Two New Flavonoids from Andrographis rothii.

Abstract

Two New Flavonoids from Andrographis rothii. -(REDDY, M. K.; REDDY, M. V. B.; JAYAKRISHNA, G.; GUNASEKAR*, D.; CAUX, C.; BODO, B.; Chem. Pharm. Bull. 51 (2003) 2, 191-193; Dep. Chem., Sri Venkateswara Univ., Tirupati 517 502, India; Eng.) -M. Paetzel 31-235

Preferentially Cytotoxic Constituents of Andrographis paniculata and their Preferential Cytotoxicity against Human Pancreatic Cancer Cell Lines

“…Fraction 11 (94.0 mg) was subjected to reversed-phase preparative TLC with MeOH-CH 3 CN-H 2 O (5:5:1) to give pinocembrin (6, 2.5 mg) [20], ermanin (7, 2.4 mg) [21], ergosterol peroxide (8, 4.2 mg) [22], oleanolic acid (9, 11.6 mg) [23], and 5,3′,4′-trihydroxy-7-methoxyflavone (10, 1.6 mg) [24]. Fraction 12 (104 mg) was subjected to reversed-phase preparative TLC with MeOH-CH 3 CN-H 2 O (5:5:1) to give andrograpanin (11, 1.3 mg) [25], skullcapflavone I (12, 1.6 mg) [26], and loliolide (13, 2.2 mg) [27]. Fraction 13 (102 mg) was separated by reversed-phase preparative TLC with MeOH-CH 3 CN-H 2 O (3:3:1) to give 5,2′-dihydroxy-7,8-dimethoxyflavone (12, 8.0 mg) and 5-hydroxy-7,8,2′,5′-tetramethoxyflavone (14, 2.6 mg) [28].…”

“…Thus, the CHCl 3 -soluble fraction was subjected to a series of chromatographic separations, which led to the isolation of 21 compounds. Their structures were identified by analyses of spectroscopic data and comparison with literature data to be: stearic acid (1) [15], pinostrobin (2) [16], -sitosterol (3) [17], bis(2ethylhexyl) phthalate (4) [18], 5-hydroxy-6,7-dimethoxyflavone (5) [19], pinocembrin (6) [20], ermanin (7) [21], ergosterol peroxide (8) [22], oleanolic acid (9) [23], 5,3′,4′-trihydroxy-7-methoxyflavone (10) [24], andrograpanin (11) [25], skullcapflavone I (12) [26], loliolide (13) [27], 5-hydroxy-7,8,2′,5′-tetramethoxyflavone (14) [28] 14-deoxy-11,12-didehydroandrographolide (17) [31], isoandrographolide (18) [32], andrographolide (19) [33], apigenin (20) [34], and 14-deoxyandrographolide (21) [35] (Figure 1). Among these compounds, compounds 2, 4, and 6 have been isolated for the first time from an Andrographis species.…”

Naturally Occurring Flavanones: An Overview

“…It has already been established that a good number of naturally occurring flavanones exhibit promising biological and pharmacological activities as summarized in Table 2, and discussed below. (only non-H substituents are indicated) 1 R 2 =R 4 =R 6 =R 7 = R 8 = OMe 2 R 2 =R 6 =OH, R 4 =OMe 3 R 2 =R 6 =OH, R 4 =R 5 =OMe 4 R 2 =R 4 = R 6 =R 9 =OMe 5 R 2 =OH, R 3 = 2-hydroxy-5-methoxybenzyl, R 4 =R 5 =OMe 6 R 2 =OH, R 3 = R 4 =OMe, R 5 = 2-hydroxy-5-methoxybenzyl 7 R 2 =R 4 =R 7 =OH, R 3 =R 8 =R 9 =OMe 8 R 2 =R 7 =OH, R 3 =R 4 =R 8 =R 9 =OMe 9 R 4 =2,3-epoxy-3-methylbutyl, R 8 =OH 10 R 2 =R 4 =R 6 =R 8 =OMe, R 5 =Me 11 R 4 =R 8 =OH, R 5 =R 7 =OMe 12 R 2 =R 4 =R 8 =OH, R 5 = CH2CH(OH)C(Me)=CH2 13 R 2 =R 4 =R 7 =R 9 =OH, R 3 =R 5 =prenyl 14 R 2 =R 4 =R 7 =OH, R 3 =R 5 =R 9 =isoprenyl, R 8 =OMe 15 R 2 =R 4 =OH, R 5 =2,3-epoxy-3-methylbutyl, R 6 =R 8 =OMe 16 R 2 =R 4 =OMe, R 7 ,R 8 = -OCH2O-17 R 2 =R 4 =R 6 =R 8 =OH, R 5 = isoprenyl, R 9 = -CMe2CH=CH2 (2S) 18 R 2 =R 4 =R 8 =OH, R 5 = isoprenyl, R 9 = -CMe2CH=CH2 (2S) 19 R 2 =R 4 =R 7 = OH, R 5 = R 6 =prenyl, R 8 = OMe (2S) 20 R 2 =R 4 =OH, R 3 =OMe, R 5 =prenyl 21 R 2 =R 4 =R 6 =OH, R 3 = prenyl, R 5 =OMe 22 R 4 =R 7 =OH, R 8 =OMe, R 9 = prenyl 23 R 4 =R 8 =OH, R 7 =OMe, R 9 = prenyl 23a R 4 =R 7 =R 8 =OH, R 9 = prenyl 24 R 2 =R 4 =OH, R 8 =OMe, R 7 =R 9 =prenyl 25 R 2 =R 4 =OH, R 8 =OMe, R 7 =-CH=CHC(OH)(Me)CH3, R 9 = prenyl 26 R 2 =R 4 =R 8 =OH, R 3 = prenyl, R 5 =Me 27 R 2 =R 4 =R 8 =OH, R 3 6 =OH, R 5 =prenyl 35 R 2 =R 4 =R 6 =R 8 =OH, R 3 =prenyl, R 9 =OMe 36 R 2 =R 4 =R 6 =R 8 =OH, R 5 =prenyl, R 9 =OMe 37 R 2 =OMe, R 4 =R 8 =OH, R 5 = Lavandulyl 38 R 2 =OMe, R 4 =R 6 =R 8 =OH, R 5 = Lavandulyl 39 R 2 =OH, R 4 =OMe, R 5 = -CH=CHCOMe (E) 40 R 2 =R 6 =OH, R 4 =R 8 =R 9 =OMe (2S) 41 R 4 =R 8 =OH, R 2 =R 7 =OMe 42 R 2 =R 8 =OH, R 4 =OMe, R ...…”