Boophiline, an antimicrobial sterol amide from the cattle tick boophilus microplus

Abstract

Boophiline (1), a new sterol amide was isolated from the cattle tick Boophilus microplus (Ixodidae). The structure was assigned as N‐[3‐(sulfooxy)‐25ξcholest‐5‐en‐26‐oyl]‐L‐isoleucine by detailed 2D NMR investigations in conjunction with FAB mass spectrometry and acidic hydrolyses. Complete assignment of the diastereotopic methylene protons of the ring system could be deduced from the NMR data. In agar dilution assays, 1 exhibited antifungal properties against Cladosporium cucumerinum and antibacterial activity against Bacillus subtilis and Escherichia coli.

Two New Phenolic Amides from the Seeds of Pharbitis nil

“…14) These data indicated that the side chain of 1 is threo-2,3-dihydroxyputrescine (threo-1,4-diamino-2,3-butanediol), NMR data of which were in agreement with those of related synthetic compounds. 14) The absolute configuration of the side chain of 1 was confirmed by acidic hydrolysis 16) that afforded threo-1,4-diamino-2,3butanediol (1b). 14) In order to identify its absolute configuration, 1b was converted to 2,2-dimethyl-4,5-bis(aminomethyl)-1,3-dioxolane (1c) by treatment with 2,2-dimethoxypropane and p-toluenesulfonic acid (PTSA) in MeOH (see Chart 2), 14,17) which was identical to (4S,5S)-2,2-dimethyl-4,5bis(aminomethyl)-1,3-dioxolane.…”

Concise synthesis of (25S)-Δ4-dafachronic acid and desulfated boophiline enabled by photoinduced decarboxylative allylation and asymmetric hydrogenation

“…Boophiline is an antimicrobial sterol amide from the cattle tick Boophilus microplus , which inhibits the expression of fliC (flagellin) and cdrA (biofilm scaffold), whose products are necessary for biofilm formation in Pseudomonas aeruginosa . 3 Despite interest in its bioactivity, the configuration of the C-25 chiral center has not yet been assigned (Scheme 1a).…”

A Nature-Inspired Design Yields a New Class of Steroids Against Trypanosomatids

“…A steroid molecule isolated from the eggshell of the tick Rhipicephalus microplus , HIT1 ( N -(3-sulfoxy-25-cholest-5-en-26-oil)- L -isoleucine) was identified as an antimicrobial agent. This compound is a cholesterol sulfate attached to a residue of L-isoleucine via an amide bond (Figure 1) [9]. HIT2 (cholest-4,20,24-trien-3-one), a cholesterol derivative extracted from Pentalinon andrieuxii roots exhibited potent activity against Leishmania mexicana promastigote and amastigote forms.…”

“…HIT2 (cholest-4,20,24-trien-3-one), a cholesterol derivative extracted from Pentalinon andrieuxii roots exhibited potent activity against Leishmania mexicana promastigote and amastigote forms. In addition, a similar compound from Trametes versicolor was characterized with anti-Leishmania activity with an IC 50 in L. mexicana amastigotes of 15 µM [10,11] Furthermore, steroid molecules similar to the synthetic HIT3 (Figure 1) were described with antibacterial, antifungal, antiparasitic, and anticarcinogenic activity [9,12,13,14]. These compounds are less toxic to mammalian cells than nitroaromatic compounds used as antiparasitic drugs.…”