Anti-inflammatory Coumarin and Benzocoumarin Derivatives from Murraya alata

Abstract

Two new rare 8-methylbenzo[h]coumarins, muralatins A and B (1, 2), nine new C-8-substituted coumarins, muralatins C-K (3-11), and 22 known analogues (12-33) were isolated from the leaves of Murraya alata. The absolute configurations of compounds 5, 11, 23, 24, 27, 30, and 33 were assigned via comparison of their specific rotations, by Mosher's method, and by single-crystal X-ray diffraction and electronic circular dichroism (ECD) data of the in situ formed transition metal complexes. A putative biosynthesis pathway to 1 and 2 is proposed, and the chemical synthesis of 1 was accomplished through electrocyclization of 5,7-dimethoxy-8-[(Z)-3-methylbut-1,3-dienyl)]coumarin (12). Compounds 1, 2, 8, 12, and 31 showed inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages with IC50 values of 6.0-14.5 μM.

Prenylated Coumarins from Heracleum stenopterum, Peucedanum praeruptorum, Clausena lansium, and Murraya paniculata

“…The NMR spectra (Table 3) showed the presence of a 5,6,7,8-tetrasubstituted coumarin skeleton [ δ H 6.33 (d, J  = 9.6 Hz, H-3) and 7.92 (d, J  = 9.6 Hz, H-4); δ C 161.2 (s, C-2), 114.5 (d, C-3), 138.3 (d, C-4), 140.9 (s, C-5), 138.4 (s, C-6), 149.4 (s, C-7), 118.9 (s, C-8), 110.0 (s, C-4a), and 146.0 (s, C-8a)], two methoxys [ δ H 3.96, 3.91 (each s); δ C 62.1, 61.7 (each q)], a prenyl [ δ H 3.50 (d, J  = 7.0 Hz, H-1′), 5.22 (br t, J  = 7.0, H-2′), 1.68 (br s, H-4′), and 1.83 (br s, H-5′); δ C 22.5 (t, C-1′), 121.3 (d, C-2′), 132.8 (s, C-3′), 25.7 (q, C-4′), 18.0 (q, C-5′)], and a phenolic hydroxy group [ δ H 5.56 (s, 6-OH)]. All of the above spectroscopic data were generally consistent with those of 6-methoxycoumurrayin [16], except that a methoxy group was replaced by a hydroxy group. The two methoxy groups were located at C-5 and C-7 on the basis of the HMBC correlations from H-4 to C-5, 5-OCH 3 to C-5, H-1′ to C-7/C-8a, and from 7-OCH 3 to C-7.…”

“…for C 15 H 14 O 5 Na, 297.0733). The NMR data (Table 3) revealed the presence of a 6,7-disubstituted coumarin skeleton [ δ H 6.33 (d, J  = 9.6 Hz, H-3), 7.69 (d, J  = 9.6 Hz, H-4), 7.97 (s, H-5), and 6.83 (s, H-8)], a methoxy group ( δ H 3.89; δ C 56.5), and a set of signals originated from a prenyl unit [ δ H 3.15 (heptet, J  = 7.0, H-3′), 1.24 (d, J  = 7.0, H-4′ and H-5′); δ C 193.6 (s, C-1′), 205.6 (s, C-2′), 36.3 (d, C-3′), 17.2 (q, C-4′ and C-5′)], which were further established as a 3-methyl-2-oxobutyroyl unit by the HMBC correlations of H-4′ and H-5′ with C-2′ as well as comparison with literature data [16]. This unit was attached to C-6 from the HMBC correlation of H-5 to C-1′, while the methoxy at C-7 by a weak but clear 4 J correlation from the methoxy protons to C-8.…”

Four new phenolic glycosides from Baoyuan decoction

“…Cell maintenance, experimental procedures, and data determination for the inhibition of NO production and the viability assay are the same as previously described 5 15 .…”

N,N,N′,N′‐Tetrabromobenzene‐1,3‐disulfonamide Catalyzed Synthesis of New Spiro[chroman‐3,2′‐chromeno[2,3‐b]furan]‐2,4,4′‐(3′H)‐trione Derivatives

“…Also, these moieties are widely used in anti‐arrhythmic and anti‐hypertensive drugs ( B ). Cumarins and their derivatives (well known as the therapeutic agents) are a class of privileged medicinal scaffold, which have been possessing wide spectrum of biological and pharmacological activities such as anti‐proliferative , anti‐coagulant ( C ), inhalation aerosol ( D ), anti‐oxidant , anti‐inflammatory , HIV inhibitory potency , and central nervous system activities (Fig. ).…”