Skip to main content
SpringerLink
Log in

Biologically Active Constituents from Plants of the Genus Desmos

  • Chapter
  • First Online:
Progress in the Chemistry of Organic Natural Products 116

Part of the book series: Progress in the Chemistry of Organic Natural Products ((POGRCHEM,volume 116))

Abstract

The combination of traditional knowledge of medicinal plants with scientific rationale has yielded positive results in recent years. Bioactive compounds isolated from herbaceous plants have long been used as drugs that benefit human health, as well as providing useful compounds for drug development lead compound optimization. This chapter aims to provide a systematic overview of the structural types of Desmos secondary metabolites, along with their biological potential. Various chromatographic and spectroscopic methods have been utilized for isolating, purifying, and elucidating the structures of compounds from Desmos species. From 1982 to the present time, more than 200 metabolites have been isolated from members of this genus. Desmos spp. constituents include terpenoids, phytosterols, polyoxygenated cyclohexanes and cyclohexenes, oxepinones, fatty acids, with flavonoids, alkaloids, and miscellaneous phenols being the predominant compounds. The essential oils of Desmos species have also been investigated. Both crude plant extracts and isolated compounds from this genus have been evaluated for their biological activities. Desmos constituents have been found to exhibit cytotoxic, antimicrobial, antioxidative, anti-inflammatory, and aromatase and NFAT transcriptive inhibition effects.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 299.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 379.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 379.99
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

  1. Nguyen NT, Pham VC, Litaudon M, Guéritte F, Grellier P, Nguyen VT, Nguyen VH (2008) Antiplasmodial alkaloids from Desmos rostrata. J Nat Prod 71:2057

    Article  CAS  PubMed  Google Scholar 

  2. Bajgai SP, Prachyawarakorn V, Mahidol C, Ruchirawat S, Kittakoop P (2011) Hybrid flavan-chalcones, aromatase and lipoxygenase inhibitors, from Desmos cochinchinensis. Phytochemistry 72:2062

    Article  CAS  PubMed  Google Scholar 

  3. Rittiwong T, Mutarapat T, Ponglimanont C, Mahabusarakam W, Chakthong S (2011) Saiyutones A-D: four new unusual biflavones from Desmos chinensis. Tetrahedron 67:5444

    Article  CAS  Google Scholar 

  4. Wu JH, McPhail AT, Bastow KF, Shiraki H, Ito J, Lee KH (2002) Desmosdumotin C, a novel cytotoxic principle from Desmos dumosus. Tetrahedron 43:1391

    Article  CAS  Google Scholar 

  5. Tuntipaleepu M, Chakthong S, Ponglimanont C, Plodpai P, Voravuthikuncha SP (2012) Antifungal and cytotoxic substances from the stem barks of Desmos chinensis. Chin Chem Lett 23:587

    Article  Google Scholar 

  6. Dej-adisai S, Meechai I, Puripattanavong J, Kummee S (2014) Antityrosinase and antimicrobial activities from Thai medicinal plants. Arch Pharmacal Res 37:473

    Article  CAS  Google Scholar 

  7. Linh NTT, Ha NTT, Tra NTT, Anh LTT, Tuyen NV, Son NT (2021) Medicinal plant Centipeda minima: a resource of bioactive compounds. Mini Rev Med Chem 21:273

    Article  PubMed  Google Scholar 

  8. Son NT, Elshamy AI (2021) Flavonoids and other non-alkaloidal constituents of genus Erythrina: phytochemical review. Comb Chem High Throughput Screen 24:20

    Google Scholar 

  9. Son NT (2017) An overview of the genus Prismatomeris: phytochemistry and biological activity. Bull Fac Pharm Cairo Univ 55:11

    Google Scholar 

  10. Son NT (2017) A review on the medicinal plant Dalbergia odorifera species: phytochemistry and biological activity. Evid-Based Compl Alt Med 2017, ID 7142370

    Google Scholar 

  11. Son NT (2018) Notes on the genus Paramignya: phytochemistry and biological activity. Bull Fac Pharm Cairo Univ 56:1

    Google Scholar 

  12. Son NT (2019) Genus Miliusa: a review of phytochemistry and pharmacology. Evid-Based Compl Alt Med 2019, ID 8314693

    Google Scholar 

  13. Son NT (2019) Genus Erythrophleum: botanical description, traditional use, phytochemistry and pharmacology. Phytochem Rev 18:571

    Article  CAS  Google Scholar 

  14. Son NT (2019) Secondary metabolites of genus Pandanus-an aspect of phytochemistry. Mini Rev Org Chem 16:689

    Article  CAS  Google Scholar 

  15. Son NT (2020) A mini-review of the tropical plant Cratoxylum fomosum ssp. pruniflorum: phytochemical and pharmacological aspects. Lett Org Chem 17:327

    Google Scholar 

  16. Son NT, Linh NTT, Tra NT, Ha NTT, Anh LTT, Cham BT, Anh DTT, Tuyen NV (2021) Genus Styrax: a resource of bioactive compounds. Stud Nat Prod Chem 69:299

    Article  Google Scholar 

  17. Suthiphasilp V, Maneerat W, Andersen RJ, Phukhatmuen P, Pyne SG, Laphookhieo S (2019) Dasymaschalolactams A-E, aristolactams from a twig extract of Dasymaschalon dasymaschalum. J Nat Prod 82:3176

    Article  CAS  PubMed  Google Scholar 

  18. Meesakul P, Richardson C, Pyne SG, Laphookhieo S (2019) α-Glucosidase inhibitory flavonoids and oxepinones from the leaf and twig extracts of Desmos cochinchinensis. J Nat Prod 82:741

    Article  CAS  PubMed  Google Scholar 

  19. Qais N, Rahman MM, Rashid MA, Koshino H, Nagasawa K, Nakata T (1996) Antibacterial flavonoids from Desmos chinensis. Fitoterapia 67:554

    CAS  Google Scholar 

  20. Suthiphasilp V, Maneerat T, Duangyod T, Charoensup R, Raymond JA, Stephen GP, Laphookhieo S (2020) Polyoxygenated seco-cyclohexenes derivatives from flower and leaf extracts of Desmos cochinchinensis and their α-glucosidase inhibitory activity. Heliyon 6:e05791

    Google Scholar 

  21. Suthiphasilp V, Maneerat T, Raymond JA, Brian OP, Stephen GP, Surat L (2021) α-Glucosidase inhibitory activity of compounds isolated from the twig and leaf extracts of Desmos dumosus. Heliyon 7:e06180

    Google Scholar 

  22. Nguyen NT, Pham VC, Litaudon M, Guéritte F, Bodo B, Nguyen VT, Nguyen VH (2009) Novel cyclopeptide and unique flavone from Desmos rostrata. Total synthesis of desmorostratone. Tetrahedron 65:7171

    Google Scholar 

  23. Wu JH, Mao SL, Liao SX, Yi YH, Lan CQ, Su ZW (2001) Desmosdumotin B: a new special flavone from Desmos dumosus Chin Chem Lett 12:49

    Google Scholar 

  24. Kuo PC, Tran DT, Huang GJ, Huang BS, Le TMH, Yang ML, Wu TS (2015) Flavonoids from the fruits of Desmos cochinchinesis var. fulvescens and their inhibitory effects on NO production. Chem Nat Compd 51:1

    Google Scholar 

  25. Ju J, Yu J (1999) Studies on chemical constituents of seeds of Desmos chinensis Lour. China J Chin Mater Med 24:418

    CAS  Google Scholar 

  26. Wu JH, Liao SX, Liang HQ, Mao SL (1994) Isolation and identification of flavones from Desmos cochinchinensis Lour. Acta Pharm Sin B 29:621

    CAS  Google Scholar 

  27. Wu JH, Wang XH, Yi YH, Lee KH (2003) Anti-AIDS agents 54. A potent anti-HIV chalcone and flavonoids from genus Desmos. Bioorg Med Chem Lett 13:1813

    Google Scholar 

  28. Shi M, Pan Q, Min Z (2003) Study on chemical constituents from leaves of Desmos chinensis Lour. Zhongguo Yaoke Daxue Xuebao 34:503

    CAS  Google Scholar 

  29. Liao SX, Han GY, Zhang YR, Zheng QT, He CH (1989) Chemical constituents of the root of Desmos cochinchinensis Lour. Acta Pharm Sin B 24:110

    CAS  Google Scholar 

  30. Rittiwong T (2010) Chemical constituents from the leaves of Desmos chinensis Lour. MS thesis, Prince of Songkla University, Hat Yai, Thailand

    Google Scholar 

  31. Clement JA, Ondeyka JG, Goetz MA (2017) Benzoate esters and flavonoids from Desmos pedunculosus. Phytochem Lett 22:117

    Article  CAS  Google Scholar 

  32. Liu XT, Zhang Q, Liang JY, Min ZD (2004) A new oxoaporphine from Desmos chinensis Lour. Chin J Nat Med 2:205

    CAS  Google Scholar 

  33. Wu JH, Liao SX, Mao SL, Yi Y, Takeya K, Su Z, Lan C (1999) Studies on chemical constituents from Desmos dumosus Saff. Acta Pharm Sin B 34:682

    Google Scholar 

  34. Kiem PV, Minh CV, Huong HT, Lee JJ, Lee IS, Kim YH (2005) Phenolic constituents with inhibitory activity against NFAT transcription from Desmos chinensis. Arch Pharm Res 28:1345

    Article  CAS  PubMed  Google Scholar 

  35. Wu JH, Lan C, Mao SL, Liao SX, Su Z (2000) Chemical constituents from the root of Desmos chinensis. Chin Tradit Herbal Drugs 31:567

    Google Scholar 

  36. Jin Z (1992) Chemical constituents on the roots of Desmos chinensis. Yunnan Zhiwu Yanjiu 14:97

    Google Scholar 

  37. Liao SX, Mi HM, Yang GJ, Su ZW (1997) Isolation and identification of constituents from Desmos dumosus. Chin Trad Herbal Drugs 28:515

    Google Scholar 

  38. Wu JH, Mao SL, Liao SX, Shi WH, Su ZW, Lan CQ (2000) Studies on chemical constituents in the root of Desmos grandifolius (I). China J Chin Mater Med 25:419

    CAS  Google Scholar 

  39. Kakeya H, Imoto M, Tabata Y, Iwami J, Matsumoto H, Nakamura K, Koyano T, Tadano K, Umezawa K (1993) Isolation of a novel substrate-competitive tyrosine kinase inhibitor, desmal, from the plant Desmos chinensis. FEBS Lett 320:169

    Article  CAS  PubMed  Google Scholar 

  40. Prachyawarakorn V, Sangpetsiripan S, Surawatanawong P, Mahidol C, Ruchirawatacd S, Kittakoop P (2013) Flavans from Desmos cochinchinensis as potent aromatase inhibitors. Med Chem Commun 4:1590

    Article  CAS  Google Scholar 

  41. Wu JH, Liao SX, Mao SL, Liang HQ, Wang YL, Su ZW (1997) Desmosflavanone II: a new flavanone from Desmos cochinchinensis Lour. J Chin Pharm Sci 6:119

    CAS  Google Scholar 

  42. Wu JH, Mao SL, Liao SX, Yi YH, Su ZW (2001) Desmosdumotin A, a new compound from Desmos dumosus. J Chin Pharm Sci 10:1

    CAS  Google Scholar 

  43. Connolly JD, Dagli S, Haque ME (2005) Constituents of the Annonaceae species Miliusa velutina and Desmos longiflorus. J Indian Chem Soc 80:1169

    Google Scholar 

  44. Rahman MM, Qais N, Rashid MA (2003) A new C-benzylated chalcone from Desmos chinensis. Fitoterapia 74:511

    Article  Google Scholar 

  45. Nakagawa-Goto K, Lee KH (2006) Anti-AIDS agents 68. The first total synthesis of a unique potent anti-HIV chalcone from the genus Desmos. Tetrahedron Lett 47:8263

    Google Scholar 

  46. Abdullah Z, Awang K (2005) Chemical constituents of Desmos dunalii (Hk. f. et. Th.) Sanfford. Mal J Sci 24:267

    Google Scholar 

  47. Chan KC, Ton HT (1986) 7-Hydroxyaporphine alkaloid from Desmos dasymachalus. Phytochemistry 25:1999

    Article  CAS  Google Scholar 

  48. Leboeuf M, Cavé A, Tohami ME, Pusset J, Forgacs P, Provost J (1982) Alkaloids of Annonaceae. XXXV. Alkaloids of Desmos tiebaghiensis. J Nat Prod 45:617

    Google Scholar 

  49. Awang K, Abdullah Z, Mukhtar MR, Litaudon M, Jaafar FM, Hadi HAA, Thomas NF (2009) Dunaliine A, a new amino diketone from Desmos dunalii (Annonaceae). Nat Prod Res 23:652

    Article  CAS  PubMed  Google Scholar 

  50. Sun NJ, Ho DK, Hu XE, Sneddon JM, Stephens RE, Cassady JM (1995) New cytotoxic fatty acid from Desmos cochinchinensis (Annonaceae). Nat Prod Lett 7:35

    Article  CAS  Google Scholar 

  51. Sulaiman M, Martin MT, Pas M, Hadi AHA, Awang K (1998) Desmosine, an artefact alkaloid from Desmos dumosus. Phytochemistry 49:2191

    Article  CAS  Google Scholar 

  52. Plodpai P, Chuenchitt S, Petcharat V, Chakthong S, Voravuthikunchai S (2013) Anti-Rhizoctonia solani activity by Desmos chinensis extracts and its mechanism of action. J Crop Prot 43:65

    Article  Google Scholar 

  53. Zhi QQ, Yan QH, Wang Q, Sun PF, Zhou HY, He ZM (2020) Purification and characterization of two grandiuvarones from Desmos chinensis leaves and their antimicrobial activities. Nat Prod Res 34:1105

    Article  CAS  PubMed  Google Scholar 

  54. Wu TY, Cheng YB, Cheng FT, Hsu YM, Dinh TT, Chang FR, Wu YC (2014) Chemical constituents of the leaves of Desmos cochinchinensis var. fulvescens Ban. Helv Chim Acta 97:1714

    Google Scholar 

  55. Sun NJ, Ho DK, Sneddon JM, Stephens RE, Cassady JM (1992) New cytotoxic cycloartane triterpenoids from Desmos cochinchinensis (Annonaceae). Nat Prod Lett 1:109

    Article  CAS  Google Scholar 

  56. Connolly JD, Haque MDE, Hasan CM, Hossain MS (1994) l5α-Hydroxy-24-methylenelanosta-7,9(1l)-dien-3-one from the stem bark of Desmos longiflorus. Phytochemistry 36:1337

    Google Scholar 

  57. Silva GND, Dutra LM, Lorenzo VP, Silva GD (2021) Phytochemicals and biological properties of Annona coriacea Mart. (Annonaceae): a systematic review from 1971 to 2020. Chem Biol Interact 336:109390

    Google Scholar 

  58. Plodpai P, Petcharat V, Chuenchit S, Chakthong S, Joycharat N, Voravuthikunchai S (2013) Desmos chinensis: a new candidate as natural antifungicide to control rice diseases. Ind Crops Prod 42:324

    Article  Google Scholar 

  59. Son NT, Anh LT, Thuy DTT, Luyen ND, Tuyen TT (2021) Essential oils of Polythia suberosa leaf and twig and their cytotoxic and anti-microbial activities. Chem Biodivers 18:e21000284

    Google Scholar 

  60. Dai DN, Hoi TM, Thang TD, Ogunwande IA (2012) The leaf essential oils of five Vietnamese Desmos species (Annonaceae). Nat Prod Commun 7:231

    CAS  PubMed  Google Scholar 

  61. Hisham A, Rameshkumar KB, Sherwani N, Al-Saidi S, Al-Kindy S (2012) The composition and antimicrobial activities of Cyperus conglomeratus, Desmos chinensis var. lawii and Cyathocalyx zeylanicus essential oils. Nat Prod Commun 7:663

    Google Scholar 

  62. Dai DN, Thanh BV, Thang TD, Ogunwande IA (2014) Identification of volatile constituents of the stem bark and fruits of Desmos cochinchinensis Lour. Am J Essent Oil 1:20

    Google Scholar 

  63. Brophy JJ, Goldsack RJ, Forster PI (2002) The leaf essential oils of the Australian species of Desmos (Annonaceae). J Essent Oil Res 14:298

    Article  CAS  Google Scholar 

  64. Dai DN, Thang TD (2012) Chemical composition of the leaf essential oil of Desmos chinensis Lour. (Annonaceae) from Vietnam. J Essent Oil Bear Plants 15:1044

    Google Scholar 

  65. Dai DN, Hoi TM, Thang TD, Ogunwande IA (2014) Analysis of essential oil constituentsof three Dasymaschalon species (Annonaceae) from Vietnam. Nat Prod Res 28:156

    Article  CAS  PubMed  Google Scholar 

  66. Wang Z (2010) Baker-Venkataraman rearrangement. Comprehensive organic name reactions and reagents. Part 1. Wiley, Hoboken NJ, USA, p 168

    Google Scholar 

  67. Kummee S, Intaraksa N (2008) Antimicrobial activity of Desmos chinensis leaf and Maclura cochinchinensis wood extracts. Songklanakarin J Sci Technol 30:635

    Google Scholar 

  68. Kim JH, Campbell BC, Mahoney N, Chan KL, Molyneux RJ, Balajee A (2010) Augmenting the activity of antifungal agents against aspergilli using structural analogues of benzoic acid as chemosensitizing agents. Fungal Biol 114:817

    Article  CAS  PubMed  Google Scholar 

  69. Batovsk D, Todorova I (2010) Trends in utilization of the pharmacological potential of chalcones. Curr Clin Pharmacol 5:1

    Article  Google Scholar 

  70. Grodin JM, Siiteri PK, Macdonald PC (1973) Source of estrogen production in postmenopausal women. J Clin Endocrinol Metab 36:207

    Article  CAS  PubMed  Google Scholar 

  71. Ghosh D, Lo J, Morton D, Valette D, Xi J, Griswold J, Davies HML (2012) Novel aromatase inhibitors by structure-guided design. J Med Chem 55:8464

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  72. Abbas AK, Lichtman AH, Pober JS (1997) Cellular and molecular immunology, 3rd ed. WB Saunders, Philadelphia, USA, p 315

    Google Scholar 

Download references

Acknowledgments

The compilation of information described in this chapter was supported by the Vietnam Academy of Science and Technology, Vietnam-2021.

Author information

Authors and Affiliations

  1. Department of Chemistry, Institute of Chemistry, Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay, Hanoi, Vietnam

    Nguyen Thi Thuy Linh

  2. Department of Applied Biochemistry, Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay, Hanoi, Vietnam

    Ninh The Son

Authors
  1. Nguyen Thi Thuy Linh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ninh The Son
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ninh The Son .

Editor information

Editors and Affiliations

  1. College of Pharmacy, Ohio State University, Columbus, OH, USA

    A. Douglas Kinghorn

  2. Institute of Organic Chemistry, Johannes Kepler University, Linz, Austria

    Heinz Falk

  3. School of Pharmacy, University of East Anglia, Norwich, UK

    Simon Gibbons

  4. Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan

    Yoshinori Asakawa

  5. School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan, China

    Ji-Kai Liu

  6. Department of Pharmacognosy, University of Vienna, Vienna, Wien, Austria

    Verena M. Dirsch

Rights and permissions

Reprints and permissions

Copyright information

© 2021 The Author(s), under exclusive license to Springer Nature Switzerland AG

About this chapter

Check for updates. Verify currency and authenticity via CrossMark

Cite this chapter

Linh, N.T.T., Son, N.T. (2021). Biologically Active Constituents from Plants of the Genus Desmos. In: Kinghorn, A.D., Falk, H., Gibbons, S., Asakawa, Y., Liu, JK., Dirsch, V.M. (eds) Progress in the Chemistry of Organic Natural Products 116. Progress in the Chemistry of Organic Natural Products, vol 116. Springer, Cham. https://doi.org/10.1007/978-3-030-80560-9_5

Download citation

Publish with us

Policies and ethics

Search

Navigation