Chemical Diversity of Indole Alkaloids from Malaysian Kopsia Species (Apocynaceae) and Their Biological Activities.

Authors

  • Wan Nur Huda Wan Hanafi Natural Products and Synthesis Organic Laboratory (NPSOLab), School of Chemical Sciences, Universiti Sains Malaysia, Pulau Pinang, Malaysia
  • Mohamad Nurul Azmi Mohamad Taib Natural Products and Synthesis Organic Laboratory (NPSOLab), School of Chemical Sciences, Universiti Sains Malaysia, Pulau Pinang, Malaysia
  • Pinus Jumaryatno Department of Pharmacy, Faculty of Mathematics and Natural Sciences, Universitas Islam Indonesia, Yogyakarta, 55584, Indonesia.

DOI:

https://doi.org/10.37134/jsml.vol12.2.3.2024

Keywords:

Apocynacae, Kopsia, indole alkaloids, aspidofractinine, aspidospermane, eburnane

Abstract

The genus Kopsia, which belongs to the family Apocynaceae, has been used extensively in traditional treatment. This mini-review provides a comprehensive analysis of the chemical diversity of indole alkaloids from Malaysian Kopsia species and their biological activities. Fifteen species with 164 indole alkaloids have already been studied and successfully isolated and characterised. Most of them are categorised as aspidofractinine, aspidospermane and eburnane types. The literature and references for this manuscript were obtained from various sources including SciFinder®, Reaxys®, ScienceDirect®, PubMed Central®, NIH National Library of Medicine, Google Scholar and The Plant List®.

Downloads

Download data is not yet available.

References

Awang K, Pais M, Sévenet T, Schaller H, Nasir AM, Hadi AHA. (1991). Eburnaminol and larutensine, alkaloids from Kopsia larutensis. Phytochemistry, 30(9), 3164-3167.

Chan EWC, Wong SK, Chan HT. (2016). Apocynaceae species with antiproliferative and/or antiplasmodial properties: A review of ten genera. Journal of Integrative Medicine, 14(4), 269-284

Gan CY, Yoganathan K, Sim KS, Low YY, Lim SH, Kam TS. (2014). Corynanthean, eburnan, secoleuconoxine, and pauciflorine alkaloids from Kopsia pauciflora. Phytochemistry, 108, 234-242.

Gilbert B. (1965). The alkaloids of Aspidosperma, Diplorrhyncus, Kopsia, Ochrosia, Pleiocarpa, and related genera. In R. H. F. Manske (Ed.) Alkaloids: Chemistry and Physiology, Academic Press.

Kam TS. (1999). Alkaloids from Malaysian flora. In S. W. Pelletier (Ed.) Alkaloids: Chemical and biological perspectives, Pergamon.

Kam TS, Arasu L, Yoganathan K. (1996b). Alkaloids from Kopsia pauciflora. Phytochemistry, 43(6), 1385-1387.

Kam TS, Choo YM, Chen W, Yao JX. (1999a). Indole and monoterpene alkaloids from the leaves of Kopsia dasyrachis. Phytochemistry, 52(5), 959-963.

Kam TS, Lim KH, Yoganathan K, Hayashi M, Komiyama K. (2004). Lundurines A–D, cytotoxic indole alkaloids incorporating a cyclopropyl moiety from Kopsia tenuis and revision of the structures of tenuisines A–C. Tetrahedron, 60(47), 10739-10745.

Kam TS, Sim KM. (1998). Alkaloids from Kopsia griffithii. Phytochemistry, 47(1), 145-147.

Kam TS, Sim KM, Koyano T, Komiyama K. (1999b). Leishmanicidal alkaloids from Kopsia griffithii. Phytochemistry, 50(1), 75-79.

Kam TS, Subramaniam G, Chen W. (1999c). Alkaloids from Kopsia dasyrachis. Phytochemistry, 51(1), 159-169.

Kam TS, Subramaniam G, Sim KM, Yoganathan K, Koyano T, Toyoshima M, Rho MC, Hayashi M, Komiyama K. (1998). Reversal of multidrug resistance (MDR) by aspidofractinine-type indole alkaloids. Bioorganic & Medicinal Chemistry Letters, 8(19), 2769-2772.

Kam TS, Tan PS, Chuah CH. (1992). Alkaloids from leaves of Kopsia larutensis. Phytochemistry, 31(8), 2936-2938.

Kam TS, Tan PS. (1995). Dehydropleiocarpine alkaloids from Kopsia profunda. Phytochemistry, 39(2), 469-471.

Kam TS, Yoganathan K. (1996a). Three aspidofractinine-type alkaloids from Kopsia teoi. Phytochemistry, 42(2), 539-541.

Kam TS, Yoganathan K. (1997). Lahadinines A and B, new cyano-substituted indole alkaloids from Kopsia pauciflora. Phytochemistry, 46(4), 785-787.

Kam TS, Yoganathan K, Koyano T, Komiyama K. (1996c). Pauciflorines A and B, novel melanin biosynthesis inhibitors from Kopsia. Tetrahedron letters, 37(32), 5765-5768.

Kan-Fan C, Sevenet T, Hadi HA, Bonin M, Quirion JC, Husson HP. (1995). Monoterpene alkaloids from Kopsia macrophylla. Natural Product Letters, 7(4), 283-290.

Khozirah S, Noor Rain A, Siti Najila MJ, Imiyabir Z, Madani L, Rohaya C, Rosilawati M, Nuziah H, Goh SH, Zakiah I. (2011). In vitro antiplasmodial properties of selected plants of Sabah. Pertanika Journal of Science and Technology, 19(1), 11-17.

Lim KH, Kam TS. (2008). Methyl chanofruticosinate alkaloids from Kopsia arborea. Phytochemistry, 69(2), 558-561.

Lim KH, Komiyama K, Kam TS. (2007). Arboricine and arboricinine, unusual tetracyclic indole regioisomers from Kopsia. Tetrahedron Letters, 48(7), 1143-1145.

Mauger A, Jarret M, Kouklovsky C, Poupon E, Evanno L, Vincent G. (2021). The chemistry of mavacurane alkaloids: A rich source of bis-indole alkaloids. Natural Product Reports, 38(10), 1852-1886.

Middleton DJ. (2004). A revision of Kopsia (Apocynaceae : Rauvolfioideae). Harvard Papers in Botany, 9(1), 89-142.

Mok SL, Yoganathan K, Lim TM, Kam TS. (1998). Cardiovascular effects of aspidofractinine-type alkaloids from Kopsia. Journal of Natural Products, 61(3), 328-332.

Raal A, Meos A, Hinrikus T, Heinämäki J, Romāne E, Gudienė V, Jaktas V, Koshovyi O, Kovaleva A, Fursenco C, Chiru T, Nguyen HT. (2020). Dragendorff's reagent: Historical perspectives and status of a versatile reagent introduced over 150 years ago at the University of Dorpat, Tartu, Estonia. Die Pharmazie-An International Journal of Pharmaceutical Sciences, 75(7), 299-306

Saxton JE. (1998). Alkaloids of the aspidospermine group. Academic Press.

Sevenet T, Allorge L, David B, Awang K, Hadi AHA, Quirion J, Remy F, Schaller H, Teo LE. (1994). A preliminary chemotaxonomic review of Kopsia (Apocynaceae). Journal of Ethnopharmacology, 41(3), 147-183.

Shahari MS, Ismail AF, Kumolosasi E, Rajab NF, Husain K. (2017). Isolation of indole alkaloids from Kopsia larutensis King & Gamble and their effects on histamine and β-hexosaminidase inhibitory in RBL-2H3 cell line. Journal of Innovations in Pharmaceutical and Biological Sciences, 4(3), 80-86.

Shiobara T, Nagumo Y, Nakajima R, Fukuyama T, Yokoshima S, Usui T. (2021). A novel translation inhibitor, mersicarpine, inhibits S-phase progression and induces apoptosis in HL60 cells. Bioscience, Biotechnology and Biochemistry, 85(1), 92-96.

Subramaniam G, Hiraku O, Hayashi M, Koyano T, Komiyama K, Kam TS. (2007). Biologically active aspidofractinine, rhazinilam, akuammiline, and vincorine alkaloids from Kopsia. Journal of Natural Products, 70(11), 1783-1789.

Teo LE, Pachiaper G, Chan KC, Hadi HA, Weber JF, Deverre JR, David B, Sévenet T. (1990). A new phytochemical survey of Malaysia V. Preliminary screening and plant chemical studies. Journal of Ethnopharmacology, 28(1), 63-101.

Uzir S, Mustapha AM, Hadi AHA, Awang K, Wiart C, Gallard JF, Pais M. (1997). Terengganensines A and B, dihydroeburnane alkaloids from Kopsia terengganensis. Tetrahedron Letters, 38(9), 1571-1574.

Wong SK, Lim YY, Abdullah NR, Nordin FJ. (2011). Assessment of antiproliferative and antiplasmodial activities of five selected Apocynaceae species. BMC Complementary and Alternative Medicine, 11(1), 1-8.

Wong SK, Yeap JSY, Tan CH, Sim KS, Lim SH, Low YY, Kam TS. (2021). Arbolodinines A−C, biologically-active aspidofractinine-aspidofractinine, aspidofractinine-strychnan, and kopsine-strychnan bisindole alkaloids from Kopsia arborea. Tetrahedron, 78, 131802.

Wong SP, Chong KW, Lim KH, Lim SH, Low YY, Kam TS. (2016). Arborisidine and arbornamine, two monoterpenoid indole alkaloids with new polycyclic carbon-nitrogen skeletons derived from a common pericine precursor. Organic Letters, 18(7), 1618-1621.

Downloads

Published

2024-05-15

How to Cite

Wan Hanafi, W. N. H., Mohamad Taib, M. N. A., & Pinus Jumaryatno. (2024). Chemical Diversity of Indole Alkaloids from Malaysian Kopsia Species (Apocynaceae) and Their Biological Activities. Journal of Science and Mathematics Letters, 12(2), 34–49. https://doi.org/10.37134/jsml.vol12.2.3.2024

Issue

Section

Articles