4-Benzyloxylonchocarpin and muracatanes A-C from Ranunculus muricatus L. and their biological effects

Hidayat Hussain; Iftikhar Ali; Daijie Wang; Nilufar Z. Mamadalieva; Wahid Hussain; René Csuk; Anne Loesche; Lucie Fischer; Dan Stærk; Syariful Anam; Mashail N. AlZain; Maria Mushtaq; Zaheer Ul-Haq; Riaz Ullah; Omar M. Noman; Ghulam Abbas; Ivan R. Green

doi:10.3390/biom10111562

4-Benzyloxylonchocarpin and muracatanes A-C from Ranunculus muricatus L. and their biological effects

Hidayat Hussain^*, Iftikhar Ali, Daijie Wang, Nilufar Z. Mamadalieva, Wahid Hussain, René Csuk, Anne Loesche, Lucie Fischer, Dan Stærk, Syariful Anam, Mashail N. AlZain, Maria Mushtaq, Zaheer Ul-Haq, Riaz Ullah, Omar M. Noman, Ghulam Abbas, Ivan R. Green

^*Corresponding author af dette arbejde

Biologiske lægemidler

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

9 Citationer (Scopus)

49 Downloads (Pure)

Abstract

Ranunculus muricatus L. is a spiny fruit buttercup that is used in various traditional medicinal systems. In the current investigation of R. muricatus, the new chalcone 4-benzyloxylonchocarpin (1), the new anthraquinone muracatanes A (2), the new-to-nature anthraquinone muracatanes B (3), and the
new naphthalene analog muracatanes C (4) were isolated, in addition to the three previously reported
compounds, 4-methoxylonchocarpin (5), β-sitosterol (6), and β-sitosterol β-D-glucopyranoside (7). Their structures were elucidated using 1D (¹H and ¹³C) and 2D (COSY, HSQC, and HMBC) NMR
spectroscopy and HR-ESI-MS. Chalcone 1 showed potent acetylcholinesterase inhibitory effects with
K_i of 5.39 μM and K_i' of 3.54 μM, but none of the isolated compounds showed inhibitory activity
towards butyrylcholinesterase. Anthraquinone 3 illustrated α-glucosidase inhibitory effects with
IC₅₀-values of 164.46 ± 83.04 μM. Compound 5 displayed moderate cytotoxic activity towards ovarian carcinoma (A2780, IC₅₀ = 25.4 μM), colorectal adenocarcinoma (HT29, IC₅₀ = 20.2 μM), breast cancer (MCF7, IC₅₀ = 23.7 μM), and thyroid carcinoma (SW1736, IC₅₀ = 26.2 μM) while it was inactive towards pharynx carcinoma (FaDu: IC⁵⁰ > 30 μM).

Originalsprog	Engelsk
Artikelnummer	1562
Tidsskrift	Biomolecules
Vol/bind	10
Udgave nummer	11
Antal sider	15
ISSN	2218-273X
DOI	https://doi.org/10.3390/biom10111562
Status	Udgivet - 2020

Adgang til dokumentet

10.3390/biom10111562

biomolecules-10-01562-v2Forlagets udgivne version, 2,72 MBLicens: CC BY

Citationsformater

Hussain, H., Ali, I., Wang, D., Mamadalieva, N. Z., Hussain, W., Csuk, R., Loesche, A., Fischer, L., Stærk, D., Anam, S., AlZain, M. N., Mushtaq, M., Ul-Haq, Z., Ullah, R., Noman, O. M., Abbas, G., & Green, I. R. (2020). 4-Benzyloxylonchocarpin and muracatanes A-C from Ranunculus muricatus L. and their biological effects. Biomolecules, 10(11), Artikel 1562. https://doi.org/10.3390/biom10111562

Hussain, H, Ali, I, Wang, D, Mamadalieva, NZ, Hussain, W, Csuk, R, Loesche, A, Fischer, L, Stærk, D, Anam, S, AlZain, MN, Mushtaq, M, Ul-Haq, Z, Ullah, R, Noman, OM, Abbas, G & Green, IR 2020, '4-Benzyloxylonchocarpin and muracatanes A-C from Ranunculus muricatus L. and their biological effects', Biomolecules, bind 10, nr. 11, 1562. https://doi.org/10.3390/biom10111562

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title = "4-Benzyloxylonchocarpin and muracatanes A-C from Ranunculus muricatus L. and their biological effects",

abstract = "Ranunculus muricatus L. is a spiny fruit buttercup that is used in various traditional medicinal systems. In the current investigation of R. muricatus, the new chalcone 4-benzyloxylonchocarpin (1), the new anthraquinone muracatanes A (2), the new-to-nature anthraquinone muracatanes B (3), and thenew naphthalene analog muracatanes C (4) were isolated, in addition to the three previously reportedcompounds, 4-methoxylonchocarpin (5), β-sitosterol (6), and β-sitosterol β-D-glucopyranoside (7). Their structures were elucidated using 1D (1H and 13C) and 2D (COSY, HSQC, and HMBC) NMRspectroscopy and HR-ESI-MS. Chalcone 1 showed potent acetylcholinesterase inhibitory effects withKi of 5.39 μM and Ki' of 3.54 μM, but none of the isolated compounds showed inhibitory activitytowards butyrylcholinesterase. Anthraquinone 3 illustrated α-glucosidase inhibitory effects withIC50-values of 164.46 ± 83.04 μM. Compound 5 displayed moderate cytotoxic activity towards ovarian carcinoma (A2780, IC50 = 25.4 μM), colorectal adenocarcinoma (HT29, IC50 = 20.2 μM), breast cancer (MCF7, IC50 = 23.7 μM), and thyroid carcinoma (SW1736, IC50 = 26.2 μM) while it was inactive towards pharynx carcinoma (FaDu: IC50 > 30 μM).",

author = "Hidayat Hussain and Iftikhar Ali and Daijie Wang and Mamadalieva, {Nilufar Z.} and Wahid Hussain and Ren{\'e} Csuk and Anne Loesche and Lucie Fischer and Dan St{\ae}rk and Syariful Anam and AlZain, {Mashail N.} and Maria Mushtaq and Zaheer Ul-Haq and Riaz Ullah and Noman, {Omar M.} and Ghulam Abbas and Green, {Ivan R.}",

year = "2020",

doi = "10.3390/biom10111562",

language = "English",

volume = "10",

journal = "Biomolecules",

issn = "2218-273X",

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TY - JOUR

T1 - 4-Benzyloxylonchocarpin and muracatanes A-C from Ranunculus muricatus L. and their biological effects

AU - Hussain, Hidayat

AU - Ali, Iftikhar

AU - Wang, Daijie

AU - Mamadalieva, Nilufar Z.

AU - Hussain, Wahid

AU - Csuk, René

AU - Loesche, Anne

AU - Fischer, Lucie

AU - Stærk, Dan

AU - Anam, Syariful

AU - AlZain, Mashail N.

AU - Mushtaq, Maria

AU - Ul-Haq, Zaheer

AU - Ullah, Riaz

AU - Noman, Omar M.

AU - Abbas, Ghulam

AU - Green, Ivan R.

PY - 2020

Y1 - 2020

N2 - Ranunculus muricatus L. is a spiny fruit buttercup that is used in various traditional medicinal systems. In the current investigation of R. muricatus, the new chalcone 4-benzyloxylonchocarpin (1), the new anthraquinone muracatanes A (2), the new-to-nature anthraquinone muracatanes B (3), and thenew naphthalene analog muracatanes C (4) were isolated, in addition to the three previously reportedcompounds, 4-methoxylonchocarpin (5), β-sitosterol (6), and β-sitosterol β-D-glucopyranoside (7). Their structures were elucidated using 1D (1H and 13C) and 2D (COSY, HSQC, and HMBC) NMRspectroscopy and HR-ESI-MS. Chalcone 1 showed potent acetylcholinesterase inhibitory effects withKi of 5.39 μM and Ki' of 3.54 μM, but none of the isolated compounds showed inhibitory activitytowards butyrylcholinesterase. Anthraquinone 3 illustrated α-glucosidase inhibitory effects withIC50-values of 164.46 ± 83.04 μM. Compound 5 displayed moderate cytotoxic activity towards ovarian carcinoma (A2780, IC50 = 25.4 μM), colorectal adenocarcinoma (HT29, IC50 = 20.2 μM), breast cancer (MCF7, IC50 = 23.7 μM), and thyroid carcinoma (SW1736, IC50 = 26.2 μM) while it was inactive towards pharynx carcinoma (FaDu: IC50 > 30 μM).

AB - Ranunculus muricatus L. is a spiny fruit buttercup that is used in various traditional medicinal systems. In the current investigation of R. muricatus, the new chalcone 4-benzyloxylonchocarpin (1), the new anthraquinone muracatanes A (2), the new-to-nature anthraquinone muracatanes B (3), and thenew naphthalene analog muracatanes C (4) were isolated, in addition to the three previously reportedcompounds, 4-methoxylonchocarpin (5), β-sitosterol (6), and β-sitosterol β-D-glucopyranoside (7). Their structures were elucidated using 1D (1H and 13C) and 2D (COSY, HSQC, and HMBC) NMRspectroscopy and HR-ESI-MS. Chalcone 1 showed potent acetylcholinesterase inhibitory effects withKi of 5.39 μM and Ki' of 3.54 μM, but none of the isolated compounds showed inhibitory activitytowards butyrylcholinesterase. Anthraquinone 3 illustrated α-glucosidase inhibitory effects withIC50-values of 164.46 ± 83.04 μM. Compound 5 displayed moderate cytotoxic activity towards ovarian carcinoma (A2780, IC50 = 25.4 μM), colorectal adenocarcinoma (HT29, IC50 = 20.2 μM), breast cancer (MCF7, IC50 = 23.7 μM), and thyroid carcinoma (SW1736, IC50 = 26.2 μM) while it was inactive towards pharynx carcinoma (FaDu: IC50 > 30 μM).

U2 - 10.3390/biom10111562

DO - 10.3390/biom10111562

M3 - Journal article

C2 - 33212893

SN - 2218-273X

VL - 10

JO - Biomolecules

JF - Biomolecules

IS - 11

M1 - 1562

ER -