A novel sesquiterpenoid from the leaves of Cinnamomum subavenium

Abstract

syringaldehyde (3), trans-coumaric acid (4), cis-coumaric acid (5), vanillic acid (6), and p-hydroxybenzoic acid (7), were isolated from the leaves of Cinnamomum subavenium Miq (Lauraceae). These compounds were identified and characterized by physical and spectral evidence.

Pharmacological properties and their medicinal uses ofCinnamomum: a review

“…Root 3,4-Methylenedioxy-5-methoxy cinnamyl alcohol; eugenol; isoobtusilactone A; myristicin; obtusilactone A, [255] subamol. [256] isoobtusilactone A, obtusilactone A, eugenol, myristicin, cinnamyl alcohol [255] Anticancer activity, [130,257] antiinflammatory, [130] antioxidant, [130,172,255] antityrosinase, [258] , enzyme inhibitory [259] Abdominal pain, chest pain, diarrhoea, hernia, nausea, rheumatism, stomach aches, swellings, vomiting [260] Stem (+)-Catechin, (+)-syringaresinol, (À)-epicatechin, (À)sesamin, ferulic acid, isolinderanolide B, linderanolide B6, p-hydroxybenzaldehyde, palmitic acid, secosubamolide, stearic acid, stigmasterol, stigmasteryl-D-glucoside, subamolides A-C, syringaldehyde, vanillic acid, vanillin, b-sitosterol, bsitosterol-D-glucoside [257] epicatechin; gibberellin; hydroxytyrosol; nine flavonoids, catechin; phloridzin; two tannins, cinnamtannins B-1 [259] Fatty acids: Hexadecanoic acid [262] Hydrocarbons: Cadalene; pentacosane; tridecane; acopaene; d-cadinene. [262] Others: (E)-Methyl cinnamate; (E)-a-ionone; (Z)isoeugenol; benzyl benzoate; cis-calamenene; cis-⍺bergamotene; cubenol; dodecene; elemol; geranyl acetate; geranyl formate; methyl eugenol; transpinocarveol; a-cubebene; a-cyperone.…”

Total Synthesis of (±)‐Dihydroisosubamol

“…3368,2934,2853,1707,1608,1589,1496,1452,1373,1260,1159,1039,982,875,823,798 The spectroscopic data correspond to that reported in literature. [1] In the original data a CH group was assigned to a very weak peak at 41.5 ppm, which was not detected in our sample. We instead believe that the broad signal at 43.7 ppm is correctly assigned to this CH group, since the original spectra also show this signal.…”

“…Chemical shifts are given in ppm and coupling constants in Hz. 1 H and 13 C spectra were calibrated in relation to the deuterated solvents. The following appreviations were used for 1 H NMR to indicate the signal multiplicity: s (singlet), d (doublet), t (triplet), q (quartet), quint (quintet), m (multiplet), dd (doublet of doublet), dt (doublet of triplet), bs (broad singlet).…”

“…Some members of this class of natural products display interesting biological activities like inhibition of Cyctochrome P450 (CYP3 A4), inhibition of a-Glucosidase Typ IV (Bacillus stearothermophilus) and antiprofilerative activity against cancer cell line DU145. [1] One particularly interesting member is (aR,7R)-Dihydroisosubamol, which was isolated from the leaves of Cinnamomun subavenum together with five other new and sixteen known compounds. This compound constitutes the first dibenzocycloheptadiene isolated from nature and had not been synthesised so far.…”

Highly Efficient Gold‐Catalyzed Synthesis of Dibenzocycloheptatrienes

“…In the last years, several natural products belonging to the class of dibenzocycloheptanoids have been isolated from different sources 7. Figure 1 depicts, as selected representatives, tenuifolin,7d, f which shows antiproliferative activity against tumor cell line DU145, the strongly related reticuol as an inhibitor of cytochrom P450 (CYP3 A4),7b,i subavenoside E,7c showing inhibitory activity against α‐glucosidase type IV from Bacillus stearothermophilus , dibenzocycloheptadiene sihydroisosubamol,7c and subamol 7a,e…”