Characterization and Bioactive Potential of Secondary Metabolites Isolated from Piper sarmentosum Roxb.

Abstract

Piper sarmentosum Roxb. (Piperaceae) is a traditional medicinal plant in South-East Asian countries. The chemical investigation of leaves from this species resulted in the isolation of three previously not described compounds, namely 4″-(3-hydroxy-3-methylglutaroyl)-2″-β-D-glucopyranosyl vitexin (1), kadukoside (2), and 6-O-trans-p-coumaroyl-D-glucono-1,4-lactone (3), together with 31 known compounds. Of these known compounds, 21 compounds were isolated for the first time from P. sarmentosum. The structures were established by 1D and 2D NMR techniques and HR-ESI-MS analyses. The compounds were evaluated for their anthelmintic (Caenorhabditis elegans), antifungal (Botrytis cinerea, Septoria tritici and Phytophthora infestans), antibacterial (Aliivibrio fischeri) and cytotoxic (PC-3 and HT-29 human cancer cells lines) activities. Methyl-3-(4-methoxyphenyl)propionate (8), isoasarone (12), and trans-asarone (15) demonstrated anthelmintic activity with IC50 values between 0.9 and 2.04 mM. Kadukoside (2) was most active against S. tritici with IC50 at 5.0 µM and also induced 94% inhibition of P. infestans growth at 125 µM. Trans-asarone (15), piperolactam A (23), and dehydroformouregine (24) displayed a dose-dependent effect against B. cinerea from 1.5 to 125 µM up to more than 80% inhibition. Paprazine (19), cepharadione A (21) and piperolactam A (23) inhibited bacterial growth by more than 85% at 100 µM. Only mild cytotoxic effects were observed.

Comparative metabolite analysis of Piper sarmentosum organs approached by LC–MS-based metabolic profiling

“…Finally, Cluster VII is mostly represented by flavonoids (apigenin derivatives), including flavone- C -glycosides, and other phenolic metabolites such as phenylpropanoids and specific lignans. The compounds present in this cluster were found in relatively high amounts in leaves and are congruent with the constituents isolated from leaves of P. sarmentosum in our previous study [ 17 ].…”

“…Several previous studies on P. sarmentosum focused mainly on the constituents and pharmacological activities of the leaves [ 6 , 15 – 17 ]. Pharmacological studies recently conducted in Malaysia showed that the extract of P. sarmentosum leaves has vascular protective, neuroprotective, anti-obesity, and anti-hyperlipidemia activity [ 18 – 20 ].…”

A screen of plant-based natural products revealed that quercetin prevents amyloid-β uptake in astrocytes as well as resulting astrogliosis and synaptic dysfunction

“…4) natural product (NP) or simple NP derivative, preferentially from plant or mushroom; 5) derived from a plant with reported Anti-Alzheimer or similar neurological activity, including such data from our previous research; or: from a compound class reported bene cial to neuro-in ammation; or: compound with structural similarity to such with reported activity in mental health [12,20,21,[24][25][26][27]. The tested natural products comprised a wide range of compound classes, including avonoids, alkaloids, lignans, anthraquinones, other diverse phenolics and triterpenoids.…”

Anti-Xanthine Oxidase 5′-Hydroxyhericenes A–D from the Edible Mushroom Hericium erinaceus and Structure Revision of 3-[2,3-Dihydroxy-4-(hydroxymethyl)tetrahydrofuran-1-yl]-pyridine-4,5-diol

“…According to the values of Δδ S-R of the (S) and (R)-MTPA esters, the absolute configuration at C5′ was concluded to be R. (Figure 3) During the purification of bioactive compounds from the n-BuOH extract of H. erinaceus, we obtained compound 5, and analysis of NMR data revealed that a structure of 5 might be 3- 4A,4B). This alkaloid was first isolated from the mealworm T. molitor, 16 and later from the leaves of P. erosus 17 and P. sarmentosum, 18 and the whole plants of H. cordata Thunb. 19 Compound 5 had identical 1 H and 13 C NMR data (DMSO-d 6 ) to those of the alkaloid from the mealworm (Table 2) as well as the published NMR data of the alkaloid from plants.…”

“…erinaceus showed the most promising results, but there is little information available for breast cancer therapies using this mushroom. In this paper, we describe the isolation and structure elucidation of new geranyl-resorcinol derivatives and propose a structure revision of an alkaloid, 3-[2,3-dihydroxy-4-(hydroxymethyl)­tetrahydrofuran-1-yl]-pyridine-4,5-diol, previously isolated from the mealworm Tenebrio molitor, and later from the leaves of Pachyrhizus erosus and Piper sarmentosum, and the whole plants of Houttuynia cordata Thunb . Biological screening revealed potential drug candidates for breast cancer treatments.…”