ent-Pimarane diterpenoids from Siegesbeckia glabrescens with anti-inflammatory activity

Sesquiterpene Lactones from Sigesbeckia glabrescens Possessing Potent Anti-inflammatory Activity by Directly Binding to IKKα/β

“…Compound 6 was isolated as a colorless oil and exhibited the molecular formula C 20 H 24 O 7 as determined by its HREIMS ion peak at m/z 399.1412 [M + Na] + (calcd for C 20 H 24 NaO 7 , 399.1420). On comparing the 1 H and 13 C NMR data for 5 and 6, the differences were the replacement of the angeloyloxy group in 5 by a tigloyloxy group in 6 and of a methoxy group in 5 by a hydroxy group in 6. This was in agreement with the observed HMBC and 1 H− 1 H COSY correlations.…”

“…The 1 H NMR spectrum exhibited typical signals for three olefinic protons at δ H 6.28 (1H, d, J = 3.6 Hz, H-13a), 5.70 (1H, d, J = 3.6 Hz, H-13b), and 6.21 (1H, m, H-3′), three oxymethine protons at δ H 4.63 (1H, dd, J = 11.4, 9.6 Hz, H-6), 5.64 (1H, dd, J = 4.2, 1.8 Hz, H-8), and 3.88 (1H, d, J = 4.8 Hz, H-9), two oxymethylene protons at δ H 3.70 (2H, s, H 2 -14), a methoxy proton at δ H 3.49 (3H, s, OCH 3 -9), and two methyl protons at δ H 1.95 (3H, m, Me-4′), and 1.83 (3H, m, Me-5′). In the 13 C NMR spectrum, apart from five characteristic carbon signals for the angeloyloxy group, 15 carbon resonances were observed, and these were ascribed to one methyl, four methylenes (including one olefinic carbon at δ C 122.2), six methines, and four quaternary carbons (including one olefinic carbon at δ C 136.5 and two carbonyl carbons at δ C 170.6 and 211.3), with the aid of an HSQC experiment. These characteristic signals, in combination with the HRESIMS data, implied that 8 is a highly oxidized sesquiterpenoid possessing an angeloyloxy group substitution.…”

“…In addition, according to records of “Herbal for Relief of Famines”, after cooking, the bitter taste of Siegesbeckiae Herba disappears, and it can be used as a food to alleviate hunger and prevent various diseases in times of famine. Sigesbeckia glabrescens Makino, one of the basic plants of Sigesbeckiae Herba, belongs to the genus Sigesbeckia in the family Compositae, and is utilized for the treatment of rheumatoid arthritis, thrombogenesis, hypertension, and snakebites . However, current studies on the chemical constituents and pharmacological activities of S. glabrescens focus mainly on the properties of its diterpenoids, such as the anti-inflammatory and antiangiogenic effects of kirenol .…”

“…Sigesbeckia glabrescens Makino, one of the basic plants of Sigesbeckiae Herba, belongs to the genus Sigesbeckia in the family Compositae, and is utilized for the treatment of rheumatoid arthritis, thrombogenesis, hypertension, and snakebites. 13 However, current studies on the chemical constituents and pharmacological activities of S. glabrescens focus mainly on the properties of its diterpenoids, such as the anti-inflammatory and antiangiogenic effects of kirenol. Meanwhile, the large number of sesquiterpenes present have been neglected.…”

Simultaneous Quantification of Kirenol, Daurutoside, and Darutigenol in Siegesbeckia orientalis L. by HLPC-DPA Method

“…Địa chỉ email: anhthu23081985@gmail.com https://doi.org/10.25073/2588-1132/vnumps.4399 truyền, hy thiêm được dùng để điều trị phong thấp, nhức xương, yếu chân, bán thân bất toại, gân cốt nhức lạnh, lưng gối tê dại, khớp sưng nóng đỏ và đau nhức, đau lưng, mỏi gối, mụn nhọt lở ngứa, kinh nguyệt không đều [3]. Một số nghiên cứu tác dụng sinh học của dịch chiết hy thiêm cho thấy chúng có nhiều hoạt tính ý nghĩa như chống viêm, chống dị ứng, chống nhiễm khuẩn, và chống oxy hóa [4][5][6][7]. Về thành phần hóa học, nhiều công trình nghiên cứu đã công bố chỉ ra trong hy thiêm chứa các nhóm chất chính là sesquiterpenoid, diterpenoid, steroid và phenolic,… [5][6][7][8].…”