Bioactive natural products derived from mangrove-associated microbes

Jing Xu *
Key Laboratory of Protection and Development Utilization of Tropical Crop Germplasm Resources, Ministry of Education, College of Material and Chemical Engineering, Hainan University, Haikou 570228, P. R. China. E-mail: happyjing3@163.com; Fax: +86 898 6627 9010; Tel: +86 898 6627 9226

First published on 19th November 2014

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Jing Xu

Jing Xu obtained her BS and MS degrees from Hainan University. In 2006, she began her doctoral research with Professor Huashi Guan at the College of Medicine and Pharmaceutics, Ocean University of China. In 2007, she continued with her doctoral research in a group working with Professor Peter Proksch and received her PhD degree in 2010 at Heinrich-Heine-Universität Düsseldorf, Germany. She joined the faculty at Hainan University after her graduation where she is currently an Associate Professor of Pharmaceutical Chemistry. Simultaneously, she undertook a postdoctoral appointment at Nanjing University, with Professor Renxiang Tan from 2011 to 2014. Her research interests are focused on natural products originating from endophytic microbes and medicinal plants.

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1. Introduction

Microorganisms from special ecological niches such as the mangrove endosymbionts are a rich source of diverse and structurally unique bioactive natural products. Microbes inhabiting mangrove ecosystems adapt to frequent and sporadic environmental changes, including high salinity, low oxygen, nutrient limitation, tidal gradients, high temperatures, excessively high light, and drought.¹ The warm and damp conditions result in an active microbial community, which can act as an effective selector for metabolic pathway adaptations via generation of unique functional metabolites of pharmaceutical importance.

Mangrove forests are complex ecosystems that harbor diverse groups of microorganisms including actinomycetes, bacteria, fungi, cyanobacteria, microalgae, macroalgae and fungus-like protozoa. In the tropical mangrove microbial community, bacteria and fungi constitute 91% of the total microbial biomass, whereas algae and protozoa represent only 7% and 2%, respectively. Although the mangrove ecosystem has extensive microbial diversity, culture-dependent technologies reveal only a small percentage (<1%) of the microbial community while 99% of the microorganisms remain undiscovered. Among the isolated microbes, less than 5% of species have been presently chemically estimated, and these include the actinomycetes, bacteria and fungi. The advent of modern techniques provides the opportunity to find novel metabolites.²

Mangrove associated microbial natural products have been the subject of several review articles. Advances in the chemistry and bioactivity of fungi from mangroves have been reviewed periodically in Natural Product Reports by Blunt and his co-workers.^3,4 Wang et al. reviewed the studies on structure and bioactivity of metabolites isolated from mangrove-derived fungi in the South China Sea.⁵ Prof. Proksch' group compiled a comprehensive review detailing a decade of studies on potential of mangrove-derived endophytic fungi as promising bioactive natural products.^6,7 Our previous review discussed the role of these endophytic fungi as a major source of antimicrobial agents. These fungi produce a wide range of medicinal compounds, including antitumor, neuroprotective, antioxidant, anti-AChE, anti-BK_Ca channel agents, and 348 molecules were discovered before 2011.⁸

However, 464 new metabolites have been discovered recently; therefore, we describe here the source, chemistry, and biology of the newly discovered biomolecules from the mangrove-associated microbes. We also summarize the chemical synthesis and the biosynthetic relationship of metabolites. All relevant studies focusing on known secondary metabolites in terms of bioactivity, the source of the microorganism, and the location of collection are examined, and particular emphasis is given to their potential use as drug leads. The running titles are presented in the following order: actinomycetic, bacterial, and fungal producers with structures classified within a biogenetic context as polyketides, terpenes, and nitrogenated compounds. Bioassays showed that the antitumor, anti-influenza A H1N1, anti-enzyme, anti- or activate-subintestinal vessel plexus and brine shrimp lethality activities were the most notable bioactivities of secondary metabolites isolated during 2011–2013. Possible biogenetic relationships between several alkaloids, quinones, phenols, lactones, sesquiterpenes, sesterterpenoids, and meroterpenes are discussed. The biomacromolecules originating from the title microbes were not within the scope of this review. The Metabolites Name Index in conjunction with the Microbial and Host Source Index, the Bioactivity Index and the Leading References on isolation in the accompanying tables, will help understand the fascinating chemistry and biology of naturally occurring mangrove-associated microbial metabolites.

2. Actinomyces-derived molecules

Due to the high rediscovery rate of known compounds from Actinomycetes, there has been a renewed interest in the development of new antimicrobial agents from this species. These compounds can help combat the increasing number of multidrug-resistant human pathogens.⁹ Mangrove-derived actinomycetes are a potentially vast resource of structurally diverse natural products with unusual biological activity. Streptomyces are Gram-positive bacteria known for the production of an enormous variety of biologically active secondary metabolites, including antibiotics, immunosuppressants, and anticancer agents and have been become the focus of antibiotic research in the past three years.

2.1. Terpenoids

Eudesmene sesquiterpenes are proposed to be originated from further cyclization of the monocyclic germacranes.¹⁰ They are most abundant as eukaryotic secondary metabolites and may be referred to as selinanes, commonly metabolized by a variety of plants, such as Inula japonica,¹¹ Blumea balsamifera,¹² and Nectandra cissiflora.¹³ The only examples from prokaryotes are the recently described selina-4(14),7(11)-diene-8,9-diol from a marine Streptomyces sp.;¹⁴ and 1,6,11-eudesmanetriol and 11-eudesmene-1,6-diol from an endophytic Streptomyces sp. of Drymaria diandra.¹⁵ Five new members of this family, kandenols A–E (1–5), were characterized from a culture filtrate of endophytic Streptomyces sp. HKI0595 isolated from Kandelia candel (L.) (Xiamen, Fujian, China) using an HPLC-MS hyphenated system. The configuration of these eudesmenes was rigorously established by a combination of the Mosher method and comparison of CD spectra with α-rotunol and β-rotunol. Hydroperoxide moieties are relatively rare in compounds 3 and 4. Metabolite 5 is the first actinomycete agarofuran, which belongs to an important group of antibiotics. Unfortunately, none of these sesquiterpenes exhibited any cytotoxicity against the 12 selected human cell lines tested. However, weak to moderate antimicrobial activities were detected against Bacillus subtilis ATCC 6633 and Mycobacterium vaccae IMET 10670, with MIC values ranging from 12.5–50 μg mL⁻¹.¹⁶

2.2. Nitrogenated compounds

Indole terpenoids encompass a highly diverse group of natural products, including infamous psychotropic agents such as lysergic acid derivatives, the aphrodisiac yohimbine, and the potassium channel blockers paxilline and lolitrem. A remarkable fact about this multifarious class is that practically all indole terpene alkaloids have been isolated from plants and fungi. Further work on the aforementioned Streptomyces sp. HKI0595 endophyted in K. candel and another endophyte Streptomyces sp. GT2002/1503 associated in Bruguiera gymnorrhiza revealed five new pentacyclic indolosesquiterpene congeners, xiamycin A (6) and its methyl ester (7), xiamycin B (8), the seco-derivative indosespene (9), and the novel bridged spiro compound sespenine (10) by the same research team.^17,18 Their most likely biosynthetic pathway and interrelationship are proposed based on the heterologous gene expression and mutational analysis as shown in Scheme 1.¹⁹ A broad bioactivity screen revealed that compound 6 was moderately active against HIV, specifically blocked R5, but had no effects on X4 tropic HIV-1 infection. Compound 7 exhibited potential cytotoxicity compared with 6 in a modified propidium iodide assay, with IC₅₀ values of 10.13 μM. Compound 8–10 showed moderate to strong antimicrobial activities in agar diffusion assays against several bacteria, including methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus faecalis; however, these compounds did not show cytotoxicity against human tumor cell lines. These rare endophyte metabolites likely play an ecological role in their habitat because their diverse antiviral, antibacterial, and antifungal activities may contribute to the antibiotic reservoir of the mangrove plants.¹⁸ It is intriguing that these prokaryotes are endophytes producing typical plant metabolites. A unique diazaphenanthrene alkaloid, named 1-N-methyl-3-methylamino-[N-butanoic acid-3′-(9′-methyl-8′-propen-7′-one)-amide]-benzo[f][1,7]naphthyridine-2-one (11) and a known metabolite N-[[3,4-dihydro-3S-hydroxy-2S-methyl-2-(4′R-methyl-3′S-pentenyl)-2H-1-benzopyran-6-yl]carbonyl]-threonine (12) were isolated from Streptomyces albogriseolus and Streptomyces xiamenensis, respectively. Both of these compounds were obtained from mangrove sediments collected in the national mangrove reserve in Fujian province of China. A bioassay disclosed that the compound 12 inhibited the proliferation of human lung fibroblasts (WI26); blocks adhesion of human acute monocytic leukemia cells (THP-1) to a monolayer of WI26 cells; and reduces the contractile capacity of WI26 cells in three-dimensional free-floating collagen gels.^20,21 The total synthesis of 11 was accomplished by coupling the tricyclic heteroaromatic carboxylic acid with the chiral unsaturated amino ketoacid to yield a fused tricyclic heteroaromatic system as shown in Scheme 2 and the absolute configuration of 11 was firstly determined.²² A new benzamide, 3-hydroxyl-2-N-iso-butyryl-anthranilamide (13), together with two known benzamides (14, 15) and three known quinazolines (16–18), was isolated from a mangrove actinomycetes Streptomyces sp. no. 061316 isolated from mangrove soils (Wenchang, Hainan, China). Although the extract from which it was isolated displayed in vitro inhibitory caspase-3 activity, the pure natural products only 14 and 18 were found to be moderately active with IC₅₀ values of 32 and 36 μM, respectively.²³ Several studies have demonstrated that Streptomyces is a successful source of bioactive benzoxazole metabolites, such as antitumor agents UK-1 (ref. 24) and nataxazole,²⁵ antibiotics A33853 (ref. 26) and caboxamycin.²⁷ An antitumour benzoxazole derivative AJI956 (19), originally obtained from the actinomycete strain Streptomyces sp., was purified from Streptomyces sp. A1626 in Kandelia candel.²⁸ Micro-broth dilution assay disclosed its additional strength in moderating antifungal activity against fungal strains Candida albicans ATCC90028, Cryptococcus neoformans SLA1017 and Aspergillus fumigatus SIA1524, with IC₅₀/MIC values of 0.78/1.25, 1.5/2.5, and 15/20 μg mL⁻¹. Halogenation was reported to be an important feature for the bioactivity of a large number of distinct natural products. Chlorination was the most frequently found modification, followed by bromination, while iodination and fluorination are rare in nature.²⁹ Using PCR-based genetic screening techniques on mangrove sediments, 163 strains of actinomycetes were isolated and investigated for their potential to produce halogenated metabolites. A previously known antibiotic, enduracidin (20), was identified in the mangrove-derived Streptomyces atrovirens MGR140.^30,31

3. Bacterial metabolites

Information on bacterial strains, hosts, natural products, their biological activities, and relevant articles is included in Table 1. A predominant focus of natural products study of mangrove-associated bacteria has been on species of the genus Bacillus. However other bacteria, such as Gram-negative Erythrobacter have also proven to be an additional source of biologically and chemically interesting natural products. Chemical examination of an extract from an Erythrobacter sp. isolated from mangrove sediments yielded erythrazoles A (21) and B (22). The erythrazoles are of mixed biosynthetic origin containing a tetrasubstituted benzothiazole, an appended diterpene side chain, and a glycine unit. Based on the structural analysis, formation of the benzothiazole moiety was proposed to include a series of well precedented steps found in ubiquinone biosynthesis, i.e. prenylation, decarboxylation, hydroxylation, methylation, oxidation, and cyclisation. Their most likely biosynthetic pathway and interrelationship are shown in Scheme 3. Compound 21 is cytotoxic to a panel of non-small cell lung cancer (NSCLC) cell lines, with IC₅₀ values of 1.5, 2.5, and 6.8 μM against H1325, H2122, and HCC366, respectively.³² This encouraged subsequent efforts to investigate other bacteria that were not necessarily scarce in nature, but were rarely ever brought into culture and study.

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4. Fungal metabolites

Mangrove-associated fungi produce a larger number of secondary metabolites compared to any other mangrove-derived microbes, especially the endophytic fungi.⁸ Many of these fungi are capable of synthesizing bioactive compounds that may contribute to their adaptation to harsh environmental factors such as predation and microbial infection during long co-evolution. An ever-increasing number of compounds are being reported from fungi associated with mangrove plants and soils. Some of these compounds have been shown to have a broad spectrum of biological activity, and they can be grouped into several categories, including isocoumarins, chromones, flavonoids, quinones, xanthones, phenols and phenolic acids, lactones, terpenoids, nitrogenated compounds, steroids, etc. Table 2 lists the hosts, natural products, biological activities, and articles related to these fungi and their products.

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4.1. Polyketides

4.2. Terpenoids

4.3. Nitrogenated compounds

4.4. Steroids

Sterols with a 5,8-epidioxy moiety are well-known metabolites from marine organisms, such as corals, sponges, and mangrove-derived fungi, as well as terrestrial macrofungi.^234–238 In contrast, sterols with the 5,9-epidioxy motif have been rarely reported. So far, only five 5,9-epidioxy-sterols have been isolated from several edible mushrooms; however, none of them were extracted from mangrove organisms. Nigerasterols A and B (456, 457) representing the first 5,9-epidioxy-sterols of mangrove origin were characterized from Aspergillus niger MA-132 isolated from Avicennia marina. Both 456 and 457 displayed potent activity against tumor cell lines HL60 (IC₅₀ 0.30/1.50 μM) and A549 (IC₅₀ 1.82/5.41 μM) in a preliminary bioassay. The absolute configuration of compound 456 was determined by the application of a modified version of Mosher's method.²³² Apart from a known neuritogenic compound NGA0187 (458), compounds 3β,5α-dihydroxy-(22E,24R)-ergosta-7,22-dien-6-one (459), 3β,5α,14α-trihydroxy-(22E,24R)-ergosta-7,22-dien-6-one (460) were also purified from the culture of Aspergillus terreus (no. GX7-3B) obtained from Brugnieria gymnoihiza. Metabolite 458 induced significant neurite outgrowth in PC12 cells and was found to show potent inhibitory activity against MCF-7, A549, HL-60 and KB cell lines. MCF-7, A549, HL-60 and KB cell lines had IC₅₀ values of 4.98, 1.95, 0.68, 1.50 μM, respectively.^61,239,240 The 3β-hydroxy sterols and their oxygenated analogues include a large group of metabolites found in lower terrestrial organisms, marine organisms, lichens and fungi.²⁴¹ Several ubiquitous microbial secondary metabolites such as ergosta-4,6,8(14),22-tetraen-3-one (461) were isolated from Pestalotiopsis clavispora from the stem of Bruguiera sexangula.⁸⁷ The sterol 7,22-(E)-diene-3β,5α,6β-triol-ergosta (462) was discovered using a mixed fermentation technique on unidentified mangrove endophytic fungal strains Kandelia candel endophytic K38 and Eucheuma muricatum endophytic E33.³⁷

5. Concluding remarks

Mangrove-associated microbes continue to be the focus for much of natural products research that has been well documented. In this review, we systematically summarized the new findings regarding the chemistry and bioactivities of most natural products found in mangrove microbial ecosystems during the last three years. These include 464 naturally occurring small-biomolecules. The rate at which these metabolites have been discovered within the past three years has increased sharply (33%). Furthermore, they have contributed to increasing chemical diversity in the compounds discovered over the past twenty years. This increase is largely due to improvements in isolation procedures and structural analysis. These trends are shown graphically in Fig. 1, which compares outputs for 1989 through to Nov. 2010 with those for the recent three years. The compounds are shown according to their structural classification.

At the domain level, <5% of the species examined originated from the actinomyces or bacteria while the majority (>95%) originated from fungi. Actinomycetes are of special interests (4%) as they are known to produce chemically diverse compounds with an extraordinarily high proportion (60%) of their metabolites showing a wide range of biological activities. The endophytic fungi have been found to produce a significant number of interesting metabolites (>83%) with biologically active substances. The endophytic fungi have been found to produce a significant number of interesting metabolites >83% with 32% biologically active substances, occur in considerably higher numbers than those produced by rhizosphere soil or sediments microorganisms <12% but of 38% of bioactive substances. The high rate of inactive metabolite discovery in previous studies was probably because of bias in the screening programmes and limitations in analytical technology. It is noteworthy that Aspergillus, Penicillium, and Pestalotiopsis are predominant as producers of promising chemical diversity. Furthermore, they constitute 46% of the compounds reported, and if five other prolific genera such as Streptomyces, Acremonium, Phomopsis, Sporothrix, and Xylaria are considered, they account for nearly 68% of all of the metabolites. The remaining 26% are scattered across another 17 genera, and less than 6% of the metabolites are from unidentified microorganisms. Rhizophora apiculata (14%), rhizosphere soil and sediment (11%), Kandelia candel (10%), Bruguiera gymnoihiza (8%) and Rhizophora stylosa (6%) were considered to be the main sources of metabolic microbes. The emergence of plants native to China and Thailand as significant sources of new compounds may be of particular significance. Our last review discussed the problem of ambiguously described microorganisms; however, since then the ratio of ambiguous microbes and sources reported in the ensuing three years have declined dramatically, and most microbes are properly documented and characterized (Tables 1 and 2).

Some compounds intrigue the natural product researchers because of their unusual structures including the unusual 5/8/6/6 tetracyclic ring or 5/7/(3)6/5 pentacyclic sesterterpenoids asperterpenoid A (317), asperterpenols A (318) and B (319) from Aspergillus sp. Some metabolites have provided valuable access to novel hybrid chemotypes derived from different biosynthetic routes. These include NRPS, terpene, shikimate and polyketide mixed biosynthetic tetrasubstituted benzothiazole erythrazoles A (21) and B (22) from Erythrobacter sp., hybrid sesquiterpene-polyketide metabolites pestalotiopens A and B (336, 337) from Pestalotiopsis sp. JCM2A4. Among the 130 or so bioactive components presented in this review, several have fascinating bioactivities comparable to those of modern pharmacological products. These include the antitumor agents paeciloxocin A (179), sumalarins A–C (240–242), and merulin A and C (287, 289). Paeciloxocin A from Paecilomyces sp. exhibited strong cytotoxicity effects against the growth of hepG2 cell line at 1 μg mL⁻¹. Sumalarins A–C (240–242) from Penicillium sumatrense MA-92 showed potent cytotoxicity against some of the tested tumor cell lines, whereas merulin A and C (282, 284) were identified from an unidentified fungus XG8D isolated from the leaves of Xylocarpus granatum, which displayed significant cytotoxicity against human breast cancer line (BT474) with IC₅₀ values of 4.98 and 1.57 μg mL⁻¹, respectively. Merulin C 284 displayed promising activity in a rat aortic ring sprouting (ex vivo) and a mouse Matrigel (in vivo) assay. Anti-H1N1 agents such as isoaspulvinone E (232) from Aspergillus terreus Gwq-48 showed significant anti-influenza A H1N1 virus activities with IC₅₀ value of 32.3 μg mL⁻¹ and exhibited effective inhibitory activity against H1N1 viral neuraminidase (NA). Indole-diterpenoid alkaloids 398–400 and 402–408 from Penicillium camemberti OUCMDZ-1492 exhibited significant in vitro anti-H1N1 with IC₅₀ values of 6.6–89 μM, respectively. The compounds 417b, 420, 422–424, and 426 from Cladosporium sp. PJX-41 showed significant activities against the influenza virus A (H1N1) with IC₅₀ values of 82–89 μM, which is much more effective than ribavirin (IC₅₀ 113.1 μM). Anti-enzyme agents such as p-terphenyls 125–127 showed strong inhibitory effects against R-glucosidase with IC₅₀ values of 0.9, 4.9, and 2.5 μM, respectively. The compound 317 displayed strong inhibitory activity against Mycobacterium tuberculosis protein tyrosine phosphatase B (mPTPB) with an IC₅₀ value of 2.2 μM while compounds 318 and 319 strongly inhibited acetylcholinesterase (AChE) with IC₅₀ values of 2.3 and 3.0 μM, respectively. Arigsugacin I (338) from Penicillium sp. sk5GW1L showed potential anti-AChE activity with IC₅₀ values of 0.64 ± 0.08 μM. Compounds, 27, 46 and 439 from Phomopsis sp. were demonstrated to accelerate the growth of subintestinal vessel plexus (SIV) markedly, whereas phomopsis-H76 C (451) was shown to be a subintestinal vessel plexus (SIV) branch growth inhibitor. Strong brine shrimp lethality was detected by aniquinazolines A–D (429–432) from Aspergillus nidulans. MA-143 showed potent lethality with LD₅₀ values of 1.27, 2.11, 4.95 and 3.42 μM, respectively, which were over 40 times stronger than that of the positive control colchicines. This makes many of these compounds suitable candidates for drug discovery and will trigger groundbreaking synthesis studies of these compounds in the coming years.

Biogenetic hypotheses have become increasingly valuable in the screening of structurally related missing precursors/intermediates/products. Metabolites are biologically compatible with many living systems and often possess unique and useful biological activities, largely because their scaffolds are the result of evolutionarily significant selective pressures. Activation of these attenuated or silenced genes of biosynthetic pathways to obtain either improved titers of known compounds or new ones altogether has been the subject of particular interest. “One Strain Many Compounds” (OSMAC) approach has been popular towards the discovery of new metabolites. Consequently, the manipulation of biosynthetic pathways, epigenetic modifications (cytosporone R 150 from concomitant supplementation of Leucostoma persoonii), varying culture conditions (compounds 47–58 from Aspergillus tubingensis) and co-culturing two organisms together (compounds 221–227 from Pestalotiopsis sp. PSU-MA92/PSU-MA119) have been applied to stimulate the production of new compounds.

The anticancer drug taxol (316) was purified from Fusarium oxysporum of Rhizophora annamalayana. This drug implicated mangrove endophytes as a sustainable, economically feasible and alternative source of therapeutic compounds. The production of bioactive substances by mangrove microbes is directly related to the independent evolution of these microorganisms, which may have incorporated genetic information from their biotope and carry out certain functions. For example, austin-like derivatives 325–329 represent a class of compounds (identified from Emericella sp.) that are toxic to insects and play crucial ecological roles such as the capacity to protect its host plant against insect invaders. Thus, they contribute to a range of defense substances secreted by plants that can be further investigated. Interesting biotopes such as the mangrove microbial communities are especially productive since they accumulate a diverse array of bioactive compounds with novel scaffolds. As yet, the potential of this area remains virtually untapped. Substantial evidence now exists showing that in the long-term maintenance of the biodiversity profile, mangrove ecosystems can provide a valuable function in wave and storm surge attenuation, and erosion reduction. However, nowadays approximately one-third of the global cover of these ecosystems has been lost; this is particularly true in Southeast Asia. The most challenging goals concerning secondary metabolites are the elucidation of their true function in their native mangrove habitats and, closely associated with this, the identification of the physiological and ecological conditions that have led to the activation of secondary metabolism gene clusters. Many of the extensive areas of mangrove restoration throughout the world have cited expected ecosystem protection benefits, which will also support the continued provision of functional, diverse, inhabitated microbes. Multidisciplinary research and collaborative endeavors amongst biotechnologists, microbiologists, chemists and pharmacologists would result in the isolation of unusual or rare microorganisms that produce structurally interesting and biologically active molecules with potential use in medicinal and agricultural applications.

Acknowledgements

Co-Financed by grants of National Natural Science Foundation of China for Young Scholar (no. 81202456), Hainan Provincial Natural Science Foundation (no. 814285), Special Foundation for Modernization of Traditional Chinese Medicine of Hainan (ZY201429) and the programs for New Century Excellent Talents in University (NCET-13-0760) are gratefully acknowledged.

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