Skip to main content

Recent Advances in the Insect Natural Product Chemistry: Structural Diversity and Their Applications

  • Chapter
  • First Online:
Natural Materials and Products from Insects: Chemistry and Applications

Abstract

Phylum Arthropoda is the largest phylum of animal kingdom with around one million different species comprising more than 80% of all known animal species. These include insects, spiders, ticks, lice, centipedes, shrimp, and crabs with several less known species as well. Arthropod natural products represent structurally and functionally diverse chemical compounds ranging from fatty acids, polyketide, terpenoids to nucleosides. Most of the chemical compounds from arthropods are of polyacetate or fatty acid origin with highly nonpolar structures. Chemical analysis and spectroscopic identifications of new and fascinating structures have led to analyze the biological roles of identified compounds. More recently, small-molecule metabolites are facilitating for identification of novel types of chemical and ecological interactions. Besides metabolic chemistry and various biological applications, insect natural products are found to be active ingredients of various natural dyes (cochineal and lac dye). The semisynthetic derivative carmine later found its use as a biological staining and as a food coloring agent.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

eBook
USD 16.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  • Abubakar MB, Abdullah WZ, Sulaiman SA, Suen AB (2012) A review of molecular mechanisms of the anti-leukemic effects of phenolic compounds in honey. Int J Mol Sci 13:15054–15073

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Aguilar F, Crebelli R, Di Domenico A, Dusemund B, Frutos MJ, Galtier P, Gott D, Gundert-Remy U, Lambré C, Leblanc J-C, Lindtner O, Moldeus P, Mortensen A, Mosesso P, Oskarsson A, Parent-Massin D, Stankovic I, Waalkens-Berendsen IW, Woutersen RA, Wright M, Maged Y (2015) EFSA ANS panel (EFSA panel on food additives and nutrient sources added to food). Scientific opinion on the re-evaluation of cochineal, carminic acid, carmines (E120) as a food additive. Eur Food Saf Auth J 13:4288

    Google Scholar 

  • Ahmad I, Beg AZ (2001) Antimicrobial and phytochemical studies on 45 Indian medicinal plants against multi-drug resistant human pathogens. J Ethnopharmacol 74:113–123

    Article  CAS  PubMed  Google Scholar 

  • Ahn MY, Shim SH, Jeong HK, Ryu KS (2008) Purification of a dimethyladenosine compound from silkworm pupae as a vasorelaxation substance. J Ethnopharmacol 117:115–122

    Article  CAS  PubMed  Google Scholar 

  • Aldrich JR, Bartelt RJ, Dickens JC, Knight AL, Light DM, Tumlinson JH (2003) Insect chemical ecology research in the United States Department of Agriculture–Agricultural Research Service. Pest Manag Sci 59:777–787

    Article  CAS  PubMed  Google Scholar 

  • Alonso-Castro AJ (2014) Use of medicinal fauna in Mexican traditional medicine. J Ethnopharmacol 152:53–70

    Article  PubMed  Google Scholar 

  • Behroozi J, Divsalar A, Saboury AA (2014) Honey bee venom decreases the complications of diabetes by preventing hemoglobin glycation. J Mol Liq 199:371–375

    Article  CAS  Google Scholar 

  • Bellik Y (2015) Bee venom: its potential use in alternative medicine. Anti Infec Agents 13:3–16

    Article  CAS  Google Scholar 

  • Benítez G (2011) Animals used for medicinal and magico-religious purposes in western Granada Province, Andalusia (Spain). J Ethnopharmacol 137:1113–1123

    Article  PubMed  Google Scholar 

  • Berthold N, Czihal P, Fritsche S, Sauer U, Schiffer G, Knappe D, Alber G, Hoffmann R (2013) Novel apidaecin1b analogs with superior serum stabilities for treatment of infections by gram-negative pathogens. Antimicrob Agents Chemother 57:402–409

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Bexfield A, Bond AE, Morgan C (2010) Amino acid derivatives from Lucilia sericata excretions/secretions may contribute to the beneficial effects of maggot therapy via increased angiogenesis. Br J Dermatol 162:554–562

    Article  CAS  PubMed  Google Scholar 

  • Bingham SJ, Tyman JHP (2000) The synthesis of kermesic acid by acetylation-aided tautomerism of 6-chloro-2,5,8-trihydroxynaphtho-1,4-quinone. Chem Commun:925–926

    Google Scholar 

  • Blum MS (1996) Semiochemical parsimony in the Arthropoda. Annu Rev Entomol 41:353–374

    Article  CAS  PubMed  Google Scholar 

  • Borges ME, Tejera RL, Diaz L, Esparza P, Ibáñez E (2012) Natural dyes extraction from cochineal (Dactylopius coccus). New extraction methods. Food Chem 132:1855–1860

    Article  CAS  Google Scholar 

  • Brudzynski K, Abubaker K, Wang T (2012) Powerful killing by buckwheat honeys is concentration dependent, involves complete DNA degradation and requires hydrogen peroxide. Front Microbiol 3(242):2012

    Google Scholar 

  • Budhraja A, Gao N, Zhang Z, Son Y-O, Cheng S, Wang X, Ding S, Hitron A, Chen G, Luo J, Shi X (2012) Apigenin induces apoptosis in human leukemia cells and exhibits anti-leukemic activity in vivo. Mol Cancer Ther 11:132–142

    Article  CAS  PubMed  Google Scholar 

  • Bulet P, Stocklin R (2005) Insect antimicrobial peptides: structures, properties and gene regulation. Protein Pept Lett 12:3–11

    Article  CAS  PubMed  Google Scholar 

  • Burwood R, Read G, Schofield K, Wright D (1965) The pigments of stick lac. Part I. isolation and preliminary examination. J Chem Soc 0:6067–6073

    Article  CAS  Google Scholar 

  • Burwood R, Read G, Schofield K, Wright DE (1967) The pigments of stick lac: part II. The structure of laccaic acid A. J Chem Soc 9:842–851

    Google Scholar 

  • Campos JF, Dos Santos UP, Macorini LF, De Melo AM, Balestieri JB, Paredes-Gamero EJ et al (2014) Antimicrobial, antioxidant and cytotoxic activities of propolis from Melipona orbignyi (Hymenoptera, Apidae). Food Chem Toxicol 65:374–380

    Article  CAS  PubMed  Google Scholar 

  • Campos JF, Dos Santos UP, Dos Santos Da Rocha P, Damião MJ, Balestieri JB, Cardoso CA et al (2015, 2015) Antimicrobial, antioxidant, antiinflammatory, and cytotoxic activities of propolis from the stingless bee Tetragonisca fiebrigi (Jataí). Evid Based Complement Alternat Med:296186

    Google Scholar 

  • Cazander G, Schreurs MWJ, Renwarin L, Dorresteijn C, Hamann D, Jukema GN (2012) Maggot excretions affect the human complement system. Wound Repair Regen 20:879–886

    Article  PubMed  Google Scholar 

  • Chairat M, Rattanaphani S, Bremner JB, Rattanaphani V (2005) An adsorption and kinetic study of lac dyeing on silk. Dyes Pigments 64:231–241

    Article  CAS  Google Scholar 

  • Chambers L, Woodrow S, Brown AP, Harris PD, Phillips D, Hall M, Church JC, Pritchard DI (2003) Degradation of extracellular matrix components by defined proteinases from the greenbottle larva Lucilia sericata used for the clinical debridement of non-healing wounds. Br J Dermatol 148:14–23

    Article  CAS  PubMed  Google Scholar 

  • Chen J, Lariviere WR (2010) The nociceptive and anti-nociceptive effects of bee venom injection and therapy: a double-edged sword. Prog Neurobiol 92:151–183

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Chen L, Lu YY, Hu QB, Fadamiro Y (2012) Similarity in venom alkaloid chemistry of alate queens of imported fire ants: implication for hybridization between Solenopsis richteri and S. invicta in the southern United States. Chem Biodivers 9:702–713

    Article  CAS  PubMed  Google Scholar 

  • Cherniack EP (2010) Bugs as drugs, part 1: insects. The “new” alternative medicine for the 21st century? Altern Med Rev 15:124–135

    PubMed  Google Scholar 

  • Chernysh S, Irina K, Irina A (2012) Anti-tumor activity of immunomodulatory peptide alloferon-1 in mouse tumor transplantation model. Int Immunopharmacol 12:312–314

    Article  CAS  PubMed  Google Scholar 

  • Coelho GR, Mendonça RZ, De Senna Vilar K, Figueiredo CA, Badari JC, Taniwaki N et al (2015) Antiviral action of hydromethanolic extract of geopropolis from Scaptotrigona postica against antiherpes simplex virus (HSV-1). Evid Based Complement Alternat Med 2015:296086

    Article  PubMed  PubMed Central  Google Scholar 

  • Cooksey CJ (2018) The red insect dyes: carminic, kermesic and laccaic acids and their derivatives. Biotech Histochem. https://doi.org/10.1080/10520295.2018.1511065

  • Cooper RA, Lindsay E, Molan PC (2011) Testing the susceptibility to manuka honey of streptococci isolated from wound swabs. J ApiProd ApiMed Sci 3:117–122

    Article  Google Scholar 

  • Corti A (1851) Recherches sur l’organe de l’ouie des mummifères. Z Wiss Zool 3:109–169

    Google Scholar 

  • Costa-Neto EM (2002) The use of insects in folk medicine in the state of Bahia, northeastern Brazil, with notes on insects reported elsewhere in Brazilian folk medicine. Human Ecol 30:245–263

    Article  Google Scholar 

  • Daleprane JB, Abdalla DS (2013) Emerging roles of propolis: antioxidant, cardioprotective, and antiangiogenic actions. Evid Based Complement Alternat Med 2013:175135

    Article  PubMed  PubMed Central  Google Scholar 

  • Dang Y-J, Zhu C-Y (2013) Oral bioavailability of cantharidin loaded solid lipid nanoparticles. BMC Chin Med 8:8

    Article  Google Scholar 

  • Danneels EL, Rivers DB, de Graaf DC (2010) Venom proteins of the parasitoid wasp Nasoniavitri pennis: recent discovery of an untapped pharmacopee. Toxins 2:494–516

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Degenhardt J, Gershenzon J, Baldwin IT, Kessler A (2003) Attracting friends to feast on foes: engineering terpene emission to make crop plants more attractive to herbivore enemies. Curr Opin Biotechnol 14:169–176

    Article  CAS  PubMed  Google Scholar 

  • Dimroth O, Kämmerer H (1920) Ṻeber die Carminsäure. Ber Dtsch Chem Ges 53:471–480

    Article  Google Scholar 

  • Dossey AT (2010) Insects and their chemical weaponry: new potential for drug discovery. Nat Prod Rep 27:1737–1757

    Article  CAS  PubMed  Google Scholar 

  • Erejuwa OO, Sulaiman SA, Wahab MS (2012) Honey: a novel antioxidant. Molecules 17:4400–4423

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Farrell BD (1998) “Inordinate fondness” explained: why are there so many beetles? Science 281:555–559

    Article  CAS  PubMed  Google Scholar 

  • Fernandez-Cabezudo MJ, El-Kharrag R, Torab F, Bashir G, George JA, El-Taji H, al Ramadi BK (2013) Intravenous administration of manuka honey inhibits tumor growth and improves host survival when used in combination with chemotherapy in a melanoma mouse model. PLoS One 8:0055993

    Article  CAS  Google Scholar 

  • Ferreira ESB, Hulme AN, McNab H, Quye A (2004) The natural constituents of historical textile dyes. Chem Soc Rev 33:329–336

    Article  CAS  PubMed  Google Scholar 

  • Freires IA, De Alencar SM, Rosalen PL (2016) A pharmacological perspective on the use of Brazilian red Propolis and its isolated compounds against human diseases. Eur J Med Chem 110:267–279

    Article  CAS  PubMed  Google Scholar 

  • Gadgil DD, Rao AVR, Venkatarman K (1968) Structure of kermesic acid. Tetrahedron Lett 9:2223–2227

    Article  Google Scholar 

  • Galvis CEP, Mendez LYV, Kouznetsov VV (2013a) Cantharidin-based small molecules as potential therapeutic agents. Chem Biol Drug Des 82:477–499

    Article  CAS  Google Scholar 

  • Galvis CE, Méndez LY, Kouznetsov VV (2013b) Cantharidin-based small molecules as potential therapeutic agents. Chem Biol Drug Des 82:477–499

    Article  CAS  Google Scholar 

  • Gomes A, Alam MA, Bhattacharya S, Dasgupta SC, Mukherjee S, Bhattacharya S, Gomes A (2011) Ethno biological usage of zoo products in rheumatoid arthritis. Indian J Exp Biol 49:565–573

    PubMed  Google Scholar 

  • Graetz TJ, Tellor BR, Smith JR, Avidan MS (2011) Desirudin: a review of the pharmacology and clinical application for the prevention of deep vein thrombosis. Expert Rev Cardiovasc Ther 9:1101–1109

    Article  CAS  PubMed  Google Scholar 

  • Heinen TE, De Veiga AB (2011) Arthropod venoms and cancer. Toxicon 57:497–511

    Article  CAS  PubMed  Google Scholar 

  • Henriques AF, Jenkins RE, Burton NF, Cooper RA (2011) The effect of manuka honey on the structure of Pseudomonas aeruginosa. Eur J Clin Microbiol Infect Dis 30:167–171

    Article  CAS  PubMed  Google Scholar 

  • Hoffman DR (2010) Ant venoms. Curr Opin Allergy Clin Immunol 10:342–346

    Article  CAS  PubMed  Google Scholar 

  • Hoskin DW, Ramamoorthy A (2008) Studies on anticancer activities of antimicrobial peptides. Biochim Biophys Acta 1778:357–375

    Article  CAS  PubMed  Google Scholar 

  • Huber JT (2009) Biodiversity of Hymenoptera. In: Foottit RG, Adler PH (eds) Insect biodiversity: science and society. Blackwell Publishing Ltd, West Sussex, pp 303–323

    Chapter  Google Scholar 

  • Itokawa H, Takeya K, Hitotsuyanagi Y, Morita H (2000) Antitumor compounds isolated from higher plants. In: Atta-ur-Rahman (ed) Studies in natural products chemistry. Elsevier Science, Amsterdam, pp 269–350

    Google Scholar 

  • Jaroli DP, Mahawar MM, Vyas N (2010) An ethno zoological study in the adjoining areas of Mount Abu wildlife sanctuary, India. J Ethnobiol Ethnomed 6:6

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Jenkins RE, Cooper R (2012) Synergy between oxacillin and manuka honey sensitizes methicillin-resistant Staphylococcus aureus to oxacillin. J Antimicrob Chemother 67:1405–1407

    Article  CAS  PubMed  Google Scholar 

  • Jull AB, Rodgers A, Walker N (2008) Honey as a topical treatment forwounds. Cochrane Database of Systematic Rev 4:CD005083

    Google Scholar 

  • Kaltenpoth M, Göttler W, Dale C, Stubblefield JW, Herzner G, Röser-Müller K, Strohm E (2006) Candidatus Streptomyces philanthi’, an endosymbiotic streptomycete in the antennae of Philanthus digger wasps. Int J Syst Evol Microbiol 56:1403–1411

    Article  CAS  PubMed  Google Scholar 

  • Kamel MM, El-Shishtawy RM, Youssef BM, Mashaly H (2007) Ultrasonic assisted dyeing. IV. Dyeing of cationised cotton with lac natural dye. Dyes Pigments 73:279–284

    Article  CAS  Google Scholar 

  • Kang SJ, Kim DH, Mishig-Ochir T et al (2012) Antimicrobial peptides: their physicochemical properties and therapeutic application. Arch Pharm Res 35:409–413

    Article  CAS  PubMed  Google Scholar 

  • Kazemzadeh-Narbat M, Noordin S, Masri BA et al (2012) Drug release and bone growth studies of antimicrobial peptide-loaded calcium phosphate coating on titanium. J Biomed Mater Res B Appl Biomater 100:1344–1352

    Article  CAS  PubMed  Google Scholar 

  • Kazimırova M, Stibraniova I (2013) Tick salivary compounds: their role in modulation of host defences and pathogen transmission. Cell Infect Microbiol 3:2013

    Google Scholar 

  • Khan MA, Khan M, Srivastava PK, Mohammad F (2004) Extraction of lac red dye and its application on wool. Colourage 51:27–30

    CAS  Google Scholar 

  • Khan MI, Shahid M, Khan SA, Yusuf M, Khan MA, Mohammad F (2012) Studies on application of lac natural dye on wool using eco-friendly metal mordants. Colourage 59:42–51

    CAS  Google Scholar 

  • Klos D (2005) The Dyer’s companion. Interweave Press, Loveland

    Google Scholar 

  • Knecht E (1941) A manual of dyeing for the use of practical dyers, manufacturers, students and all interested in the art of dyeing, London, vol 1, 9th edn. Griffin and Company Ltd

    Google Scholar 

  • Koehler S, Doubský J, Kaltenpoth M (2013) Dynamics of symbiont-mediated antibiotic production reveal efficient long-term protection for beewolf offspring. Front Zool 10(3)

    Google Scholar 

  • Kongkachuichay P, Shitangkoon A, Chinwongamorn N (2002) Thermodynamics of adsorption of laccaic acid on silk. Dyes Pigments 53:179–185

    Article  CAS  Google Scholar 

  • Koren CZ (1994) HPLC analysis of the natural scale insect, madder and indigoid dyes. J Soc Dye Colour 110:273–277

    Article  CAS  Google Scholar 

  • Kroiss J, Kaltenpoth M, Schneider B, Schwinger MG, Hertweck C, Maddula RK, Strohm E, Svatoš A (2010) Symbiotic Streptomycetes provide antibiotic combination prophylaxis for wasp offspring. Nat Chem Biol 6:261–263

    Article  CAS  PubMed  Google Scholar 

  • Kwakman PHS, te Velde AA, de Boer L, Vandenbroucke-Grauls CMJE, Zaat SAJ (2011) Two major medicinal honeys have different mechanisms of bactericidal activity. PLoS One 6(3):0017709

    Article  CAS  Google Scholar 

  • Lee KH (1993) Antineoplastic agents and their analogues from Chinese traditional medicine. In: Kinghorn AD, Balandrin M (eds) Human medicinal agents from plants, vol 534. ACS Symp Ser, pp 170–190

    Google Scholar 

  • Lee DS, Sinno S, Khachemoune A (2011) Honey and wound healing: an overview. Am J Clin Dermatol 12:181–190

    Article  CAS  PubMed  Google Scholar 

  • Lee WR, Park KK, Pak SC (2015) The protective effect of bee venom on fibrosis causing inflammatory diseases. Toxins 7:4758–4772

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Li W, Xie L, Chen Z, Zhu Y, Sun Y, Miao Y, Xu Z, Han X (2010) Cantharidin, a potent and selective PP2A inhibitor, induces an oxidative stress-independent growth inhibition of pancreatic cancer cells through G2/M cell cycle arrest and apoptosis. Cancer Sci 101:1226–1233

    Article  CAS  PubMed  Google Scholar 

  • Li Y, Xiang Q, Zhang Q, Huang Y, Su Z (2012) Overview on the recent study of antimicrobial peptides: origins, functions, relative mechanisms and application. Peptides 37:207–215

    Article  CAS  PubMed  Google Scholar 

  • Li X, Liu N, Xia X (2013) The effects of maggot secretions on the inflammatory cytokines in serum of traumatic rats. Afr J Tradit Complement Altern Med 10:151–154

    CAS  PubMed  PubMed Central  Google Scholar 

  • Lissina E, Young B, Urbanus ML, Guan XL, Lowenson J, Hoon S, Baryshnikova A, Riezman I, Michaut M, Riezman H, Cowen LE, Wenk MR, Clarke SG, Giaever G, Nislow C (2011) A systems biology approach reveals the role of a novel methyl transferase in response to chemical stress and lipid homeostasis. PLoS Genet 7:e1002332

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lloyd A (1980) Extraction and chemistry of cochineal. Food Chem 5:91–107

    Article  CAS  Google Scholar 

  • Lockhart GJ (2007) Ants and other great medicines. partially published online by Jacobson AL. http://www.arthurleej.com/ants.pdf

  • Lu J, Sun Q, Tu ZC, Lv Q, Shui PX, Cheng YX (2015) Identification of Nacetyldopamine dimers from the dung beetle Catharsius molossus and their COX-1 and COX-2 inhibitory activities. Molecules 20:15589–15596

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Luetchford KA, Chaudhuri JB, De Bank PA (2020) Silk fibroin/gelatin microcarriers as scaffolds for bone tissue engineering. Mater Sci Eng C 106:110116–110124

    Article  CAS  Google Scholar 

  • MacIntosh AC, Kearns VR, Crawford A, Hatton PV (2008) Skeletal tissue engineering using silk biomaterials. J Tissue Eng Regen Med 2:71–80

    Article  CAS  PubMed  Google Scholar 

  • Maddocks SE, Jenkins RE (2013) Honey: a sweet solution to the growing problem of antimicrobial resistance? Future Microbiol 8:1419–1429

    Article  CAS  PubMed  Google Scholar 

  • Mahawar MM, Jaroli DP (2008) Traditional zoo therapeutic studies in India: a review. J Ethnobiol Ethnomed 4:17

    Article  PubMed  PubMed Central  Google Scholar 

  • Mandal V, Mohan Y, Hemalatha S (2007) Microwave assisted extraction – an innovative and promising extraction tool for medicinal plant research. Pharmacog Rev 1:7–10

    CAS  Google Scholar 

  • Mandala MD, Mandal S (2011) Honey: its medicinal property and antibacterial activity. Asian Pac J Trop Biomed 1:154–160

    Article  Google Scholar 

  • Mayer F, Cook AH (1943) The chemistry of natural coloring matters: the constitutions, properties, and biological relations of the important natural pigments. Reinhold Publishing Corporation, New York

    Book  Google Scholar 

  • McLoone P, Warnock M, Fyfe L (2015) Honey: a realistic antimicrobial for disorders of the skin. J Microbiol Immunol Infect 49:161–167

    Article  CAS  PubMed  Google Scholar 

  • Mehandale AR, Rao AVR, Shaikh IN, Venkataraman K (1968) Desoxyerythrolaccin and laccaic acid D. Tetrahedron Lett 9:2231–2234

    Article  Google Scholar 

  • Meinel L, Betz O, Fajardo R, Hofmann S, Nazarian A, Cory E, Hilbe M, McCool J, Langer R, Vunjak-Novakovic G, Merkle HP, Rechenberg B, Kaplan DL, Kirker-Head C (2006) Silk based biomaterials to heal critical sized femur defects. Bone 39:922–931

    Article  CAS  PubMed  Google Scholar 

  • Mlcek J, Borkovcova M, Bednarova M (2014) Biologically active substances of edible insects and their use in agriculture, veterinary and human medicine – a review. J Cent Eur Agric 15:225–237

    Article  Google Scholar 

  • Monteiro MC, Romão PRT, Soares AM (2009) Pharmacological perspectives of wasp venom. Protein Pept Lett 16:944–952

    Article  CAS  PubMed  Google Scholar 

  • Ntwasa M, Goto A, Kurata S (2012) Coleopteran antimicrobial peptides: prospects for clinical applications. Int J Microbiol 2012:101989

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Numata K, Subramanian B, Currie HA, Kaplan DL (2009) Bioengineered silk protein-based gene delivery systems. Biomaterials 30:5775–5784

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Oka H, Ito Y, Yamada S, Kagami T, Hayakawa J, Harada K, Atsumi E, Suzuki M, Suzuki M, Odani H, Akahori S, Maeda K, Nakazawa H, Ito Y (1998) Separation of lac dye components by high-speed counter-current chromatography. J Chromatogr A 813:71–77

    Article  CAS  PubMed  Google Scholar 

  • Orsolic N (2009) Bee honey and cancer. J ApiProd ApiMed Sci 1:93–103

    Article  Google Scholar 

  • Oršolić N (2012) Bee venom in cancer therapy. Cancer Metast Rev 31:173–194

    Article  CAS  Google Scholar 

  • Ostorhazi E, Holub MC, Rozgonyi F, Harmos F, Cassone M, Wade JD, Otvos L Jr (2011) Broad-spectrum antimicrobial efficacy of peptide A3-APO in mouse models of multidrug-resistant wound and lung infections cannot be explained by in vitro activity against the pathogens involved. Int J Antimicrob Agents 37:480–484

    Article  CAS  PubMed  Google Scholar 

  • Overeem JC, Van der Kerk GJM (1964) Mollisin, a naturally occurring chlorine-containing quinone. Part IV. Revised structures for cochenillic acid and for the insect pigments, carminic and kermesic acids. Recl Trav Chim Pays-Bas 83:1023–1035

    Article  CAS  Google Scholar 

  • Pandhare ED, Rao AVR, Srinivasan R, Venkataraman K (1966) Lac pigments. Tetrahedron 8:229–239

    Article  Google Scholar 

  • Pandhare ED, Rao AVR, Shaikh IN, Venkataraman K (1967) The constitution of laccaic acid B. Tetrahedron Lett 8:2437–2440

    Article  Google Scholar 

  • Park JH, Jeong YJ, Park KK, Cho HJ, Chung IK, Min KS, Kim M, Lee KG, Yeo JH, Park KK, Chang YC (2010) Melittin suppresses PMA-induced tumor cell invasion by inhibiting NF-kB and AP-1-dependent MMP-9 expression. Mol Cells 29:209–215

    Article  CAS  PubMed  Google Scholar 

  • Patricia V, Oliverio V, Triny L, Favián M (2015) Meliponini biodiversity and medicinal uses of pot-honey from ElOro province in Ecuador. Emir J Food Agric 27:502–506

    Article  Google Scholar 

  • Pemberton RW (1999) Insects and other arthropods used as drugs in Korean traditional medicine. J Ethnopharmacol 65:207–216

    Article  CAS  PubMed  Google Scholar 

  • Perez-Riverol A, Aparecido dos Santos-Pinto JR, Lasa AM, Palma MS, Brochetto-Braga MR (2017) Wasp venomic: unravelling the toxins arsenal of Polybia Paulista venom and its potential pharmaceutical applications. J Proteome 161:88–103

    Article  CAS  Google Scholar 

  • Perkin AG, Everest AE (1918) The natural organic colouring matters. Longmans, Green and Co, London

    Google Scholar 

  • Poinar GO Jr, Marshall CJ, Buckley R (2007) One hundred million years of chemical warfare by insects. J Chem Ecol 33:1663–1669

    Article  CAS  PubMed  Google Scholar 

  • Quinones JP, Roschger C, Zierer A, Peniche C, Bruggemann O (2019) Steroid-grafted silk fibroin conjugates for drug and agrochemical delivery. Eur Poly J 119:169–175

    Article  CAS  Google Scholar 

  • Rao VR, Shaikh IN, Venkataraman K (1968) Laccaic acid C, the first natural anthraquinone with an amino acid side chain. Indian J Chem 7:188–189

    Google Scholar 

  • Ratcliffe NA, Mello CB, Garcia ES, Butt TM, Azambuja P (2011) Insect natural products and processes: new treatments for human disease. Insect Biochem Mol Biol 41:747–769

    Article  CAS  PubMed  Google Scholar 

  • Rattanaphani S, Chairat M, Bremner JB, Rattanaphani V (2007) An adsorption and kinetic study of lac dyeing on cotton pretreated with chitosan. Dyes Pigments 72:88–96

    Article  CAS  Google Scholar 

  • Roberts AE, Maddocks SE, Cooper RA (2012) Manuka honey is bactericidal against Pseudomonas aeruginosa and results in differential expression of OprF and algD. Microbiol 158:3005–3013

    Article  CAS  Google Scholar 

  • Rosenberg E (2008) Characterisation of historical organic dyestuffs by liquid chromatography-mass spectrometry. Anal Bioanal Chem 391:33–57

    Article  CAS  PubMed  Google Scholar 

  • Sachetto ATA, Mackman N (2019) Modulation of the mammalian coagulation system by venoms and other proteins from snakes, arthropods, nematodes and insects. Thrombosis Res 178:145–154

    Article  CAS  Google Scholar 

  • Saidemberg DM, Da Silva-Filho LC, Tognoli LM, Tormena CF, Palma MS (2010) Polybioside, a neuroactive compound from the venom of the social wasp Polybia paulista. J Nat Prod 73:527–531

    Article  CAS  PubMed  Google Scholar 

  • Schmitt P, Günther H, Hägele G, Stilke R (1984) A 1H and 13C NMR study of carminic acid. Magn Reson Chem 22:446–449

    CAS  Google Scholar 

  • Seckam A, Cooper R (2013) Understanding how honey impacts on wounds: an update on recent research findings. Wounds Int 4:20–24

    Google Scholar 

  • Seybold SJ (2004) Preface: the eighth day of discovery: molecular biology comes to chemical ecology. J Chem Ecol 30:2327–2333

    Article  CAS  PubMed  Google Scholar 

  • Sforcin JM, Bankova V (2011) Propolis: is there a potential for the development of new drugs? J Ethnopharmacol 133:253–260

    Article  CAS  PubMed  Google Scholar 

  • Sherman RA, Hall MJR, Thomas S (2000) Medicinal maggots: an ancient remedy for some contemporary afflictions. Annu Rev Entomol 45:55–81

    Article  CAS  PubMed  Google Scholar 

  • Silva JC, Rodrigues S, Feás X, Estevinho LM (2012) Antimicrobial activity, phenolic profile and role in the inflammation of propolis. Food Chem Toxicol 50:1790–1795

    Article  CAS  PubMed  Google Scholar 

  • Slocinska M, Marciniak P, Rosinski G (2008) Insects antiviral and anticancer peptides: new leads for the future? Protein Pept Lett 15:578–585

    Article  CAS  PubMed  Google Scholar 

  • Son DJ, Lee JW, Lee YH (2007) Therapeutic application of anti-arthritis, pain-releasing, and anti-cancer effects of bee venom and its constituent compounds. Pharmacol Ther 115:246–270

    Article  CAS  PubMed  Google Scholar 

  • Song ZW, Liu P, Yin WP, Jiang YL, Ren YL (2012) Isolation and identification of antibacterial neo-compounds from the red ants of ChangBai Mountain, Tetramorium sp. Bioorg Med Chem Lett 22:2175–2181

    Article  CAS  PubMed  Google Scholar 

  • Spagnuolo C, Russo M, Bilotto S, Tedesco I, Laratta B, Russo GL (2012) Dietary polyphenols in cancer prevention: the example of the flavonoid quercetin in leukemia. Ann N Y Acad Sci 1259:95–103

    Article  CAS  PubMed  Google Scholar 

  • Stewart RJ, Wang CS (2010) Adaptation of caddisfly larval silks to aquatic habitats by phosphorylation of H-fibroin serines. Biomacromolecules 11:969–974

    Article  CAS  PubMed  Google Scholar 

  • Szliszka E, Krol W (2013) Polyphenols isolated from propolis augment TRAIL-induced apoptosis in cancer cells. Evid Based Comp Altern Med 2013:731940

    Google Scholar 

  • Takeuchi I, Shimamur Y, Kakami Y, Kameda T, Hattori K, Miura S, Shirai H, Okumura M, Inagi T, Terada H, Makino K (2019) Transdermal delivery of 40-nm silk fibroin nanoparticles. Colloid Surf B Biointerf 175:564–568

    Article  CAS  Google Scholar 

  • Tang JJ, Zhang L, Jiang LP, Di L, Yan YM, Tu ZC et al (2014) Dopamine derivatives from the insect Polyrhachis dives as inhibitors of ROCK1/2 and stimulators of neural stem cell proliferation. Tetrahedron 70:8852–8857

    Article  CAS  Google Scholar 

  • Tiedemann EJ, Yang Y (1995) Fiber-safe extraction of red mordant dyes from hair fibers. J Am Inst Conserv 34:195–206

    Article  Google Scholar 

  • Tonks AJ, Dudley E, Porter NG, Parton J, Brazier J, Smith EL, Tonks A (2007) A5.8-kDa component of manuka honey stimulates immune cells via TLR4. J Leukoc Biol 82:1147–1155

    Article  CAS  PubMed  Google Scholar 

  • Torrent M, Pulido D, Rivas L (2012) Antimicrobial peptide action on parasites. Curr Drug Targets 13:1138–1147

    Article  CAS  PubMed  Google Scholar 

  • Tseng I-J, Sheu S-Y, Lin P-Y, Lee J-A, Ou K-L, Lee L-W (2012) Synthesis and evaluation of cantharidinimides on human cancer cells. J Exp Clin Med 4:280–283

    Article  CAS  Google Scholar 

  • Uçkan F, Sinan S, Savasçi S, Ergin E (2004) Determination of venom components from the endoparasitoid wasp Pimplaturionellae L. (Hymenoptera: Ichneumonidae). Ann Entomol Soc Am 97:775–780

    Article  Google Scholar 

  • Ulm H, Wilmes M, Shai Y, Sahl H-G (2012) Antimicrobial host defensins - specific antibiotic activities and innate defense modulation. Front Immunol 3:249

    Article  PubMed  PubMed Central  Google Scholar 

  • Verhecken A (1989) Dyeing with kermes is still alive. J Soc Dye Colour 105:389–391

    Article  CAS  Google Scholar 

  • Wang GS (1989) Medical uses of mylabris in ancient China and recent studies. J Ethnopharmacol 26:147–162

    Article  CAS  PubMed  Google Scholar 

  • Wouters J, Verhecken A (1989) The coccid insect dyes: HPLC and computerized diode-array analysis of dyed yarns. Stud Conserv 34:189–200

    CAS  Google Scholar 

  • Xu X, Liu W, Li W, Liu S (2016) Anticoagulant activity of crude extract of Holotrichia diomphalia larvae. J Ethnopharmacol 177:28–34

    Article  CAS  PubMed  Google Scholar 

  • Yan YM, Li LJ, Qin XC, Lu Q, Tu ZC, Cheng YX (2015) Compounds from the insect Blaps japanensis with COX-1 and COX-2 inhibitory activities. Bioorg Med Chem Lett 25:2469–2472

    Article  CAS  PubMed  Google Scholar 

  • Yavuz B, Zeki J, Taylor J, Harrington K, Coburn JM, Ikegaki N, Kalpan DL, Chiu B (2019) Silk reservoirs for local delivery of cisplatin for neuroblastoma treatment: In Vitro and In Vivo evaluations. J Pharam Sci 108:2748–2755

    Article  CAS  Google Scholar 

  • Yi HY, Chowdhury M, Huang YD, Yu XQ (2014) Insect antimicrobial peptides and their applications. Appl Microbiol Biotechnol 98:5807–5822

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Yin WP, Zhao CJ, Liao CY, Trowell S, Rickards RW (2013) Preparative isolation of novel antimicrobial compounds from Pergidae sp. by reversed-phase high-performance liquid chromatography. Chem Nat Compd 49:41–45

    Article  CAS  Google Scholar 

  • Zarchi K, Jemec GB (2012) The efficacy of maggot debridement therapy - a review of comparative clinical trials. Int Wound J 9:469–477

    Article  PubMed  PubMed Central  Google Scholar 

  • Zhang Z, Wang S, Diao Y, Zhang J, Lv D (2010) Fatty acid extracts from Lucilia sericata larvae promote murine cutaneous wound healing by angiogenic activity. Lipids Health Dis 9:24

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgments

Financial support provided by Southwest University Chongqing, China, as Postdoctoral Fellow for Dr. Luqman Jameel Rather is highly acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Qing Li .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2020 Springer Nature Switzerland AG

About this chapter

Check for updates. Verify currency and authenticity via CrossMark

Cite this chapter

Rather, L.J., Ansari, M.F., Li, Q. (2020). Recent Advances in the Insect Natural Product Chemistry: Structural Diversity and Their Applications. In: Kumar, D., Shahid, M. (eds) Natural Materials and Products from Insects: Chemistry and Applications. Springer, Cham. https://doi.org/10.1007/978-3-030-36610-0_5

Download citation

Publish with us

Policies and ethics