Arctigenin

Separation of chloroformic fraction of raw material by a polyamide sorbent with the following individual fractions elution and crystallization allowed to study lignans of burdock with IR-, mass- and NMR spectroscopy. In result, aixtiin, arctigenin, lappaols were identified. Sepai ation of essential oils was provided by the method two of State Phaiiuacopeias of the Ukraine. Essential oils were analyzed by the means of gas chromatography. 

Apomorphine 169, 170 Aporphine alkaloids 151, 152 Apparicine 16, 147 Arborine 105, 106 Arctigenin 39 Aren tin 41, 47 Arecaidine 86... 

Lappa communis Coss et Germ. L. edulis Sieb. L. major Gaerth. L. minor DC (Syn. Arctium lappa) Niu Bang, Zong Shi (seed, root) Seed arctin, arctigenin, gobosterin, essential oil, fatty oil. Root Inulin, lappine, lappatin, resin, essential oil, tannins.49 Diuretic, antipyretic, expectorant, antiphlogistic in throat infections, pneumonia, scarlet fever, measles, smallpox, syphilis. 

Arctium lappa L. China Arctin, arctigenin, matai-resinol, sesquilignins, stereoisomer.1,9 For dermatitis, tumors, antibacterial, relieve sore throat. 

Eich E, Pertz H, Kaloga M, Schulz J, Fesen MR, Mazumder A, Pommier Y. (-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase. J Med Chem 1996 ... 

As a result of these developments, Doyle and co-workers have synthesized several lignans, among which are (-)-enterolactone, (+)-isodeoxypodophyllotoxin, and (-)-arctigenin [126], Selected examples have been reported of impressive results from C-H insertion reactions of diazoacetamides that result in [3-lactams. For example, [3-lactam formation was the sole C-H insertion process to occur with 51 (Eq. 5.33) [128] or other seven-membered ring diazoacetamides. 

The dibenzylbutyrolactone lignan matairesinol was also found to be an anti-HIV agent [110], although the sample used in this bioassay was not isolated from a Taxus species. Another dibenzylbutyrolactone lignan, arctigenin, as well as its unsubstituted benzyl derivative exhibited anti-HIV replication activity, with EC50 values of 0.16 and 22 ig/mL and therapeutic index values of 5 and 9.1, respectively [111]. 

Sun, W. 1992. Determination of arctiin and arctigenin in Frustus arctii by reverse phase HPLC. Acta Pharm. Sin. 27(7), 549. 

Arctigenin Ipomoea cairica (Convolvulaceae) HIV-1 RT [metabolites inhibit... 

Foldeak S., Ilcgyes, P., and Dombi, G., Extraction of arctigenin and synthesis of its amino derivatives. Acta Phys. Chem.. 20,459, 1974 Chent. Abstr. 83. 58560, 1975. 

As in the case of antibiotics, this group of substrates may be readily functionalized by aminomethylation due to the presence of phenolic rings, which permit preparation of pnxlucts with basic properties. Flavonoids such as rutin " and silymarin pos.sess two hydroxylated aromatic nuclei, both of which may undergo aminomethylation, thus preventing the clear detection of the site of attack however, the products obtained usually maintain the pharmacological activity of the initial material. In the case of arctigenin, aminomethylation can lake place only in the ortho position with respect to the hydroxy group, and chrysin (487, Fig. 180) reacts at position 8. 

Arctigenin, a natural product from Arctium lappa (L.), inhibits Ap production by suppressing p-site APP cleavage enzyme 1 expression and promotes Ap clearance by enhancing autophagy through AKT/mTOR signaling inhibition and AMPK/Raptor... 

Zhu Z, Yan J, Jiang W, Yao XG, Chen J, Chen L et al (2013) Arctigenin effectively ameliorates memory impairment in Alzheimer s disease model mice targeting both P-amyloid production and clearance. J Neurosci 33 13138-13149... 

Arctigenin (472), prepared from 3,4-dimethoxybenzaldehyde, was submitted to PhI(OCOCF3)2-promoted oxidation in trifluoroethanol (TFE) (room temp., 24 h) to afford spirodienone 473 and a mixture of two cyclooctadienes (474 and 475) in 13 and 14% yields, respectively. When the reaction was repeated in hexafluoroisopropanol for 3.5 h, a 1 1 mixture of stegaue 474 and isostegane 475 was obtained in 26% yield (Scheme 93). Acid-catalyzed rearrangement of 473 with HCIO4 in CHCI3 provided a quantitative... 

Arctigenin (38), (-)-tracheloside (189) and etoposide (VP-16-213, 65) showed a strong cyto-protective effect against human immunodeficiency virus type-l(HIV-l) in vitro, and efficiently inhibited both cellular topoisomerase II activity and the... 

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