, Description de la feuille de Mesua lepidota T

, Analyse de l'huile essentielle des fruits de Mesua lepidota

, Spectres de RMN du lépidotol A (94)

. Annexe, Spectres de RMN du lépidotol B (95)

, Annexe 8. Spectres de RMN du lépidotol C (96)

, Annexe 9, Spectres de RMN du lépidotol D (97)

, Annexe 10, Spectres de RMN du lépidotol E (98)

, Spectres de RMN de la lépidotine A (99)

, Spectres de RMN de la lépidotine B (100)

. .. , Spectres de RMN du mélange mammea A/OB (101) / mammea A/OC (102), p.277

, Extraction des fruits de Mesua lepidota par divers solvants « verts »

, Spectres de RMN de la tétraptérone (105)

, Spectres de RMN de la tétraptérine (106)

, Spectres de RMN de l'acide tétraptérique (115)

, 254 nm) des fractions F5, F6, F7 et F9 de l'extrait 5442L_DCM (Mesua assamica)

, Evaluation de l'hépatotoxicité de quatre polyphénols prénylés d'intérêt

A. A. Agrawal and M. G. Weber, On the study of plant defence and herbivory using comparative approaches: how important are secondary plant compounds, Ecology letters, vol.18, pp.985-991, 2015.

P. Coulerie and C. Poullain, New Caledonia: a 'hot spot' for valuable chemodiversity, Chemistry & Biodiversity, vol.12, pp.841-858, 2015.
URL : https://hal.archives-ouvertes.fr/hal-01178978

B. T. Dang, C. Geny, P. Blanchard, C. Rouger, P. Richomme et al., Advanced glycation inhibition and protection against endothelial dysfunction induced by coumarins and procyanidins from Mammea neurophylla, Fitoterapia, vol.96, pp.65-75, 2014.
URL : https://hal.archives-ouvertes.fr/hal-01059141

H. Ait-oufella, E. Maury, B. Guidet, and G. Offenstadt, L'endothélium : un nouvel organe, Bibliographie du chapitre I, vol.1, pp.126-136, 2008.

M. E. Widlansky, N. Gokce, J. F. Keaney, . Jr, and J. A. Vita, The clinical implications of endothelial dysfunction, Journal of the American College of Cardiology, vol.42, pp.1149-1160, 2003.

M. Salvadori and E. Bertoni, What's new in clinical solid organ transplantation by 2013, World Journal of Transplantation, vol.4, pp.243-266, 2014.

F. Filipponi, S. P. De, A. Saviozzi, and G. Bozzi, Tissue procurement and transplantation: a Tuscany perspective, Transplantation Proceedings, vol.40, pp.1811-1813, 2008.
DOI : 10.1016/j.transproceed.2008.05.048

D. Farge, L. Terriou, R. Dulery, I. Yakoub-agha, M. Badoglio et al., Autogreffe des cellules souches hématopoïétiques dans les maladies auto-immunes : recommendations de la SFGM-TC, vol.62, pp.204-208, 2014.
DOI : 10.1016/j.patbio.2014.05.012

C. Brick, O. Atouf, N. Benseffaj, and M. Essakalli, Rejet de la greffe rénale : mécanisme et prévention
DOI : 10.1016/j.nephro.2010.10.002

. Néphrologie-&-thérapeutique, , vol.7, pp.18-26, 2011.

, Agence de la biomédecine -Chiffres préliminaires, 2013.

P. Chandak and C. Callaghan, The immunology of organ transplantation, Surgery, vol.32, pp.325-332, 2014.

J. Glicenstein, Un livre d'or de la chirurgie plastique française, Annales de Chirurgie Plastique Esthétique, vol.55, pp.338-353, 2010.
DOI : 10.1016/j.anplas.2010.07.012

E. Haddad, Evolution des concepts de l'immunosuppression dans le cadre de la transplantation d'organe. Archives de Pédiatrie, vol.11, pp.532-534, 2004.

M. Kolopp-sarda, C. Malcus, and C. Kohler, Immunologie de la transplantation : rejets et infections en transplantation d'organes solides. Revue Francophone des Laboratoires, pp.23-30, 2008.
DOI : 10.1016/s1773-035x(08)73332-x

W. G. Land, Chronic allograft dysfunction: a model disorder of innate immunity, Biomedical Journal, vol.36, pp.209-228, 2013.

Q. Lin, M. Li, D. Fang, J. Fang, and S. B. Su, The essential roles of toll-like receptor signaling pathways in sterile inflammatory diseases, International Immunopharmacology, vol.11, pp.1422-1432, 2011.

J. R. Beijnum, W. A. Buurman, and A. W. Griffioen, Convergence and amplification of toll-like receptor (TLR) and receptor for advanced glycation end products (RAGE) signaling pathways via high mobility group B1 (HMGB1), Angiogenesis, vol.11, pp.91-99, 2008.

N. Angaswamy, V. Tiriveedhi, N. J. Sarma, V. Subramanian, C. Klein et al., Interplay between immune responses to HLA and non-HLA self-antigens in allograft rejection, Human Immunology, vol.74, pp.1478-1485, 2013.
DOI : 10.1016/j.humimm.2013.07.002
URL : http://europepmc.org/articles/pmc3813452?pdf=render

A. L. Taylor, C. J. Watson, and J. A. Bradley, Immunosuppressive agents in solid organ transplantation: mechanisms of action and therapeutic efficacy, Critical Reviews in Oncology/Hematology, vol.56, pp.23-46, 2005.

É. Thervet, J. Zuber, R. Sberro, G. Canaud, D. Anglicheau et al., Traitements immunosuppresseurs : mécanismes d'action et utilisation clinique, Néphrologie & Thérapeutique, vol.7, pp.566-581, 2011.
DOI : 10.1016/s1762-0945(09)50344-0

R. F. Saidi and K. S. Hejazii, Clinical transplantation and tolerance: are we there yet?, International Journal of Organ Transplantation Medicine, vol.5, pp.137-145, 2014.

R. E. Marker and R. B. Wagner, Steroidal sapogenins, Journal of the American Chemical Society, vol.69, pp.2167-2230, 1947.

S. A. Survase, L. D. Kagliwal, U. S. Annapure, and R. S. Singhal, Cyclosporin A -A review on fermentative production, downstream processing and pharmacological applications, Biotechnology Advances, vol.29, pp.418-435, 2011.

C. Li and L. Li, Tacrolimus in preventing transplant rejection in Chinese patients -optimizing use. Drug Design, Development and Therapy, vol.9, pp.473-485, 2015.
DOI : 10.2147/dddt.s41349
URL : https://www.dovepress.com/getfile.php?fileID=23233

C. J. Watson and J. A. Bradley, Sirolimus and everolimus: inhibitors of mammalian target of rapamycin in liver transplantation, Transplantation Reviews, vol.20, pp.104-114, 2006.

Y. Dong, R. Xu, L. Wang, J. Zhang, C. Bai et al., A combined feeding strategy for enhancing mycophenolic acid production by fed-batch fermentation in Penicillium brevicompactum, Process Biochemistry, vol.50, pp.336-340, 2015.

M. L. Herrmann, R. Schleyerbach, and B. J. Kirschbaum, Leflunomide: an immunomodulatory drug for the treatment of rheumatoid arthritis and other autoimmune diseases, Immunopharmacology, vol.47, pp.273-289, 2000.

X. Su, M. Zhang, L. Li, C. Huo, Y. Gu et al., Chemical constituents of the plants of the genus Calophyllum, Chemistry & Biodiversity, vol.5, pp.2579-2608, 2008.

D. Obolskiy, I. Pischel, N. Siriwatanametanon, M. Heinrich, and L. Garcinia, Phytotherapy Research, vol.23, pp.1047-1065, 2009.

S. Kumar, S. Sharma, and S. K. Chattopadhyay, The potential health benefit of polyisoprenylated benzophenones from Garcinia and related genera: ethnobotanical and therapeutic importance, Fitoterapia, vol.89, pp.86-125, 2013.

J. B. Lambert, E. W. Donnelly, E. A. Heckenbach, C. L. Johnson, M. A. Kozminski et al., Molecular classification of the natural exudates of the rosids, Phytochemistry, vol.94, pp.171-183, 2013.

F. V. Cechinel, C. Meyre-silva, and R. Niero, Chemical and pharmacological aspects of the genus Calophyllum, Chemistry & Biodiversity, vol.6, pp.313-327, 2009.

L. J. Rao, H. Yada, H. Ono, M. Ohnishi-kameyama, and M. Yoshida, Occurrence of antioxidant and radical scavenging proanthocyanidins from the Indian minor spice nagkesar (Mammea longifolia planch and triana syn), Bioorganic & Medicinal Chemistry, vol.12, pp.31-36, 2004.

C. V. Da-silveira, M. T. Trevisan, J. B. Rios, G. Erben, R. Haubner et al., Secondary plant substances in various extracts of the leaves, fruits, stem and bark of Caraipa densifolia Mart, Food and Chemical Toxicology, vol.48, pp.1597-1606, 2010.

A. Lavaud, P. Richomme, J. Gatto, M. Aumond, C. Poullain et al., A tocotrienol series with an oxidative terminal prenyl unit from Garcinia amplexicaulis, Phytochemistry, vol.109, pp.103-110, 2015.
DOI : 10.1016/j.phytochem.2014.10.024
URL : https://hal.archives-ouvertes.fr/hal-01113163

S. L. Crockett and N. K. Robson, Taxonomy and chemotaxonomy of the genus Hypericum, Medicinal and Aromatic Plant Science and Biotechnology, vol.5, pp.1-13, 2011.

M. Ilyas, M. Kamil, M. Parveen, and M. S. Khan, Isoflavones from Garcinia nervosa, Phytochemistry, vol.36, pp.807-809, 1994.
DOI : 10.1016/s0031-9422(00)89823-4

J. Z. Deng, D. A. Sun, S. R. Starck, S. M. Hecht, R. L. Cerny et al., Chrysochlamic acid, a new diterpenoid-substituted quinol from Chrysochlamys ulei that inhibits DNA polymerase beta, Journal of the Chemical Society-Perkin Transactions, vol.1, pp.1147-1149, 1999.

M. S. Camargo, M. T. Oliveira, M. M. Santoni, F. A. Resende, A. P. Oliveira-hohne et al., Effects of nemorosone, isolated from the plant Clusia rosea, on the cell cycle and gene expression in MCF-7 BUS breast cancer cell lines, Phytomedicine, vol.22, pp.153-157, 2015.

A. P. Silva, M. P. Silva, C. G. Oliveira, D. C. Monteiro, P. L. Pinto et al., Garcinielliptone FC: antiparasitic activity without cytotoxicity to mammalian cells, Toxicology in Vitro, vol.29, pp.681-687, 2014.
DOI : 10.1016/j.tiv.2014.12.014

F. Gutierrez-orozco and M. L. Failla, Biological activities and bioavailability of mangosteen xanthones: a critical review of the current evidence, Nutrients, vol.5, pp.3163-3183, 2013.

R. Reyes-chilpa, E. Estrada-muniz, A. T. Ramirez, B. Amekraz, A. Aumelas et al., Cytotoxic effects of mammea type coumarins from Calophyllum brasiliense, Life Sciences, vol.75, pp.1635-1647, 2004.

, Bibliographie du chapitre II

B. T. Dang, C. Geny, P. Blanchard, C. Rouger, P. Richomme et al., Advanced glycation inhibition and protection against endothelial dysfunction induced by coumarins and procyanidins from Mammea neurophylla, Fitoterapia, vol.96, pp.65-75, 2014.
DOI : 10.1016/j.fitote.2014.04.005
URL : https://hal.archives-ouvertes.fr/hal-01059141

D. Susanti, M. Taher, N. Attoumani, and F. Ahmad, Free radical scavenging and antibacterial activities of Malaysian Guttiferae plants, Journal of Medicinal Plants Research, vol.5, pp.6714-6718, 2011.

L. Ferchichi, S. Derbré, K. Mahmood, K. Touré, D. Guilet et al., Bioguided fractionation and isolation of natural inhibitors of advanced glycation end-products (AGEs) from Calophyllum flavoramulum, Phytochemistry, vol.78, pp.98-106, 2012.
URL : https://hal.archives-ouvertes.fr/hal-00740990

T. C. Mckee, C. D. Covington, R. W. Fuller, H. R. Bokesch, S. Young et al., Pyranocoumarins from tropical species of the genus Calophyllum: a chemotaxonomic study of extracts in the National Cancer Institute collection, Journal of Natural Products, vol.61, pp.1252-1256, 1998.

C. L. Cantrell, M. A. Berhow, B. S. Phillips, S. M. Duval, D. Weisleder et al., Bioactive crude plant seed extracts from the NCAUR oilseed repository, Phytomedicine, vol.10, pp.325-333, 2003.
DOI : 10.1078/094471103322004820

F. Kawamura, A. Muhamud, R. Hashim, O. Sulaiman, and S. Ohara, Two antifungal xanthones from the heartwood of Calophyllum Symingtonianum. Jarq-Japan Agricultural Research Quarterly, vol.46, pp.181-185, 2012.

S. Subeki;-nomura, H. Matsuura, M. Yamasaki, O. Yamato, Y. Maede et al.,

T. Yoshihara, Anti-babesial activity of some Central Kalimantan plant extracts and active oligostilbenoids from Shorea balageran, Planta Medica, vol.71, pp.420-423, 2005.

A. Kijjoa, A. P. Rauter, F. B. Palma, J. Justino, and M. E. Araujo, Natural products in the new millennium: prospects and industrial application, vol.47, pp.299-309, 2002.

V. Rukachaisirikul, W. Naklue, Y. Sukpondma, and S. Phongpaichit, An antibacterial biphenyl derivative from Garcinia bancana Miq, Chemical & Pharmaceutical Bulletin, vol.53, pp.342-343, 2005.
DOI : 10.1002/chin.200537209

I. Siridechakorn, W. Maneerat, T. Sripisut, T. Ritthiwigrom, S. Cheenpracha et al., Biphenyl and xanthone derivatives from the twigs of a Garcinia sp (Clusiaceae), Phytochemistry Letters, vol.8, pp.77-80, 2014.

C. Auranwiwat, K. Trisuwan, A. Saiai, S. G. Pyne, and T. Ritthiwigrom, Antibacterial tetraoxygenated xanthones from the immature fruits of Garcinia cowa, Fitoterapia, vol.98, pp.179-183, 2014.

B. Y. Tay, Chemical constituents of Garcinia mangostana, G. parvifolia, G. griffiti and G. diversifolia (Guttiferae) and their biological activities, FSAS, vol.125, 1996.

S. Hartati, A. Soemiati, H. Wang, L. B. Kardono, M. Hanafi et al., A novel polyisoprenyl benzophenone derivative from Garcinia eugeniaefolia, Journal of Asian Natural Products Research, vol.10, pp.509-513, 2008.
DOI : 10.1080/10286020801966922

Y. W. Leong, L. J. Harrison, G. J. Bennett, and H. T. Tan, Forbesione, a modified xanthone from Garcinia forbesii, Journal of Chemical Research-S, pp.392-393, 1996.

Y. J. Xu, S. C. Yip, S. Kosela, E. Fitri, M. Hana et al., Novel cytotoxic, polyprenylated heptacyclic xanthonoids from Indonesian Garcinia gaudichaudii (Guttiferae), Xanthones and benzophenones from Garcinia griffithii and Garcinia mangostana, vol.2, pp.1718-1723, 2000.
DOI : 10.1021/ol006730t

N. Jamila, M. Khairuddean, S. N. Khan, N. Khan, and H. Osman, Phytochemicals from the bark of Garcinia hombroniana and their biological activities. Records of Natural Products, vol.8, pp.312-316, 2014.

M. Ilyas, M. Kamil, M. Parveen, and M. S. Khan, Isoflavones from Garcinia nervosa, Phytochemistry, vol.36, pp.807-809, 1994.
DOI : 10.1016/s0031-9422(00)89823-4

N. M. Seruji, H. Y. Khong, and C. J. Kutoi, Antioxidant, anti-inflammatory, and cytotoxic activities of Garcinia nervosa (Clusiaceae), p.913406, 2013.

V. Rukachaisirikul, K. Tadpetch, A. Watthanaphanit, N. Saengsanae, and S. Phongpaichit, Benzopyran, biphenyl, and tetraoxygenated xanthone derivatives from the twigs of Garcinia nigrolineata, Journal of Natural Products, vol.68, pp.1218-1221, 2005.

S. H. Goh, I. Jantan, A. I. Gray, and P. G. Waterman, Prenylated xanthones from Garcinia opaca, Phytochemistry, vol.31, pp.1383-1386, 1992.
DOI : 10.1016/0031-9422(92)80296-q

R. Mori, A. E. Nugroho, Y. Hirasawa, C. P. Wong, T. Kaneda et al., Opaciniols A-C, new terpenoids from Garcinia opaca, vol.68, pp.186-191, 2014.
DOI : 10.1007/s11418-013-0764-1

. Bibliographie, E. Boer, and A. B. Ella, , vol.18, 2000.

G. King, Materials for a flora of the Malayan Peninsula, Journal of the Asiatic Society of Bengal, vol.1890, p.185

J. S. Vesque, Epharmosis sive materiae ad instruendam anatomiam systematis naturalis. Delapierre: Vincennes, 1889, Genitalia foliaque garciniearum et calophyllearum, vol.2
DOI : 10.5962/bhl.title.828

I. Carpenter, E. J. Mcgarry, and F. Scheinmann, Extractives from Guttiferae. Part XXI. The isolation and structure of nine coumarins from the bark of Mammea africana G. Don, Journal of the Chemical Society C: Organic, pp.3783-3790, 1971.

D. Guilet, J. Helesbeux, D. Seraphin, T. Sevenet, P. Richomme et al., Novel Cytotoxic 4-Phenylfuranocoumarins from Calophyllum dispar, Journal of Natural Products, vol.64, pp.563-568, 2001.
DOI : 10.1021/np000517o

L. Verotta, E. Lovaglio, G. Vidari, P. V. Finzi, M. G. Neri et al., 4-Alkyl-and 4-phenylcoumarins from Mesua ferrea as promising multidrug resistant antibacterials, Phytochemistry, vol.65, pp.2867-2879, 2004.

J. Wittenauer, S. Falk, U. Schweiggert-weisz, and R. Carle, Characterisation and quantification of xanthones from the aril and pericarp of mangosteens (Garcinia mangostana L.) and a mangosteen containing functional beverage by HPLC-DAD-MSn, Food Chemistry, vol.134, pp.445-452, 2012.

M. Yang, W. Wang, J. Sun, Y. Zhao, Y. Liu et al., Characterization of phenolic compounds in the crude extract of Hedysarum multijugum by high-performance liquid chromatography with electrospray ionization tandem mass spectrometry. Rapid Communications in Mass Spectrometry, vol.21, pp.3833-3841, 2007.

A. E. Hay, D. Guilet, C. Morel, G. Larcher, D. Macherel et al., Antifungal chromans inhibiting the mitochondrial respiratory chain of pea seeds and new xanthones from Calophyllum caledonicum, Planta Medica, vol.69, pp.1130-1135, 2003.

V. Reutrakul, P. Leewanich, P. Tuchinda, M. Pohmakotr, T. Jaipetch et al., Cytotoxic coumarins from Mammea harmandii, Planta Medica, vol.69, pp.1048-1051, 2003.

L. Crombie, R. C. Jones, and C. J. Palmer, Synthesis of mammeins and surangin A, Tetrahedron Letters, vol.26, pp.2929-2932, 1985.

F. Ramiandrasoa, N. Kunesch, J. Poisson, G. Kunesch, and . Le-calofloride, Tetrahedron, vol.39, pp.3923-3928, 1983.

M. K. Chahar, K. D. Sanjaya, T. Lokesh, and K. P. Manohara, In-vivo antioxidant and immunomodulatory activity of mesuol isolated from Mesua ferrea L. seed oil, International Immunopharmacology, vol.13, pp.386-391, 2012.

L. Crombie, R. C. Jones, and C. J. Palmer, Synthesis of the Mammea coumarins. Part 1. The coumarins of the Mammea A, B, and C series, Journal of the Chemical Society, Perkin Transactions, vol.1, pp.317-331, 1987.

L. P. Sandjo, A. J. Foster, J. Rheinheimer, H. Anke, T. Opatz et al., Coumarin derivatives from Pedilanthus tithymaloides as inhibitors of conidial germination in Magnaporthe oryzae, Tetrahedron Letters, vol.53, pp.2153-2156, 2012.

C. Morel, C. Dartiguelongue, T. Youhana, J. Oger, D. Seraphin et al., New coumarins from Mesua racemosa: isolation and synthesis, Heterocycles, vol.51, pp.2183-2191, 1999.

M. M. Ballantyne, R. D. Murray, and A. B. Penrose, An out-of-ring Claisen rearrangement during the synthesis of nieshoutin and obliquetin, Tetrahedron Letters, pp.4155-4158, 1968.

T. R. Chamberlain, J. F. Collins, and M. F. Grundon, Claisen rearrangements in the biosynthesis of 1,1-and 1,2-dimethylallyl derivatives. Biosynthesis of the quinoline alkaloid, ravenoline, Journal of the Chemical Society D: Chemical Communications, pp.1269-1270, 1969.

L. Du, F. Mahdi, M. B. Jekabsons, D. G. Nagle, and Y. Zhou, Natural and semisynthetic mammeatype isoprenylated dihydroxycoumarins uncouple cellular respiration, Journal of Natural Products, vol.74, pp.240-248, 2011.
DOI : 10.1021/np100762s
URL : http://europepmc.org/articles/pmc3045645?pdf=render

M. J. Begley, L. Crombie, R. C. Jones, and C. J. Palmer, Synthesis of the Mammea coumarins. Part 4. Stereochemical and regiochemical studies, and synthesis of (-)-Mammea B/BB, Journal of the Chemical Society, vol.1, pp.353-357, 1987.

P. J. Stephens, D. M. Mccann, J. R. Cheeseman, and M. J. Frisch, Determination of absolute configurations of chiral molecules using ab initio time-dependent density functional theory calculations of optical rotation: how reliable are absolute configurations obtained for molecules with small rotations?, Chirality, vol.17, pp.52-64, 2005.

I. Chapitre, Etude phytochimique des extraits sélectionnés

R. Caroline, Activité pharmacologique de dérivés polyphénoliques isolés de Clusiaceae et de Calophyllaceae malaisiennes : effets régulateurs sur des marqueurs endothéliaux de l'inflammation et de l'immunité 158 22, Autschbach, J, vol.12, pp.3224-3235, 2011.

G. Mazzeo, E. Giorgio, R. Zanasi, N. Berova, and C. Rosini, Absolute configuration through the DFT simulation of the optical rotation. Importance of the correct selection of the input geometry: a caveat, Journal of Organic Chemistry, vol.75, pp.4600-4603, 2010.

Y. Dai, J. Van-spronsen, G. Witkamp, R. Verpoorte, and Y. H. Choi, Natural deep eutectic solvents as new potential media for green technology, Analytica Chimica Acta, vol.766, pp.61-68, 2013.

G. King, Materials for a flora of the Malayan Peninsula, Journal of the Asiatic Society of Bengal, vol.1890, p.175

H. N. Ridley and J. Hutchinson, The flora of the Malay Peninsula, 1922.

. Polypetalae, , vol.918

A. Arboretum, Global Biodiversity Information Facility (GBIF), vol.61, p.28, 1980.

L. Verotta, G. Appendino, E. Belloro, F. Bianchi, O. Sterner et al., Synthesis and biological evaluation of hyperforin analogues. Part I. Modification of the enolized cyclohexanedione moiety, Journal of Natural Products, vol.65, pp.433-438, 2002.

P. B. Derogis, F. T. Martins, S. T. De, M. E. Moreira, F. J. Souza et al., Complete assignment of the 1 H and 13 C NMR spectra of garciniaphenone and keto-enol equilibrium statements for prenylated benzophenones, Magnetic Resonance in Chemistry, vol.46, pp.278-282, 2008.

A. L. Piccinelli, L. Campone, F. Dal-piaz, O. Cuesta-rubio, and L. Rastrelli, Fragmentation pathways of polycyclic polyisoprenylated benzophenones and degradation profile of nemorosone by multiple-stage tandem mass spectrometry, Journal of the American Society for Mass Spectrometry, vol.20, pp.1688-1698, 2009.

K. R. Gustafson, J. W. Blunt, M. H. Munro, R. W. Fuller, T. C. Mckee et al., The guttiferones, HIV-inhibitory benzophenones from Symphonia globulifera, Garcinia livingstonei, Garcinia ovalifolia and Clusia rosea, vol.48, pp.1197-1199, 1992.

M. S. Ali, S. Mahmud, S. Perveen, V. U. Ahmad, and G. H. Rizwani, Epimers from the leaves of Calophyllum inophyllum, Phytochemistry, vol.50, pp.1385-1389, 1999.

Y. Li, Z. Li, S. Yin, G. Shi, M. Liu et al., Triterpenoids from Calophyllum inophyllum and their growth inhibitory effects on human leukemia HL-60 cells, Fitoterapia, vol.81, pp.586-589, 2010.

D. Silva, F. M. Koolen, H. H. Barisson, A. De-souza, A. D. Pinheiro et al., Steroids and triterpene from the bark of Unonopsis guatterioides R. E. FR. (Anonnaceae), International Journal of Pharmacy and Pharmaceutical Sciences, vol.4, pp.522-523, 2012.

K. Husain, J. A. Jamal, and J. Jalil, Phytochemical study of Cananga odorata Hook. F. & Thoms (Annonaceae), International Journal of Pharmacy and Pharmaceutical Sciences, vol.4, pp.465-467, 2012.

G. C. Ee, S. H. Mah, S. S. Teh, M. Rahmani, R. Go et al., Soulamarin, a new coumarin from stem bark of Calophyllum soulattri, Molecules, vol.16, pp.9721-9727, 2011.

S. H. Mah, G. C. Ee, S. S. Teh, M. Rahmani, Y. M. Lim et al., Phylattrin, a new cytotoxic xanthone from Calophyllum soulattri, Molecules, vol.17, pp.8303-8311, 2012.
DOI : 10.3390/molecules17078303
URL : https://www.mdpi.com/1420-3049/17/7/8303/pdf

P. M. Dey and J. B. Harborne, Methods in plant biochemistry, vol.1, 1989.

A. M. Habib, K. S. Reddy, T. G. Mccloud, C. J. Chang, and J. M. Cassady, New xanthones from Psorospermum febrifugum, Journal of Natural Products, vol.50, pp.141-145, 1987.
DOI : 10.1021/np50050a001

H. Wang, Q. Sun, F. Yang, C. Long, Y. Wang et al., Chromanone derivatives from the pericarps of Calophyllum polyanthum, Helvetica Chimica Acta, vol.93, pp.2183-2188, 2010.

L. D. Ha, P. E. Hansen, F. Duus, H. D. Pham, and L. D. Nguyen, A new chromanone acid from the bark of Calophyllum dryobalanoides, Phytochemistry Letters, vol.5, pp.287-291, 2012.

G. H. Stout and K. D. Sears, Calophyllum products. III. Structure of blancoic acids, Journal of Organic Chemistry, vol.33, pp.4185-4190, 1968.
DOI : 10.1021/jo01275a038

A. B. Alarcon, O. Cuesta-rubio, P. J. Cardenas, A. L. Piccinelli, and L. Rastrelli, Constituents of the Cuban endemic species Calophyllum pinetorum, Journal of Natural Products, vol.71, pp.1283-1286, 2008.

. Bibliographie, H. Fouotsa, A. M. Lannang, J. P. Dzoyem, S. J. Tatsimo et al., Antibacterial and antioxidant xanthones and benzophenone from Garcinia smeathmannii, Planta Medica, vol.81, pp.594-599, 2015.

F. V. Santa-cecilia, L. A. Freitas, F. C. Vilela, C. D. Veloso, C. Q. Da-rocha et al., Antinociceptive and anti-inflammatory properties of 7-epiclusianone, a prenylated benzophenone from Garcinia brasiliensis, European Journal of Pharmacology, vol.670, pp.280-285, 2011.

M. Ali, M. Arfan, M. Ahmad, K. Singh, I. Anis et al., Antiinflammatory xanthones from the twigs of Hypericum oblongifolium Wall, Planta Medica, vol.77, 2011.

J. Chao, A. Gapor, and A. Theriault, Inhibitory effect of ?-tocotrienol, a HMG CoA reductase inhibitor, on monocyte-endothelial cell adhesion, Journal of Nutritional Science and Vitaminology, vol.48, pp.332-337, 2002.

S. Tanaka, Y. Sakata, K. Morimoto, Y. Tambe, Y. Watanabe et al., Influence of natural and synthetic compounds on cell surface expression of cell adhesion molecules

, Planta Medica, vol.67, pp.108-113, 2001.

J. Li, Y. Tu, L. Tong, W. Zhang, J. Zheng et al., Immunosuppressive activity on the murine immune responses of glycyrol from Glycyrrhiza uralensis via inhibition of calcineurin activity, Pharmaceutical Biology, vol.48, pp.1177-1184, 2010.

Y. Fu, H. Zhou, M. Wang, J. Cen, and Q. Wei, Immune regulation and anti-inflammatory effects of isogarcinol extracted from Garcinia mangostana L. against collagen-induced arthritis, Journal of Agricultural and Food Chemistry, vol.62, pp.4127-4134, 2014.

I. Raad, R. Terreux, P. Richomme, E. Matera, C. Dumontet et al., Structureactivity relationship of natural and synthetic coumarins inhibiting the multidrug transporter P-glycoprotein

, Bioorganic & Medicinal Chemistry, vol.14, pp.6979-6987, 2006.

C. Rouger, S. Derbre, B. Charreau, A. Pabois, T. Cauchy et al., Lepidotol A from Mesua lepidota inhibits inflammatory and immune mediators in human endothelial cells, Journal of Natural Products, vol.78, pp.2187-2197, 2015.
URL : https://hal.archives-ouvertes.fr/hal-01391725

B. T. Dang, C. Geny, P. Blanchard, C. Rouger, P. Richomme et al., Advanced glycation inhibition and protection against endothelial dysfunction induced by coumarins and procyanidins from Mammea neurophylla, Fitoterapia, vol.96, pp.65-75, 2014.
DOI : 10.1016/j.fitote.2014.04.005
URL : https://hal.archives-ouvertes.fr/hal-01059141

A. Hay, J. Helesbeux, O. Duval, M. Labaied, P. Grellier et al., Antimalarial xanthones from Calophyllum caledonicum and Garcinia vieillardii, Life Sciences, vol.75, pp.3077-3085, 2004.
DOI : 10.1016/j.lfs.2004.07.009
URL : https://hal.archives-ouvertes.fr/mnhn-02070126

J. Merza, S. Mallet, M. Litaudon, V. Dumontet, D. Seraphin et al., New cytotoxic guttiferone analogues from Garcinia virgata from New Caledonia, Planta Medica, vol.72, pp.87-89, 2006.
URL : https://hal.archives-ouvertes.fr/hal-00020661

B. Charreau, S. Coupel, F. Goret, C. Pourcel, and J. Soulillou, Association of glucocorticoids and cyclosporin A or rapamycin prevents E-selectin and IL-8 expression during LPS-and TNF?-mediated endothelial cell activation, Transplantation, vol.69, pp.945-953, 2000.

A. H. Zhang, X. Q. Wang, W. B. Han, Y. Sun, Y. Guo et al., Discovery of a new class of immunosuppressants from Trichothecium roseum co-inspired by cross-kingdom similarity in innate immunity and pharmacophore motif, Chemistry -An Asian Journal, vol.8, pp.3101-3107, 2013.

A. Bringmann, S. M. Schmidt, M. M. Weck, K. M. Brauer, K. Schwarzenberg et al., Zoledronic acid inhibits the function of Toll-like receptor 4 ligand activated monocyte-derived dendritic cells, Leukemia, vol.21, pp.732-738, 2007.

M. Muraro, O. M. Mereuta, F. Carraro, E. Madon, and F. Fagioli, Osteosarcoma cell line growth inhibition by zoledronate-stimulated effector cells, Cellular Immunology, vol.249, pp.63-72, 2007.

R. Reyes-chilpa, E. Estrada-muniz, A. T. Ramirez, B. Amekraz, A. Aumelas et al., Cytotoxic effects of mammea type coumarins from Calophyllum brasiliense, Life Sciences, vol.75, pp.1635-1647, 2004.

,. El-hentati, C. Iobagiu, and C. Lambert, Cytométrie et ses applications en immunologie clinique. Revue Francophone des Laboratoires, pp.23-32, 2009.

I. V. Chapitre, Etude de l'activité anti-inflammatoire et immunorégulatrice d'un panel de polyphénols

A. K. Hubbard and R. Rothlein, Intercellular adhesion molecule-1 (ICAM-1) expression and cell signaling cascades, Free Radical Biology & Medicine, vol.28, pp.1379-1386, 2000.

N. Bardin, M. Mutin, and G. Lesaule, Analyse des cellules endothéliales. Revue Française des Laboratoires, vol.4, pp.96-100, 1996.
DOI : 10.1016/s0338-9898(96)80215-0

P. Beauparlant and J. Hiscott, Biological and biochemical inhibitors of the NF-?B/Rel proteins and cytokine synthesis, Cytokine & Growth Factor Reviews, vol.7, pp.175-190, 1996.

J. S. Pober and G. Tellides, Participation of blood vessel cells in human adaptive immune responses, Trends in Immunology, vol.33, pp.49-57, 2012.

I. Riederer, W. Sievert, G. Eissner, M. Molls, and G. Multhoff, Irradiation-induced up-regulation of HLA-E on macrovascular endothelial cells confers protection against killing by activated natural killer cells, International Congress Series, vol.5, pp.181-191, 2002.

M. Iwaszko and K. Bogunia-kubik, Clinical significance of the HLA-E and CD94/NKG2 interaction

, Archivum Immunologiae et Therapia Experimentalis, vol.59, pp.353-367, 2011.

R. Christova, T. Jones, P. Wu, A. Bolzer, A. P. Costa-pereira et al., P-STAT1 mediates higher-order chromatin remodelling of the human MHC in response to IFN?, Journal of Cell Science, vol.120, pp.3262-3270, 2007.

T. Collins, A. J. Korman, C. T. Wake, J. M. Boss, D. J. Kappes et al., Immune interferon activates multiple class II major histocompatibility complex genes and the associated invariant chain gene in human endothelial cells and dermal fibroblasts, Proceedings of the National Academy of Sciences of the United States of America, vol.81, pp.4917-4921, 1984.

S. Coupel, A. Moreau, M. Hamidou, V. Horejsi, J. Soulillou et al., Expression and release of soluble HLA-E is an immunoregulatory feature of endothelial cell activation, Blood, vol.109, pp.2806-2814, 2007.

C. Zhang, J. Niu, J. Zhang, Y. Wang, Z. Zhou et al., Opposing effects of interferon-? and interferon-? on the expression of major histocompatibility complex class I chain-related A in tumors, Cancer Science, vol.99, pp.1279-1286, 2008.

A. Chauveau, P. Tonnerre, A. Pabois, P. Gavlovsky, M. Chatelais et al., Endothelial cell activation and proliferation modulate NKG2D activity by regulating MICA expression and shedding, Journal of Innate Immunity, vol.6, pp.89-104, 2014.
DOI : 10.1159/000351605

E. Lee, S. Shin, J. Kim, E. Woo, and Y. Kim, Anti-inflammatory effects of amentoflavone on modulation of signal pathways in LPS-stimulated RAW264.7 cells, Bulletin of the Korean Chemical Society, vol.33, pp.2878-2882, 2012.

P. Singh, D. Kohr, M. Kaps, and F. Blaes, Influence of statins on MHC class I expression, Annals of the New York Academy of Sciences, pp.746-751, 1173.
DOI : 10.1111/j.1749-6632.2009.04646.x

J. F. Bukowski, C. C. Dascher, and H. Das, Alternative bisphosphonate targets and mechanisms of action, Biochemical and Biophysical Research Communications, vol.328, pp.746-750, 2005.
DOI : 10.1016/j.bbrc.2004.11.075

M. Ii and D. W. Losordo, Statins and the endothelium, Vascular Pharmacology, vol.46, pp.1-9, 2007.
DOI : 10.1016/j.vph.2006.06.012

G. Belliard, S. Coupel, and B. Charreau, Effet de la fluvastatine sur l'expression du CMH de classe I par les cellules endothéliales humaines, Néphrologie & Thérapeutique, vol.1, pp.221-227, 2005.
DOI : 10.1016/j.nephro.2005.06.008

L. Peng, Y. Qi, H. Wu, and Q. Wei, Interaction of glycyrol with calcineurin A studied by spectroscopic methods and docking. International Union of Biochemistry and Molecular Biology Life, vol.63, pp.14-20, 2011.

R. O'kennedy and R. D. Thornes, Coumarins: biology, applications and mode of action, vol.348, 1997.

J. Cen, M. Wang, G. Jiang, Y. Yin, Z. Su et al., The new immunosuppressant, isogarcinol, binds directly to its target enzyme calcineurin, unlike cyclosporin A and tacrolimus, Biochimie, vol.111, pp.119-124, 2015.

D. Roux, H. A. Hadi, S. Thoret, D. Guenard, O. Thoison et al., Structure-activity relationship of polyisoprenyl benzophenones from Garcinia pyrifera on the tubulin/microtubule system, Journal of Natural Products, vol.63, pp.1070-1076, 2000.

J. T. Lyles, A. Negrin, E. J. Kennelly, S. I. Khan, and K. He, In vitro antiplasmodial activity of benzophenones and xanthones from edible fruits of Garcinia species, Planta Medica, vol.80, pp.676-681, 2014.

B. D. Kahan, Individuality: the barrier to optimal immunosuppression, Nature Reviews Immunology, vol.3, pp.831-838, 2003.

S. Sun, The noncanonical NF-?B pathway, Immunological Reviews, vol.246, pp.125-140, 2012.
DOI : 10.1111/j.1600-065x.2011.01088.x
URL : http://europepmc.org/articles/pmc3313452?pdf=render

C. Auger and V. B. Schini-kerth, Potentiel des polyphénols à améliorer la protection vasculaire en stimulant la fonction endothéliale. Cahiers de Nutrition et de Diététique, vol.49, pp.160-172, 2014.
DOI : 10.1016/j.cnd.2014.03.005

I. V. Chapitre, Etude de l'activité anti-inflammatoire et immunorégulatrice d'un panel de polyphénols

X. Chao, X. Zhou, G. Zheng, C. Dong, W. Zhang et al., Osthole induces G2/M cell cycle arrest and apoptosis in human hepatocellular carcinoma HepG2 cells, Pharmaceutical Biology, vol.52, pp.544-550, 2014.

T. Uehara, N. Kiyosawa, T. Shimizu, K. Omura, M. Hirode et al., Species-specific differences in coumarin-induced hepatotoxicity as an example toxicogenomics-based approach to assessing risk of toxicity to humans, Human & Experimental Toxicology, vol.27, pp.23-35, 2008.

G. L. Pardo-andreu, Y. Nunez-figueredo, V. G. Tudella, O. Cuesta-rubio, F. P. Rodrigues et al., The anti-cancer agent guttiferone-A permeabilizes mitochondrial membrane: ensuing energetic and oxidative stress implications, Toxicology and Applied Pharmacology, vol.253, pp.282-289, 2011.

F. H. Reis, G. L. Pardo-andreu, Y. Nunez-figueredo, O. Cuesta-rubio, J. Marin-prida et al., Clusianone, a naturally occurring nemorosone regioisomer, uncouples rat liver mitochondria and induces HepG2 cell death, Chemico-Biological Interactions, vol.212, pp.20-29, 2014.
DOI : 10.1016/j.cbi.2014.01.015
URL : https://doi.org/10.1016/j.cbi.2014.01.015

A. G. Huebschmann, J. G. Regensteiner, H. Vlassara, and J. E. Reusch, Diabetes and advanced glycoxidation end products, Diabetes Care, vol.29, pp.1420-1432, 2006.

S. Feske, H. Okamura, P. G. Hogan, and A. Rao, Ca2+/calcineurin signalling in cells of the immune system, Biochemical and Biophysical Research Communications, vol.311, pp.1117-1132, 2003.

G. Cheeseman, V. Scalmani, B. Barone, G. A. Mennucci, H. Petersson et al.,

A. F. Hratchian, J. Izmaylov, G. Bloino, J. L. Zheng, M. Sonnenberg et al.,

J. B. Knox, V. Cross, C. Bakken, J. Adamo, R. Jaramillo et al., , 2009.

J. P. Perdew, K. Burke, and M. Ernzerhof, Generalized gradient approximation made simple, Physical Review Letters, vol.77, pp.3865-3868, 1996.
DOI : 10.1103/physrevlett.77.3865

C. Adamo and V. Barone, Toward reliable density functional methods without adjustable parameters: the PBE0 model, The Journal of Chemical Physics, vol.110, pp.6158-6170, 1999.

P. J. Stephens, F. J. Devlin, J. R. Cheeseman, and M. J. Frisch, Calculation of optical rotation using density functional theory, The Journal of Physical Chemistry A, vol.105, pp.5356-5371, 2001.

D. M. Mccann and P. J. Stephens, Determination of absolute configuration using density functional theory calculations of optical rotation and electronic circular dichroism: chiral alkenes, Journal of Organic Chemistry, vol.71, pp.6074-6098, 2006.

J. R. Cheeseman, M. J. Frisch, F. J. Devlin, and P. J. Stephens, Hartree-fock and density functional theory ab initio calculation of optical rotation using GIAOs: basis set dependence, The Journal of Physical Chemistry A, vol.104, pp.1039-1046, 2000.

N. M. O'boyle, A. L. Tenderholt, and K. M. Langner, Software news and updates cclib: a library for package-independent computational chemistry algorithms, Journal of Computational Chemistry, vol.29, pp.839-845, 2008.

C. Morel, C. Dartiguelongue, T. Youhana, J. Oger, D. Seraphin et al., New coumarins from Mesua racemosa: isolation and synthesis, Heterocycles, vol.51, pp.2183-2191, 1999.

M. S. Ali, S. Mahmud, S. Perveen, V. U. Ahmad, and G. H. Rizwani, Epimers from the leaves of Calophyllum inophyllum, Phytochemistry, vol.50, pp.1385-1389, 1999.

Y. Li, Z. Li, S. Yin, G. Shi, M. Liu et al., Triterpenoids from Calophyllum inophyllum and their growth inhibitory effects on human leukemia HL-60 cells, Fitoterapia, vol.81, pp.586-589, 2010.

K. Husain, J. A. Jamal, and J. Jalil, Phytochemical study of Cananga odorata Hook. F. & Thoms (Annonaceae), International Journal of Pharmacy and Pharmaceutical Sciences, vol.4, pp.465-467, 2012.

A. M. Habib, K. S. Reddy, T. G. Mccloud, C. J. Chang, and J. M. Cassady, New xanthones from Psorospermum febrifugum, Journal of Natural Products, vol.50, pp.141-145, 1987.

G. H. Stout and K. D. Sears, Calophyllum products. III. Structure of blancoic acids, Journal of Organic Chemistry, vol.33, pp.4185-4190, 1968.

R. Caroline, Activité pharmacologique de dérivés polyphénoliques isolés de Clusiaceae et de Calophyllaceae malaisiennes : effets régulateurs sur des marqueurs endothéliaux de l'inflammation

L. Sero, L. Sanguinet, P. Blanchard, B. T. Dang, S. Morel et al., Tuning a 96-well microtiter plate fluorescence-based assay to identify AGE inhibitors in crude plant extracts, Molecules, vol.18, pp.14320-14339, 2013.

G. Rakotomalala, C. Agard, P. Tonnerre, A. Tesse, S. Derbre et al., Extract from Mimosa pigra attenuates chronic experimental pulmonary hypertension, Journal of Ethnopharmacology, vol.148, pp.106-116, 2013.

S. Coupel, F. Leboeuf, G. Boulday, J. Soulillou, and B. Charreau, RhoA activation mediates phosphatidylinositol 3-kinase-dependent proliferation of human vascular endothelial cells: an alloimmune mechanism of chronic allograft nephropathy, Journal of the American Society of Nephrology, vol.15, pp.2429-2439, 2004.

G. Belliard, S. Coupel, and B. Charreau, Effet de la fluvastatine sur l'expression du CMH de classe I par les cellules endothéliales humaines, Néphrologie & Thérapeutique, vol.1, pp.221-227, 2005.

M. Muraro, O. M. Mereuta, F. Carraro, E. Madon, and F. Fagioli, Osteosarcoma cell line growth inhibition by zoledronate-stimulated effector cells, Cellular Immunology, vol.249, pp.63-72, 2007.

. O. Botanique and . Fenêtre,

, ANSM. Glossaire des termes anatomiques utiles pour l'identification B (Drogues végétales), vol.602, 1998.

M. Botineau, Botanique systématique et appliquée des plantes à fleurs, 2010.

.. .. -prednisone, , vol.40, pp.33-34

. .. 6-dihydroxyxanthone, , pp.33-34

. .. -hydroxyxanthone, , pp.33-35

.. .. -hydroxyxanthone, 36 33e -Mesuaxanthone B ou 1,5,6-trihydroxyxanthone, pharmacologique de dérivés polyphénoliques isolés de Clusiaceae et de Calophyllaceae malaisiennes : effets régulateurs sur des marqueurs endothéliaux de l'inflammation, pp.33-37

.. .. -méthoxyxanthone, 36 33i -5-Hydroxy-1-méthoxyxanthone, pp.33-36

.. .. -méthoxyxanthone, 36 33k -Mesuaxanthone A ou 1,5-dihydroxy-3-méthoxyxanthone, pp.33-35

. .. -hydroxyxanthone, , vol.36, p.33

C. .. 33o--tovopyrifoline, , vol.36, pp.6-7

G. .. 33r--cudraxanthone,

. .. -désoxyjacareubine, , pp.34-40

. .. 34b--jacareubine,

C. .. 34c--caloxanthone,

. .. 34d--macluraxanthone,

. .. 36a--ananixanthone,

. .. 36b--mesuasinone,

A. .. ,

B. .. ,

A. .. 41c--mesuabixanthone,

B. .. 41d--mesuabixanthone, 43 Annexes Caroline ROUGER | Activité pharmacologique de dérivés polyphénoliques isolés de Clusiaceae et de Calophyllaceae malaisiennes : effets régulateurs sur des marqueurs endothéliaux de l'inflammation et de l'immunité, p.249

. .. 56--oblongulide,

. .. 60a--assamène,

C. .. 60b--surangine,

. .. Ab,

. .. Ac,

. .. 61e--racémosone, -méthylbutanoyl)-8-[(E)-3,7-diméthylocta-2,6-dienyl]-4-phényl-2H-chromèn-2-one, vol.46, pp.61-66

. .. 61i--racémosol,

. .. Ba,

. .. Bc, -méthylbutanoyl)-6-[(E)-3,7-diméthylocta-2,6-dienyl]-4-phényl-2H-chromèn-2-one, vol.46, pp.62-67

. .. 62f--isoracémosol,

C. .. 62g--mesuagénine,

A. .. 63a--mesuagenine,

B. .. 63b--mesuagenine,

D. .. 64a--mesuagenine,

. .. 65e--mesuarine, , vol.46, p.3

, 46 Annexes Caroline ROUGER | Activité pharmacologique de dérivés polyphénoliques isolés de Clusiaceae et de Calophyllaceae malaisiennes : effets régulateurs sur des marqueurs endothéliaux de l'inflammation

A. 66b--mammea and F. .. , , vol.46, pp.66-74

, Dihydro-5-hydroxy-6-(3-méthylbutanoyl)-4-phényl-8-(prop-1-èn-2-yl)furo[2,3-h]chromèn-2-one, vol.9, pp.66-74

. .. 67--furanoracémosone,

.. .. ,

.. .. -friedélanol, , pp.77-80

. .. 77c--acide-myrtifolique,

.. .. Amyrine,

.. .. 78c--acide-oléanolique,

. .. 80a--simiarénol,

. .. 80b--simiarénone,

. .. 81a--lupéol,

.. .. -oxo-bétuline, , vol.50, p.251

C. .. Lépidotol,

, 138 111 -3-Hydroxy-2-méthoxyxanthone

Y. H. Choi, J. Van-spronsen, Y. Dai, M. Verberne, F. Hollmann et al., Are natural deep eutectic solvents the missing link in understanding cellular metabolism and physiology? Plant Physiology, vol.156, pp.1701-1705, 2011.

A. P. Abbott, D. Boothby, G. Capper, D. L. Davies, and R. K. Rasheed, Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids, Journal of the American Chemical Society, vol.126, pp.9142-9147, 2004.

Y. Dai, J. Van-spronsen, G. Witkamp, R. Verpoorte, and Y. H. Choi, Ionic liquids and deep eutectic solvents in natural products research: mixtures of solids as extraction solvents, Journal of Natural Products, vol.76, pp.2162-2173, 2013.

Y. Dai, G. Witkamp, R. Verpoorte, and Y. H. Choi, Natural deep eutectic solvents as a new extraction media for phenolic metabolites in Carthamus tinctorius L, Analytical Chemistry, vol.85, pp.6272-6278, 2013.

, Annexes

, Spectres de RMN de l'acide tétraptérique (115) RMN 1 H du composé 115 (300 MHz

, COSY du composé, vol.115