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Article

Bioactive Abietane-Type Diterpenoid Glycosides from Leaves of Clerodendrum infortunatum (Lamiaceae)

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Pharmazeutisches Institut, Abteilung Pharmazeutische Biologie, Christian-Albrechts-Universität zu Kiel, Gutenbergstrasse 76, 24118 Kiel, Germany
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Department of Pharmacy, International Islamic University Chittagong, Chittagong 4318, Bangladesh
3
Department of Science, University of Basilicata, Viale dell’ Ateneo Lucano 10, 85100 Potenza, Italy
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Spinoff BioActiPlant s.r.l., Viale dell’ Ateneo Lucano 10, 85100 Potenza, Italy
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Department of Experimental Pathology, Graduate School of Comprehensive Human Sciences, University of Tsukuba, Ibaraki 305-8575, Japan
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Department of Pharmacy, University of Rajshahi, Rajshahi 6205, Bangladesh
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Otto Diels Institute for Organic Chemistry, University of Kiel, Otto-Hahn-Platz 4, 24118 Kiel, Germany
*
Author to whom correspondence should be addressed.
Academic Editors: Raffaele Pezzani and Sara Vitalini
Molecules 2021, 26(14), 4121; https://doi.org/10.3390/molecules26144121
Received: 31 May 2021 / Revised: 26 June 2021 / Accepted: 29 June 2021 / Published: 6 July 2021
(This article belongs to the Special Issue Biological and Pharmacological Activity of Plant Natural Compounds II)
In this study, two previously undescribed diterpenoids, (5R,10S,16R)-11,16,19-trihydroxy-12-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-17(15→16),18(4→3)-diabeo-3,8,11,13-abietatetraene-7-one (1) and (5R,10S,16R)-11,16-dihydroxy-12-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-17(15→16),18(4→3)-diabeo-4-carboxy-3,8,11,13-abietatetraene-7-one (2), and one known compound, the C13-nor-isoprenoid glycoside byzantionoside B (3), were isolated from the leaves of Clerodendrum infortunatum L. (Lamiaceae). Structures were established based on spectroscopic and spectrometric data and by comparison with literature data. The three terpenoids, along with five phenylpropanoids: 6′-O-caffeoyl-12-glucopyranosyloxyjasmonic acid (4), jionoside C (5), jionoside D (6), brachynoside (7), and incanoside C (8), previously isolated from the same source, were tested for their in vitro antidiabetic (α-amylase and α-glucosidase), anticancer (Hs578T and MDA-MB-231), and anticholinesterase activities. In an in vitro test against carbohydrate digestion enzymes, compound 6 showed the most potent effect against mammalian α-amylase (IC50 3.4 ± 0.2 μM) compared to the reference standard acarbose (IC50 5.9 ± 0.1 μM). As yeast α-glucosidase inhibitors, compounds 1, 2, 5, and 6 displayed moderate inhibitory activities, ranging from 24.6 to 96.0 μM, compared to acarbose (IC50 665 ± 42 μM). All of the tested compounds demonstrated negligible anticholinesterase effects. In an anticancer test, compounds 3 and 5 exhibited moderate antiproliferative properties with IC50 of 94.7 ± 1.3 and 85.3 ± 2.4 μM, respectively, against Hs578T cell, while the rest of the compounds did not show significant activity (IC50 > 100 μM). View Full-Text
Keywords: Clerodendrum infortunatum; terpenoids; phenylpropanoids; antidiabetic; breast cancer Clerodendrum infortunatum; terpenoids; phenylpropanoids; antidiabetic; breast cancer
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MDPI and ACS Style

Uddin, M.J.; Russo, D.; Haque, M.A.; Çiçek, S.S.; Sönnichsen, F.D.; Milella, L.; Zidorn, C. Bioactive Abietane-Type Diterpenoid Glycosides from Leaves of Clerodendrum infortunatum (Lamiaceae). Molecules 2021, 26, 4121. https://doi.org/10.3390/molecules26144121

AMA Style

Uddin MJ, Russo D, Haque MA, Çiçek SS, Sönnichsen FD, Milella L, Zidorn C. Bioactive Abietane-Type Diterpenoid Glycosides from Leaves of Clerodendrum infortunatum (Lamiaceae). Molecules. 2021; 26(14):4121. https://doi.org/10.3390/molecules26144121

Chicago/Turabian Style

Uddin, Md. J., Daniela Russo, Md. A. Haque, Serhat S. Çiçek, Frank D. Sönnichsen, Luigi Milella, and Christian Zidorn. 2021. "Bioactive Abietane-Type Diterpenoid Glycosides from Leaves of Clerodendrum infortunatum (Lamiaceae)" Molecules 26, no. 14: 4121. https://doi.org/10.3390/molecules26144121

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