IRIDOID GLUCOSIDES FROM Barleria lupulina LINDL.
DOI:
https://doi.org/10.18173/2354-1059.2025-0007Keywords:
Barleria lupulina, iridoid glycoside, cytotoxicity, anti-inflammatory activityAbstract
Four iridoid glycosides, 6-O-trans-p-coumaroyl-8-O-acetylshanzhiside methyl ester (1), 6-O-p-methoxy-trans-cinnamoyl-8-O-acetylshanzhiside methyl ester (2), 6-O-cis-p-coumaroylshanzhiside methyl ester (3), and ipolamiide (4) have been purified and structurally elucidated from Barleria lupulina Lindl. (Acanthaceae) collected in Luang Namtha province, Laos. Compound 1, at a concentration of 128 μg/mL, inhibited the growth of the A549 cancer cell line by 31% and nitric oxide production in RAW 264.7 cells by 30%. This is the first report on the chemical constituents of Lao’s Barleria lupulina.
References
[1] Bunyapraphatsara N, Chokechaijaroenporn O, (2000). Thai Medicinal Plants (Vol. 4). Faculty of Pharmacy, Mahidol University and National Center for Genetic Engineering and Biotechnology, Bangkok, p. 675-677.
[2] Goya C, Sungyu Y, Jun-Ho S, (2021). Handbook of Cambodian Medicinal Plants, Korea Institute of Oriental Medicine, p. 136.
[3] Do HB, Dang QC, Bui XC, Nguyen TD, Do TD, Pham VH, Vu NL, Pham DM, Pham KM, Doan TN, Nguyen T & Tran T, 2006. Medicinal Plant and Animal (Vol. 2). Science and Technics Publishing House, Hanoi.
[4] Onvilay S, Muachanh S, Khamman P, (2019). Medicinal Plants of the Ex-situ Medicinal Plants Preserve in Veunkham. Institute of Traditional Medicine (ITM), Ministry of Health, Laos. [5] Yoosook C, Panpisutchai Y, Chaichana S, Santisuk T, Reutrakul V, (1999). Evaluation of anti-HSV-2 activities of Barleria lupulina and Clinacanthus nutans. Journal of Ethnopharmacology, 67(2), 179-187.
[6] Ismail-Suhaimy NW, Gani SSA, Zaidan UH, Halmi MIE, Bawon P, (2021). Optimizing Conditions for Microwave-Assisted Extraction of Polyphenolic Content and Antioxidant Activity of Barleria lupulina Lindl. Plants, 10(4), 682.
[7] Kumari R, Dubey RC, (2016a). HPTLC and GC-MS profile of Barleria lupulina Lindl. extracts and their effect on enteric bacterial pathogens. Journal of Applied Pharmacy, 8(3), 61-68.
[8] Suba V, Murugesan T, Kumaravelrajan R, Mandal SC, Saha BP, (2005). Antiinflammatory, analgesic, and antiperoxidative efficacy of Barleria lupulina Lindl. Extract. Phytotherapy Research, 19(8), 695-699.
[9] Kumari R, Dubey RC, (2016b). Phytochemical analysis and antibacterial and cytotoxic properties of Barleria lupulina Lindl. Extracts. Journal of Plant Pathology & Microbiology, 7(10), 2.
[10] Suba V, Murugesan T, Arunachalam G, Mandal SC, Saha BP, (2004). Anti-diabetic potential of Barleria lupulina extract in rats. Phytomedicine, 11, 202-205.
[11] Suksamrarn A, (1986). Iridoid glucosides from Barleria lupulina. Journal of Natural Products, 49(1), 179-179.
[12] Byrne LT, Sasse JM, Skelton BW, Suksamrarn A, White AH, (1987). The minor iridoid glucosides of Barleria lupulina: isolation, crystal structure and plant growth-inhibiting properties of 6-O-acetylshanzhiside methyl ester. Australian Journal of Chemistry, 40(5), 785-794.
[13] Tuntiwachwuttikul P, Pancharoen O, Taylor WC, (1998). Iridoid glucosides of Barleria lupulina. Phytochemistry, 49(1), 163-166.
[14] Kanchanapoom T, Kasai R, Yamasaki K, (2001). Iridoid glucosides from Barleria lupulina. Phytochemistry, 58(2), 337-341.
[15] Suksamrarn S, Wongkrajang K, Kirtikara K, Suksamrarn A, (2003). Iridoid glucosides from the flowers of Barleria lupulina. Planta Medica, 69(09), 877-879.
[16] Widyowati R, Tezuka Y, Miyahara T, Awale S, Kadota S, (2010). Alkaline phosphatase (ALP) enhancing iridoid glucosides from the Indonesian medicinal plant Barleria lupulina. Natural Product Communications, 5(11), 1711-1716.
[17] Kim KH, Park YJ, Chung KH, Yip MLR, Clardy J, Senger D, Cao S, (2015). Iridoid glycosides from Barleria lupulina. Journal of Natural Products, 78(2), 320-324.
[18] Kim KH, Clardy J, Senger D, Cao S, (2015). Chakyunglupulins A and B, two novel 4,8,8-trimethylcyclooct-2-enone derivatives from Barleria lupulina. Tetrahedron Letters, 56(21), 2732-2734.
[19] Scudiero DA, Shoemaker RH, Kenneth DP, Monks A, Tierney S, Nofziger TH, Currens MJ, Seniff D, Boyd MR, (1988). Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Research, 48, 4827-4833. [20] Cheenpracha S, Park EJ, Rostama B, Pezzuto JM, Chang LC, (2010). Inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage RAW 264.7 cells by the norsesterterpene peroxide, epimuqubilin A. Marine Drugs, 8(3), 429-437.
[21] Harraz FMH, El-Halawany AM, El-Gayed SH, Abdel-Sattar E, (2009). Iridoid glycosides from Barleria trispinosa. Natural Product Research, 23(10), 903-908.
[22] Chen JL, Blanc P, Stoddart CA, Bogan M, Rozhon EJ, Parkinson N, Ye Z, Cooper R, Balick M, Nanakorn W, Kernan MR, (1998). New iridoids from the medicinal plant Barleria prionitis with potent activity against respiratory syncytial virus. Journal of Natural Products, 61(10), 1295-1297.
[23] Xu HT, Chen Y, Zhang CG, Ju ZC, Wang YL, Chuo GX, (2021). Acylated iridoid glucosides from Pseudocaryoperis paniculata (C.B. Clark) P.D. Cantino, Phytochemistry, 181, 112569.
[24] Köroğlu E, Çelebioğlu HU, Akşit H, Taş R, (2019). Insight into Effects of Ipolamiide isolated from Plantago euphratica on Probiotic Properties of Lactobacillus acidophilus and Lactobacillus. European Journal of Science and Technology, 17, 995-1000.
