Phytochemical Investigation of the Roots of Ipomoea asarifolia and Antiproliferative Activity of the Isolated Compounds against Multiple Myeloma Cells.

Ipomoea asarifolia is a herbaceous plant belonging to the family Convolvulaceae and is native to tropical regions of Africa, America, and Asia. A dichloromethane root extract showed antiproliferative activity against multiple myeloma cells (RPMI 8226). The phytochemical investigation led to the isolation of 15 compounds. Compounds 1-4, named (4S,8S)-1-(furan-3-yl)-9-hydroxy-4,8-dimethylnonane-1,6-dione, isoferulic acid hexadecyl ester, caffeic acid hexadecyl ester, and asarifolin I, respectively, are described for the first time. The structures of these molecules were established from their NMR, UV, IR spectroscopic, and MS data. 4-Hydroxycinnamic acid hexadecyl ester (5), 4-hydroxycinnamic acid octadecyl ester (6), 4-hydroxycinnamic acid eicosyl ester (7), caffeic acid octadecyl ester (8), pescapreins III, IV, XXI, XXIII, XXV, and XXVI (9-14), and stoloniferin III (15) were also isolated. All compounds were tested against a multiple myeloma cell line (RPMI 8226). When their IC50 value was lower than 10 µM, the compounds were also tested against two other multiple myeloma cell lines, MM.1S and MM.1R. Compound 3 was the most potent, with an IC50 value of 3.0 µM against RPMI 8226 cells.

Isolation and Structure Elucidation of Compounds from Sesamum alatum and Their Antiproliferative Activity against Multiple Myeloma Cells.

The phytochemical investigation of the dichloromethane root extract of Sesamum alatum led to the isolation of 18 compounds. Among these, compounds 3-8, defined as 9-hydroxy-2,2-dimethyl-2H-benzo[g]chromene-5,10-dione 6-O-ß-d-glucopyranoside (3), (2S,3R)-3,4,7-trihydroxy-2-(3'-methylbut-2'-en-1'-yl)-2,3-dihydro-1H-inden-1-one (4), (Z)-2-(1',4'-dihydroxy-4'-methylpent-2'-en-1'-ylidene)-4,7-dihydroxy-1H-indene-1,3(2H)-dione (5), (S)-2,5,8-trihydroxy-3-(2'-hydroxy-3'-methylbut-3'-en-1'-yl)naphthalene-1,4-dione (6), 6-hydroxy-3-(3'-methylbut-2'-en-1'-yl)-4-oxo-4H-chromene-5-carboxylic acid (7), and (S)-2-(1'-hydroxy-4'-methylpent-3'-en-1'-yl)anthracene-9,10-dione (8), respectively, have not yet been described. Their structures were elucidated based on spectroscopic data analysis, including IR, NMR, HRESIMS and ECD measurements. Additional known compounds, namely, hydroxysesamone (1), anthrasesamone A (2), 2,6-dimethoxy-1,4-benzoquinone (9), syringic acid (10), syringaresinol (11), 2,3-epoxysesamone 8-O-ß-d-glucopyranoside (12), 2,3-diacetylmartinoside (13), 2,3-epoxy-4,5,8-trihydroxy-2-prenyl-1-tetralone (14), ursolic acid (15), chlorosesamone (16), 2,3-epoxysesamone (17), and 2-(4-methyl-3-pentenyl)anthraquinone (18) were isolated. The antiproliferative activity of the compounds was tested against the RPMI 8226 multiple myeloma cell line. When compounds presented an IC50 value <10 µM, they were tested against two other multiple myeloma cell lines, MM.1S and MM.1R. Compound 17 was found to be the most potent, with IC50 values of 0.6, 0.7, and 0.9 µM, respectively, for the three cell lines.

Pyridine-4(1H)-one Alkaloids from Waltheria indica as Antitrypanosomatid Agents.

Twelve new pyridine-4(1H)-one derivatives, namely, 8-demethoxywaltherione F (1), waltheriones R-V (2, 6, 7, 10, and 11), 1-methoxywaltherione O (3), (S)-15-hydroxywaltherione G (4), (8R)-8-hydroxywaltherione M (5), (9S,13S)-2-hydroxymethylwaltherione C (8), (9S,10S,13S)-10-hydroxywaltherione C (9), and (S)-13-methoxywaltherione V (12), as well as melovinone (13) and 5'-methoxywaltherione A (14) were isolated from the CH2Cl2 extract of the aerial parts of Waltheria indica. Their chemical structures were determined by means of a comprehensive analysis including 1H NMR, DEPTQ, HSQC, HMBC, 1H-1H COSY, ROESY, and HRESIMS data. The absolute configurations were assigned via comparison of the experimental and calculated ECD data. In addition, the isolated constituents as well as the known waltheriones M-Q were evaluated for their in vitro antitrypanosomal activity. Compounds 2, 5, and 7 as well as waltheriones M, P, and Q showed potent growth inhibition toward Trypanosoma cruzi with IC50 values of 2.1, 0.8, 2.1, 1.3, 0.5, and 0.1 µM, respectively, and selectivity indices of >12, >33, >13, 5, 25, and 14. These findings further demonstrate that the waltheriones are a promising class of antichagasic compounds worthy of further investigations.

Antitrypanosomal quinoline alkaloids from the roots of Waltheria indica.

Chemical investigation of the dichloromethane root extract of Waltheria indica led to the isolation and characterization of 10 quinoline alkaloids, namely, 8-deoxoantidesmone (1), waltheriones E-L (2-9), and antidesmone (10). Among these, compounds 2-9 have not yet been described in the literature. Their chemical structures were established by means of spectroscopic data interpretation including (1)H and (13)C NMR, HSQC, HMBC, COSY, and NOESY experiments and UV, IR, and HRESIMS. The absolute configurations of the compounds were established by comparison of experimental and TDDFT-calculated ECD spectra. In addition, the isolated constituents were evaluated for their in vitro antitrypanosomal activity. Compounds 4, 5, and 8 showed potent and selective growth inhibition toward Trypanosoma cruzi with IC50 values between 0.02 and 0.04 µM. Cytotoxicity for mouse skeletal L-6 cells was also determined for these compounds.

Antiproliferative activity of compounds isolated from the root bark of Lannea acida in multiple myeloma cell lines.

Lannea acida A. Rich. is a native plant of West Africa used in traditional medicine against diarrhea, dysentery, rheumatism, and women infertility. Eleven compounds were isolated from the dichloromethane root bark extract using various chromatographic techniques. Among those, nine compounds have not been previously reported, i.e. one cardanol derivative, two alkenyl 5-hydroxycyclohex-2-en-1-ones, three alkenyl cyclohex-4-ene-1,3-diols, two alkenyl 7-oxabicyclo[4.1.0]hept-4-en-3-ols, and one alkenyl 4,5-dihydroxycyclohex-2-en-1-one, together with two known cardanols. The structure of the compounds was elucidated using NMR, HRESIMS, ECD, IR, and UV. Their antiproliferative activity was evaluated in three multiple myeloma cell lines: RPMI 8226, MM.1S, and MM.1R. Two compounds showed activity in all cell lines with IC50 values < 5 µM. Further investigations are needed to understand the mechanism of action.

Antiprotozoal activity of natural products from Nigerien plants used in folk medicine.

In the course of the screening of plants from Niger for antiprotozoal activity, the methanol extract of Cassia sieberiana, and the dichloromethane extracts of Ziziphus mauritiana and Sesamun alatum were found to be active against protozoan parasites, namely Trypanosoma brucei rhodesiense, Trypanosoma cruzi, Leishmania donovani and/or Plasmodium falciparum. Myricitrin (1), quercitrin (2) and 1-palmitoyl-lysolecithin (3) were isolated from C. sieberiana. From Z. mauritiana, the three triterpene derivatives 13, 15, and 16 are described here for the first time. Their chemical structures were determined by 1D and 2D NMR experiments, UV, IR and HRESIMS data. The absolute configurations were assigned via comparison of the experimental and calculated ECD spectra. In addition, eight known cyclopeptide alkaloids (4, 5, 7-12), and five known triterpenoids (6, 14, 17-19) were isolated. The antiprotozoal activity of the isolated compounds, as well as of eleven quinone derivatives (20-30) previously isolated from S. alatum was determined in vitro. The cytotoxicity in L6 rat myoblast cells was also evaluated. Compound 18 showed the highest antiplasmodial activity (IC50 = 0.2 µm) and compound 24 inhibited T. b. rhodesiense with an IC50 value of 0.007 µM. However, it also displayed significant cytotoxicity in L6 cells (IC50 = 0.4 µm).