• Journal of Life Science
• /
• v.15 no.1 s.68
• /
• pp.147-151
• /
• 2005

A$(-)-\alpha$-narcotine from Papaver sommiferum was refluxed with ethyl chloroformate to give the diastereomeric chloro-carbamate mixture and the Z/E-enol lactones as Z:E=1:1.1 ratio in HPLC analysis. After photoisomerization with UV (254 nm), the Z/E ratio was drastically changed to Z:E=7:1, which may indicate that the E-isomer was easily converted to the Z-isomer due to photoisomerization. The photoisomerization of the Z/E-enol lactones and the different stereochemistry of the degradation product of $\beta-narcotine$, deuterated $\beta-narcotine$ and $\beta-narcotine$ with ethyl chloroformate will also be discussed.

• Natural Product Sciences
• /
• v.13 no.3
• /
• pp.247-250
• /
• 2007

A new sphingosine (1) was isolated from the MeOH extract of a marine sponge Haliclona (Reniera) sp. by bioactivity-guided fractionation. The 1D and 2D NMR, and MS spectroscopic analyses were used to establish the planar structure of 1. The stereochemistry of the compound was defined on the basis of modified Mosher's method, comparison of optical rotation and NMR data with those of the reported. Compound 1 was mildly cytotoxic to a panel of five human solid tumor cell lines.

• Journal of Photoscience
• /
• v.9 no.2
• /
• pp.362-363
• /
• 2002

Since chlorophyll a and bacteriochlorophyll a are asymmetric molecules, an external ligand can coordinate to the central Mg atom either from the chiorin macrocycle side where the C13$^2$-methoxycarbonyl moiety protrudes (denoting as the 'back' side) or frome the other side (the 'face' side). We investigated which side of the macrocycle is favored for the ligand coordination, by survey of the highly resolved crystal structures of various photosynthetic proteins and theoretical model calculations. It is found that chlorophyll a as well as bacteriochlorophyll a and b in the photosynthetic proteins mostly bind their ligands on the 'back' sides. This finding was confirmed by the theoretical calculations for methyl chlorophyllide a and methyl bacteriochlorophyllide a as models: the 'back' type ligand-(bacterio )chlorophyll complex was more stable than the 'face' type one. The calculations predicted influence of the Cl3$^2$-stereochemistry on the choice of the side of the ligand coordination, which is discussed in relation to the presence of the Cl3$^2$-epimer of chlorophyll a in photosystem I reaction center [I].

• Bulletin of the Korean Chemical Society
• /
• v.34 no.9
• /
• pp.2640-2644
• /
• 2013

The all-hydrocarbon i,i+4 stapling system using an oct-4-enyl crosslink is one of the most widely employed chemical tools to stabilize an ${\alpha}$-helical conformation of a short peptide. This crosslinking system has greatly extended our ability to modulate intracellular protein-macromolecule interactions. The helix-inducing property of the i,i+4 staple has shown to be highly dependent on the length and the stereochemistry of the oct-4-enyl crosslink. Here we show that changing the double bond position within the i,i+4 staple has a considerable impact not only on the formation of the crosslink but also on ${\alpha}$-helix induction. The data further increases the understanding of the structure-activity relationships of this valuable chemical tool.

• Bulletin of the Korean Chemical Society
• /
• v.23 no.11
• /
• pp.1548-1552
• /
• 2002

$(-)-\beta-Narcotine$ (6), a phthalideisoquinoline alkaloid, was synthesized conveniently by the direct condensation of cotarnine (1) and iodomeconine (2) prepared by aromatic iodination using thallium trifluoroacetate/KI and by the successive reduction of resulting $iodo-{\beta}-narcotine$ (5) with aluminum amalgam. Its structure including a stereochemistry was confirmed by instrumental analyses. This synthetic alkaloid was degraded with ethyl chloroformate at room temperature to afford the chloro-carbamate 6b as a crystalline intermediate, which was unexpectedly converted into the carbinol 8 by exchange of Cl with OH of water contained in the solvents and the ethoxy-carbamate 9, probably because of ethanol added to chloroform as a solvent stabilizer during the purification by column chromatography.

• Journal of the Korean Magnetic Resonance Society
• /
• v.15 no.2
• /
• pp.128-136
• /
• 2011

A new sesterterpenoid, phorbaketal derivative, was isolated from the marine sponge Phorbas species. Its planar structures was completely determined from a combination of extensive 1D and 2D NMR experiments and MS data, and also the stereochemistry on the chiral centers were established by the ROESY experiment and the comparison with the $^1H$ and $^{13}C$ chemical shifts of the known phorbaketal compounds. This compound 1 moderately showed cytotoxicity effect against hepatoma cancer HepG2 cell.

• Journal of the Korean Magnetic Resonance Society
• /
• v.14 no.1
• /
• pp.1-8
• /
• 2010

Four 5,8-epidioxy sterols were isolated from the marine sponge Plakortis simplex. Their structures were completely determined by an extensive NMR analysis and comparison with NMR data of similar compounds for absolute stereochemistry of the side chain. The compounds were assigned as 5,8-epidioxy- (24S)-ethylcholesta-6,22(E),25-trien-3-ol(1), 5,8-epidioxy-(24S)-methylcholesta- 6,22(E)-dien-3-ol(2), 5,8-epidioxycholesta-6,22(E)-dien-3-ol(3) and 5,8- epidioxycholesta-6-en-3-ol (4).

• Journal of the Korean Magnetic Resonance Society
• /
• v.17 no.1
• /
• pp.47-53
• /
• 2013

Four new cyclic peroxide compounds (1~4) were isolated from the marine sponge Plakortis simplex. Their structures including relative stereochemistry were determined by MS and NMR analysis. All compounds, a side carbon chain with 10 carbons, were very unstable. After transformation into methyl ester analogues, the structure determination was conducted. Compounds 1a and 2a are stereoisomers, assigned as $3S^*$, $4S^*$, $6R^*$ and $3R^*$, $4S^*$, $6R^*$, respectively. Similarly, compounds 3a and 4a, replaced the methoxy group with an aliphatic methyl, are also stereoisomers. Compounds 1a and 2a exhibited the strong antifungal effect against the fungus Candida albicans.

• Journal of the Korean Magnetic Resonance Society
• /
• v.21 no.4
• /
• pp.145-151
• /
• 2017

Rhodiola rosea, also known as gold root or rose root, is a perennial plant in the family of Crassulaceae. The rhizhome of R. rosea has been widely used as a hemostatic, tonic for burns and contusions in traditional Chinese medicine. Recent studies reported its strong antioxidant and adaptogenic properties. In this paper, we attempted to isolate compounds from the methanolic extract of R. rosea rhizomes. Four compounds including one new compound (1), two kaempferol glycosides (3 and 4) were isolated from chloroform and ethyl acetate soluble fraction of R. rosea extract. The structures of 1~4 including relative stereochemistry were determined by MS and NMR analysis.

• YAKHAK HOEJI
• /
• v.44 no.6
• /
• pp.505-510
• /
• 2000

The synthesis of pentahydroindanoisoquinoline (4) compound has been achieved via the cyclization of 2-(N-benzylamino)-5,6-difluoro-1-indanol (10a, 10b), which was prepared by condensation and reduction of 2-amino-1-indanol and benzaldehyde in ethanol. The stereochemistry of $H_{6a}$ and $H_{11b}$ of 9,10-difluoro-5,6,6a,7,11b-pentahydroindano[2,1-c]isoquinoline (4) was the trans B/C ring fusion.