Monolaterol, the First Configurationally Assigned Phenylphenalenone Derivative with a Stereogenic Center at C-9, from Monochoria elata

Abstract

Phytochemical analysis of the roots of Monochoria elata resulted in the structure elucidation of monolaterol, the first configurationally assigned phenylphenalenone-type natural product with a stereogenic center at the phenyl-bearing carbon, C-9, and four known phenylphenalenones by MS and NMR methods. The absolute configuration of the new phenyldihydrophenalenediol was assigned by comparing the results of quantum chemical CD calculations and experimental CD spectra, and the crystal structure was determined by X-ray diffraction analysis.

Phytochemicals and Allelopathy of Induced Water Hyacinth against Microcystis aeruginosa

“…9 This assumption was supported by the HMBC correlations of H 2 -3 (δ H 3.11, d, J = 15.0 Hz, and 2.47, dt, J = 15.0, 5.0 Hz) and H-6 (δ H 7.60, d, J = 8.8 Hz) with C-4 (δ C 152.1, s) and C-9b (δ C 127.4, s), as well as the ROESY correlation between H-5 (δ H 7.12, d, J = 8.8 Hz) and 4-OCH 3 (δ H 3.90, s). The absolute configuration of C-1 was assigned as S by comparing the optical rotation value (+36.3 [c 0.10, CHDCl 3 ]) with that of monolaterol (+83.4 [c 0.10, MeOH]), 10 which also supported that the experimental CD curve of 1 matched well with that of monolaterol 10 (Figure 2). This assignment was unambiguously confirmed by using X-ray diffraction analysis with Cu Kα radiation (Figure 3).…”

“…Crystallographic data for compound 1: C 21 H 20 O 3 , M = 320.37, orthorhombic, a = 7.33390 (10) Å, b = 11.0182(2) Å, c = 20.2959(4) Å, α = 90.00°, β = 90.00°, γ = 90.00°, V = 1640.04(5) Å 3 , T = 296(2) K, space group P212121, Z = 4, μ(Cu Kα) = 0.686 mm −1 , 8791 reflections measured and 2787 independent reflections (R int = 0.0526). The final R 1 was 0.0506 (I > 2σ[I]), and the final wR(F 2 ) was 0.1398 (I > 2σ[I]).…”

Aminocatalyzed Synthesis of Enantioenriched Phenalene Skeletons through a Friedel–Crafts/Cyclization Strategy

“…Therefore, phenalenone derivatives elicit antifungal, antimicrobial, and anticancer activities . Optically active 1 H -phenalene framework is also found in natural products such as monolaterol 4 which has been isolated from the roots of Monochoria elata , belonging to the plant family Pontederiaceae . This natural product represents the first isolated phenylphenalene-related compound with a chiral center at the phenyl-bearing atom.…”

Ammonificins C and D, Hydroxyethylamine Chromene Derivatives from a Cultured Marine Hydrothermal Vent Bacterium, Thermovibrio ammonificans

“…The corresponding oscillator and rotatory strengths thus obtained were summed and energetically weighted, following the Boltzmann statistics. Finally, the overall UV and CD spectra were simulated as sums of Gaussian functions centered at the wavelengths of the respective electronic transitions and multiplied by the corresponding oscillator or rotatory strengths, transformed into absorption and Δε values, respectively [13,14,15,16]. …”