Isoprenylated Naphthoquinone Dimers Firmianones A, B, and C from Firmiana platanifolia

Abstract

Three new compounds designated as firmianones A, B, and C (1-3), along with 13 known compounds, were isolated from the roots of Firmiana platanifolia. Their structures were elucidated by interpretation of HRESIMS, 1H-1H COSY, HMQC, HMBC, and NOESY. The absolute configurations of firmianones A and B with a rare hexacyclic skeleton were determined by CD exciton-coupling experiments. Firmianones A and B exhibited moderate cytotoxicity to the P388 cancer cell line.

Enzymatic production of sterculic acid from the novel Phoenix tree seed oil: Optimization and kinetic study

“…Many active components can be obtained from the stem, leaf, flower, and wood fiber of the Phoenix tree Son et al, 2015;Woo et al, 2015). The root bark of the Phoenix tree had been used to treat rheumatism, asthma, fractures, and tumors (Bai et al, 2005). The seeds of the Phoenix tree have also been used as traditional Chinese herbs for promoting digestion and treating stomachache (Woo et al, 2016).…”

A STIGMASTEROL GLYCOSIDE FROM THE ROOT WOOD OF <i>Melochia Umbellata</i> (Houtt) Stapf <i>var.</i> degrabrata K.

“…The olefinic resonance at δ 121.04, 137.85, and 128.79 corresponded to C-6, C-22 and C-23 methine carbons, and a signal at δ 140.43 corresponded to the C-5 quarternary carbon of the sterol moiety. The value of J = 7.8 on 1' (anomeric proton) reflected that the proton is the axial-axial to C-2' proton which means glucopyranoside moiety binds to the sterol moiety β position [3,11]. Based on the data description above and comparison with physical and spectroscopic data of previously known compound [10], the molecular structure of compound 1 is in Fig.…”

“…The existence of long-range correlations of protons at δ 4.23 (H-1') with a carbon at δ 76.95 (C-3) and 76.63 (C-5') indicates that the group of glucose is bound to C-3 (oxy carbon sp 3 ). Long-range correlations of protons at δ 5.32 (H-6) with a methylene carbon at δ 31.30 (C-7), methine carbon at 31.38 (C-8), and the quaternary carbon at 36.15 (C-10) strengthen that the C-5 and C-6 are as olefinic bonding in the second ring of sterol skeleton.…”

“…Its roots are widely known having contained many bioactive compounds such as flavonoids as an antifungal from Hildegardia barteri [2], isoprenylated naphtoquinone from Firmiana platanifolia which is active against leukemia cells P-388 [3], the alkaloid quinolinone from Waltheria douradinha as antibacterial [4], melochinone and melovinone from Melochia tomentosa [5][6], and some alkaloids cyclopeptide from Melochia chamaedrys [7].…”

An alkaloidal glycoside and other constituents from Leucosceptrum japonicum

“…Previous studies on the chemical constituents of L. japonicum have reported five flavonoids [1] and five acylglycosides [2]. In the present work, a new alkaloidal glycoside (1), a new phenylpropanoid glucoside (2), a new caffeic acid derivative (3), and 26 known compounds, verbascoside (4) [2], acteoside isomer (5) [2], lipedoside A (6) [3], 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-a-L-mannopyranosyl)-4-[(2Z)-3-(4-hydroxyphenyl)-2-propenoate]-b-D-glucopyranoside (7) [4], leucosceptoside A (8) [5], jionoside D (9) [5], martynoside (10) [6], leonoside B (11) [7], scutellarein 7-glucuronide (12) [8], 6-O-methylscutellarin (13) [9], comanthoside B (14) [1], hispidulin 7-O-glucuronide methyl ester (15) [10], hispidulin 7-O-b-D-glucopyranoside (16) [11], luteoline (17) [12], scutellarein (18) [10], 6-O-methyl-scutellarein (19) [10], citrusin C (20) [13], 10-O-(E)-p-coumaroylgeniposidic acid (21) [14], tyrosol (22) [15], protocatechualdehyde (23) [16], p-hydroxybenzoic acid (24) [17], 4-hydroxybenzoic acid methyl ester (25) [18], protocatechuic acid (26) [19], trans-caffeic acid (27) [13], indole-3-aldehyde (28) [20], and indole-3-carboxylic acid (29) [21], were isolated. d 3.08 showed a long-range coupling with a carbon signal at d 109.0 which was long-range coupled with a proton signal at d 7.51.…”