Structure and absolute configuration of triterpene dimers from Maytenus scutioides

Plant use in the medicinal practices known as “strict diets” in Chazuta valley (Peruvian Amazon)

“…macrocarpa contains dammarane triterpenes (Chavez et al, 1997). This class of compounds has shown, in general, antinflammatory, analgesic (Akihisa et al, 1997;Ozaki et al, 2000;Rouf et al, 2001;Yasukawa et al, 2000) antimicrobial (Gonzalez et al, 1996), and antiviral activities (Inada et al, 1993;Kaij-A-Kamb et al, 1992;Madureira et al, 2003;Zhang et al, 2003).…”

Cheiloclines A–I. First examples of octacyclic sesquiterpene-triterpene hetero-Diels–Alder adducts

“…It has been postulated that this type of compounds is biosynthesized by hetero-Diels-Alder reactions, which was supported by the synthesis of one triterpene dimer carried out in our laboratory. 11 In this paper we report the isolation from Cheiloclinium hippocratioides (Celastraceae) of nine octacyclic hetero DielsAlder adducts (1-9) with a novel structure based on two monomer units from guaiane and D:A-friedo-nor-oleanane sesqui/triterpene skeletons. All adducts were found to be composed of one aromatic triterpene unit derived from pristimerin and one sesquiterpene unit derived from guaia-1(5),3(4),11(13)-triene, being the first examples of this kind of adducts isolated from natural sources.…”

“…8 In this sense, it has been recently reported the 1.70 Å resolution crystal structure of the natural Diels-Alderase, fungal macrophomate synthase (MPS), in complex with pyruvate. 9 Itokawa and collaborators and our group have isolated triterpene dimers [10][11][12][13][14][15][16] and triterpene trimers 17 from Celastraceae plants. It has been postulated that this type of compounds is biosynthesized by hetero-Diels-Alder reactions, which was supported by the synthesis of one triterpene dimer carried out in our laboratory.…”

Triterpenes (C30)

“…10.18. The other triterpene dimers are 7,8-dihydroscutionin-αB, 7,8-dihydroscutionine-βB, scutidin-αA, the structures and absolute configurations of which have been elucidated [64]. González and his group [65] and Itokawa and his collaborators [66] have isolated more triterpene dimers and González et al [67] have also reported triterpene trimers from Celastraceae plants.…”

“…Triterpene dimers and triterpene trimers are also known to occur in nature. Seven dimeric compounds have been isolated [64] from the root bark of the subtropical shrub Maytenus scutioides (Celastraceae), distributed in North of Argentina and South of Paraguay and Bolivia. They were found to be composed of one quinoidtype triterpene, derived from co-occurring pristimerin or 7,8-dihydropristimerin and one aromatic triterpene, derived from pristimerin or 6-hydroxypristimerin linked together by two ether linkages between the two A rings.…”