The 3′R,4‘R absolute configuration (AC) of the angular-type pyranocoumarins (-)-3′,4′-di-O-acetylkhellactone (2), (-)-4′-O-acetyl-3′-O-angeloylkhellactone (3), (+)-3′-O-acetyl-4-O-isobutyroylkhellactone (4), and (-)-3′-O-angeloyl-4′-O-senecioylkhellactone (5), isolated from the aerial parts of Prionosciadum thapsoides, was assigned by vibrational circular dichroism exciton chirality (VCDEC), and confirmed by comparison of their VCD frequencies with those calculated using DFT at the B3LYP/DGDZVP level. This again reveals that AC assignments based on optical rotation data are not very confident. Evaluation of Flack and Hooft parameters obtained after single-crystal X-ray diffraction analysis of 3, independently confirmed this AC.
MurrayRDH. (2002) The naturally occurring coumarins. In Progress in the Chemistry of Organic Natural Products. Vol. 83, HerzW, FalkH, KirbyGW, MooreRE (Eds). Springer, Vienna, New York, 185–209.
2.
ZhangSL, LiJM, XiaoQH, WuAH, ZhaoQ, YangGR, ZhangKH. (2001) Effect of DL-praeruptorin A on ATP sensitive potassium channels in human cortical neurons. Acta Pharmacologica Sinica, 22, 813–816.
3.
ZhaoNC, JimWB, ZhangXH, GuanFL, SunYB, AdachiH, OkuyamaT. (1999) Relaxant effects of pyranocoumarins compounds isolated from a Chinese medical plant Bai-Hua Qian-Hu, on isolated rabbit tracheas and pulmonary arteries. Biological and Pharmaceutical Bulletin, 22, 984–987.
4.
LiangT, YueW, LiQ. (2010) Chemopreventive effects of Peucedanum praeruptorum DUNN and its mayor constituents on SGC7901 gastric cancer cells. Molecules, 15, 8060–8071.
GuobingX. (2013) Medical composition for treating diabetes mellitus complicated with hyperlipidemia, its preparation and detection method. Peop. Rep. China, CN 103006725 A, 20130403.
7.
JinSY, JinKK. (2014) Praeruptorin A and salts thereof for preventing and treating osteoporosis, PCT Int. Appl. WO 2014084669 A1 20140605.
MatsudaH, MurakamiT, NishidaN, KageuraT, YoshikawaM. (2000) Medicinal foodstuffs. XX. Vasorelaxant active constituents from the roots of Angelica forcjuga Kitagawa: Structures of hyuganins A, B, C, and D. Chemical and Pharmaceutical Bulletin, 48, 1429–1435.
Valencia-IslasN, AbbasH, ByeR, ToscanoR, MataR. (2002) Phytotoxic compounds from Prionosciadium watsoni. Journal of Natural Products, 65, 828–834.
18.
KongLY, LiX, PeiYH, ZhuTR. (1994) Isolation and structural elucidation of qianhucoumarin D and E from Peucedanum praeruptorum. Acta Pharmacologica Sinica, 29, 49–54.
19.
Torres-ValenciaJM, Chávez-RíosOE, Cerda-García-RojasCM, Burgueño-TapiaE, Joseph-NathanP. (2008) Dihydrofurochromones from Prionosciadium thapsoides. Journal of Natural Products, 71, 1956–1960.
20.
Buendía-TrujilloAI, Torres-ValenciaJM, Joseph-NathanP, Burgueño-TapiaE. (2014) Absolute configuration of angular 3′-acyloxypyranocoumarins by vibrational circular dichroism exciton chirality. Tetrahedron: Asymmetry, 25, 1418–1423.
21.
TaniguchiT, MondeK. (2012) Exciton chirality method in vibrational circular dichroism,. Journal of the American Chemical Society, 134, 3695–3698.
22.
AsaiT, TaniguchiT, YamamotoT, MondeK, OshimaY. (2013) Structures of spiroindicumides A and B, unprecedented carbon skeletal spirolactones, and determination of the absolute configuration by vibrational circular dichroism exciton approach. Organic Letters, 15, 4320–4323.
23.
KamoriK, TaniguchiT, MizutaniS, MondeK, KuramochiK, TsubakiK. (2014) Short synthesis of berkeleyamide D and determination of the absolute configuration by vibrational circular exciton chirality method. Organic Letters, 16, 1386–1389.
24.
WuT, YouX. (2012) Exciton coupling analysis and enolization monitoring by vibrational circular dichroism spectra of camphor diketones. The Journal of Physical Chemistry A, 116, 8959–8964.
25.
MasaA, RizzoP, MonacoG, ZanasiR. (2013) Absolute configuration assignment made easier by VCD of couplet oscillating carbonyls: the case of (-)-propanedioic acid, 2-(2,3)-dihydro-3-oxo-1H-isoindol-1-yl)-1,3-dimethyl ester. Tetrahedron Letters, 54, 6242–6246.
26.
ThadanitiS, ArchakunakornW, TuntiwachwuttikulP, BremmerJB. (1994) Chromones from Harrisonia perforata (Blanco.). Journal of the Science Society of Thailand, 20, 183–187.
27.
ShanbhagSN, MestaCK, MaheshwariML, PaknikarSN, BhattacharyyaSC. (1964) Jatamansin, a new terpenic coumarin from Nardostachys jatamansi. Tetrahedron, 20, 2605–2615.
28.
NielsenBE, SoineTO. (1967) Coumarins of Pteryxia terebentina. Structure of two new coumarins, isopteryxin and calipteryxin. Journal of Pharmaceutical Sciences, 56, 184–187.
29.
SwagerTM, CardellineJH.II (1985) Coumarins from Musineon divaricatum. Phytochemistry, 24, 805–813.
30.
MatsudaH, MurakamiT, KageuraT, NinomiyaK, ToguchidaI, NishidaN, YoshikawaM. (1998) Hepatoprotective and nitric oxide production inhibitory activities of coumarin and polyacetylene constituents from the roots of Angelica furcjuga. Bioorganic & Medicinal Chemistry Letters, 8, 2191–2196.
31.
Joseph-NathanP, Gordillo-RománB. (2015) Vibrational circular dichroism absolute configuration determination of natural products. In Progress in the Chemistry of Organic Natural Products. Vol. 100, KinghornAD, FalkH, KobayashiJ (Eds). Springer International Publishing, Switzerland, 311–451.
32.
FlackHD, BernardinelliG. (2008) The use of X-ray crystallography to determine absolute configuration. Chirality, 20, 681–690.
33.
HooftRWW, StraverLH, SpekAL. (2008) Determination of absolute structure using Bayesian statistic on Bijvoet differences. Journal of Applied Crystallography, 41, 96–103.
34.
LiuR, FengL, SunA, KongL. (2004) Preparative isolation and purification of coumarins from Peucedanum praeruptorum Dunn by high-speed counter-current chromatography. Journal of Chromatography A, 1057, 89–94.
