Quinolizidine-Based Variations and Antifungal Activity of Eight Lupinus Species Grown under Greenhouse Conditions

Abstract

Fusarium oxysporum is an aggressive phytopathogen that affects various plant species, resulting in extensive local and global economic losses. Therefore, the search for competent alternatives is a constant pursuit. Quinolizidine alkaloids (QA) are naturally occurring compounds with diverse biological activities. The structural diversity of quinolizidines is mainly contributed by species of the family Fabaceae, particularly the genus Lupinus. This quinolizidine-based chemo diversity can be explored to find antifungals and even mixtures to address concomitant effects on F. oxysporum. Thus, the antifungal activity of quinolizidine-rich extracts (QREs) from the leaves of eight greenhouse-propagated Lupinus species was evaluated to outline promising QA mixtures against F. oxysporum. Thirteen main compounds were identified and quantified using an external standard. Quantitative analysis revealed different contents per quinolizidine depending on the Lupinus plant, ranging from 0.003 to 32.8 mg/g fresh leaves. Bioautography showed that all extracts were active at the maximum concentration (5 µg/µL). They also exhibited >50% mycelium growth inhibition. All QREs were fungistatic except for the fungicidal QRE of L. polyphyllus Lindl. Angustifoline, matrine, 13α-hydroxylupanine, and 17-oxolupanine were ranked to act jointly against the phytopathogen. Our findings constitute reference information to better understand the antifungal activity of naturally afforded QA mixtures from these globally important plants.

Antifungal activity against Fusarium oxysporum of quinolizidines isolated from three controlled-growth Genisteae plants: structure–activity relationship implications

“…Lupinus and Genista plants were propagated from seeds under greenhouse conditions (vide infra). Seeds from Lupinus plants were commercially purchased from Sow Right Seeds [ 55 ]. Healthy seeds from G. monspessulana (voucher specimen No COL: 576,283 kept at Colombian National Herbarium) were collected from wild plants at Choconta municipality, Cundinamarca, Colombia (Temperature = 15 ± 3 °C, 2660 masl, 5°04′30 ″ N 73°43′05 ″ W).…”

Ruta angustifolia Pers. (Narrow-Leaved Fringed Rue): Pharmacological Properties and Phytochemical Profile

“…The name angustifolin of the product is emblematic because it derives directly from Angustifolia, but it is confusing because the same name has been given to a totally different product, an ent-kaurane diterpenoid isolated from the aerial parts of Isodon species [ 93 , 94 ]. There are also four lignans named angustifolin A-D isolated from Kadsura angustifolia [ 95 ], and an alkaloid designated angustifoline (with a “e” at the end to respect the alkaloid terminology) found in Lupinus species [ 96 , 97 ]. Hence, the possible confusion between names Angustifolin from Ruta has been rarely cited, but it cannot be ignored [ 88 ].…”

Isoflavone Content and Nutritional-Related Properties of Debittered Seeds from Two Andean Lupin (Lupinus mutabilis Sweet) Ecotypes Propagated in Two Soils

“…The method precision was evaluated through intra and inter-day lupanine analyses, whose relative standard deviations (RSD%) were 4.2 and 3.4%, respectively. The LoD, limit of quantification (LoQ), and recoveries for the GC-FID lupanine analysis were 1 µg/mL, 2 µg/mL, and 95.5-104.1%, respectively [32]. QC pooled samples were analyzed to assess the detector response variation (CV < 5%).…”