Propolins and glyasperin A from stingless bee nests

Ragasa, Consolacion Y.; Galian, Richard Anthony F.; Ebajo, Virgilio D.; Aguda, Remil; Cervancia, Cleofas R.; Shen, Chien Chang

doi:10.1016/j.bjp.2015.03.006

Cited by 12 publications

(12 citation statements)

References 16 publications

(17 reference statements)

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“…Isolation and structure elucidation: The extraction of crude extract and the isolation and structure elucidation of compounds 1-3 from T. biroi were reported previously [30].…”

Section: Methodsmentioning

confidence: 99%

“…Clerodane diterpenes, 15-oxo-3,13Z-kolavadien-17-oic acid and 15-oxo-3Z,I3E-kolavadien-17-oic acid from Brazilian propolis damaged and retarded the growth of HuH13, KB, HeLa and HLC-2 cells with ID50 of 20-30 µg/mL [29]. Glyasperin A was earlier reported as a constituent of Philippine propolis [30]. Propolins with cytotoxic activities have been isolated from propolis.…”

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confidence: 99%

“…Previously, the isolation of glyasperin A, propolin E, propolin A, propolin H, squalene, a mixture of lupeol, α-amyrin and β-amyrin and another mixture of urs-12-en-3-one, olean-12-en-3-one and lup-12-en-3-one from dichloromethane extracts of propolis collected from the stingless bee (Tetragonula biroi Friese) hives in San Roque, Sorsogon, Philippines was reported [30]. This study was expanded and we report herein the cytotoxicity potentials of the dichloromethane crude extract as well as those of the compounds, glyasperin A (1), propolin E (2) and propolin A (3), obtained from T. biroi bee hives, against three human cancer cell lines, breast (MCF-7) and colon (HT-29 and HCT-116) and a normal cell line, human dermal fibroblast, neonatal (HDFn).…”

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confidence: 99%

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Cytotoxic Prenylflavanones from Philippine Stingless Bee (Tetragonula biroi Friese) Nests

Reyes¹,

Oyong²,

Ebajo³

et al. 2018

Asian J. Chem.

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INTRODUCTIONPropolis or "bee glue" is a resinous material collected by honeybees from tree buds, sap flows or other botanical exudates and is used for sealing and coating bee hives. For many centuries, aside from its use as food, beverage and food supplement, it has long been used extensively in traditional medicine because of its wide range of therapeutic values for the treatment of common cold, flu, upper respiratory tract infections, as dermatological preparations for wounds, burns, acne, herpes simplex, genitalis and neurodermatitis, as mouthwash and toothpaste to prevent caries and gingivitis and for cosmetic applications [1,2]. Propolis was shown to exhibit a broad spectrum of biological activities which include antimicrobial [3,4], antifungal [5,6], free radical scavenging [7,8], anti-HIV [9,10], anti-inflammatory [11,12] and anti-herpes [13,14]. A recent study reported that propolis, at a concentration of 0.01 % (w/v), exhibited antiproliferative and cytotoxic actions against human fibroblasts proliferation in cell culture, followed by mild cell necrosis [15]. The dichloromethane crude extract and compounds, glyasperin A (1), propolin E (2) and propolin A (3), obtained from Philippine stingless bee (Tetragonula biroi Friese) nests, were evaluated for their cytotoxic potentials. The anti-proliferative activities of crude extract and compounds 1-3 against human cancer cell lines, breast (MCF-7) and colon (HT-29 and HCT-116), and a normal cell line, human dermal fibroblast neonatal (HDFn), were evaluated using the PrestoBlue ® cell viability assay. The crude extract was most anti-proliferative against HCT-116 cells (IC50 = 1.410 µg/mL). Glyasperin A (1) exhibited the strongest effect on MCF-7 cells (2.378 µg/mL). Propolin E (2) was most cytotoxic against HCT-116 cells (2.279 µg/mL), while propolin A (3) was most inhibitory against MCF-7 cells (2.815 µg/mL). Comparing the colorectal cancer cell lines, HCT-116 was generally more susceptible under crude extract, 2, and 3 (IC50 = 1.410, 2.279, 3.013 µg/mL, respectively) than 5.320, 5.359). Comparing the activities of propolin E and propolin A against HCT-116 cells, 2 (IC50 = 2.279 µg/mL) was more cytotoxic than 3 (3.013). The crude extract was more cytotoxic than Zeocin against HCT-116 cells. To our best of knowledge, this is the first report on the anti-proliferative properties of crude extract and compounds from T. biroi.

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“…Isolation and structure elucidation: The extraction of crude extract and the isolation and structure elucidation of compounds 1-3 from T. biroi were reported previously [30].…”

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Cytotoxic Prenylflavanones from Philippine Stingless Bee (Tetragonula biroi Friese) Nests

Reyes¹,

Oyong²,

Ebajo³

et al. 2018

Asian J. Chem.

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“…Because of their pharmacological utility,t he propolis of stingless bees has attracted much attention as ar ich source of biologically active naturalp roducts. [2,3] Many efforts have been devoted to analyzing and identifying biologically active natural products in the propolis. [2,3] However,t ot he best of our knowledge,novel natural products have not been isolated from the propolis of stingless bees.…”

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confidence: 99%

“…[2,3] Many efforts have been devoted to analyzing and identifying biologically active natural products in the propolis. [2,3] However,t ot he best of our knowledge,novel natural products have not been isolated from the propolis of stingless bees. Herein, we report the isolation and structure determination of monomeric phloroglucinol derivatives [4] tetragocarbone A( 1a)a nd B( 1b,F igure 1) isolated from the propolis of the Australian social stingless bee, Tetragonula carbonaria (= Trigona carbonaria).…”

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Structure Determination of Monomeric Phloroglucinol Derivatives with a Cinnamoyl Group Isolated from Propolis of the Stingless Bee, Tetragonula carbonaria

et al. 2016

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Tetragocarbones A and B were isolated from the propolis of an Australian stingless bee, Tetragonula carbonaria. These largely planar structures were proposed as a result of NMR analysis as well as comparison of their NMR data with those of related monomeric phloroglucinol derivatives. To elucidate relative and absolute stereochemistry of tetragocarbone A, the synthesis of the proposed structure of tetragocarbone A was performed. As a result, the synthetic compound bearing stereogenic centers 1R*,3R*,6S* was identical with naturally occurring tetragocarbone A. The absolute stereochemistry of tetragocarbone A was established to be 1R,3R,6S by chiral HPLC separation and X-ray analysis. Comparison of the NMR data of tetragocarbone A with that of tetragocarbone B indicated that tetragocarbone B would be a natural congener of tetragocarbone A.Stingless bees are a large group of social honey bees and live in tropical and subtropical areas.[1] Stingless bees produce propolis as their hive material. The propolis of stingless bees has been use in traditional medicines and health supplements worldwide. Because of their pharmacological utility, the propolis of stingless bees has attracted much attention as a rich source of biologically active natural products. [2,3] Many efforts have been devoted to analyzing and identifying biologically active natural products in the propolis. [2,3] However, to the best of our knowledge, novel natural products have not been isolated from the propolis of stingless bees. Herein, we report the isolation and structure determination of monomeric phloroglucinol derivatives [4] tetragocarbone A (1 a) and B (1 b, Figure 1) isolated from the propolis of the Australian social stingless bee, Tetragonula carbonaria (= Trigona carbonaria). Tetragocarbone A and B are the first examples of tetramethylated monomeric phloroglucinol derivatives bearing a cinnamoyl group. The relative and absolute stereochemistry of 1 a was unambiguously determined by its total synthesis and X-ray crystal analysis. Comparison of the NMR data of tetragocarbone B (1 b) with that of 1 a provides a proposed structure of 1 b that would be a natural congener of 1 a. Hexane extracts of the propolis of T. carbonaria were purified by repeated normal phase silica gel chromatography, normal phase HPLC, and chiral normal phase HPLC to give 1 a and 1 b (Scheme S1 in the supporting information). Tetragocarbone A (1 a) and B (1 b) were obtained as yellow oil. These optical rotations were found to be levorotatory (1 a: [a] = À13.6 (c = 0.28, CHCl 3 ), 1 b: [a] = À17.1 (c = 0.14, CHCl 3 )). The molecular formulas of 1 a and 1 b were putatively assigned as C 26 The planar structures of 1 a and 1 b were proposed as a result of NMR analysis and comparison of their NMR data with those of monomeric phloroglucinols 2 a, 2 b, and 3 [a] Dr.

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