Anti-AIDS Agents, 4. Tripterifordin, a Novel Anti-HIV Principle from Tripterygium wilfordii: Isolation and Structural Elucidation

Abstract

A new kaurane-type diterpene lactone, tripterifordin [1], has been isolated from the roots of Tripterygium wilfordii. The structure of 1 was elucidated by spectroscopic methods, including the concerted application of a number of 2D nmr techniques that involved the 1H-1H COSY, heteronucleus-detected variants of the heteronuclear chemical shift correlation (HETCOR), phase-sensitive NOESY, and long-range HETCOR. Compound 1 shows anti-HIV replication activity in H9 lymphocyte cells with an EC50 of 1 microgram/ml.

Enzyme‐Catalysed Transformations of ent‐Kaurane Diterpenoids

“…Apart from the same shifts observed for compound 12, the 1 H NMR spectra of compounds 13 and 14 showed additional upfield shifts for Hs-19 (δ = 3.64, d) and for H-2 (δ = 3.97, dddd). The shifts observed in the 13 C NMR spectra of compounds 13 and 14 (with respect to compound 15) were in perfect agreement with the proposed structure.…”

“…The 1 H NMR spectrum of compound 12 showed an upfield shift of H-15 (δ = 3.83, br. s) and although the chemical shift of C-15 was not changed in the 13 C NMR spectrum, an usual downfield shift (β effect) was observed for C-16 (δ = 160.0). Apart from the same shifts observed for compound 12, the 1 H NMR spectra of compounds 13 and 14 showed additional upfield shifts for Hs-19 (δ = 3.64, d) and for H-2 (δ = 3.97, dddd).…”

“…The acylating agent (0.25 mL) and an amount equiva- Table 8. 13 C NMR spectroscopic data of compounds 8, 9 and 11-17.…”

“…[34] 1 H NMR (CDCl 3 , 500 MHz): see Table 5. 13 C NMR (CDCl 3 , 62.7 MHz): see Table 7. 1 H NMR (CDCl 3 , 500 MHz): see Table 5.…”

“…In fact, antimicrobial activity has been reported for kauren-19-oic acid, [2][3][4] kaur-15-en-19-oic acid [5] and foliol (2), [6] the last isolated from some species of Sideritis (Lamiaceae) used in Spanish folk medicine. Some products have shown good cytotoxic, [7][8][9][10][11] anti-HIV, [12,13] hypotensive [14] and antiinflammatory [15,16] activities. Recently we reported on the anti-HIV [17] and the antifeedant [18] activities of linearol (3), a common metabolite of genus Sideritis, [19,20] and of several semisynthetic derivatives.…”