title: Novel urushiols with human immunodeficiency virus type 1 reverse transcriptase inhibitory activity from the leaves of Rhus verniciflua.
abstract: Two novel urushiols, 1 and 2, and two known urushiols, 3 and 4, were isolated from the leaves of Rhus verniciflua and were examined for their human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) inhibitory activity. The novel urushiols were found to be 1,2-dihydroxyphenyl-3-[7'(E),9'(Z),11'(Z)-pentadecatrienyl]-14'-ol (1) and 1,2-dihydroxyphenyl-3-[8'(Z),10'(E),12'(E)-pentadecatrienyl]-14'-ol (2) by spectroscopic analyses. The absolute configuration at C-14' in 1 and 2 was determined to be a racemic mixture of (R) and (S) isomers by ozonolysis. Compound 2 (IC50: 12.6 µM) showed the highest HIV-1 RT inhibitory activity among the four urushiols, being 2.5-fold more potent than the positive control, adriamycin (IC50: 31.9 µM). Although the known urushiols were isolated from the sap and leaves of R. verniciflua, 1 was exclusively present in the leaves, and higher amounts of 2 were found in the leaves than in the sap. Present findings indicate that the leaves of R. verniciflua represent a new biological resource from which novel and known urushiols may be prepared, and the possible use of novel urushiols as bioactive products.
authors.affiliation: Food Material Center for R and D, Kibun Foods Inc., 86 Yanokuchi, Inagi, Tokyo, 2060812, Japan, kazunari_kadokura@kibun.co.jp.
authors.forename: Kazunari
authors.initials: K
authors.lastname: Kadokura
authors.forename: Kohei
authors.initials: K
authors.lastname: Suruga
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Tomita
authors.forename: Wataru
authors.initials: W
authors.lastname: Hiruma
authors.forename: Motoyuki
authors.initials: M
authors.lastname: Yamada
authors.forename: Akio
authors.initials: A
authors.lastname: Kobayashi
authors.forename: Akira
authors.initials: A
authors.lastname: Takatsuki
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Nishio
authors.forename: Tadatake
authors.initials: T
authors.lastname: Oku
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Sekino
mesh_terms: D002396:Catechols / Q000737:chemistry* / Q000494:pharmacology*; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry; D029045:Rhus / Q000737:chemistry*
chemical_list: D002396:Catechols; D010936:Plant Extracts; C003747:urushiol; C514824:reverse transcriptase, Human immunodeficiency virus 1; D054303:HIV Reverse Transcriptase