A novel homosesquiterpenoid from the stems ofCinnamomum burmanii

Abstract

A novel homosesquiterpenoid, burmanol (1), along with 16 known compounds, including one triterpenoid, one quinol, two chlorophylls, two coumarins, two steroids, three lignans and five benzenoids were obtained from the stems of Cinnamomum burmanii (Lauraceae). The structures of these compounds were determined on the basis of spectroscopic analysis.

Anti-Inflammatory and Antibacterial Activity Constituents from the Stem of Cinnamomum validinerve

“…The known compounds lincomolide A ( 3 ) [ 24 ], linderanolide B ( 4 ) [ 25 ], isolinderanolide B ( 5 ) [ 25 ], isophilippinolide A ( 6 ) [ 26 ], secosubamolide ( 7 ) [ 27 ], reticuol ( 8 ) [ 28 ], burmanol ( 9 ) [ 29 ], (−)-5,7-dimethoxy-3′,4′-methylenedioxy-flavan-3-ol ( 10 ) [ 30 ], taxifolin ( 11 ) [ 31 ], (−)-yangambin ( 12 ) [ 32 ], (−)-pinoresinol ( 13 ) [ 33 ], (+)-monomethylpinoresinol ( 14 ) [ 34 ], (+)-syringaresinol ( 15 ) [ 33 ], erythro -guaiacylglycerol- β - O -4′-(5′)-methoxylariciresinol ( 16 ) [ 35 ], caryolane-1,9 β -diol ( 17 ) [ 36 ], β -sitosterol ( 18 ) [ 37 ], and cinnamtannin B1 ( 19 ) [ 38 ] were identified by comparisons of physical and spectroscopic data ([α] D , UV, IR, 1 H NMR, and MS) with authentic samples or literature data. Among them, cinnamtannin B1 ( 19 ) (3.6 g) was obtained as the major constituent.…”

“…It has been previously synthesized and yielded as a mixture [19,20]. The known compounds lincomolide A (3) [24], linderanolide B (4) [25], isolinderanolide B (5) [25], isophilippinolide A (6) [26], secosubamolide (7) [27], reticuol (8) [28], burmanol (9) [29], (−)-5,7-dimethoxy-3 ,4 -methylenedioxy-flavan-3-ol (10) [30], taxifolin (11) Compounds 6, 7, and 19 were evaluated for their ability to inhibit the growth of Propionibacterium acnes. Compounds 6 and 7 showed anti-microbial activity against P. acnes, with a minimal inhibitory concentration (MIC) value of 16 µg/mL.…”

Chemical Structures of Lignans and Neolignans Isolated from Lauraceae

“…(+)-De-4’’-O-methylmagnolin ( 49 ) and (+)-syringaresinol ( 50 ) both were found to occur in the methanolic extract of the stems of Actinodaphne lancifolia [30]. The leaves of C. macrostemon Hayata [31] and the stems of C. burmanii [32] both contained (+)-syringaresinol ( 50 ) and yangambin ( 51 ), which showed various pharmacological effects. Moreover, C. burmanii also contained (+)-sesamin ( 46 ) [32].…”

“…The leaves of C. macrostemon Hayata [31] and the stems of C. burmanii [32] both contained (+)-syringaresinol ( 50 ) and yangambin ( 51 ), which showed various pharmacological effects. Moreover, C. burmanii also contained (+)-sesamin ( 46 ) [32]. (+)-Demethoxyexcelsin ( 52 ), (+)-piperitol ( 53 ), and (+)-methoxypiperitol ( 54 ) were obtained from the bark and wood of N. turbacensis , together with (+)-sesamin ( 46 ) [33].…”

Burmannic Acid Inhibits Proliferation and Induces Oxidative Stress Response of Oral Cancer Cells

“…C. burmannii is a commonly used spice in Indonesia [19], and its bark is the source of the spice cinnamon. Some homosesquiterpenoids [20] and amides have been isolated from C. burmannii stems. Using C. burmannii roots, we identified a new apocarotenoid and a novel β-ionone derivative, burmannic acid (BURA) [21], with a carboxylic acid group binding to C-5 of 3-hydroxy-5,6-epoxy-β-ionone.…”