Two new compounds from the roots of Swietenia macrophylla

Abstract

Phytochemical investigation on the roots of Swietenia macrophylla yielded one new pharagmalin-type limonoid named 2-dehydroxyl-swietephragmin C (1) and one new xanthone, 1,5-dihydroxy-6-methoxy-6',6'-dimethyl-2H-pyrano[2',3':3,2]xanthone (2), in addition to three known compounds. The structures of the new compounds were unambiguously determined by comprehensive spectroscopic methods (NMR, UV, IR, MS), as well as by comparison with the reported data in the literature. Xanthones were reported from Swietenia genus for the first time.

Chemistry and Biology of Novel Meliaceae Limonoids

“…The carbonyl group at C3 in Toonasinenine G ( 388) is reduced with oxirane ring formation at C1/2 in Toonacilianin D (410) and Toonasinenine F (411). Toonacilianin B, C (412,413) and Toonaciliatone H (414) share the same skeleton as compound (409) except the cleavage of C1/11 ether bridge and formation of ∆ 1,2 double bond. Ciliatasecone G ( 415) is C15 acetyl analog of compound (412).…”

“…The epoxide ring at C14, C15 in compound (390) and compound (393) is replaced by ∆ 14,15 double bond in Ciliatasecone O (428) and Ciliatasecone P (429) respectively. Ciliatasecone D (430) differs from compound (413) with presence of hydroxyl group at C14 and ∆ 8,9 double bond with cleavage of C8,C14 epoxide ring. Ciliatasecone E (431) differs from compound (430) with reduction of C3 carbonyl and shifting of double bond from ∆ 8,9 to ∆ 8,30 .…”

“…At 10 µM, compounds (1155, 1241, 1242) exhibited inhibitory activity against lipopolysaccharide induced NF-κB activation, but showed no obvious toxicity on RAW264.7 macrophage cells 372,375 . Compounds (1013, 1085, 1090, 1116, 1188, 1190, 1195) were inactive for inhibition of in vitro αglucosidase and acetylcholinesterase activities 386,413 . At 1 µg/mL, compounds (1021, 1032, 1089, 1113, 1114, 1295, 1296, 1309) exhibited inhibitory activity against lipopolysaccharide induced NF-κB production in NF-κB luciferaseexpressing human embryonic kidney 293 (HEK293-NF-κB-luc) cells in vitro with relative inhibitory potency of 0.25, 0.18, 0.11, 0.23, 0.23, 0.10, 0.33, 0.69 respectively compared to positive control hydrocortisone with relative inhibitory value of 0.29 390 395,409,410,468,478 .…”

“…. Compounds (265, inhibitory effect against the Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells with IC 50 value of 452,401, 496,482, 488, 521, 495, 530, 528, 497, 493, 453, 497,431,299,318,413,475,481 and 418 mol ratio/32 pmol TPA respectively…”

Polyacetylenes from the Roots of Swietenia macrophylla King

“…It is necessary to expand the scope of research on S. macrophylla and discover or develop additional biologically active constituents of this plant genus [31]. Our recent study on the roots of S. macrophylla led to the isolation of a series of xanthones, limonoids, and other chemical components [32,33]. As a continuation of our studies on the biologically active agents from this plant, five new and two known acyclic C 18 –C 14 polyacetylenes have been further isolated here, and their cytotoxic activities against the human hepatocellular carcinoma cell line BEL-7402, human myeloid leukemia cell line K562, and human gastric carcinoma cell line SGC-7901 were investigated.…”