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In vitro acetylcholinesterase inhibitory activities of fractions and iso-agelasine C isolated from the marine sponge Agelas nakamurai

Yıl 2022, Cilt: 26 Sayı: 2, 279 - 286, 28.06.2025

Andhika Dwi Aristyawan Valentika Fitria Setyaningtyas Tutik Sri Wahyuni Aty Widyawaruyanti Kornkanok Ingkaninan Suciati Suciati

Öz

The marine sponges with their unique and wide range of biodiversity, producing unusual metabolites emerge as a good candidate for new therapeutic agents, including as acetylcholinesterase (AChE) inhibitor. The aims of this study are to evaluate the potency of fractions and isolated compound from Agelas nakamurai as AChE inhibitor, as well as to determine the structure of the isolated compound. The bioassay-guided isolation protocol was carried out in this study. The AChE inhibitory assay was carried out based on the modified Ellman’s method. The structure of the isolated compound was determined by NMR spectroscopy and mass spectrometry. A diterpene alkaloid was isolated from the active fraction of A. nakamurai. This compound exhibited a molecular ion at m/z 422.3280 [M]+ in mass spectrometry. The UV profile of the isolated compound showed a strong peak at 269 nm, and the specific rotation value is [α]20D +28,0 (MeOH, c 0.25). These data together with the 1H and 13C NMR spectroscopy data are similar to that reported for iso-agelasine C. The isolated iso-agelasine C gave moderate inhibition against AChE enzyme with an IC50 value of 30.68 ± 0.92 µg/mL, which was lower compared to the extract and fractions. The stronger AChE inhibitory activity in the extract and fractions is possibly due to the synergistic activity of compounds present in the extract and fractions of A. nakamurai. Iso-agelasine C could serve as a lead for the development of diterpene alkaloid as an AChE inhibitor.

Anahtar Kelimeler

Alzheimer’s diseas acetylcholinesterase inhibitor marine sponge Agelas nakamurai iso-agelasine C

Kaynakça

  • [1] Alzheimer's Association. 2020 Alzheimer’s disease facts and figures. Alzheimer’s Dement. 2020; 16(3): 391-460. [CrossRef]
  • [2] Alzheimer's Association. 2015 Alzheimer’s disease facts and figures. Alzheimer’s Dement. 2015;11(3):332-384. [CrossRef]
  • [3] Konrath EL, Passos CDS, Klein-Júnior LC, Henriques AT. Alkaloids as a source of potential anticholinesterase inhibitors for the treatment of Alzheimer’s disease. J Pharm Pharmacol. 2013; 65(12): 1701-1725. [CrossRef]
  • [4] Breijyeh Z, Karaman R. Comprehensive review on Alzheimer's disease: causes and treatment. Molecules. 2020; 25(24): 5789. [CrossRef]
  • [5] Dev K, Maurya R. Marine-derived anti-Alzheimer’s agents of promise. In: Brahmachari G. (Ed). Neuroprotective Natural Products, Clinical Aspects and Mode of Action. Wiley-VCH., Weinheim, 2017, pp. 153-184.
  • [6] Mathew M, Subramanian S. In vitro screening for anti-cholinesterase and antioxidant activity of methanolic extracts of ayurvedic medicinal plants used for cognitive disorders. Plos one. 2014; 9(1): e86804. [CrossRef]
  • [ 7] Hostettmann K, Borloz A, Urbain A, Marston A. Natural product ınhibitors of acetylcholinesterase. Curr Org Chem. 2006; 10(8): 825-847. [CrossRef]
  • [8] Heinrich M, Teoh HL. Galanthamine from snowdrop - the development of a modern drug against Alzheimer’s disease from local Caucasian knowledge. J Ethnopharmacol. 2004; 92(2-3): 147-162. [CrossRef]
  • [9] Ahmed F, Ghalib R, Sasikala P, Mueen AK. Cholinesterase inhibitors from botanicals. Pharmacogn Rev. 2013; 7(14): 121-130. [CrossRef]
  • [10] Murray A, Faraoni M, Castro M, Alza N, Cavallaro V. Natural AChE ınhibitors from plants and their contribution to Alzheimer’s disease therapy. Curr Neuropharmacol. 2013; 11(4): 388-413. [CrossRef]
  • [11] Zhang H, Dong M, Chen J, Wang H, Tenney K, Crews P. Bioactive secondary metabolites from the marine sponge genus Agelas. Mar Drugs. 2017; 15(11): 351. [CrossRef]
  • [12] Suciati, Rabgay K, Fachrunniza Y, Saesong T, Hadi TA, Wahyuni TS, Widyawaruyanti A, Ingkaninan K. Enzyme ınhibitory activities of marine sponges against cholinesterase and 5α-reductase. Malays Appl Biol. 2019; 48(3): 77- 83.
  • [13] Chu M, Tang X, Qin G, Sun Y, Li L, Li P, Li G. Pyrrole derivatives and diterpene alkaloids from the South China Sea sponge Agelas nakamurai. Chem Biodivers. 2017; 14(7). e1600446. [CrossRef]
  • [14] Roncero AM, Tobal IE, Moro RF, Díez D, Marcos IS. Halimane diterpenoids: sources, structures, nomenclature and biological activities. Nat Prod Rep. 2018; 35(9): 955-991. [CrossRef]
  • [15] García PA, Valles E, Díez D, Castro MÁ. Marine Alkylpurines: A promising group of bioactive marine natural products. Mar Drugs. 2018; 16(1): 6. [CrossRef]
  • [16] Stout EP, Yu LC, Molinski TF. Antifungal diterpene alkaloids from the Caribbean sponge Agelas citrina: Unified configurational assignments of agelasidines and agelasines. Eur J Org Chem. 2012; 2012(27): 5131-5135. [CrossRef]
  • [17] Hattori T, Adachi K, Shizuri Y. New agelasine compound from the marine sponge Agelas mauritiana as an antifouling substance against macroalgae. J Nat Prod. 1997; 60(4): 411-413. [CrossRef]
  • [18] Nisar M, Ahmad M, Wadood N, Lodhi MA, Shaheen F, Choudhary MI. New diterpenoid alkaloids from Aconitum heterophyllum Wall: Selective butyrylcholinestrase inhibitors. J Enzyme Inhib Med Chem. 2009; 24(1):47-51. [CrossRef]
  • [19] Ahmad H, Ahmad S, Shah SAA, Latif A, Ali M, Khan FA, Tahir MN, Shaheen F, Wadood A, Ahmad M. Antioxidant and anticholinesterase potential of diterpenoid alkaloids from Aconitum heterophyllum. Bioorg Med Chem. 2017; 25(13): 3368-3376. [CrossRef]
  • [20] Ahmad VU, Khan A, Farooq U, Kousar F, Khan SS, Nawaz SA, Abbasi MA, Choudhary MI. Three new cholinesterase-inhibiting cis-clerodane diterpenoids from Otostegia limbata. Chem Pharm Bull. 2005; 53(4): 378-381. [CrossRef]
  • [21] Ellman GL, Courtney KD, Andres V Jr, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol. 1961; 7(2): 88-95. [CrossRef]
  • [22] Ingkaninan K, Temkitthawon P, Chuenchom K, Yuyaem T, Thongnoi W. Screening for acetylcholinesterase inhibitory activity in plants used in Thai traditional rejuvenating and neurotonic remedies. J Ethnopharmacol. 2003; 89(2-3): 261-264. [CrossRef]
  • [23] Sirimangkalakitti N, Olatunji OJ, Changwichit K, Saesong T, Chamni S, Chanvorachote P, Ingkaninan K, Plubrukarn A, Suwanborirux K. Bromotyrosine alkaloids with acetylcholinesterase inhibitory activity from the thai sponge Acanthodendrilla sp. Nat Prod Commun. 2015; 10(11): 1945-1949. [CrossRef]
  • [24] Suciati, Laili ER, Poerwantoro D, Hapsari AP, Gifanda LZ, Rabgay K, Ekasari W, Ingkaninan K. Evaluation of cholinesterase inhibitory activity of six Indonesian Cassia species. J Res Pharm. 2020; 24(4): 472-478. [CrossRef]
  • [25] Suciati, Poerwantoro D, Widyawaruyanti A, Ingkaninan K. Acetylcholinesterase inhibitory activity of extract and fractions from the root of Rauvolfia serpentina(L.) Bth.ex Kurz. J Basic Clin Physiol Pharmacol. 2021; 32(4): 313-317. [CrossRef]

Yıl 2022, Cilt: 26 Sayı: 2, 279 - 286, 28.06.2025

Andhika Dwi Aristyawan Valentika Fitria Setyaningtyas Tutik Sri Wahyuni Aty Widyawaruyanti Kornkanok Ingkaninan Suciati Suciati

Öz

Kaynakça

  • [1] Alzheimer's Association. 2020 Alzheimer’s disease facts and figures. Alzheimer’s Dement. 2020; 16(3): 391-460. [CrossRef]
  • [2] Alzheimer's Association. 2015 Alzheimer’s disease facts and figures. Alzheimer’s Dement. 2015;11(3):332-384. [CrossRef]
  • [3] Konrath EL, Passos CDS, Klein-Júnior LC, Henriques AT. Alkaloids as a source of potential anticholinesterase inhibitors for the treatment of Alzheimer’s disease. J Pharm Pharmacol. 2013; 65(12): 1701-1725. [CrossRef]
  • [4] Breijyeh Z, Karaman R. Comprehensive review on Alzheimer's disease: causes and treatment. Molecules. 2020; 25(24): 5789. [CrossRef]
  • [5] Dev K, Maurya R. Marine-derived anti-Alzheimer’s agents of promise. In: Brahmachari G. (Ed). Neuroprotective Natural Products, Clinical Aspects and Mode of Action. Wiley-VCH., Weinheim, 2017, pp. 153-184.
  • [6] Mathew M, Subramanian S. In vitro screening for anti-cholinesterase and antioxidant activity of methanolic extracts of ayurvedic medicinal plants used for cognitive disorders. Plos one. 2014; 9(1): e86804. [CrossRef]
  • [ 7] Hostettmann K, Borloz A, Urbain A, Marston A. Natural product ınhibitors of acetylcholinesterase. Curr Org Chem. 2006; 10(8): 825-847. [CrossRef]
  • [8] Heinrich M, Teoh HL. Galanthamine from snowdrop - the development of a modern drug against Alzheimer’s disease from local Caucasian knowledge. J Ethnopharmacol. 2004; 92(2-3): 147-162. [CrossRef]
  • [9] Ahmed F, Ghalib R, Sasikala P, Mueen AK. Cholinesterase inhibitors from botanicals. Pharmacogn Rev. 2013; 7(14): 121-130. [CrossRef]
  • [10] Murray A, Faraoni M, Castro M, Alza N, Cavallaro V. Natural AChE ınhibitors from plants and their contribution to Alzheimer’s disease therapy. Curr Neuropharmacol. 2013; 11(4): 388-413. [CrossRef]
  • [11] Zhang H, Dong M, Chen J, Wang H, Tenney K, Crews P. Bioactive secondary metabolites from the marine sponge genus Agelas. Mar Drugs. 2017; 15(11): 351. [CrossRef]
  • [12] Suciati, Rabgay K, Fachrunniza Y, Saesong T, Hadi TA, Wahyuni TS, Widyawaruyanti A, Ingkaninan K. Enzyme ınhibitory activities of marine sponges against cholinesterase and 5α-reductase. Malays Appl Biol. 2019; 48(3): 77- 83.
  • [13] Chu M, Tang X, Qin G, Sun Y, Li L, Li P, Li G. Pyrrole derivatives and diterpene alkaloids from the South China Sea sponge Agelas nakamurai. Chem Biodivers. 2017; 14(7). e1600446. [CrossRef]
  • [14] Roncero AM, Tobal IE, Moro RF, Díez D, Marcos IS. Halimane diterpenoids: sources, structures, nomenclature and biological activities. Nat Prod Rep. 2018; 35(9): 955-991. [CrossRef]
  • [15] García PA, Valles E, Díez D, Castro MÁ. Marine Alkylpurines: A promising group of bioactive marine natural products. Mar Drugs. 2018; 16(1): 6. [CrossRef]
  • [16] Stout EP, Yu LC, Molinski TF. Antifungal diterpene alkaloids from the Caribbean sponge Agelas citrina: Unified configurational assignments of agelasidines and agelasines. Eur J Org Chem. 2012; 2012(27): 5131-5135. [CrossRef]
  • [17] Hattori T, Adachi K, Shizuri Y. New agelasine compound from the marine sponge Agelas mauritiana as an antifouling substance against macroalgae. J Nat Prod. 1997; 60(4): 411-413. [CrossRef]
  • [18] Nisar M, Ahmad M, Wadood N, Lodhi MA, Shaheen F, Choudhary MI. New diterpenoid alkaloids from Aconitum heterophyllum Wall: Selective butyrylcholinestrase inhibitors. J Enzyme Inhib Med Chem. 2009; 24(1):47-51. [CrossRef]
  • [19] Ahmad H, Ahmad S, Shah SAA, Latif A, Ali M, Khan FA, Tahir MN, Shaheen F, Wadood A, Ahmad M. Antioxidant and anticholinesterase potential of diterpenoid alkaloids from Aconitum heterophyllum. Bioorg Med Chem. 2017; 25(13): 3368-3376. [CrossRef]
  • [20] Ahmad VU, Khan A, Farooq U, Kousar F, Khan SS, Nawaz SA, Abbasi MA, Choudhary MI. Three new cholinesterase-inhibiting cis-clerodane diterpenoids from Otostegia limbata. Chem Pharm Bull. 2005; 53(4): 378-381. [CrossRef]
  • [21] Ellman GL, Courtney KD, Andres V Jr, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol. 1961; 7(2): 88-95. [CrossRef]
  • [22] Ingkaninan K, Temkitthawon P, Chuenchom K, Yuyaem T, Thongnoi W. Screening for acetylcholinesterase inhibitory activity in plants used in Thai traditional rejuvenating and neurotonic remedies. J Ethnopharmacol. 2003; 89(2-3): 261-264. [CrossRef]
  • [23] Sirimangkalakitti N, Olatunji OJ, Changwichit K, Saesong T, Chamni S, Chanvorachote P, Ingkaninan K, Plubrukarn A, Suwanborirux K. Bromotyrosine alkaloids with acetylcholinesterase inhibitory activity from the thai sponge Acanthodendrilla sp. Nat Prod Commun. 2015; 10(11): 1945-1949. [CrossRef]
  • [24] Suciati, Laili ER, Poerwantoro D, Hapsari AP, Gifanda LZ, Rabgay K, Ekasari W, Ingkaninan K. Evaluation of cholinesterase inhibitory activity of six Indonesian Cassia species. J Res Pharm. 2020; 24(4): 472-478. [CrossRef]
  • [25] Suciati, Poerwantoro D, Widyawaruyanti A, Ingkaninan K. Acetylcholinesterase inhibitory activity of extract and fractions from the root of Rauvolfia serpentina(L.) Bth.ex Kurz. J Basic Clin Physiol Pharmacol. 2021; 32(4): 313-317. [CrossRef]
Toplam 25 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Eczacılık Bilimleri
Bölüm Articles
Yazarlar

Andhika Dwi Aristyawan 0000-0002-4955-1343

Valentika Fitria Setyaningtyas 0000-0003-1591-2005

Tutik Sri Wahyuni 0000-0003-2049-7774

Aty Widyawaruyanti 0000-0003-4639-1599

Kornkanok Ingkaninan 0000-0002-4415-8489

Suciati Suciati 0000-0003-2436-4119

Yayımlanma Tarihi 28 Haziran 2025
Yayımlandığı Sayı Yıl 2022 Cilt: 26 Sayı: 2

Kaynak Göster

APA Aristyawan, A. D., Setyaningtyas, V. F., Wahyuni, T. S., Widyawaruyanti, A., vd. (2025). In vitro acetylcholinesterase inhibitory activities of fractions and iso-agelasine C isolated from the marine sponge Agelas nakamurai. Journal of Research in Pharmacy, 26(2), 279-286.
AMA Aristyawan AD, Setyaningtyas VF, Wahyuni TS, Widyawaruyanti A, Ingkaninan K, Suciati S. In vitro acetylcholinesterase inhibitory activities of fractions and iso-agelasine C isolated from the marine sponge Agelas nakamurai. J. Res. Pharm. Haziran 2025;26(2):279-286.
Chicago Aristyawan, Andhika Dwi, Valentika Fitria Setyaningtyas, Tutik Sri Wahyuni, Aty Widyawaruyanti, Kornkanok Ingkaninan, ve Suciati Suciati. “In Vitro Acetylcholinesterase Inhibitory Activities of Fractions and Iso-Agelasine C Isolated from the Marine Sponge Agelas Nakamurai”. Journal of Research in Pharmacy 26, sy. 2 (Haziran 2025): 279-86.
EndNote Aristyawan AD, Setyaningtyas VF, Wahyuni TS, Widyawaruyanti A, Ingkaninan K, Suciati S (01 Haziran 2025) In vitro acetylcholinesterase inhibitory activities of fractions and iso-agelasine C isolated from the marine sponge Agelas nakamurai. Journal of Research in Pharmacy 26 2 279–286.
IEEE A. D. Aristyawan, V. F. Setyaningtyas, T. S. Wahyuni, A. Widyawaruyanti, K. Ingkaninan, ve S. Suciati, “In vitro acetylcholinesterase inhibitory activities of fractions and iso-agelasine C isolated from the marine sponge Agelas nakamurai”, J. Res. Pharm., c. 26, sy. 2, ss. 279–286, 2025.
ISNAD Aristyawan, Andhika Dwi vd. “In Vitro Acetylcholinesterase Inhibitory Activities of Fractions and Iso-Agelasine C Isolated from the Marine Sponge Agelas Nakamurai”. Journal of Research in Pharmacy 26/2 (Haziran 2025), 279-286.
JAMA Aristyawan AD, Setyaningtyas VF, Wahyuni TS, Widyawaruyanti A, Ingkaninan K, Suciati S. In vitro acetylcholinesterase inhibitory activities of fractions and iso-agelasine C isolated from the marine sponge Agelas nakamurai. J. Res. Pharm. 2025;26:279–286.
MLA Aristyawan, Andhika Dwi vd. “In Vitro Acetylcholinesterase Inhibitory Activities of Fractions and Iso-Agelasine C Isolated from the Marine Sponge Agelas Nakamurai”. Journal of Research in Pharmacy, c. 26, sy. 2, 2025, ss. 279-86.
Vancouver Aristyawan AD, Setyaningtyas VF, Wahyuni TS, Widyawaruyanti A, Ingkaninan K, Suciati S. In vitro acetylcholinesterase inhibitory activities of fractions and iso-agelasine C isolated from the marine sponge Agelas nakamurai. J. Res. Pharm. 2025;26(2):279-86.