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Triterpene Sapogenins with Oleanene Skeleton: Chemotypes and Biological Activities Kamil Jatczak and Grzegorz Grynkiewicz*

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Triterpene Sapogenins with Oleanene Skeleton: Chemotypes and Biological Activities Kamil Jatczak and Grzegorz Grynkiewicz* Vol. 61, No 2/2014 227–243 on-line at: www.actabp.pl Review Triterpene sapogenins with oleanene skeleton: chemotypes and biological activities Kamil Jatczak and Grzegorz Grynkiewicz* Pharmaceutical Research Institute, Warsaw, Poland Critical survey of a selected class of pentacyclic triter- ic transformations: 2,3-oxidosqualene cyclization, which penes — the oleanane family, is presented based on results in formation of such triterpene skeletons as ole- current literature in order to underline their value for anane, ursane, hopane, etc. (Pollier et al., 2013); action medicinal chemistry and drug development potential. of cytochrome type multifunctional oxidases, which are Oleanenes may be considered as a renewable resource responsible for introduction of hydroxyl groups and also of valuable research materials which are structurally di- their subsequent oxidations (Fukushima et al., 2011); ac- verse, inherently biocompatible and have built-in affin- tion of acylases and glycosyltransferases, which complete ity for many categories of functional proteins. Although the chain of events leading to saponins which are the availability of particular compounds from natural sourc- end products of chemical defence and allelopathic chem- es may be very low, synthetic methods elaborated by icals mediating interspecies interactions (Geisler et al., generations of chemists, secure a way to obtaining desir- 2013). Historically, biological activity of saponins attract- able structures from commercial starting materials. ed more attention than their respective triterpene agly- cons (genins) (Hostettmann & Marston, 2005; Negi et al., Key words: pentacyclic triterpenes, oleanane derivatives, oleanolic 2013). More recently, it has been realized that various acid exploratory chemistry and experimental pharmacology natural triterpenes exhibit pleiotropic activity towards Received: 18 February, 2014; revised: 16 April, 2014; accepted: plethora of molecular targets, generating much interest 29 April, 2014; available on-line: 11 June, 2014 of researchers and considerable potential for pharmaco- logical studies (Sun et al., 2006; Zwenger & Basu, 2008; Sheng & Sun, 2011). Yet, in general perception signif- icance of triterpenes as prospective new drug leads is rather underscored. In order to explore and discuss their INTRODUCTION potential in some methodical way, we decided to present some structural, chemical and biological activity research Pentacyclic triterpenes (PTT) constitute a large class data, for a restricted group of compounds, representing of natural products widespread in the Plant Kingdom various chemotypes placed within strictly defined molec- (Azimova, 2013; Dinda et al., 2010). Extraordinary struc- ular framework of a particular type of triterpene skeleton tural diversity in this category of secondary metabolites originating from typical biogenetic pathway. Our choice has fascinated chemists and biologists alike for well of β-amyrin (BAR, 3) sub-class of pentacyclic triterpenes over half a century. Chemical concept of the biogene- stems from their considerable widespread occurrence tic “isoprene rule” as a basis of terpenoid assembly in and relatively good availability of pure chemical entities, plants, advanced in a seminal paper by Swiss chemists which were studied as biologically active plant constit- (Eschenmoser et al., 1955) has been recapitulated upon uents but also gave rise to several generations of semi- the publication 50-thieth anniversary, with appropriate synthetic derivatives bearing functionalities not found commentaries, outlining the substantial field of natural in Nature. Obviously, such choice is artificial in view of product research related to biomimetic carbocyclization well known diversity of the squalene cyclization process- which leads to triterpenoids and steroids (Eshenmoser es, which involves variety of OSC enzymes of different & Arigoni, 2005). Parallel effort of biosynthetic studies selectivity (Augustin et al., 2011). Although many plants afforded definite conclusion, that despite many possible contain terpenoid secondary metabolites which result pathways executed by highly specific squalene cyclases from various parallel biogenetic pathways, this review (OSC), a given PTT comprising five carbocycles and purposely focuses on only one selected type of terpenoid eight centers of chirality is assembled in a single enzy- framework (scaffold), in order to seek and discuss pos- matic step from common linear precursor (Lodeiro et al., 2007; Pollier et al., 2013). Although knowledge of *e-mail: [email protected] biosynthesis, including active sites topology of specific Abbreviations: API, active pharmaceutical ingredient; BAR, squalene cyclases, and structures of terpenoids in plants β-amyrin; BAC, β-amyrin cyclase; BAS, β-amyrin synthase; CYP, cy- tochrome P450, heme-related monooxidase; COX-2, cyclooxyge- is presently well established, their biological functions nase type 2; CDDO, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic are not entirely understood. Nevertheless, it is general- acid; CDDOMe, bardoxolone, 2-cyano-3,12-dioxooleana-1,9(11)-di- ly recognized that biogenesis of terpenes as such and en-28-oic acid methyl ester; DMAP, 4-dimethylaminopyridine; EDCI, also in their glycosylated forms (e.g. as saponins) must 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; GTS, glycosyltransferase; HCSE, horse chestnut seed extract; HCV, offer some advantage of environmental nature to the hepatitis C virus; IKKβ, subunit of IkappaB kinase complex; iNOS, plant host, which tends to be evolutionary favored and inducible nitrogen oxide synthase; NFκB, nuclear factor kappa B; genetically preserved. The present view of triterpene bio- Nrf2, nuclear protein activating Antioxidant Response Element; synthesis constitute of three distinct groups of enzymat- OSC, oxidosqualene cyclase; PTT, pentacyclic triterpenes; SAR, structure-activity relationship 228 K. Jatczak and G. Grynkiewicz 2014 sible differences in biological activities between various products of enzymatic oxidations and secondary derivat- izations. Triterpenes are abundant in many dicotyledon- ous plants (over 80 families are involved; there are over 20 000 of individual triterpenoid natural products), main- ly in glycosylated form, as mono- and bis-desmosidic sa- ponins (Azimova 2013; Dinda et al., 2010) and β-amyrin can be considered the simplest, most popular aglycone of the class and a model scaffold structure for triterpene based natural and semisynthetic pharmacophores. Since 1985, newly isolated triterpenes are regularly covered in Figure 1. Conventional representations of β-amyrin structure annual review initiated by the Royal Chemical Society (equivalent). (Hill & Connolly, 2013 and earlier annual reports). tional names usually do not reveal essential structural features; quite frequently a single PTT has several syn- HYDROXYLATED PENTACYCLIC TRITERPENES (PTT) onymic names, which can be misleading. Neutral BAR DERIVED FROM OLEANYL CATION derivatives usually feature a double bond (relatively un- reactive; typical olean-12-enes are reported to resist cata- (S)-2,3-Epoxysqualene, which results from biogene- lytic hydrogenation and exhibit atypical reactivity towards tic condensation of isoprenoid phosphates, undergoes oxidative reagents), hydroxyl groups, primary and sec- in Nature a sequence of enzymatic transformations, ondary, of different reactivity. Stereochemistry of sec- producing carbocationic PTT intermediates (Xue et al., ondary hydroxyl groups reflects specificity of particular 2012), which can undergo Wagner-Merwein type rear- hydroxylases, which are P450 cytochrome type enzymes rangements but are also susceptible to a spontaneous (Geisler et al., 2013) characteristic for a given plant spe- stabilization with concomitant formation of an olefinic cies. Typically hydroxylated positions of oleanene skele- bond as illustrated on the Scheme 1. Condensed penta- ton, such as: 2, 3, 6, 11, 15, 16, 21 and 22 can carry cyclic framework formed, features characteristic pattern hydroxyl groups of either α- or β-configuration. Oxo of substitution with residual 3-β hydroxyl group, double functions are occasionally encountered within BAR an- bond Δ-12,13; eight methyl groups forming two geminal alogues, both as aldehyde or keto group. It has to be arrangements (at C-4 and C-20), trans- junction of the mentioned that “epoxy” prefix is applied in convention- cyclohexane ABCD rings and cis-fused rings DE. The al nomenclature of PTT in two different meanings: as corresponding hydrocarbon is known as olean-12-ene, vicinal and non-vicinal anhydro-diol arrangement, which which is a convenient entry for semi-systematic nomen- can be misleading. Acidic function is usually (but not clature for natural and synthetic derivatives. This molec- always) revealed in the trivial name of a natural triter- ular arrangement, presented on Fig. 1 with some stereo- pene. Frequently encountered ending: “genin” testifies chemical details elucidated from X-ray structure determi- to origin of newly identified specimen at the time of its nation (Maartmann-Moe et al., 1987; Froelich & Gzella, discovery as an aglycone of saponins. Apart from ven- 2010) and key carbon atom numbering, is characterized erable attempts at total synthesis, chemistry of simpler by relatively high thermodynamic stability as evidenced PTT have not been particularly developed, thus relatively by conformational energetics study conducted by EJ Co- succinct descriptions of some hydroxylated oleanenes
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