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

• Published in: Molecules (Basel, Switzerland) Switzerland), 2021-07, Vol.26 (14), p.4121
• Main Authors: Uddin, Md Josim, Russo, Daniela, Haque, Md Anwarul, Çiçek, Serhat Sezai, Sönnichsen, Frank D, Milella, Luigi, Zidorn, Christian
• Format: Article
• Language: English
• Subjects: Abietanes - chemistry; Acarbose; Age; alpha-Amylases - antagonists & inhibitors; Amylases; antidiabetic; Antidiabetics; Antimicrobial agents; Antineoplastic Agents - pharmacology; Breast cancer; Cancer; Carbohydrates; Cholinesterase Inhibitors - pharmacology; Clerodendrum - chemistry; Clerodendrum infortunatum; Diabetes; Diabetes mellitus; Diterpenes; Enzymes; Glucose; Glucosidase; Glycoside Hydrolase Inhibitors - pharmacology; Glycosides; Glycosides - pharmacology; Humans; Hydrocarbons; In vitro methods and tests; Lamiaceae; Natural products; Neoplasms - drug therapy; Phenylpropanoids; Phytochemicals; Plant Leaves - chemistry; Spectrometry; terpenoids; Tumor Cells, Cultured; Tumors; Yeasts; α-Amylase; α-Glucosidase
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules26144121

In this study, two previously undescribed diterpenoids, (5 ,10 ,16 )-11,16,19-trihydroxy-12- -β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-17(15→16),18(4→3)- -3,8,11,13-abietatetraene-7-one ( ) and (5 ,10 ,16 )-11,16-dihydroxy-12- -β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-17(15→16),18(4→3)- -4-carboxy-3,8,11,13-abietatetraene-7-one ( ), and one known compound, the C -nor-isoprenoid glycoside byzantionoside B ( ), were isolated from the leaves of 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'- -caffeoyl-12-glucopyranosyloxyjasmonic acid ( ), jionoside C ( ), jionoside D ( ), brachynoside ( ), and incanoside C ( ), 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 showed the most potent effect against mammalian α-amylase (IC 3.4 ± 0.2 μM) compared to the reference standard acarbose (IC 5.9 ± 0.1 μM). As yeast α-glucosidase inhibitors, compounds , , , and displayed moderate inhibitory activities, ranging from 24.6 to 96.0 μM, compared to acarbose (IC 665 ± 42 μM). All of the tested compounds demonstrated negligible anticholinesterase effects. In an anticancer test, compounds and exhibited moderate antiproliferative properties with IC 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 (IC > 100 μM).