Highly Aromatic Flavan-3-ol Derivatives from Palaeotropical Artocarpus lacucha Buch.-Ham Possess Radical Scavenging and Antiproliferative Properties.

Weerasak Songoen,Witthawat Phanchai,Wanchai Pluempanupat,Michael A Jakupec,Dominik Wenisch,Johann Schinnerl,Lothar Brecker

doi:10.3390/molecules26041078

Weerasak Songoen, Witthawat Phanchai + Show 5 more

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https://doi.org/10.3390/molecules26041078

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Abstract

Phytochemical investigation of leaves and stembark of Artocarpus lacucha collected in Thailand resulted in three yet undescribed isomeric flavan-3-ol derivatives (1–3), the four known compounds gambircatechol (4), (+)-catechin (5), (+)-afzelechin (6) and the stilbene oxyresveratrol (7). Compounds 1 to 3 feature 6/6/5/6/5/6 core structures. All structures were deduced by NMR and MS, while density functional theory (DFT) calculations on B3LYP theory level were performed of compounds 1 to 3 to support the stereochemistry in positions 2 and 3 in the C-ring. Possible biosynthetic pathways leading to 4 are discussed. The DPPH assay revealed high radical scavenging activities for 1 (EC50 = 9.4 ± 1.0 µmol mL−1), 2 (12.2 ± 1.1), 3 (10.0 ± 1.5) and 4 (19.0 ± 2.6), remarkably lower than ascorbic acid (EC50 = 34.9) and α-tocopherol (EC50 = 48.6). A cytotoxicity assay revealed moderate but consistent antiproliferative properties of 1 in CH1/PA-1 (ovarian teratocarcinoma) and SW480 (colon carcinoma) cells, with IC50 values of 25 ± 6 and 34 ± 4 µM, respectively, whereas effects in A549 (non-small cell lung cancer) cells were rather negligible. The performed DCFH-DA assay of 1 in the former cell lines confirmed potent antioxidative effects even in the cellular environment.

Highlights

IntroductionIntroduction iationsArtocarpus lacucha Buch.-Ham. (syn A. lakoocha Wall. ex Roxb.; Mulberry family; Moraceae) is a widespread tree species in South-East Asia [1,2,3]
Introduction iationsArtocarpus lacucha Buch.-Ham. is a widespread tree species in South-East Asia [1,2,3]
Due to these structural features, we suggest to assign these compounds to flavan-benzofuran, which would be a novel subclass of flavanols

Summary

Introduction

Introduction iationsArtocarpus lacucha Buch.-Ham. (syn A. lakoocha Wall. ex Roxb.; Mulberry family; Moraceae) is a widespread tree species in South-East Asia [1,2,3]. Ex Roxb.; Mulberry family; Moraceae) is a widespread tree species in South-East Asia [1,2,3]. This species is known under the vernacular names Mahat or Ma-Haad in Thailand. Other well-known and important species of this genus are A. altilis (Parkinson) Fosberg and A. heterophyllus Lam., both are important fruit trees in tropical areas. Despite its wide distribution in natural forests and common uses for ethnomedicinal purposes, e.g., against tapeworm infections and as component in whitening solutions [4], A. lacucha has not been extensively studied in a phytochemical view.

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