15575-68-5Relevant academic research and scientific papers
COMPARATIVE CHARACTERIZATION OF THE COUMARIN COMPOSITION OF Seseli campestre GROWING IN MOLDAVIA AND IN THE CAUCASUS
Abyshev, A. Z.,Sidorova, I. P.,Abyshev, D. Z.,Florya, V. N.,Zmeikov, V. P.,Kerimov, Yu. B.
, p. 400 - 407 (1982)
The results are given of the identification of (-)-trans-khellactone and its 4'-methyl ether and (-)-3'(S),4'(S)-trans-3'-senecioyloxy-4'-angeloyloxy-3',4'-dihydroseselin and of the establishment of the structure of three new khellactone derivatives - campestrol (VII), C19H22O6, D20+32 deg (c 7.8; chloroform), campestrinol (X), C24H26O7, mp 116-118 deg C, and campestrinoside (I), C20H24O10, mp 172-173 deg C, D -272.5 deg (c 4.7; ethanol).It has been shown on the basis of chemical and spectral characteristics that campesol, earlier described as a new substance, is a mixture of two isomeric compounds - 4'-hydroxy-3'-senecioyloxy-3',4'-dihydroseselin and 3'-angeloyloxy-4'-hydroxy-3',4'-dihydroseselin.
Improved Biological Activities of Isoepoxypteryxin by Biotransformation
Mira, Amira,Amen, Yhiya M.,Alkhiary, Wael,Zhu, Qinchang,Nakagawa, Toshinori,Tran, Hai-Bang,Shimizu, Kuniyoshi
, p. 1307 - 1315 (2016)
Isoepoxypteryxin is the major coumarin of a Japanese medicinal plant Angelica shikokiana. This research was designed to study the effect of structural changes through fungal biotransformation on the reported biological activities of isoepoxypteryxin. Among the tested microorganisms, only Cordyceps sinensis had enzymes that could catalyze the ester hydrolysis and the reductive cleavage of the epoxide ring of isoepoxypteryxin, separately, to give two more polar metabolites (+)-cis-khellactone (P1) and a new coumarin derivative (+)-cis-3′-[(2-methyl-3-hydroxybutanoyl)oxy]-4′-acetoxy-3′,4′-dihydroseselin (P2), respectively. The polar metabolite P2 showed stronger cytotoxicity and higher selectivity than isoepoxypteryxin. On the molecular level, P2 showed more in vitro inhibition of both tubulin polymerization and histone deacetylase 8 (HDAC8). Similarly, P2 showed more neuroprotection against amyloid beta fragment 1 – 42 (Aβ1 – 42)-induced neurotoxicity in human neuroblastoma cells (SH-SY5Y) and exhibited more inhibition of the in vitro aggregation of Aβ1 – 42. Both metabolites showed stronger antiplatelet aggregation by increased inhibition of thromboxane-A2 synthase (TXS) activity and thromboxane-A2 (TXA2) production. This study is the first to describe the improved cytotoxic, neuroprotective, and antiplatelet aggregation activities of isoepoxypteryxin through its biotransformation by C. sinensis.
(±)-3′-O, 4′-O-dicynnamoyl-cis-khellactone, a derivative of (±)-praeruptorin A, reverses P-glycoprotein mediated multidrug resistance in cancer cells
Shen, Xiaoling,Chen, Guangying,Zhu, Guoyuan,Fong, Wang-Fun
, p. 7138 - 7145 (2006)
P-glycoprotein (Pgp) is an ATP-driven membrane exporter for a broad spectrum of hydrophobic xenobiotics. Pgp-overexpression is a common cause of multidrug resistance (MDR) in cancer cells and could lead to chemotherapeutic failure. Through an extensive he
Antidiabetic effect, antioxidant activity, and toxicity of 3′,4′-Di-O-acetyl-cis-khellactone in Streptozotocin-induced diabetic rats
Domínguez-Mendoza, Elix Alberto,Cornejo-Garrido, Jorge,Burgue?o-Tapia, Eleuterio,Ordaz-Pichardo, Cynthia
, p. 4086 - 4091 (2016)
Pyranocoumarins are compounds with an important pharmacological profile, such as anti-inflammatory, antioxidant, cytotoxic, antiviral, antibacterial, and hypoglycemic effects. These molecules have a widespread presence as secondary metabolites in medicinal plants used to treat Diabetes Mellitus (DM). The aim of this work was to evaluate antidiabetic activity in Streptozotocin (STZ)-induced diabetic rats and the antioxidant effects of 3′,4′-Di-O-acetyl-cis-khellactone (DOAcK), as well as its toxic potential. We obtained DOAcK with an enantiomeric excess of 70% by chemical synthesis. Our results showed that this compound exerts an important antidiabetic effect: blood glucose decreased in groups treated with DOAcK by 60.9% at dose of 15?mg/kg (p?50) >2000?mg/kg and, at this dose, no signs of toxicity or death were reported after 14?days of observation. These results indicate that DOAcK can improve glucose metabolism, which may be due to the increased antioxidant activity of CAT, GPx and SOD. In addition, DOAcK is not toxic in the studies tested.
Medicinal foodstuffs. XX. Vasorelaxant active constituents from the roots of Angelica furcijuga Kitagawa: Structures of hyuganins A, B, C, and D
Matsuda,Murakami,Nishida,Kageura,Yoshikawa
, p. 1429 - 1435 (2000)
From the methanolic extract with vasorelaxant activity obtained from Angelica furcijuga Kitagawa, four new khellactone-type coumarins, hyuganins A, B, C, and D, were isolated together with twelve known coumarins, two known acetylenic compounds, and a known lignan. The structures of hyuganins A, B, C, and D were determined on the basis of chemical and physicochemical evidence. Nine principal coumarins (hyuganin A, anomalin, pteryxin, isopteryxin, isoepoxypteryxin, praerosides II and IV, apiosylskimmin, (R)-peucedanol 7-O-β-D-glucopy-ranoside), two acetylenic compounds [(-)-falcarinol and falcarindiol], and related compounds were examined for inhibitory activities on high concentration of K+ (High K+)- and dl-norepinephrine (NE)-indueed contractions. The results indicate that the 3'- and 4'-acyl groups of khellactone-type coumarins are essential for the inhibitory activity on the contractions by High K+. Hyuganin A and anomalin showed inhibitory effects on High K+-induced contraction, but not on NE-induced contraction. Other active coumarins (pteryxin, isopteryxin, isoepoxypteryxin) and an acetylenic compound (falcarindiol) non-selectively inhibited both contractions by High K+ and NE.
Characterization of metabolism of (+)-praeruptorin B and (+)-praeruptorin E in human and rat liver microsomes by liquid chromatography coupled with ion trap mass spectrometry and time-of-flight mass spectrometry
Song, Yue-Lin,Yan, Ru,Jing, Wang-Hui,Zhao, Hai-Yu,Wang, Yi-Tao
, p. 719 - 730 (2011)
Peucedani Radix is a Chinese medicinal herb noted for its effects on treatments of respiratory and pulmonary disorders. As a part of a systematic pharmacokinetic evaluation of the herb in our laboratory, the present study investigated, for the first time, the metabolic profile of (+)-praeruptorin B (dPB) and (+)-praeruptorin E (dPE), two main bioactive constituents of Peucedani Radix in pooled liver microsomes of rats (RLMs) and humans (HLMs). dPE was eliminated faster than dPB in both species. The incubation of dPB with RLMs and HLMs resulted in eight (B1-B8) and nine (B1-B9) metabolites, respectively, while both RLMs and HLMs converted dPE into 13 metabolites (E1-13). Structures of all the metabolites were proposed through comparing their mass data obtained via tandem mass spectrometry on an MSD ion trap system (IT-MS/MS) coupled with high-resolution mass measurement by time-of-flight mass spectrometry (TOF-MS) with those of the respective parent compound. B1 and E1 were unambiguously identified as (-)-cis-khellactone. The formations of all the metabolites were NADPH-dependent. Oxidation and hydrolysis were demonstrated to be two predominant metabolic pathways of dPB and dPE. Oxidation initiated at either the C-3′ or C-4′ substituent, while hydrolysis only started from the C-3′ substituent. Fragmentation of all metabolites followed similar pathways to those of the parent pyranocoumarins. The information on metabolic properties of dPB and dPE and the mass fragmentation profiles of their metabolites obtained in the present study will aid in characterization of metabolic profiles of other angular-type pyranocoumarins and further investigation of in vivo fates of these pyranocoumarins and the herb. Copyright
Chromones and coumarins from Saposhnikovia divaricata (Turcz.) Schischk. Growing in Buryatia and Mongolia and their cytotoxicity
Frolova, Tatyana S.,Ganbaatar, Jamsranjav,Petrova, Tatyana N.,Pokrovskii, Andrey G.,Radnaeva, Larisa D.,Rybalova, Tatyana V.,Shults, Elvira E.,Taraskin, Vasilii V.,Urbagarova, Bayarma M.
, (2020)
Ethnopharmacological relevance: Saposhnikovia divaricata (family Apiaceae) a traditional medicinal plant distributed in many provinces of China, is well known for the pharmaceutical value and has been used for rheumatic arthritis, and anxiety in children. Antiviral, antioxidant and antiproliferative activities were also mentioned. The application of this plant are recorded in the Chinese Medicine (CM) classical text the Shen Nong's Materia Medica (Shen Nong Ben Cao Jing). In this monograph S. divaricata (syn Radix Ledebouriella divaricata) is graded as a premium-grade herb, with their broad-spectrum of therapeutic applications for the treatment of cough, common cold, arthralgia, as well as in rheumatic disorders. Aim of the study: To isolate and identify chemical constituents (chromones and coumarins) from S. divaricata, collected in Buryatia and Mongolia and to study their in vitro anticancer activity against MEL-8, U-937, DU-145, MDA-MB-231 and ВТ-474 cell lines. Materials and methods: An 40% aqueous ethanol extract of the roots of S. divaricata was prepared and further successively fractionated by extraction with petroleum ether, diethyl ether, tert-butyl methyl ether and ethyl acetate. The obtained extracts were subjected to a series of chromatographic separations on silica gel for isolation of individual compounds. Isolated compounds were tested for their cytotoxicity with respect to model cancer cell lines using the conventional MTT assays. Results: Total of 15 individual compounds: coumarins scopoletin 2, bergapten 3, isoimperatorin 4, marmesin 5, (+)-decursinol 9, (?)-praeruptorin B 10, oxypeucedanin hydrate 11, chromones: hamaudol 6, cimifugin 7, 5-О-methylvisamminol 8, chromone glycosides: prim-O-glucosylcimifugin 12, sec-O-glucosylhamaudol 13, 4′-O-β-D-glucopyranosyl-5-О-methylvisamminol 14, 4′-O-β-D-glucopyranosylvisamminol (15) and also polyyne compound panaxinol 1 were isolated and characterized. The structure of dihydropyranocoumarin 10 was confirmed by X-ray diffraction analyses. HPLC-UV method was used for determination of the content of most abundant chromones 7, 12 and 14 in the roots of S. divaricata, collected in Mongolia. Compounds 3–11 and 13, 14 were evaluated for their cytotoxicity with respect to model cancer cell lines. All the compounds were non-toxic in the hemolysis test. Conclusion: This report about the phytochemical profiles of S. divaricata growing in Mongolia and Buryatia led to the identification of 14 compounds including coumarins and chromones. The available coumarins and chromones may serve as new leads for the discovery of anticancer drugs.
DIHYDROPYRANOCOUMARINS FROM ROOTS OF PEUCEDANUM JAPONICUM
Ikeshiro, Yasumasa,Mase, Izumi,Tomita, Yutaka
, p. 4303 - 4306 (1992)
Two new angular-type dihydropyranocoumarins, peujaponisin and (-)-visnadin, were isolated from the roots of Peucedanum japonicum and the structures determined as 3'(S)-senecioyloxy-4'(S)-isovaleryloxy-3',4'-dihydroseselin and 3'(S)-2-methylbutyryloxy-4'(S
Coumarins from the fruits of Seseli devenyense
Widelski, Jarek,Melliou, Eleni,Fokialakis, Nikolas,Magiatis, Prokopios,Glowniak, Kazimierz,Chinou, Ioanna
, p. 1637 - 1641 (2005)
Eight new coumarins were isolated from the fruits of Seseli devenyense Simonkai. Their structures were established from NMR and mass data and their absolute configurations from chemical degradation correlation reactions. The new structures are the decanoic and dodecanoic esters of (+)-lomatin (3, 4), the decanoates of (+)-cis-khellactone at positions 4′ (5) and 3′ (6) as well as the 2′S epimer of 8-(2,3-dihydroxy-3-methylbutyl)-7- hydroxychromen-2-one (7) named devenyol, its two O-monoglucosides at positions 3′ and 7 named devenyosides A (8) and B (9), and the corresponding 3′- and 7-O-diglucoside named devenyoside C (10). This plant is an interesting example of stereochemical diversity based on biodiversity given that other members of the Apiaceae family produce exclusively the 2′R epimers of compounds 7-9.
Plant Coumarins. 3. (-temp)-PTeryxin from Peucedanum terebinthaceum
Ganbaatar,Gantumur,Osadchii,Shul'ts,Shakirov,Tolstikov
, p. 578 - 581 (2008)
The potentially medically valuable pyranocoumarin (+)-pteryxin was isolated for the first time from Peucedanum terebinthaceum Fischer et Turcz. The structure of (+)-pteryxin was rigorously proved using mass spectrometry, NMR, IR, and UV spectroscopy and c
