Dalbergia ecastaphyllum (L.) Taub. and Symphonia globulifera L.f.: The Botanical Sources of Isoflavonoids and Benzophenones in Brazilian Red Propolis

Abstract

The Brazilian red propolis (BRP) constitutes an important commercial asset for northeast Brazilian beekeepers. The role of Dalbergia ecastaphyllum (L.) Taub. (Fabaceae) as the main botanical source of this propolis has been previously confirmed. However, in addition to isoflavonoids and other phenolics, which are present in the resin of D. ecastaphyllum, samples of BRP are reported to contain substantial amounts of polyprenylated benzophenones, whose botanical source was unknown. Therefore, field surveys, phytochemical and chromatographic analyses were undertaken to confirm the botanical sources of the red propolis produced in apiaries located in Canavieiras, Bahia, Brazil. The results confirmed D. ecastaphyllum as the botanical source of liquiritigenin (1), isoliquiritigenin (2), formononetin (3), vestitol (4), neovestitol (5), medicarpin (6), and 7-O-neovestitol (7), while Symphonia globulifera L.f. (Clusiaceae) is herein reported for the first time as the botanical source of polyprenylated benzophenones, mainly guttiferone E (8) and oblongifolin B (9), as well as the triterpenoids β-amyrin (10) and glutinol (11). The chemotaxonomic and economic significance of the occurrence of polyprenylated benzophenones in red propolis is discussed.

Accessible Methodologies for Quantification of Flavonoids and Total Phenols in Propolis

“…36 Na própolis marrom, foi encontrado o composto 2-[1-hidroximetil]vinil-5-acetil-hidroxicumarano (I) (Figura 2) e na vermelha, isoflavonoides e benzofenonas preniladas. 21…”

“…Nas própolis brasileiras, poucos flavonoides foram identificados, tais como: 5,6,7-tri-idroxi-3,4'-di-idroxiflavona, aromadendrina-4-metil éter, pinobanksina, kaempferida, além de crisina e . [21][22][23][24][25][26] Apesar de não estarem em quantidades expressivas na própolis de alecrim-do-campo (comercialmente a mais importante própolis brasileira) os flavonoides podem estar presentes em menores quantidades e serem responsáveis por diversas atividades biológicas importantes, como anti-inflamatória e antioxidante. Entretanto, outras própolis de grande interesse comercial, como a vermelha e a verde da caatinga apresentam, quantidades expressivas de flavonoides.…”

The Strong Anti-Kinetoplastid Properties of Bee Propolis: Composition and Identification of the Active Agents and Their Biochemical Targets

“…Flavonoids are abundant in the leaves, flowers, and fruits of the plants [53,54] from which bees collect resins and sticky exudates to make their propolis. Triterpenoids are widely distributed in African propolis [15,16,55,57,58] but have also been reported in Bolivia [62,63], Brazil [61], Indonesia [28], and Thailand [67]. The most common triterpenes isolated from propolis are cycloartanes [15,28,58,[61][62][63].…”

“…Other phytochemicals isolated from propolis within the period under review were not as widely distributed across all regions as the flavonoids and triterpenoids. However, studies indicate surprising similarity between propolis from Nigeria, Thailand, and Brazil, countries that could hardly be further apart, in their composition of triterpenoids, xanthones, and their prenylated derivatives [14,15,61,67]. Isolation of diterpenes is reported most from mainland Australia and the islands [71,72].…”

Evaluation of the antiproliferative activity of red propolis hydroalcoholic extract and its fractions obtained by partition

“…Propolis is a product of honeybee hives, containing mainly beeswax and a resin obtained from various plant sources such as apical buds, young leaves and exudates (Salatino & Salatino 2018). Red propolis, with Dalbergia ecastaphyllum (Daugsch et al, 2008;Silva et al, 2008) and Symphonia globulifera (Ccana-Ccapatinta et al, 2020) as its main botanical sources, has recently stood out as a natural medicinal product due to its various biological properties such as anti-inflammatory (Batista et al 2018), antitumoral (Salatino & Salatino 2018) antioxidant, cytotoxic (de Oliveira Reis et al, 2019), antimicrobial (Miranda et al 2019) activities and healing capacity (Picolotto et al 2019). The biological activity of red propolis is mainly related to isoflavones, which act in synergy with the other compounds.…”