Aristolochia Aristolochic acids

A. indica L. Indian Aristolochia, also known as Indian birthwort, ishvara (Sanskrit), or adagam (Tamil), is a bitter climber native to India. The medicinal material consists of the rhizome, which is to resolve inflammation (India), counteract insect poison, and as an antipyretic (Philippines and Vietnam). The rhizome contains aristolochic acid, which inhibits in vitro and dose-dependent phospholipid hydrolysis by the human synovial fluid phospholipase A2, snake venom phospholipase A2, porcine pancreatic phospholipase A2, and human platelet phospholipase A2 (2). 

Wu TS, Leu YL, Chan YY. Aristofolin-A, a denitro-aristolochic acid glycoside and other constituents from aristolochia kaempferi. Phytochemistry 1998 49 2509-2510. 

Tree sparrow Passer Swallowtail butterfly Aristolochic acids (from Aristolochia Nishida and... 

Aristolochic acid derivatives have been found only among plants of the family Aristolochiaceae (Aristolochia spp. and Asarum canadense var. reflexum (34)) and in Bragantia wallichii (35,36). In all derivatives, substitution of nitro group is present at C-10, the carboxy group is present at C-1, and a methylenedioxy is substituted at C-3 and C-4 only. This general structure will be very interesting in biosynthesis and plant biochemistry. 

The IR spectra are useful for detecting functional groups of Aristolochia alkaloids. Aristolochic acids show two characteristic bands at 1550 and 1350 cm due to the absorption of nitro group, and the carboxy OH group appears at 3000-2500 cm as a broad continuous absorption. Hydroxy derivatives of aristolochic acids or aristolactams show OH and NH absorptions at 3300-3500 and 3200-3400 cm The carboxy or lactam carbonyl is present at 1690 cm i. In general, the aromatic ring system shows stretches at 1625-1575 and 1525-1475 cm 1 as usual, and observation of the 900-700 cm region is often used for analysis of substitution type in aromatic derivatives 28). 

The mass spectra of Aristolochia N-containing compounds were first reported by Pailer et al., who studied the electron impact-induced fragmentation of the esters of aristolochic acids. They found that the nitro radical is very easily split off from the molecular ion, giving the base peak (M — 46) +, and then the CH3, CO, etc. were removed. Pailer etal. concluded the fragmentation was as shown in Scheme 3 (26). 

The genus Aristolochia comprises approximately 200 species, many of which have played important roles in folk medicine for treating sore throat, venomous snakebites, wounds, fevers, and tuberculosis. The chemistry and pharmacology of aristolochic acid, the main active principle, was researched by many scientists. Many worthy achievements in the pharmacology of aristolochic acid have been published. 

The roots of Aristolochia indica, commonly known as an Indian birthwort, are reputedly used in Indian folk medicine as an emmenagogue and as an abor-tifacient. Aristolochic acid and its methyl ester, sesquiterpene (12S)-7,12-secoishwaran-12-ol, isolated from this plant, possessed significant antifertility activity in mice (103-105). 

In addition, intraamniotic injection of aristolochic acid I in mid-term pregnant dogs and rats led to termination of pregnancy (106). Later, Che et al. reported that four Aristolochia alkaloids, aristolochic acid I and its methyl ester, aristolic acid, and (125)-7,12-secoish-waran-12-ol were ineffective in antifertility tests, when administered to mice, hamsters, or rats (707). 

Aristolochia species (Aristolochiaceae), stores the constituents of the host plant (Aristolochia clematis), aristolochic acid I (143 see Section in body... 

Aristolochia contorta Bunge. A. kaempferi Willd. A. longa Thunb. A. recurvilabra Hance Ma Dou Ling (stem) Aristolochic acid A, aristolochic acid D, aristoloside, magnoflorine, oleanolic acid, beta-sitosterol, hederagenin.48 This herb is toxic. Treat pulmonary disorders, antitussive, an expectorant in asthma and bronchitis. 

Aristolochia debilis Sieb. et Zucc. Qing Mu Xiang (root) Aristolochic acid, debilic acid, magnoflorine, dibilone, cyclanoline, aristolone.33 Antihypertensive, lower heart rate and myocardial contractility, vasodilatation. 

Aristolochia shimadai Hayata Taiwan Ma Dou Ling (stem) Aristolochic acid.54 Relieve pain, a diuretic, externally for snakebite. 

China Aristolochia manshuriensis Kom. Aristolochic acid, saponin akebin, triterpenoids.2533 Diuretic, antibacterial. 

N.A. Aristolochia clematitis L. A. serpentaria L. Aristolochic acids, volatile oil, tannins.99 Treat wounds, sores, snakebite, taken after childbirth to prevent infection, heal ulcers, treat asthma and bronchitis. 

Aristolochic acid (60), aristolochic acid-D (61), and aristolactam-/3-D-glucoside (62), reported by earlier workers, have been re-isolated from Aristolochia indica (Aristolochiaceae). Of greater interest, five phenanthrene derivatives, (63)—(67), were also found in the plant. Compound (65) was labelled aristolamide, (66) is aristolinic acid methyl ester, and (67) is methyl aristolochate.71... 

Aristolochic acid (phenanthrene) Aristolochia clematis, A. debilis, A.indica, A. longa, Asarum canadense (Aristolochiaceae) MLCK, PKA, PKC... 

The larvae of the blue butterfly (Plebejus icaroides) feed only on lupines, rich in alkaloids. As far as we know, the larvae do not sequester or store the dietary alkaloids (506). Helopeltis feeds on Cinchona bark, which is rich in cinchonine-like alkaloids it stores and uses them for its own defense (506). Larvae of the butterflies Pachlioptera aristolochiae, Zerynthia po-tyxena, Ornithoptera priamus, and Battus philenor live on Aristolochia plants and were shown to take up and sequester aristolochic acid, a carcinogenic alkaloid discussed earlier, as an effective defense compound (4,28,236). 

In the study of the patients with kidney cancer associated with the use of aristolochia, samples of kidney tissue were taken from patients. When analysed these were found to contain aristolochic acid, a known constituent of the herb. Molecules related to aristolochic acid were found bound to DNA from aU the kidney samples analysed. When molecules of a chemical become bound to DNA, dysfunction of the molecule can result in various ways. The binding to DNA can lead to mutations or other disturbances in DNA function which underlie cancer, such as switching on cancer genes or oncogenes. Many carcinogens (or their active metabolites) have been found to bind to DNA and this is believed to be part of the process by which chemicals cause cancer. 

Plants belonging to the genns of Aristolochia are rich in aristolochic acids and aristolactams. 

On 11 April 2001 the FDA cautioned consumers to immediately discontinue any dietary supplements or traditional medicines that contain aristolochic acid, including products with Aristolochia, Bragantia, or Asarum listed as their ingredients. 

Like Aristolochia fangchi, A. debilis contains the highly toxic aristolochic acid and was therefore the likely cause of the toxic hepatitis. 

Numerous reports from many countries have confirmed that plants from the Aristolochia species are the cause of the nephropathy (12,13), and the toxic agent has been confirmed to be aristolochic acid (14). 

In Japan two cases of Chinese herb nephropathy were associated with chronic use of Aristolochia manchuriensis (Kan-mokutsu) (24). The diagnosis was confirmed by renal biopsy and the toxic constituents were identified as aristolochic acids I, II, and D. 

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