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1 June 2016

Sorbicillinoids from Fungi and Their Bioactivities

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Key Laboratory of Plant Pathology, Ministry of Agriculture/Department of Plant Pathology, College of Plant Protection, China Agricultural University, Beijing 100193, China
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Molecules2016, 21(6), 715;https://doi.org/10.3390/molecules21060715
This article belongs to the Special Issue Polyketides
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Abstract

Sorbicillinoids are important hexaketide metabolites derived from fungi. They have a variety of biological activities including cytotoxic, antioxidant, antiviral and antimicrobial activity. The unique structural features of the sorbicillinoids make them attractive candidates for developing new pharmaceutical and agrochemical agents. About 90 sorbicillinoids have been reported in the past few decades. This mini-review aims to briefly summarize their occurrence, structures, and biological activities.

1. Introduction

Sorbicillinoids (also called vertinoids) belong to hexaketide metabolites in which the cyclization has taken place on the carboxylate terminus [1]. They have highly diverse bioactivities and have been isolated from either marine [2,3,4] or terrestrial fungi [5,6,7]. Many of them possess elaborate bicyclic or tricyclic systems that appear to arise from the oxidative dearomatizaton and subsequent dimerization/trimerization of sorbicillin (5). The presence of the C1’–C6’ sorbyl sidechain is another structural feature of these compounds. The term “sorbicillinoid” has come to encompass the family as a whole and generally refers to any compound that contains the carbon skeleton of sorbicillin.
Since first reported in 1948 by Cram et al., sorbicillinoids have been extensively studied [8,9]. In 2011, Harned and Volp reviewed the structures of 62 sorbicillinoids [1]. Since then, many new members of this family were isolated and great progress has been made [4,10,11,12,13]. According to the structural features, sorbicillinoids can be divided into four groups: monomeric sorbicillinoids, bisorbicillinoids, trisorbicillinoids, and hybrid sorbicillinoids. Biosynthesis and chemical synthesis have been extensively studied and reviewed [1,11,14,15,16,17]. In this mini-review, we focus on the occurrence and biological activities of sorbicillinoids, and 28 additional sorbicillinoids were added on the basis of the previous review [1].

2. Occurrence

Sorbicillinoids have a diverse distribution in fungi (Table 1, Table 2, Table 3 and Table 4). Accordingly, their structures are shown in Figure 1, Figure 2, Figure 3 and Figure 4. In total, about 90 sorbicillinoids have been isolated, and they were found mainly in terrestrial fungi, which contained nine genera, namely Acremonium, Aspergillus, Clonostachys, Emericella, Penicillium, Phaeoacremonium, Scytalidium, Trichoderma, and Verticillium, and partly in marine fungi that included five genera (i.e., Paecilomyces, Penicillium, Phialocephala, Trichoderma and Trichothecium). All these fungi belong to ascomycetes.
Table 1. Occurrence of the monomeric sorbicillinoids (1–30) in fungi.
Table 2. Occurrence of the bisorbicillinoids (31–60) in fungi.
Table 3. Occurrence of the trimeric sorbicillinoids (61–65) in fungi.
Table 4. Occurrence of the hybrid sorbicillinoids (66–90) in fungi.
Figure 1. Structures of the monomeric sorbicillinoids (1–30) isolated from fungi.
Figure 2. Structures of the bisorbicillinoids (31–60) isolated from fungi.
Figure 3. Structures of the trimeric sorbicillinoids (61–65) isolated from fungi.
Figure 4. Structures of the hybrid sorbicillinoids (66–90) isolated from fungi.

2.1. Monomeric Sorbicillinoids

To date, 30 monomeric sorbicillinoids (Table 1 and Figure 1) have been isolated from Clonostachys, Emericella, Penicillium, Phaeoacremonium, Phialocephala, Scytalidium, Trichoderma, Trichothecium and Verticillium species.
Sorbicillinol (1) was found to be highly reactive and it was the biosynthetic precursor of the other sorbicillinoid family members [11].
Sorrentanone (=3-hydroxy-2,5-dimethyl-6-(1′-oxo-2′,4′-dienylhexyl)-1,4-benzoquinone, 26) was the benzoquinone structure of sohirnone B (8), meaning that it was imagined arising from the oxidation of sohirnone B (8) [5,18]. Similarly, 2-(2′,3′-dihydrosorbyl)-3,6-dimethyl-5-hydroxy-1,4-benzoquinone (25) was the benzoquinone of sohirnone C (15) [5,19].

2.2. Bisorbicillinoids

Bisorbicillinoids are also called dimeric sorbicillinoids, which consist of two sorbicillinoid monomers (Table 2), whose structures are shown in Figure 2. Up to now, 30 bisorbicillinoids have been isolated from fungi. These compounds are mainly distributed in the genera Acremonium, Aspergillus, Clonostachys, Penicillium, Phialocephala, Trichoderma, Trichothecium and Verticillium.

2.3. Trisorbicillinoids

Trisorbicillinoids are also called trimeric sorbicillinoids. Up to date, only five trimeric sorbicillinoids have been isolated from marine fungi (i.e., Penicillium sp. F23-2 and Phialocephala sp. FL30r) (Table 3 and Figure 3). Among them, sorbicillamine E (65) was a compound containing N element [10].

2.4. Hybrid Sorbicillinoids

Hybrid sorbicillinoids are proposed to be derived from either a Diels-Alder or a Michael reaction of a monomeric sorbicillinoid diene and a second non-sorbicillinoid dienophile. About 25 hybrid sorbicillinoids have been isolated from fungi so far.
The structure of sorbicillamine A (78) was a tentative assignment for the C-2/C-7 unit, which might exist as either enol or keto tautomers, and they were interconverting on the NMR timescale in solution [10].
Compound 73 from an intertidal marine fungus Paecilomyces marquandii was an unnamed sorbicillinoid urea [57]. Chloctanspirones A (74) and B (75) containing chlorine were isolated from Penicillium terrestre derived from a marine sediment. The differences between them were their absolute configuration at C-19 [58]. Similarly, both sorbicatechols A (76) and B (77) were isolated from the marine sediment-derived fungus Penicillium chrysogenum PJX-17, and their differences were the absolute configuration at C-7 [59].
Unnamed urea (73), sorbicillamine A (78), sorbicillactone A (85), and sorbicillactone B (86) were a class of N-containing compounds [10,21,57]. Interestingly, the N-containing sorbicillinoids including dimeric sorbicillamines D (39), B (40), C (41), and trimeric sorbicillamine E (65) were all isolated from marine fungi (Table 2, Table 3 and Table 4). Except urea 73 from the genus Paecilomyces, others were isolated from the genus Penicillium.

3. Biological Activities

3.1. Cytotoxic Activity

Many sorbicillinoids were screened to have cytotoxic activities, which are summarized in Table 5. (2S)-2,3-Dihydro-7-hydroxy-6,8-dimethyl-2-[(E)-prop-1-enyl]-chroman-4-one (21) and (2S)-2,3-dihydro-7-hydroxy-6-methyl-2-[(E)-prop-1-enyl]-chroman-4-one (22) displayed significant activities against the human breast cancer cell line MCF-7 with IC50 values of 9.51 and 7.82 μg/mL, respectively, and 2′,3′-dihydrosorbicillin (13) showed moderate cytotoxicity against various human cancer cell lines (colon cancer cell line Lovo, hepatic cancer cell line Bel-7402, lung cancer line A549, nasopharyngeal carcinoma cell lines CNE1, CNE2, KB and SUNE1) with IC50 values ranging from 9.19 to 21.93 μg/mL [4].
Table 5. Cytotoxic activity of the screened sorbicillinoids from fungi.
5′-Formyl-2′-hydroxyl-4′-methoxy-(E,E)-sorbophenone (10) showed cytotoxic activity on OSU-CLL (lymphocytic leukemia) cell lines with IC50 value of 3.1 µM at 48 h, on MDA-MB-435 (melanoma) and SW-620 (colon) cell lines with IC50 values of 1.5 and 0.5 µM at 72 h, respectively. Similarly, 1-(2′-hydroxy-4′-methoxy-5′-methylphenyl)-E,E-2,4-hexadien-1-one (9) on MDA-MB-435 and SW-620 cell lines with IC50 values of 65.2 and 15.1 µM, scalbucillin B (12) on MDA-MB-435 and SW-620 cell lines with IC50 values of 67.9 and 16.0 µM, and 5′-formyl-2′-hydroxy-4′-methoxy-(E)-4-hexenophenone (18) on MDA-MB-435 and SW-620 cell lines with IC50 values of 2.3 and 2.5 µM at 72 h, respectively [12].
(E)-6-(2,4-Dihydroxyl-5-methylphenyl)-6-oxo-2-hexenoic acid (23) and 6-(2,4-dihydroxyl-5-methylphenyl)-6-oxohexanoic acid (24) from a saline lands-derived fungus Trichoderma sp. showed cytotoxic effects on P388 cell line with IC50 values of 72.8 and 44.5 μM, and on HL-60 cell line with IC50 values of 52.5 and 81.2 μM, respectively [6].
Dihydrotrichodermolide (56) and dihydrodemethylsorbicillin (17) displayed cytotoxic effects against P388 cell line (IC50 values of 11.5 and 0.1 μM, respectively) and K562 cell line (IC50 values of of 22.9 and 4.8 μM, respectively) [36].
Chloctansprirone A (74) was active against HL-60 and A549 cell lines with IC50 values of 9.2 and 39.7 μM, respectively. Chloctansprirone B (75) showed relatively weak activity against HL-60 cells with IC50 value of 37.8 μM [58].
By comparing the structure-activity relationships of the compounds, the sorbyl sidechain was very important. Sorbicillinoids with their C2′-C3′ double bond being reduced were less active. For example, sorbicllin (5) showed significant inhibitory activity on HeLa and HepG2 cells with IC50 values of 1.6 and 27.2 μM, respectively. On the contrary, 2′,3′-dihydrosorbicillin (13) with the C2′-C3′ double bond being reduced showed less activity on HeLa and HepG2 cells with IC50 values of 7.4 and 44.4 μM, respectively. The same phenomena were observed for the compounds 6-demethylsorbicillin (7) vs. sohirnone A (14) [27], bisvertinolone (34) vs. 10,11-dihydrobisvertinolone (36) [27], and 5′-formyl-2′-hydroxyl-4′-methoxy-(E,E)-sorbophenone (10) vs. 5′-formyl-2′-hydroxy-4′-methoxy-(E)-4-hexenophenone (18) [12].

3.2. Antimicrobial Activity

Some sorbicillinoids exhibited antimicrobial activities that are shown in Table 6. 5′-Formyl-2′-hydroxyl-4′-methoxy-(E,E)-sorbophenone (10) and 5′-formyl-2′-hydroxy-4′-methoxy-(E)-4-hexenophenone (18) displayed strong antifungal activity on A. niger with MIC values of 0.05 and 0.04 μg/mL (0.20 and 0.16 μM), respectively, much more potent than the positive control (amphotericin B, MIC value of 31 μg/mL). Scalbucillin B (12) showed an MIC value of 0.60 μg/mL (2.42 μM) against Aspergillus niger. Considering the potent antimicrobial activity, a hemolytic assay toward sheep red blood cells in vitro was carried out to assess the toxicity of these compounds (10, 12, 18). They showed a similarly low toxicity on sheep red blood cells, which indicated the promising safety for their potential application as the anti-Aspergillus agents [12].
Table 6. Antimicrobial activity of the screened sorbicillinoids from fungi.
Dihydrotrichodimerol (44) and tetrahydrotrichodimerol (45) exhibited strong antibacterial activity on Bacillus megaterium with MIC values of 25 and 12.5 μg/mL, respectively. Dihydrotrichodimer ether A (59) and dihydrotrichodimer ether B (60) had strong antibacterial activity on Escherichia coli with MIC values of 25 and 50 μg/mL, respectively. Furthermore, dihydrotrichodimer ether B (60) showed preferable antibacterial activity against Ballus subtilis with MIC value of 50 μg/mL [13].

3.3. Antiviral Activity

Sorbicatechols A (76) and B (77) from the marine-derived fungus Penicillium chrysogenum PJX-17 showed potent antiviral activity against influenza A virus (H1N1) with IC50 values of 85 and 113 μM, respectively (ribavirin as the positive control with IC50 value of 84 μM) [59].
Sorbicillactone A (85) from a sponge-derived fungus Penicillium chrysogenum displayed anti-HIV activity. It protected human T lymphocytes (H9 cells) against the cytopathic effect of HIV-1 in the concentration range of 0.3 and 3.0 μg/mL [21]. This hybrid sorbicillinoid was considered to be a potential inhibitor to VP40 matrix protein of the Ebola virus [63].

3.4. Antioxidant Activity

Active oxygen species cause many diseases such as atherosclerosis, inflammation, ischemia-reperfusion injury, rheumatioid arthritis and central nervous diseases. Furthermore, senility, cancer initiation and progression are also believed to involve active oxygen species [64,65]. Thus, it is expected that the effective antioxidant agents may prevent the onset and development of these diseases. Some sorbicillinoids exhibited obviously antioxidant activity. The DPPH radical scavenging activity of the sorbicillinoids isolated before 2011 was well summarized [1]. After 2011, only one sorbicillinoid JBIR-124 (81) from Penicillium citrinum Sp1080624G1f01 was screened to have DPPH radical scavenging activity with IC50 value of 30 µM [62].

3.5. Other Biological Activities

Other biological activities of the sorbicillinoids are shown in Table 7. Dihydrotrichodimerol (44) and bislongiquinolide (=bisorbibutenolide=trichotetronine, 49) from Trichoderma citrinoviridev influenced aphid feeding preferences [48]. Isobisvertinol (38) from Aspergillus sp. FKI-1746 inhibited lipid droplet accumulation in macrophages [40].
Table 7. Other biological activities of the screened sorbicillinoids from fungi.
In addition, dihydrotrichodimerol (44) from an unidentified fungus activated peroxisome proliferator-activated receptor γ (PPAR γ) with an ED50 value of 80 ng/mL [50]. Bisvertinolone (34) from Verticillium intertextum inhibited the biosynthesis of β-l,6-glucan [42].
Trichodimerol (=MS-182123, 42) from Penicillium chrysogenum strain V39673 inhibited the production of tumor necrosis factor-α (TNF-α) by macrophages (IC50 value of 200 ng/mL) and monocytes (IC50 value of 200 ng/mL) [46]. Subsequently, trichodimerol was screened to show an inhibitory effect on lipopolysaccharide-induced eicosanoid secretion in THP-1 human monocytic cells [66].
6′-Hydroxyoxosorbicillinol (4) showed inhibition on soybean lipoxygenase activity with an IC50 value of 16 µM, about 10 folds higher than oxosorbicillinol (3). 6′-Hydroxyoxosorbicillinol (4) also exhibited prostaglandin D2 and leukotriene B4 release suppression activity with IC50 values of 10 and 100 µM, respectively [22].
Sorbiterrin A (79) showed moderate acetylcholinesterase (AChE) inhibitory effect with IC50 value of 25 µg/mL [61].

4. Conclusions

About 90 sorbicillinoids have been isolated from terrestrial and marine ascomycetous fungi in the past few decades. Some of them exhibited promising bioactivities, especially cytotoxic, antioxidant, antimicrobial, and antiviral activities. In recent years, more and more new members of sorbicillinoids have been isolated. All these sorbicillinoids could be the rich resources of biologically active substances with significant medicinal and agricultural potential.
The biosynthesis studies of sorbicillinoids have been carried out [11,14,15,16,17] and well summarized [1]. Sorbicillinol (1) has been hypothesized as a precursor of most sorbicillinoids that were biosynthesized by polyketide synthases (PKs) [14]. In addition, the PKS gene cluster containing SorbA, SorbB and SorbC has been characterized for sorbicillin (5) biosynthesis, and sorbicillinol (1) was proved as a key intermediate [11]. The extensive 13C enrichment studies carried out by Abe and co-workers have unequivocally demonstrated that many of biosynthetic hypotheses of sorbicillinoids are correct [14,15,16,17]. There are still some uncertainties. Furthermore, the specific polyketide synthases in the biosynthetic pathway of sorbicillinoids in fungi have not been characterized. Chemical syntheses of sorbicillinoids have attracted pharmaceutical chemists as they have potential applications in the agriculture, pharmaceutical and food industries. Some sorbicillinoids such as sorbicillin (5), vertinolide (28), epoxysorbicillinol (2), and trichodimerol (=MS-182123, 42) have been synthesized successfully, and well summarized [1].
In most cases, biological activities, structure-activity relations, and mode of action of sorbicillinoids have been investigated based on in vitro studies or animal models. Few studies have been performed at the level of clinical trials in patients. Future studies should be emphasized on the improvement in methodological quality and warrant further clinical research on the effects of these compounds. The applications of sorbicillinoids as antitumor agents, antimicrobials, antivirus agents and antioxidants, as well as their underlying bioactivities, have led to considerable interest within the pharmaceutical community and health-care industry. With a good understanding of the biosynthetic pathways of some sorbicillinoids, we can not only increase outputs of the bioactive sorbicillinoids but also block biosynthesis of some harmful sorbicillinoids by specific interferences.

Acknowledgments

This work was co-financed by the grants from the National Natural Science Foundation of China (31271996 and 31471729), and the Hi-Tech R&D Program of China (2011AA10A202).

Author Contributions

Jiajia Meng performed bibliographic research, drafted and corrected the manuscript. Xiaoxiang Fu, Xiaohan Wang, Dan Xu and Xuping Zhang retrieved literature, participated in the discussions and supported manuscript corrections. Daowan Lai reviewed the manuscript and helped to revise it. Ligang Zhou and Guozhen Zhang conceived the idea, designed the review structure, supervised manuscript drafting, and revised the manuscript. All authors read and approved the final manuscript.

Conflicts of Interest

The authors declare no conflict of interest.

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Simultaneous Determination of Purpurin, Munjistin and Mollugin in Rat Plasma by Ultra High Performance Liquid Chromatography-Tandem Mass Spectrometry: Application to a Pharmacokinetic Study after Oral Administration of Rubia cordifolia L. Extract
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