Studies on Aristolochia III. Isolation and Biological Evaluation of Constituents of Aristolochia indica Roots for Fertility-Regulating Activity

Abstract

An ethanol extract of Aristolochia indica roots decreased fertility in both rats and hamsters when administered postcoitally (days 1-10 and 1-6, respectively). Petroleum ether (A), CHCl3 (B), and aqueous (C) fractions, tested similarly in rats, were inactive and/or toxic. Partition of fraction B afforded non-acidic (D) and acidic (E) fractions. Savinin (1), isolated from fraction D and not previously reported from the Aristolochiaceae , was inactive when administered postcoitally to rats. Aristolochic acid-I (2), reported previously from A. indica and isolated from fraction E, was inactive when administered postcoitally to rats and toxic when administered postcoitally to hamsters. (12S)-7,12- Secoishwaran -12-ol (3), previously reported from A. indica and isolated from fraction A, did not interrupt pregnancy when administered to mice on day 6 of pregnancy. Four additional compounds, aristolic acid (4) [prepared from aristolochic acid-I (2)], methyl aristolate (5) [prepared by methylating aristolic acid (4)], and cis- and trans-p-coumaric acid (both oblate commercially), were similarly tested in mice and found to be inactive. Aristolic acid (4), and the cis- and trans-p-coumaric acids also were inactive when administered postcoitally (days 1-10) to rats. Seven compounds reported previously from A. indica were also isolated, as were a new naphthoquinone, aristolindiquinone (6) (fraction E), and magnoflorine (fraction C).

Two New Aristolochic Acid Derivatives from the Roots of Aristolochia fangchi and Their Cytotoxicities

“…14,15) One singlet signal at d 6.48 (2H, s) was attributed to methylenedioxyl protons. 11,13) All substituted groups and positions were confirmed by heteronuclear multiple bond connectivity (HMBC) and nuclear Overhauser effect spectroscopy (NOESY) experiments ( These spectral findings confirmed that the hydroxyl group was substituted at C-7. Based on the above evidence, compound 4 was determined as a new constituent, and named Aristolochic Acid F.…”

“…The three known compounds were identified as aristolochic acid A (1), aristolochic acid B (2), and aristolochic acid C (3) by comparison of their spectral data with data reported in the literature [11][12][13][14][15] (Fig. 1).…”

“…The UV absorption of 4 at 218, 256, 295, 351, and 371 nm showed it was a phenanthro type derivative. 11,15) Its IR spectrum showed absorption bands due to hydroxyl, nitro, and carboxyl functions at 3438, 1337, 1520, and 1715 cm (Table 1) and 13 C-NMR spectral data (Table 2) Phytochemical investigation of 90% ethanol extracts of the roots of Aristolochia fangchi yielded two new aristolochic acid derivatives named Aristolochic Acid F and Aristolochic Acid G, together with three known compounds. Their structures were elucidated by spectral analysis.…”

“…The UV absorption of 4 at 218, 256, 295, 351, and 371 nm showed it was a phenanthro type derivative. 11,15) Its IR spectrum showed absorption bands due to hydroxyl, nitro, and carboxyl functions at 3438, 1337, 1520, and 1715 cm 14) and a hydroxyl group was believed to be connected at C-7. The remaining 2 one-proton signals at d 7.72 (1H, s) and 8.21 (1H, s) could be ascribed to H-2 and H-9, respectively, due to the anisotropic effect of the carbonyl group at C-1.…”

Safety Pharmacology and Toxicity Study of Herbal Medicines

“…Experiments have shown AA possess carcinogenic, 31 mutagenic, 32 nephrotoxic, 33 cytostatic, 34 and antifertility effects. 35 Study of its acute toxic effects in rodents 36 is given here as an example.…”