A new flavone glucoside, andrographidine G (1), was isolated from Andrographis paniculata together with 13 known compounds, including flavonoids, diterpenoids, and iridoids. The structure of 1 was established by spectroscopic and spectrometric techniques, including HR-ESI-TOF-MS, 1D and 2D NMR, and chemical methods. The known compounds were identified as andrographidine A (2), (2R)-5-hydroxy-7,8-dimethoxyflavanone-5-O-β-D-glucopyranoside (3), acanthoside B (4), neoandrographiside (5), andropanoside (6), andrographiside (7), andrographolide (8), 14-deoxy-11,12-didehydroandrographiside (9), 14-deoxy-11,12-didehydroandrographolide (10), procumbide (11), procumboside (12), 6-epi-8-O-acetylharpagide (13), and curvifloruside F (14).
(a) SubramanianR., ZainiA.M., SadikunA. (2012) A bitter plant with a sweet future? A comprehensive review of an oriental medicinal plant: Andrographis paniculata.Phytochemistry Reviews, 11, 39–75; (b) Samy RP, Thwin MM, Gopalakrishnakone P. (2007) Phytochemistry, pharmacology and clinical use of Andrographis paniculata. Natural Product Communications, 2, 607-618; (c) Xu C, Chou G-X, Wang C-H, Wang Z-T. (2012) Rare noriridoids from the roots of Andrographis paniculata. Phytochemistry, 77, 275-279; (d) Radhika P, Prasad YR, Lakshmi KR. (2010) Flavones from the stem of Andrographis paniculata Nees. Natural Product Communications, 5, 59-60; (e) Chopra RN CI, Handa KL, Kapur ID. (1958) Indigenous Drugs of India. 2nd edn. U.N. Dhar & Sons, Calcutta; (f) Dua VK, Ojha VP, Roy R, Joshi BC, Valecha N, Devi CU, Bhatnagar MC, Sharma VP, Subbarao SK. (2004) Anti-malarial activity of some xanthones isolated from the roots of Andrographis paniculata. Journal of Ethnopharmacology, 95, 247-251; (g) Dassanayake M, Fosberg F, Clayton W. (1995) A Revised Hand Book to The Flora of Ceylon, vol. IX. Amerind Co., New Delhi. 236-239; (h) Reddy VLN, Reddy SM, Ravikanth V, Krishnaiah P, Goud TV, Rao TP, Ram TS, Gonnade RG, Bhadbhade M, Venkateswarlu Y. (2005) A new bis-andrographolide ether from Andrographis paniculata Nees and evaluation of anti-HIV activity. Natural Product Research, 19, 223-230.
2.
(a) LiW., XuX., ZhangH., MaC., FongH., vanB.R., FitzloffJ. (2007) Secondary metabolites from Andrographis paniculata.Chemical and Pharmaceutical Bulletin, 55, 455–458; (b) Agrawal PK, Thakur RS. (1985) Carbon-13 NMR spectral investigations, part 9. Carbon-13 NMR spectroscopy of lignan and neolignan derivatives. Magnetic Resonance in Chemistry, 23, 389-418; (c) Fujita T, Fujitani R, Takeda Y, Takaishi Y, Yamada T, Kido M, Miura I. (1984) On the diterpenoids of Andrographis paniculata: X-ray crystallographic analysis of andrographolide and structure determination of new minor diterpenoids. Chemical and Pharmaceutical Bulletin, 32, 2117-2125; (d) Matsuda T, Kuroyanagi M, Sugiyama S, Umehara K, Ueno A, Nishi K. (1994) Cell differentiation-inducing diterpenes from Andrographis paniculata Nees. Chemical and Pharmaceutical Bulletin, 42, 1216-1225; (e) Kikuchi T, Matsuda S, Kubo Y, Namba T. (1983) New iridoid glucosides from Harpagophytum procumbens DC. Chemical and Pharmaceutical Bulletin, 31, 2296-2301; (f) Hannedouche S, Stanislas E, Moulis C, Fouraste I. (2000) Iridoids from Caryopteris x clandonensis. Phytochemistry, 54, 807-809; (g) Lai G-F, Wang X-Y, Wang Y-F, Cao J-X, Luo S-D, Ju P. (2009) Diterpenes and diterpene glucosides from Phlogacanthus curviflorus. Helvetica Chimica Acta, 92, 470-480.
3.
KuroyanagiM., SatoM., UenoA., NishiK. (1987) Flavonoids from Andrographis paniculata.Chemical and Pharmaceutical Bulletin, 35, 4429–4435.
4.
WangY-H, AvulaB., FuX., WangM., KhanI.A. (2012) Simultaneous determination of the absolute configuration of twelve monosaccharide enantiomers from natural products in a single injection by a UPLC-UV/MS method. Planta Medica, 78, 834–837.
5.
MiyaichiY., HanamitsuE., KizuH., TomimoriT. (2006) Studies on the constituents of Scutellaria species (XXII). Constituents of the roots of Scutellaria amabilis Hara. Chemical and Pharmaceutical Bulletin, 54, 435–441.