Xanthoxylum

There are several alkaloids in the structure of which are both quinazoline and indole nuclei. Evodiamine (1001 R = H) and rutaecarpine (1002) were both isolated from the seeds of Evodia rutaecarpa about 1916 and synthesized in 1927. They were found subsequently to occur also in Xanthoxylum rhetsa, which in addition yielded rhetsinine (1001 R = OH) (59T(7)257). The plant Hortia arborea afforded two more related alkaloids, hor-tiacine and hortiamine, each characterized by a methoxy group in the benzene ring of the indole portion (60JA5187). 

The K-R reaction has also been useful for structural confirmation of natural products such as tambulin (71), a flavonoid isolated from the seeds of Xanthoxylum acanthopodium In the critical reaction (O-ethoxyphloroacetophenone (72) was allowed to react with anisic anhydride (38b) in the presence of sodium anisate (73) at 170 C to deliver flavone 74 in 65% yield. Flavone 74 was then converted after multiple steps to diethyl ether 75 which corresponded to the diethyl ether of tambulin (71). 

In the course of detailed studies on the chemical constituents of rutaceous plants, genus Xanthoxylum, known to contain the antitumor benzophen-anthridine alkaloids, Ishii et al. (167-173) have isolated four seco amide alkaloids arnottianamide (206), iwamide (207), integriamide (208), and isoarnottianamide (209). Sharma et al. (174) have also found arnottianamide (206) in Toddia Asiatica. 

Xanthoxylum piperitum DC Chuan Jian (fruit) Essential oils, phellandrene, limonene, citronellol, geraniol, and sanshol in fruit sesquiterpene lactones-xanthatin, limonene in seed saponin, citral, citronellol, geraniol in leaf berberine, xanthoxylinin root.49-430 Diaphoretic properties, prophylactic against hydrophobia, used as a diuretic, stomachic, carminative, stimulant, resolving inflammatory swellings, it is sedative. 

Tomita, M. and H. Ishii. 1958. Studies on the alkaloids of rutaceous plants. IV. Alkaloids of Xanthoxylum ailanthoides Sieb. Zucc. [Fagara ailanthoides (Sieb. Zucc.) Engl.]. J. Pharm. Soc. Jpn. 78 1441-1443. 

T. thunbergii, Xanthoxylum piperitum, Zanthoxylum schinifolium Anethum graveoleus, Angelica amurensis, A. anomala, A. dahurica, A. pubescens, Dictamnus albus,... 

M. liliflora, M. purpurea, Rosa rugosa, Xanthoxylum piperitum, Thymus vulgaris, Zingiber officinale Cunninghamia lanceolata... 

Daucus carota, Elettaria cardamomum, Juniperus rigida, Plumeria rubra, Vitex nequndo, Xanthoxylum piperitum, Xanthoxylum schinifolium... 

Geraniol Chenopotium ambrosiodes, Citrus reticulata, Coriandrum sativum, Cymbopogon citratus, Daucus carota, Elettaria cardamomum, Myristica fragrans, Plumeria rubra, Rosa rugosa, Thymus vulgaris, Vitex nequndo, Xanthoxylum piperitum, Zanthaxylum bungeanum X m 2... 

Aucklandia costus, A. lappa, Cinnamomum aromaticum, C. cassia, Coriandrum sativum, Saussurea japonica, S. lappa, Valeriana alternifolia, V amurensis, V. fauriei, V subbipinnatifolia, Xanthoxylum piperitum, Zanthoxylum schinifolium, Zingiber officinale Cunninghamia lanceolata Phellodendmn amurense, P. chinensis Angelica amurensis, A. anomala, A. dahurica Sphenomeris chusana... 

Sesquiterpene Alpinia officinarum, Artemisia annua, A. apiacea, Curcuma longa, Cyperus rotundus, Dryobalanops aromatica, D. camphora, Ginkgo biloba, Hedychium coronarium, Jasminum samba, Melaleuca leucadendra, Nardostachys jatamansi, Xanthoxylum piperitum... 

Zanthoxylum schinifolium Sepium sebiferum, S. discolor Xanthoxylum piperitum... 

Argemone mexicana, Bocconia spp., Chelidonium majus [root], Eschscholtzia californica [cell culture] (Papaveraceae) ffinthoxylum zanthoxyloides (Fagara xanthoxylum) (Rutaceae) ffinthoxylum americanum, z(. spp. (Rutaceae)... 

Botanical origin Xanthoxylum americanum Xanthoxylum Clava-Herculis Citrus Aurantium Bergamia Citrus Aurantium... 

Terihanine (8) was originally isolated as its 6-oxoderivative named oxyterihanine from Zcmthoxylum nitidum DC. (synonym Xanthoxylum nitidum (Roxb.) DC. Japanese name, teriha-zan o) [53], Later Ih-Sheng Chen isolated terihanine from Taiwan Z nitidum as a new quaternary alkaloid (private communication from Professor Hisashi Ishii, Chiba University, Japan). The structures of terihanine and oxyterihanine have been established by syntheris [54,55]. 

Ishikawa, T, Seki, M., Nishigaya, K., Miura, Y., Seki, H., Chen, I.-S., and Ishii, H. (1995) Studies on the chemical constituents of Xanthoxylum nitidum (Roxb.) D. C. (Fagara nitida Roxb.). III. The chemical constituents of the wood. Chem. Pharm. Bull. 43(11), 2014-2018. 

Tincture of Prickly-aah Berries. Macerate 8 ounces prickly-osh berries (Xanthoxylum) for 14 days in 2 pints diluted alcohol or, displace 2 ounces of tincture by percolation. This tincture possesses all the virtues of the berries. In cholera, the dose is from 4 to 1 fluid ounce, repeated as often as required in ordinary cases fri)m 1 to 4 fluid drachms, given in water. Am. Dis.)... 

Xanthoxylum amottianum Unspecified NN-dimethyl tetrahydroisoquinolinium salt 83... 

New sources for known alkaloids are (+ )-reticuline, Litsea xylanica (Laura-ceae) and Hernandia jamaicensis (Hernandiaceae) (see ref. 87) coclaurine, Sarcopetalum harveyanum Muell. (Menispermaceae) (— )-armepavine, Euony-mus europaeus (Celastraceae) (+ )-armepavine N-metho-salt, Xanthoxylum inerme Koidz. (Fagara boninensis Koidz.) (Rutaceae). ... 

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