New Caledonia: A ‘ Hot Spot’ for Valuable Chemodiversity : Part 2: Basal Angiosperms and Eudicot Rosids Paul Coulerie, Cyril Poullain To cite this version: Paul Coulerie, Cyril Poullain. New Caledonia: A ‘ Hot Spot’ for Valuable Chemodiversity : Part 2: Basal Angiosperms and Eudicot Rosids. Chemistry and Biodiversity, Wiley, 2016, 13 (1), pp.18 - 36. 10.1002/cbdv.201400389. hal-01937774 HAL Id: hal-01937774 https://hal.umontpellier.fr/hal-01937774 Submitted on 23 Feb 2021 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. NewCaledonia:AHot Spotfor Valuable Chemodiversity Part 2: Basal Angiosperms and Eudicot Rosids by Paul Coulerie*a)b)and Cyril Poullainc)d) a)Institut Agronomique nØo-CalØdonien,Connaissance et AmØlioration des Agrosystmes,BPA5, 98848 Noumea Cedex, New Caledonia b)School of Pharmaceutical Sciences,University of Geneva, 30, Quai Ernest-Ansermet, CH-1211 Geneva 4 (phone: 41-22-3793409; e-mail:[email protected]) þ c)Centre de Recherche de Gif,Institut de Chimie des Substances Naturelles,CNRS,Labex LERMIT,1Avenue de la Terrasse, FR-91198 Gif-sur-YvetteCedex d)Stratoz, 5, Rue de la Baume,FR-75008 Paris Theflora of New Caledonia encompasses more than 3000 plant species and almost80% are endemic. New Caledonia is considered as ahot spot for biodiversity.With the current global loss of biodiversityand the fact that severaldrugs and pesticides becomeobsolete,there is an urgentneed to increasesampling and research on new natural products.Inthis context,wereview the chemical knowledge available on New Caledonian native flora from economicalperspectives.Weexpect that abetter knowledgeofthe economic potential of plant chemistry will encourage the plantation of native plants for the development of a sustainable economy which will participate in the conservation of biodiversity.Inthe second part of this review,wefocus on the results exposed in 60 scientific articlesand describe the identification of 225 original compounds from basal angiosperms and eudicotrosids.Wediscuss the economic potential of plants and molecules from medicinal and industrial perspectives.This review also highlights severalplants and groups,such as Amborella sp., Piperaceae,orPhyllanthaceae,that are unexplored in New Caledonia despite their high chemical interest. Those plants are consideredtohave priority in future chemical investigations. Introduction. –The importance of biodiversity for the New Caledonia, an archipelago locatedinthe South- discovery of new naturalproducts with economicalvalue West Pacific, is considered as one of the 34 majorhot spots was recognized in 1990 duringameetingofthe Interna- for marine and terrestrial biodiversity [7]. Areview tional Society of Chemical Ecology.Inthe Gçteborg published in 2004 by Laurent and Pietra highlighted the Resolution [1],natural product diversity was recognized pharmacological potential of the Neo-Caledonian marine as atreasuryofimmense value to human kind. This organisms [8], but no review of terrestrial phytochemical resolution also pointed out the currentalarming rate of investigationsisavailable yet. Considering higher plants,it species extinction that is rapidly depleting this treasury, is evaluatedthat New Caledonia contains3270 native with potentially disastrous consequences.This encouraged species,ofwhich 78% are endemictothis territory [9].This the research for valuable naturalproducts for the valor- botanical diversityalso represents ahuge reserve of ization and protectionofbiodiversity [1].From time original naturalcompounds and providesareal interest immemorial, plants have provided awide variety of foods, for green chemistry,pharmacology,cosmetics,and agrono- drugs,cosmetics,fibers, and building materials,and have my.The term hot spot also points out that the biodiversity been fundamental for the development of human societies is highly threatened by human activities and therefore, this [2]. Morerecently,studiesofplant chemistry have led to habitat must be protected [10]. Forthis purpose,the the discovery of many bioactiveproducts,such as for discovery of interesting chemicals from plantswill encour- pharmacological,agronomical, or cosmetic applications. age the reforestation and thus,the protection of biodiver- Thediscovery of aspirin from Filipendula ulmaria or of sity.Investigations of the New Caledonian chemodiversity artemisinin from Artemisia annua are among the most already provided original compounds and/or interesting popularexamples that illustrate the importance of such drugs.Asanexample,methoxyellipticine, an alkaloid research [3][4].Despite the development of combinatorial found in aNew Caledonian Apocynaceae,was used to chemistry and rational drug design,many authors argue develop adrug (Celiptium)used to treat breast and liver that natural products are likely to continuetoprovidethe cancers [11]. best lead-moleculesinthe future [5][6].Inthis context, Despite phytochemicalinterest, plant chemistry re- species-rich areas,such as tropical and subtropical forests, mains largely unexplored in New Caledonia. During the are of particular interest. second part of the 20th century, research mainlyfocused on the discovery of original compounds (e.g.,[12 –14]). Later, the published phytochemicalstudies on New Caledonian biological evaluations started to be systematically associ- angiosperms led to the isolationoforiginal naturalcom- ated to phytochemical analysis (e.g.,[15 –17]).This was the pounds.Also,severalofthem wereshown to be highly beginning of research for economical evaluation, in a bioactive,showing high potential for pharmaceutical ap- purpose of biodiversity conservation. Following the review plications. On the contrary,other economic perspectives of isolated alkaloids from New Caledonian flora by SØvenet for New Caledonian plants, such as cosmetic or agronomic and Pusset [18], we present here abroaderreview of the applications,are poorly documented. As summarized in phytochemistryofNew Caledonianplants and discuss their Fig. 1,wecan also notify that we did not find any economic potential. This review summarizespublications publication related to endemic speciesfrom 60% of the available on SciFinder from 1972, when the first formal angiosperm families. phytochemical studies of endemic plants were published, up to early 2015. Protoangiosperms, Monocots, and Basal Eudicots. – Theknowledge availableinscientific literature about Annonaceae. This family is represented by twelve species the chemistry of New Caledonian native plants is reported (includingelevenendemic species)that are divided into six exhaustively.The data are organized by families of plants, genera. Annonaceae is ahuge tropicalbotanicalfamily that according to the phylogeny proposed by the Angiosperm encompasses more than 2000 species including several Phylogeny Group III (APG III;see Fig. 1)[19].This allows comestible fruits (e.g., Annonasquamosa and Annona acomprehensive chemotaxonomicalorganizationofthis muricata)orplants used for perfumery (e.g., Cananga review.Floricalwas used as taxonomical reference for the odorata and Mkilua fragrans). Annonaceae are known to New Caledonian flora [9]. This review points out the contain polyphenols (includingunusualC-benzylflavo- economic interest of terrestrial biodiversity of New Cale- noids), terpenes, acetogenins,and alkaloids (mainly from donia and highlights new groups which have been poorly the isoquinolinegroup)asshown in many publications studied and may contain novel compounds.This compila- dedicatedtothese plants (e.g.,[22]and [23]).They are also tion highlights that the original flora from New Caledonia frequently describedinfolk medicines [24]and numerous also contains awide range of original compounds.Origi- species show strong bioactivities,such as insecticidal or nality of New Caledonian compounds was updatedusing antitumoral activities[25][26]. the Dictionary of Natural Products [20]. We considered Thechemistry of five species has beeninvestigated in compounds as originals when encounteredonly in a New Caledonia: Xylopia pancheri, Xylopia vieillardii, restricted number of endemicspecies stemming from a Meiogyne tiebaghiensis (syn.: Desmos tiebaghiensis), Hu- unique genus.1)Wealso point out that alot of work bera nitidissima (syn.: Polyalthia nitidissima), and Gonio- remains to be done for the development of economical thalamus dumontetii.Thirteen isoquinolinealkaloids,in- applications based on this biodiversity.This review is cluding an unusual morphinanedienone (pallidine;shown divided into three parts.The first part coversthe knowl- in Fig.2)were identified from M. tiebaghiensis [18].X. edge of the chemistry of New Caledonianconifers[21], pancheri and H. nitidissima containagreat variety of whereas the two followingparts focus on the metabolites aporphine and isoquinolinealkaloids from benzylisoquino- isolated from angiosperms.The secondpart, which is line and protoberberine groups, including four lindoldh- presented here,compiles the results obtained by investiga- aminederivatives (namely N,N-dimethyllindoldhamine*, tion of basal angiosperms,monocots,basal