008) | Edenia sp. (Pleosporaceae) | 23 | Antiparasitic compound especially against protozoans, antineoplastic effects via G2/M stage in mammalian cell cycle | ||
| Rugulosin (Mousa and Raizada, 2013) | Hormonema dematioides | 24 | Act as a mycotoxins due to having cell necrosis, fatty acids degeneration effects makes it a natural cytotoxic compound | ||
| Pestalachloride B (Li et al., 2008) | P. adusta | 25 | Antibiotic (antifungal) activities | ||
| CR377 (Brady and Clardy, 2000; Mousa and Raizada, 2013) | Fusarium sp. | 26 | Antibiotic (antifungal) activities | ||
| Pestalotheol C (Mousa and Raizada, 2013) | Pestalotiopsis theae | 27 | Inhibitory effect | ||
| Chaetomugilin A (Qin et al., 2009) | C. globosum | 28 | Cytotoxic effect against brine shrimp larvae | ||
| d. Phenylpropanoids and lignans | Coniferin (Falshaw et al., 1969; Chapela et al., 1991; Daubresse et al., 1997) | Xylariaceae sp. | 29 | Reduced the biosynthesis of lignins via inhibition of oxidases | |
| Syringin (Eleutheroside B) (Falshaw et al., 1969; Chapela et al., 1991; Cho et al., 2001; Li et al., 2017) | Xylariaceae sp. | 30 | Antioxidant effects, anti-inflammatory, immunomodulatory, and most remarkably used in cardiac disease (cardiac hypertrophy) | ||
| Phillyrin (Zhang Q. et al., 2012; Chen et al., 2016) | C. gloeosporioides | 31 | Antioxidant, anti-inflammatory, and antipyretic activities | ||
| Sesamin (Lee et al., 2011; Nicoletti and Fiorentino, 2015) | A. ilanense | 32 | Antitumor, antioxidantive, antihypertensive properties | ||
| Syringaresinol (Cheng et al., 2013; Nicoletti and Fiorentino, 2015; Kim et al., 2016) | A. ilanense | 33 | Activating the SIRT1 gene expression, leading to slow the cellular senescence, and enhanced the function of endothelial cells | ||
| 4-Ketopinoresinol (Chen et al., 2012; Cheng et al., 2013; Nicoletti and Fiorentino, 2015) | A. ilanense | 34 | Nrf2/ARE-mediated transcription activator and eliminate the oxidative stress effects | ||
| e. Flavonoids | Cajanol (Liang et al., 2013; Zhao et al., 2013; Nicoletti and Fiorentino, 2015) | Hypocrea lixii | 35 | Anticarcinogenic and antimalarial properties | |
| Kaempferol (Vellosa et al., 2011; Nicoletti and Fiorentino, 2015) | F. chlamydosporum | 36 | Cytotoxic and antioxidant properties | ||
| Quercetin (Materska, 2008; Huang et al., 2013; Nicoletti and Fiorentino, 2015) | A. ilanense | 37 | Reduce degenerative disease, apoptotic activity against liver cancer, antioxidant drug | ||
| Silymarin (AbouZid, 2012; Nicoletti and Fiorentino, 2015) | A. iizukae | 38a–38g including 7 flavonolignans (silybin A, B, isosilybin A, B, silychristin A, B, and silydianin) | Anti-inflammatory, anticarcinogenic, anti-asthma, hyperprolactinemia, hepatoprotective, immunostimulant | ||
| Tricin (Tan and Zou, 2001; Mousa and Raizada, 2013) | N. typhnium infected bluegrass | 39 | Toxic effect against mosquito larvae and acted as antimalarial agent | ||
| Flavones glycosides (Tan and Zou, 2001; Mousa and Raizada, 2013) | N. typhnium infected bluegrass | 40 | Antimalarial agent | ||
| f. Saponins | Diosgenin (Nicoletti and Fiorentino, 2015) | Fusarium sp., Cephalosporium sp., Paecilomyces sp. | 41 | Pharmaceutically effective drug and important precursor of progesterone, corticosteroids, and other several steroidal drugs | |
| Gymnemagenin (Nicoletti and Fiorentino, 2015) | P. oxalicum | 42 | Antidiabetic properties | ||
| g. Phenols and phenolic acids | 2-Hydroxy-6-methyl benzoic acid (Yang et al., 1994; Zou et al., 2000) | Phoma sp. | 43 | Antibiotic activity | |
| Tyrosol (Zou et al., 2000; Rodríguez-Morató et al., 2015) | E. typhina | 44 | Antifungal | ||
| cis- and trans- p-coumaric acids (Zou et al., 2000; Sigurdson et al., 2018) | E. typhina | 45, 46 | Antimicrobial activities | ||
| Colletotric acid (Zou et al., 2000) | C. gloeosporioides | 47 | Antimicrobial compound | ||
| h. Aliphatic and chlorinated metabolites | Phomodiol (Calhoun et al., 1992; Horn et al., 1996) | Phomopsis sp. | 48 | Antimicrobial, insecticidal, algicidal properties | |
| Phomopsolide B (aliphatic ester related compounds) (Tan and Zou, 2001) | Phomopsis sp. | 49 | Antimicrobial activities | ||
| Mycorrhizin A (Tan and Zou, 2001) | Phyllosticta sp. strain 76 | 50 | Antibiotic drug | ||
| Cryptosporiopsin (chlorinated compounds) (Tan and Zou, 2001) | Pezicula sp., P. livida | 51 | Algicidal drug | ||
| i. Peptides | Leucinostatin A (Tan and Zou, 2001) | Acremonium sp. | 52 | Fungicidal, antitumor, phytotoxic properties | |
| Echinocandins A, B, D, H (Tan and Zou, 2001) | A. rugulosus, Cryptosporiopsis sp., Pezicula sp. | 53 | Antibiotic activities | ||
| Cryptocandin (Tan and Zou, 2001) | Cryptosporiopsis cf. quercina | 54 | Antifungal properties | ||
| j. Steroids | 3β,5α-dihydroxy-6β-acetoxyergosta-7,22-diene and 3β,5α-dihydroxy-6β-phenylacetoxyergosta-7,22-diene (Lu et al., 2000) | Colletotricum sp. | 55, 56 | Fungicidal activity | |
| 3β-hydroxyergosta-5-ene and 3-oxoergosta-4,6,8(14),22-tetraene (Lu et al., 2000) | Colletotricum sp. | 57, 58 | Fungicidal activity | ||
| Ergosterol (Yu et al., 2010; Yang H. et al., 2015; Nowak et al., 2016) | Nodulisporium sp. | 59 | Antimicrobial activity | ||
| 5a, 8a-epidioxy ergosterol (Yu et al., 2010; Nowak et al., 2016) | Nodulisporium sp. | 60 | Antimicrobial activity |
*The chemical structure of the secondary metabolite represented by each number is shown in Figure 4.