A New Saponin with Anti-HIV-1 Protease Activity from Acacia pennata

Abstract

We investigated the phytochemicals from an ethanol extract of Acacia pennata (L.) Willd stems, a Vietnam medicinal plant, which led to the isolation of a new saponin termed 21β- O-[(2 E)-6-hydroxyl-2,6-dimethyl-2,7-octadienoyl] pitheduloside G (1), as well as pitheduloside G (2), a known saponin. The structures of compounds 1 and 2 were elucidated via spectroscopy and compared with those reported in the literature. The isolates (1 and 2) were tested for their inhibitory effects on human immunodeficiency virus type 1 (HIV-1) protease (PR). We found that the new compound, 21β- O-[(2 E)-6-hydroxyl-2,6-dimethyl-2,7-octadienoyl] pitheduloside G (1), possessed potent anti-HIV-1 PR activity, with a half-maximum inhibitory concentration (IC50) value of 2.0 ± 0.2 μM. In contrast, pitheduloside G (2) exhibited much less inhibition, with an IC50 value of 18 ± 0.5 μM. Both compounds were nontoxic in human embryonic kidney 293T cells at concentrations effective against HIV-1 PR. This is the first report regarding the isolation of an anti-HIV-1 PR compound (1) from an Acacia plant species.

Computational guided identification of potential leads from Acacia pennata (L.) Willd. as inhibitors for cellular entry and viral replication of SARS-CoV-2

“…The study was initially proposed to limit the virtual screening to isolated flavonoids only. However, a literature survey revealed that a saponin ‘21β- O -[(2 E )-6-hydroxyl-2,6-dimethyl-2,7-octadienoyl] pitheduloside G’ isolated from A. pennata exhibited an antiviral activity [ 30 ]. Therefore, in addition to flavonoids, the chances to find a potential lead from other classes of secondary metabolites also exist.…”

“…The bark of A. pennata is also traditionally used to treat gastrointestinal ailments like cholera and dysentery [ 25 , 29 ]. Pharmacological activities like antiviral [ 30 , 31 ], anti-inflammatory, antinociceptive [ 32 ], antioxidant [ 25 ], anti-parasitic [ 33 ], antimicrobial [ 34 ], and antidiabetic [ 35 ] had been scientifically investigated for A. pennata . The traditional utility of A. pennata to treat various health ailments may be attributed to the presence of flavonoids [ 26 ], terpenoids [ 27 ], phenols [ 28 ], and saponins [ 30 ] in the plant.…”

“…Pharmacological activities like antiviral [ 30 , 31 ], anti-inflammatory, antinociceptive [ 32 ], antioxidant [ 25 ], anti-parasitic [ 33 ], antimicrobial [ 34 ], and antidiabetic [ 35 ] had been scientifically investigated for A. pennata . The traditional utility of A. pennata to treat various health ailments may be attributed to the presence of flavonoids [ 26 ], terpenoids [ 27 ], phenols [ 28 ], and saponins [ 30 ] in the plant. Also, the young shoot tips of A. pennata is consumed as a vegetable as it is rich in nutrients and minerals [ 36 – 38 ].…”

Acacia pennata L. leaves: chemical profiling and impact on DNA damage, alteration of genotoxicity—related genes expression and ROS generation in hepatic tissues of acetaminophen treated male rats

“…Acacia pennata L., is a thorny woody climber distributed in South and Southeast Asia including India, China and Thailand (Lalchhandama 2013 ). Traditionally, it has been used in rheumatism, headaches and fever treatment (Nguyen et al 2018 ). Several biological reports have been performed on different plant parts, leaves possessed anti-nociceptive, anti-inflammatory (Dongmo et al 2005 ) and antifungal effects particularly towards C. albicans and K. polysporus (Malabadi and Vijay Kumar 2007 ) as well as anti-transcription activities (Rifai et al 2010 ).…”

Ethnopharmacology and phytochemistry-based review on the antimalarial potential of Acacia pennata (L.) Willd.

“…A. pennata (Family: Fabaceae) is a large thorny plant found in Bangladesh, Bhutan, India, Myanmar, Southwest China, Sri Lanka, Thailand and Vietnam. [14][15][16] There are plenty of nutrients present in A. pennata ( Figure 2) that accounts for its nutraceutical potential. 15 However, specifications on the plant part, method of preparation, route of administration, and dosing regimen adopted for the traditional treatment against malaria were missing.…”