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Hillman, P.F.;  Lee, C.;  Nam, S. Microbial Natural Products with Wound-Healing Properties. Encyclopedia. Available online: https://encyclopedia.pub/entry/40203 (accessed on 01 September 2024).
Hillman PF,  Lee C,  Nam S. Microbial Natural Products with Wound-Healing Properties. Encyclopedia. Available at: https://encyclopedia.pub/entry/40203. Accessed September 01, 2024.
Hillman, Prima F., Chaeyoung Lee, Sang-Jip Nam. "Microbial Natural Products with Wound-Healing Properties" Encyclopedia, https://encyclopedia.pub/entry/40203 (accessed September 01, 2024).
Hillman, P.F.,  Lee, C., & Nam, S. (2023, January 16). Microbial Natural Products with Wound-Healing Properties. In Encyclopedia. https://encyclopedia.pub/entry/40203
Hillman, Prima F., et al. "Microbial Natural Products with Wound-Healing Properties." Encyclopedia. Web. 16 January, 2023.
Microbial Natural Products with Wound-Healing Properties
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This entry is adapted from the peer-reviewed paper 10.3390/pr11010030

Wound healing continues to pose a challenge in clinical settings. Moreover, wound management must be performed properly and efficiently. Acute wound healing involves multiple cell divisions, a new extracellular matrix, and the process of formation, such as growth factors and cytokines, which are released at the site of the wound to regulate the process. Any changes that disrupt the healing process could cause tissue damage and prolong the healing process. Various factors, such as microbial infection, oxidation, and inflammation, can delay wound healing. In order to counter these problems, utilizing natural products with wound-healing effects has been reported to promote this process. A natural product with medicinal properties, which contribute to alleviating these factors, can facilitate the wound-healing process and be developed as a future drug. Numerous research has investigated the wound-healing properties of natural products that contain antioxidant, anti-inflammatory, collagen promotion, and antibacterial properties. Various phytochemicals, including alkaloids, tannins, flavonoids, terpenoids, phenolic, essential oils, and saponin compounds, may contribute to the medicinal effects. Natural products, including phytochemicals, play an important role in wound healing due to these properties. 

natural products flavonoids quinones

1. Biosurfactant

The ability of biosurfactants to interact with modifying surfaces makes them surface-active compounds (SACs). In nature and biotechnology, these biomolecules serve different functions due to their physiological roles and physicochemical properties due to their amphiphilic nature and their production by different microorganisms. The benefits of SACs over synthetic surfactants include low toxicity, increased biodegradability, low critical micelle concentrations, and environmental acceptability [1][2][3].
Surfactin A (1, Figure 1) isolated from Bacillus subtilis was reported to promote wound healing and the inhibition effects of scars. Amid the healing process, 1 upregulated expression of hypoxia-inducible factor-1α (HIF-1α) and vascular endothelial growth factor. Moreover, it accelerated keratinocyte migration via the mitogen-activated protein kinase and factor nuclear-κB (NF-κB) signaling pathways, followed by the regulation of pro-inflammatory cytokine secretion and macrophage phenotypic exchange. In addition, 1 could heal the wound due to its antioxidant properties, with an IC50 = 0.55 mg/mL [4][5]. It also prevented scar tissue formation by inhibiting the expression of α-smooth muscle actin (α-SMA) and transforming growth factor (TGF-β).
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Figure 1. Chemical structures of surfactin A (1), BS glycolipid (2), rhamnolipid (3), and sophorolipid (4).
An in vitro study of a biosurfactant (BS) of a glycolipid nature (2, Figure 1), isolated from Bacillus licheniformis SV1, exhibited adequate cytocompatibility and increased 3T3/NIH fibroblast proliferation. An approach using a BS ointment in vivo stimulated re-epithelialization, fibroblast proliferation, and the faster deposition of collagen in skin excision wounds in rats, thereby demonstrating its potential to improve wound healing through transdermal delivery [6].
In a previous study, mice were treated with an ointment containing rhamnolipid (3, Figure 1) after creating severe wounds on their backs. The results of histopathological studies showed that 3 improved wound closure and collagenases, and it reduced inflammation by reducing the level of TNF-α without causing any negative skin reactions. There is evidence that dirhamnolipid therapy can alleviate scarring on the skin, as it has shown effects in rabbit ear hypertrophic scar models, with a depletion in α-SMA expression, type I collagen fibers, and scar elevation index scores [7].
By substituting human skin with an in vitro model of human dermal fibroblasts, a cell culture model was utilized to demonstrate the wound-healing capacity of sophorolipid (4, Figure 1), revealing that 4 affected the human skin fibroblast expression of elastase inhibition collagen I mRNA, with IC50 = 38.5 μg/mL. Additionally, an in vitro wound-healing evaluation in the human colorectal adenocarcinoma (HT-29) cell line showed a significant increase in collagenase-1 expression in HT-29 colorectal adenocarcinoma cells after treatment for 48 h with 4 [8][9].

2. Flavonoids

The flavonoid class of compounds possesses various biological functions, making them important sources of new pharmaceuticals, including those for treating skin wounds. The structure–activity relationship is one of the main factors that contributes to the pharmaceutical properties of flavonoids [10][11][12]. Their anti-inflammatory [13], antibacterial [14], antioxidant [15], and antifibrotic [16] properties depend largely on the presence of hydroxyl groups due to high hydroxylation.
Baicalin (5, Figure 2) is a flavone glycoside with anti-inflammatory, antiviral, and photoprotective properties [17]. Compound 5 blocks the pathological keratinocyte changes in psoriatic patients [18]. An antioxidant and anti-inflammatory effect may be responsible for the wound-healing properties of the baicalin nanohydrogel preparation. Moreover, 5 inhibits nitric oxide and tumor necrosis factor-α (TNF-α), which are both important elements in the inflammatory process [19]. Finally, 5 was found to exist in the endophytic fungus Spiropes sp. and played a major role in the pharmacological action of Scutellaria baicalensis [17][20].
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Figure 2. Chemical structures of baicalin (5), kaempferol (6), and quercetin (7).
Kaempferol (6, Figure 2) is known to inhibit cancer growth; reduce inflammation; promote antioxidant activity; and protect the heart, liver, and brain [21]. With a 1% w/w ointment concentration, 6 exhibited wound-healing activity in diabetic and non-diabetic rats. This wound-healing activity was studied utilizing incision and excision wound models [22]. According to both models, kaempferol showed crucial wound-healing activity, as indicated by the increase in the granulation tissue weight and hydroxyproline content in the incision wound model, as well as a reduction in the wound area, faster epithelialization, increased dry weight of the tissue, and increased hydroxyproline content in the excision wound model [23]. Moreover, 6 was found in many edible vegetables and the extract of the endophytic fungi Fusarium chlamydosporum from Tylophora indica [24][25][26].
Bioflavonoids such as quercetin (7, Figure 2) are known for their anti-atherosclerotic, anti-hypercholesterolemic, anti-hypertensive, anti-inflammatory, and anti-obesity properties [27]. Preclinical research has shown 7 to possess wound-healing properties [28][29]. A study by Jangde et al. evaluated quercetin’s wound-healing properties in vitro and in vivo. The results indicated that wound healing was significantly accelerated, and the wound termination time significantly decreased compared to the regular dosage forms. These results suggested that connectivity tissue disorders can be treated effectively as wound-healing approaches [29]. Quercetin was found in more than 20 plants [17]. Moreover, in terms of obtaining quercetin from bacteria, it was isolated for the first time from a cyanobacterium, Anabaena aequalis Borge [30].

3. Quinones

Biochemical pigments called quinones are established in several living organisms, including fungi, bacteria, a few animals, and higher plants. There are many forms of quinones in nature, such as naphthoquinones, benzoquinones, polycyclic quinones, and anthraquinones. 
A new antibiotic, MT81 (8, Figure 3), was isolated and purified from Penicillium nigricans culture media. It was found that 8 was a polyhydroxy anthraquinone, which exhibited antibacterial properties, along with an antiprotozoal effect toward Leishmania donovani promastigotes in vitro. Moreover, 8 was investigated for its wound-healing effect in mice. The result exhibited the healing effects of an 8 ointment on mice infected with pathogenic organisms, and it was comparable to the positive control, nitrofurazone. This indicates that the antimicrobial effect of 8 helps to heal infected wounds by inhibiting microorganisms [31].
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Figure 3. Chemical structures of MT81 (8), emodin (9), and hennotanic acid (10).
Emodin (9, Figure 3) is a natural anthraquinone derivative found in a wide variety of higher plants. Emodin obtained from microorganisms was first described as frangula-emodin, which was isolated from the fungus Dermocybe sanguinea Wulf [32][33][34]. In addition, 9 was identified as one of the pigmented products in the culture extracts of Penicillium brunneum Udagawa, Cladosporium fulvum Cooke, Penicillium avellaneum, Penicilliopsis clavariaeformis, Penicillium islandicum Sopp, Aspergillus wentii Wehmer, Aspergillus ochraceus Wilhelm, and Aspergillus cristatus [35][36][37][38][39][40][41][42]. Neuroprotective, anti-inflammatory, anticancer, antibacterial, anti-osteoporotic, hepatoprotective, antiviral, anti-allergic, and immunosuppressive properties are known to be associated with 9 [43]. Furthermore, the wound-healing activity of 9 using the excisional wound model in rats has been reported at dose levels of 100, 200, and 400 μg/mL [44].
Hennotannic acid (10, Figure 3), also known as lawsone, is an orange-red dye extracted from the leaves of Lawsonia inermis L., often known as the henna tree. However, Sarang et al. reported the production of 10 from an endophytic fungus, Gibberella moniliformis, isolated from the leaf tissues of Lawsonia inermis [45]. Moreover, 10 exhibited antibacterial, antifungal, antiparasitic, antitumor, and antiviral properties [46]. By using an excision and incision model, Mandawgade and Patil investigated the wound-healing effects of 10 at dose levels of 50 mg/kg (per oral) and 0.1 mg/kg (topical/ointment). Based on the result, 10 exhibited significant wound-healing activity in both models [47]. Another study on 10 also demonstrated crucial wound-healing activity in rodents [48].

4. Phenolic Acids

Polyphenol is usually found in plants and marine organisms. Since polyphenols possess antimicrobial, regenerative, and antioxidant properties, they have significant potential for application in wound treatment [49][50][51]. Besides their antimicrobial and antioxidant activity, polyphenols are also considered to be highly bioactive agents in wound dressings for acute wound treatment, thereby playing an important role in wound healing [49][52].
Chlorogenic acid (11, Figure 4) is an ester of caffeic acid with phenolic acid (quinic acid), established in twenty medicinal plants and twenty-nine fungal taxa, including Phomopsis, Colleterotrichum, Phoma, Alternaria, and Xylariales [17][20]. Moreover, 11 showed significant wound-healing activity in both in vivo and in vitro investigations [53][54]. A recent study demonstrated that 11 promotes wound closure and capillary tube formation, as well as enhanced wound closure with keratinocytes in vitro [53]. In addition, 11 has been shown to enhance collagen synthesis by upregulating TNF-α and TGF-β during wound healing. It may promote wound healing in excision wounds due to its antioxidative properties [54].
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Figure 4. Chemical structures of chlorogenic acid (11) and gallic acid (12).
Gallic acid (12, Figure 4) is a phenolic compound that can be found in plants, as well as nineteen endophytic fungal taxa [20]; 12 exhibits strong anti-inflammatory and antioxidant properties. During in vitro experiments, 12 accelerated keratinocyte and fibroblast migration and wound healing [55]. In addition, 12 enhanced the expression of TGF-β and inhibited the nuclear factor κB (NF-κB), along with the proliferation and maturation phase of wound healing [56].

5. Peptides

Acremonamide (13, Figure 5), a new cyclic depsipeptide obtained from Acremonium sp., was isolated in an ongoing effort to discover new marine-derived natural products with wound-healing effects [57]. It is known that species of the genus Acremonium produce various secondary metabolites, such as hydroquinones, diterpenes, isocoumarins, sesquiterpenes, peptides, benzophenones, and butanolides [58]. These fungal strains also produce cyclic depsipeptides, an interesting bioactive natural product [58][59][60][61]. In in vivo experiments using the human wound healing RT2 Profiler PCR array, adjustments in the wound-healing genes’ expression were screened to determine the mechanisms behind the wound-healing properties of 13. The result demonstrated, for the first time, that 13 increased keratinocyte and fibroblast motility, as well as COL1A2 and ACTC1 expression, thereby enhancing the wound-healing process [57].
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Figure 5. Chemical structures of acremonamide (13), chondramide A (14), jasplakinolide (15), and apratyramide (16).
Chondramide A (14, Figure 5) and its analogs isolated from a terrestrial myxobacterium, Chondramyces crocatus, were examined for the growth-inhibiting activity of actin cytoskeletons [62]. The actin cytoskeleton plays a significant role in wound healing—it allows actomyosin to contract, recruits repair machinery, and migrates cells [63]. By using highly purified recombinant actin from T. gondii, in vitro polymerization assays confirmed that both synthetic and natural products target the actin cytoskeleton, with EC50 values ranging from 0.3 to 1.3 μM. The results indicate that the chondramide treatment can prevent parasitic invasion and generate faster results than standard therapeutic agents such as pyrimethamine [64].
Other studies reported the wound-healing activity of jasplakinolide (15, Figure 5) and apratyramide (16, Figure 5) [65][66]. By binding to F-actin, 15 stabilized the actin filaments in vivo, leading to actin lumps and polynucleation, which are important in wound healing [65]. Moreover, 16, a natural product isolated from a cyanobacterium, has been described to exert wound-healing effects by inducing vascular endothelial growth factor A [66].

6. Triterpenoids

Terpenoids are plant-derived phytochemicals with a large variety of chemical structures derived from isoprene and usually have polycyclic structures. They are classified into monoterpenes, diterpenes, triterpenes, tetraterpenes, sesquiterpenes, and hemiterpenes, depending on the number of isoprene units in their structures. Triterpenes either have a tetracyclic or pentacyclic structure [67][68][69]. Among pentacyclic triterpenes, oleanane, lupane, and ursane derivatives exhibit anti-inflammatory, anticancer, antioxidant, antiviral, and cardioprotective activities. In contrast, tetracyclic triterpenes have mostly been studied for their cytotoxic and anticancer biological properties [70][71][72][73]. In recent years, systematic studies have examined the efficacy of triterpenes as wound healers. Based on the results of these studies, these phytocompounds have been displayed to promote wound healing by accelerating epithelialization and collagen formation and deposition, regardless of the wound type. Furthermore, their integration into various medicinal formulations is an effective option for wound management through their long-term delivery of active compounds. In conclusion, triterpenoids have been identified as an emerging class of wound care therapies [67][74].
Asiaticoside (17, Figure 6) is a triterpenoid saponin, which is found in Centella asiatica (L.), as well as in an endophytic fungus, Colletotrichum gloeosporioides, obtained from Centella asiatica (L.) [75][76]. Based on the ability of 17 to induce the development of granulation tissue and collagenase-induced epithelialization in rabbits, it was proven that 17 exhibits wound-healing properties [77]. In addition, 17 also induces type I collagen synthesis in human dermal fibroblast cells [78].
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Figure 6. Chemical structures of asiaticoside (17).

References

  1. Araujo, J.; Monteiro, J.; Silva, D.; Alencar, A.; Silva, K.; Coelho, L.; Pacheco, W.; Silva, D.; Silva, M.; Silva, L.; et al. Surface-Active Compounds Produced by Microorganisms: Promising Molecules for the Development of Antimicrobial, Anti-Inflammatory, and Healing Agents. Antibiotics 2022, 11, 1106–1123.
  2. Uzoigwe, C.; Burgess, J.G.; Ennis, C.J.; Rahman, P.K.S.M. Bioemulsifiers Are Not Biosurfactants and Require Different Screening Approaches. Front. Microbiol. 2015, 6, 245–250.
  3. Sharma, D.; Misba, L.; Khan, A.U. Antibiotics versus Biofilm: An Emerging Battleground in Microbial Communities. Antimicrob. Resist. Infect. Control. 2019, 8, 76–86.
  4. Zouari, R.; Moalla-Rekik, D.; Sahnoun, Z.; Rebai, T.; Ellouze-Chaabouni, S.; Ghribi-Aydi, D. Evaluation of Dermal Wound Healing and in vitro Antioxidant Efficiency of Bacillus Subtilis SPB1 Biosurfactant. Biomed. Pharmacother. 2016, 84, 878–891.
  5. Yan, L.; Liu, G.; Zhao, B.; Pang, B.; Wu, W.; Ai, C.; Zhao, X.; Wang, X.; Jiang, C.; Shao, D.; et al. Novel Biomedical Functions of Surfactin A from Bacillus subtilis in Wound Healing Promotion and Scar Inhibition. J. Agric. Food Chem. 2020, 68, 6987–6997.
  6. Gupta, S.; Raghuwanshi, N.; Varshney, R.; Banat, I.M.; Srivastava, A.K.; Pruthi, P.A.; Pruthi, V. Accelerated in Vivo Wound Healing Evaluation of Microbial Glycolipid Containing Ointment as a Transdermal Substitute. Biomed. Pharmacother. 2017, 94, 1186–1196.
  7. Shen, C.; Jiang, L.; Shao, H.; You, C.; Zhang, G.; Ding, S.; Bian, T.; Han, C.; Meng, Q. Targeted Killing of Myofibroblasts by Biosurfactant di-Rhamnolipid Suggests a Therapy against Scar Formation. Sci. Rep. 2016, 6, 37553–37563.
  8. Maeng, Y.; Kim, K.T.; Zhou, X.; Jin, L.; Kim, K.S.; Kim, Y.H.; Lee, S.; Park, J.H.; Chen, X.; Kong, M.; et al. A Novel Microbial Technique for Producing High-Quality Sophorolipids from Horse Oil Suitable for Cosmetic Applications. Microb. Biotechnol. 2018, 11, 917–929.
  9. Kwak, M.-J.; Park, M.-Y.; Kim, J.; Lee, H.; Whang, K.-Y. Curative Effects of Sophorolipid on Physical Wounds: In Vitro and in Vivo Studies. Vet. Med. Sci. 2021, 7, 1400–1408.
  10. Carvalho, M.T.B.; Araújo-Filho, H.G.; Barreto, A.S.; Quintans-Júnior, L.J.; Quintans, J.S.S.; Barreto, R.S.S. Wound healing properties of flavonoids: A systematic review highlighting the mechanisms of action. Phytomedicine 2021, 90, 153636–153651.
  11. Menezes, P.D.P.; Frank, L.A.; Lima, B.S.S.; de Carvalho, Y.M.B.G.; Serafini, M.R.; Quintans-Júnior, L.J.; Pohlmann, A.R.; Guterres, S.S.; Araújo, A.A.d.S. Hesperetin-loaded lipid-core nanocapsules in polyamide: A new textile formulation for topical drug delivery. Int. J. Nanomed. 2017, 12, 2069–2079.
  12. Sak, K. Intake of individual flavonoids and risk of carcinogenesis: Overview of epidemiological evidence. Nutr. Cancer 2017, 69, 1119–1150.
  13. Pushpavalli, G.; Kalaiarasi, P.; Veeramani, C.; Pugalendi, K.V. Effect of chrysin on hepatoprotective and antioxidant status in D-galactosamine-induced hepatitis in rats. Eur. J. Pharmacol. 2010, 631, 36–41.
  14. Bagher, Z.; Ehterami, A.; Safdel, M.H.; Khastar, H.; Semiari, H.; Asefnejad, A.; Davachi, S.M.; Mirzaii, M.; Salehi, M. Wound healing with alginate/chitosan hydrogel containing hesperidin in rat model. J. Drug Deliv. Sci. Technol. 2020, 55, 101379.
  15. Feng, Y.; Sanders, A.J.; Morgan, L.D.; Harding, K.G.; Jiang, W.G. Potential roles of suppressor of cytokine signaling in wound healing. Regen. Med. 2016, 11, 193–209.
  16. Chen, R.F.; Chang, C.H.; Wang, C.T.; Yang, M.Y.; Wang, C.J.; Kuo, Y.R. Modulation of vascular endothelial growth factor and mitogen-activated protein kinase-related pathway involved in extracorporeal shockwave therapy accelerate diabetic wound healing. Wound Repair Regen. 2019, 27, 69–79.
  17. Parasuraman, S.; Perumal, P. Wound Healing Agents from Natural Sources. In Wound Healing Research, 1st ed.; Kumar, P., Kothari, V., Eds.; Springer: Singapore, 2021; pp. 95–148.
  18. Bonesi, M.; Loizzo, M.R.; Menichini, F.; Tundis, R. Flavonoids in treating psoriasis. In Immunity and Inflammation in Health and Disease, 1st ed.; Chatterjee, S., Jungraithmayr, W., Bagchi, D., Eds.; Academic Press: Cambridge, MA, USA, 2018; pp. 281–294.
  19. Manconi, M.; Manca, M.L.; Caddeo, C.; Cencetti, C.; di Meo, C.; Zoratto, N.; Nacher, A.; Fadda, A.M.; Matricardi, P. Preparation of gellan-cholesterol nanohydrogels embedding baicalin and evaluation of their wound healing activity. Eur. J. Pharm. Biopharm. 2018, 127, 244–249.
  20. Huang, W.Y.; Cai, Y.Z.; Hyde, K.D.; Corke, H.; Sun, M. Biodiversity od endophytic fungi associated with 29 traditional Chinese medicinal plants. Fungal Divers. 2008, 33, 61–75.
  21. Ren, J.; Lu, Y.; Qian, Y.; Chen, B.; Wu, T.; Ji, G. Recent progress regarding kaempferol for the treatment of various diseases. Exp. Med. 2019, 18, 2759–2776.
  22. Özay, Y.; Güzel, S.; Yumrutaş, Ö.; Pehlivanoğlu, B.; Erdoğdu, İ.H.; Yildirim, Z.; Türk, B.A.; Darcan, S. Wound healing effect of kaempferol in diabetic and nondiabetic rats. J. Surg. Res. 2019, 233, 284–296.
  23. Ambiga, S.; Narayanan, R.; Gowri, D.; Sukumar, D.; Madhavan, S. Evaluation of wound healing activity of flavonoids from Ipomoea carnea Jacq. Anc. Sci. Life 2007, 26, 45–51.
  24. Calderón-Montaño, J.M.; Burgos-Morón, E.; Pérez-Guerrero, C.; López-Lázaro, M. A review on the dietary flavonoid kaempferol. Mini Rev. Med. Chem. 2011, 11, 298–344.
  25. Liu, R.H. Health-promoting components of fruits and vegetables in the diet. Adv. Nutr. 2013, 4, 384S–392S.
  26. Pratibha, C.; Gajbhiye, S.; Roy, S.; Dudhale, R.; Chowdhary, A. Determination of Kaempferol in extracts of Fusarium chlamydosporum, an endophyticfungi of Tylophora indica (Asclepeadaceae) and its anti-microbial activity. Int. J. Pharm. Biol. Sci. 2014, 9, 51–55.
  27. David, A.V.A.; Arulmoli, R.; Parasuraman, S. Overviews of biological importance of quercetin: A bioactive flavonoid. Pharmacogn. Rev. 2016, 10, 84–89.
  28. Gomathi, K.; Gopinath, D.; Ahmed, M.R.; Jayakumar, R. Quercetin incorporated collagen matrices for dermal wound healing processes in rat. Biomaterials 2003, 24, 2767–2772.
  29. Jangde, R.; Srivastava, S.; Singh, M.R.; Singh, D. In vitro and in vivo characterization of quercetin loaded multiphase hydrogel for wound healing application. Int. J. Biol. Macromol. 2018, 115, 1211–1217.
  30. Abdel-Raouf, N.; Ibraheem, I.B.M.; Abdel-Tawab, S.; Naser, Y.A.G. Antimicrobial and antihyperlipidemic activities of isolated quercetin from anabaena aequalis(1). J. Phycol. 2011, 47, 955–962.
  31. Chatterjee, T.K.; Chakravorty, A. Wound healing properties of the new antibiotic (MT81) in mice. Indian Drugs 1993, 30, 450–452.
  32. Ismaiel, A.A.; Rabie, G.H.; Abd El-Aal, M.A. Antimicrobial and morphogenic effects of emodin produced by Aspergillus awamori WAIR120. Biologia 2016, 71, 464–474.
  33. Izhaki, I. Emodin-a secondary metabolite with multiple ecological functions in higher plants. New Phytol. 2002, 155, 205–217.
  34. Kögl, F.; Postowsky, J.J. Untersuchungen über Pilzfarbstoffe. II. Über die Farbstoffe des blutroten Hautkopfes (Dermocybe sanguinea Wulf.). Justus Liebigs Ann. Chem. 1925, 444, 1–7.
  35. Agosti, G.; Birkinshaw, J.H.; Chaplen, P. Studies in the biochemistry of micro-organisms. 112. Anthraquinone pigments of strains of Cladosporium fulvum Cooke. Biochem. J. 1962, 85, 528–530.
  36. Shibata, S.; Shoji, J.; Ohta, A.; Watanable, M. Metabolic products of fungi. XI. Some observations on the occurrence of skyrin and rugulosin in mold metabolites with reference to structural relationships between penicilliopsin and skyrin. Chem. Pharm. Bull. 1957, 5, 380–383.
  37. Shibata, S.; Udagawa, S. Metabolic products of fungi. XIX. Isolation of rugulosin from Penicillium brunneum Udagawa. Chem. Pharm. Bull. 1963, 11, 402–403.
  38. Natori, S.; Sato, F.; Udagawa, S. Anthraquinone metabolites of Talaromyces avellanens (Thom et Turreson), C.R. Benjamin and Preussia multispora (Saito et Minoura) Cain. Chem. Pharm. Bull. 1965, 13, 385–389.
  39. Ghosh, A.C.; Manmade, A.; Demain, A.L. Toxins from Penicillium islandicum Sopp. . In Mycotoxins in Human and Animal Health; Rodricks, J.V., Hesseltine, C.W., Mehlman, M.A., Eds.; Pathotox: Chicago, IL, USA, 1977; pp. 625–638.
  40. Yamazaki, M.; Maebayashi, Y.; Miyaki, K. The isolation of secalonic acid A from Aspergillus ochraceus cultured on rice. Chem. Pharm. Bull. 1971, 19, 199–201.
  41. Wells, J.M.; Cole, R.J.; Kirksey, J.W. Emodin, a toxic metabolite of Aspergillus wentii isolated from weevil-damaged chestnuts. Appl. Microbiol. 1975, 30, 26–28.
  42. Anke, H.; Kolthoum, I.; Laatsch, H. Metabolic products of microorganisms. 192. The anthraquinones of the Aspergillus glaucus group. II. Biological activity. Arch. Microbiol. 1980, 126, 231–236.
  43. Dong, X.; Fu, J.; Yin, X.; Cao, S.; Li, X.; Lin, L.; Huyiligeqi, N.J. Emodin: A review of its pharmacology, toxicity and pharmacokinetics. Phytother. Res. 2016, 30, 1207–1218.
  44. Tang, T.; Yin, L.; Yang, J.; Shan, G. Emodin, an anthraquinone derivative from Rheum officinale Baill, enhances cutaneous wound healing in rats. Eur. J. Pharm. 2007, 567, 177–185.
  45. Sarang, H.; Rajani, P.; Vasanthakumari, M.M.; Kumara, P.M.; Siva, R.; Ravikanth, G.; Shaanker, R.U. An endophytic fungus, Gibberella moniliformis from Lawsonia inermis L. produces lawsone, an orange-red pigment. Antonie Van Leeuwenhoek 2017, 110, 853–862.
  46. López López, L.I.; Nery Flores, S.D.; Silva Belmares, S.Y.; Sáenz, G.A. Naphthoquinones: Biological properties and synthesis of lawsone and derivatives-a structured review. Vitae 2014, 21, 248–258.
  47. Mandawgade, S.D.; Patil, K.S. Wound healing potential of some active principles of Lawsonia alba Lam. leaves. Indian J. Pharm. Sci. 2003, 65, 390–394.
  48. Bascha, J.; Murthy, B.R.; Likhitha, P.R.; Ganesh, Y.; Bai, B.G.; Rani, R.J.; Prakash, P.; Shanmugham, V.; Kirthi, A. In vitro and in vivo assessment of lawsone microsphere loaded chitosan scaffolds. Int. J. Phytopharm. 2016, 6, 74–84.
  49. Guimaraes, I.; Baptista-Silva, S.; Pintado, M.; Oliveira, A.L. Poplyphenols: A promising Avenue in Therapeutic Solutions for Wound Care. Appl. Sci. 2021, 11, 1230.
  50. Działo, M.A.; Mierziak, J.; Korzun, U.; Preisner, M.; Szopa, J.; Kulma, A. The potential of plant phenolics in prevention and therapy of skin disorders. Int. J. Mol. Sci. 2016, 17, 160.
  51. Ghuman, S.; Ncube, B.; Finnie, J.; McGaw, L.; Njoya, E.M.; Coopoosamy, R.; Van Staden, J. Antioxidant, anti-inflammatory and wound healing properties of medicinal plant extracts used to treat wounds and dermatological disorders. S. Afr. J. Bot. 2019, 126, 232–240.
  52. Krausz, A.E.; Adler, B.L.; Cabral, V.; Navati, M.; Doerner, J.; Charafeddine, R.A.; Chandra, D.; Liang, H.; Gunther, L.; Clendaniel, A.; et al. Curcumin-encapsulated nanoparticles as innovative antimicrobial and wound healing agent. Nanomed. Nanotechnol. Biol. Med. 2015, 11, 195–206.
  53. Moghadam, S.E.; Ebrahimi, S.N.; Salehi, P.; Moridi Farimani, M.; Hamburger, M.; Jabbarzadeh, E. Wound healing potential of chlorogenic acid and myricetin-3-O-β-rhamnoside isolated from Parrotia persica. Molecules 2017, 22, 1501.
  54. Chen, W.C.; Liou, S.S.; Tzeng, T.F.; Lee, S.L.; Liu, I.M. Effect of topical application of chlorogenic acid on excision wound healing in rats. Planta Med. 2013, 79, 616–621.
  55. Yang, D.J.; Moh, S.H.; Son, D.H.; You, S.; Kinyua, A.W.; Ko, C.M.; Song, M.; Yeo, J.; Choi, Y.H.; Kim, K.W. Gallic acid promotes wound healing in normal and hyperglucidic conditions. Molecules 2016, 21, 899.
  56. Karatas, O.; Gevrek, F. Gallic acid liposome and powder gels improved wound healing in wistar rats. Ann. Med. Res. 2019, 26, 2720–2727.
  57. Kim, S.; Lee, C.W.; Park, S.-Y.; Asolkar, R.N.; Kim, H.; Kim, G.J.; Oh, S.J.; Kim, Y.; Lee, E.-Y.; Oh, D.-C.; et al. Acremonamide, a Cyclic Pentadepsipeptide with Wound-Healing Properties Isolated from a Marine-Derived Fungus of the Genus Acremonium. J. Nat. Prod. 2021, 84, 2249–2255.
  58. Wang, X.; Gong, X.; Li, P.; Lai, D.; Zhou, L. Structural Diversity and Biological Activities of Cyclic Depsipeptides from Fungi. Molecules 2018, 23, 169–218.
  59. Ratnayake, R.; Fremlin, L.J.; Lacey, E.; Gill, J.H.; Capon, R.J. Acremolides A−D, Lipodepsipeptides from an Australian Marine-Derived Fungus, Acremonium sp. J. Nat. Prod. 2008, 71, 403–408.
  60. Sun, P.; Maloney, K.N.; Nam, S.-J.; Haste, N.M.; Raju, R.; Aalbersberg, W.; Jensen, P.R.; Nizet, V.; Hensler, M.E.; Fenical, W. Fijimycins A–C, three antibacterial etamycin-class depsipeptides from a marine-derived Streptomyces sp. Bioorg. Med. Chem. 2011, 19, 6557–6562.
  61. Amagata, T.; Morinaka, B.I.; Amagata, A.; Tenney, K.; Valeriote, F.A.; Lobkovsky, E.; Clardy, J.; Crews, P. A Chemical Study of Cyclic Depsipeptides Produced by a Sponge-Derived Fungus. J. Nat. Prod. 2006, 69, 1560–1565.
  62. Kunze, B.; Jansen, R.; Sasse, F.; Hofle, G.; Reichenbach, H. Chondramides A~D, New Antifungal and Cytostatic Depsipeptides from Chondromyces crocatus (Myxobacteria). J. Antibiot. Res. 1995, 48, 1262–1266.
  63. Abreu-Blanco, M.T.; Watts, J.J.; Verboon, J.M.; Parkhurst, S.M. Cytoskeleton Response in Wound Repair. Cell Mol. Life Sci. 2012, 69, 2469–2483.
  64. Ma, C.I.; Diraviyam, K.; Maier, M.E.; Sept, D.; Sibley, L.D. Synthetic chondramide A analogues stabilize filamentous actin and block invasion by Toxoplasma gondii. J. Nat. Prod. 2013, 76, 1565–1572.
  65. Tannert, R.; Milroy, L.G.; Ellinger, B.; Hu, T.S.; Arndt, H.D.; Waldmann, H. Synthesis and structure-activity correlation of natural-product inspired cyclodepsipeptides stabilizing F-actin. J. Am. Chem. Soc. 2010, 132, 3063–3077.
  66. Cai, W.; Salvador-Reyes, L.A.; Zhang, W.; Chen, Q.-Y.; Matthew, S.; Ratnayake, R.; Seo, S.J.; Dolles, S.; Gibson, D.J.; Paul, V.J.; et al. Apratyramide, a Marine-Derived Peptidic Stimulator of VEGF-A and Other Growth Factors with Potential Application in Wound Healing. ACS Chem. Biol. 2018, 13, 91–99.
  67. Ghiulai, R.; Roşca, O.J.; Antal, D.S.; Mioc, M.; Mioc, A.; Racoviceanu, R.; Macaşoi, I.; Olariu, T.; Dehelean, C.; Creţu, O.M.; et al. Tetracyclic and Pentacyclic Triterpenes with High Therapeutic Efficiency in Wound Healing Approaches. Molecules 2020, 25, 5557.
  68. Isah, M.B.; Tajuddeen, N.; Umar, M.I.; AlHafiz, Z.A.; Mohammed, A.; Ibrahim, M.A. Terpenoids as emerging therapeutic agents: Cellular targets and mechanisms of action against protozoan parasites. In Studies in Natural Products Chemistry, 1st ed.; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, The Netherlands, 2018; Volume 59, pp. 227–250.
  69. Furtado, N.A.J.C.; Pirson, L.; Edelberg, H.; Miranda, L.M.; Loira-Pastoriza, C.; Préat, V.; Larondelle, Y.; Andre, C.M. Pentacyclic triterpene bioavailability: An overview of in vitro and in vivo studies. Molecules 2017, 22, 400.
  70. Paduch, R.; Kandefer-Szerszen, M. Antitumor and antiviral activity of pentacyclic triterpenes. Mini-Rev. Org. Chem. 2014, 11, 262–268.
  71. Chudzik, M.; Korzonek-Szlacheta, I.; Król, W. Triterpenes as potentially cytotoxic compounds. Molecules 2015, 20, 1610–1625.
  72. Battineni, J.K.; Koneti, P.K.; Bakshi, V.; Boggula, N. Triterpenoids: A review. Int. J. Pharm. Pharm. Sci. 2018, 3, 91–96.
  73. Hill, R.A.; Connolly, J.D. Triterpenoids. Nat. Prod. Rep. 2017, 34, 90–122.
  74. Agra, L.C.; Ferro, J.N.S.; Barbosa, F.T.; Barreto, E. Triterpenes with healing activity: A systematic review. J. Dermatol. Treat. 2015, 26, 465–470.
  75. Sh Ahmed, A.; Taher, M.; Mandal, U.K.; Jaffri, J.M.; Susanti, D.; Mahmood, S.; Zakaira, Z.A. Pharmacological properties of Centella asiatica hydrogel in accelerating wound healing in rabbits. BMC Complement. Altern. Med. 2019, 19, 213.
  76. Gupta, S.; Bhatt, P.; Chaturvedi, P. Determination and quantification of asiaticoside in endophytic fungus from Centella asiatica (L.) Urban. World J. Microbiol. Biotechnol. 2018, 34, 111.
  77. Ozdemir, O.; Ozkan, K.; Hatipoglu, F.; Uyaroglu, A.; Arican, M. Effect of asiaticoside, collagenase, and alpha-chymotrypsin on wound healing in rabbits. Wounds 2016, 28, 279–286.
  78. Mukherjee, P.K.; Bahadur, S.; Chaudhary, S.K.; Harwansh, R.K.; Nema, N.K. Validation of medicinal herbs for skin aging. In Evidence-Based Validation of Berbal Medicine, 1st ed.; Mukherjee, P.K., Ed.; Elsevier: Amsterdam, The Netherlands, 2015; pp. 119–147.
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Prima F. Hillman
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Sang-Jip Nam
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Update Date: 17 Jan 2023
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