Diterpenes of Coffea seeds show antifungal and anti-insect activities and are transferred from the endosperm to the seedling after germination

Aerts, 1994, Distribution and utilization of chlorogenic acid in Coffea seedlings, J. Exp. Bot., 45, 497, 10.1093/jxb/45.4.497 Anthony, 1993, Biochemical diversity in the genus Coffea L.: chlorogenic acids, caffeine and mozambioside contents, Genet. Resour. Crop Evol., 40, 61, 10.1007/BF00052636 Anthony, 2010, Adaptive radiation in coffea subgenus coffea L. (Rubiaceae) in Africa and Madagascar, Plant Systemat. Evol., 285, 51, 10.1007/s00606-009-0255-8 Ashihara, 2008, Caffeine and related purine alkaloids: biosynthesis, catabolism, function and genetic engineering, Phytochemistry, 69, 841, 10.1016/j.phytochem.2007.10.029 Baumann, 1984, Metabolism and excretion of caffeine during germination of coffea arabica L, Plant Cell Physiol., 25, 1431, 10.1093/oxfordjournals.pcp.a076854 Biere, 2004, Plant chemical defense against herbivores and pathogens: generalized defense or trade-offs?, Oecologia, 140, 430, 10.1007/s00442-004-1603-6 Binenbaum, 2018, Gibberellin localization and transport in plants, Trends Plant Sci., 23, 410, 10.1016/j.tplants.2018.02.005 Bouarab, 2002, A saponin-detoxifying enzyme mediates suppression of plant defences, Nature, 418, 889, 10.1038/nature00950 Cheng, 2018, The coffee bean transcriptome explains the accumulation of the major bean components through ripening, Sci. Rep., 8, 1, 10.1038/s41598-018-29842-4 Clarke, 2005, Invasive phytophagous pests arising through a recent tropical evolutionary radiation: the Bactrocera dorsalis complex of fruit flies, Annu. Rev. Entomol., 50, 293, 10.1146/annurev.ento.50.071803.130428 Clifford, 2017, Chlorogenic acids and the acyl-quinic acids: discovery, biosynthesis, bioavailability and bioactivity, Nat. Prod. Rep., 34, 1391, 10.1039/C7NP00030H De-La-Cruz Chacón, 2013, Secondary metabolites during early development in plants, Phytochemistry Rev., 12, 47, 10.1007/s11101-012-9250-8 Davis, 2021, Six new species of coffee (Coffea) from northern Madagascar, Kew Bull., 76, 497, 10.1007/s12225-021-09952-5 De Meyer, 2008, Ecological niches and potential geographical distributions of Mediterranean fruit fly (Ceratitis capitata) and Natal fruit fly (Ceratitis rosa), J. Biogeogr., 35, 270, 10.1111/j.1365-2699.2007.01769.x De Roos, 1997, Levels of cafestol, kahweol, and related diterpenoids in wild species of the coffee plant Coffea, J. Agric. Food Chem., 45, 3065, 10.1021/jf9700900 Després, 2007, The evolutionary ecology of insect resistance to plant chemicals, Trends Ecol. Evol., 22, 298, 10.1016/j.tree.2007.02.010 Devappa, 2012, Localisation of antinutrients and qualitative identification of toxic components in Jatropha curcas seed, J. Sci. Food Agric., 92, 1519, 10.1002/jsfa.4736 Drenth, 2016, Fungal and oomycete diseases of tropical tree fruit crops, Annu. Rev. Phytopathol., 54, 373, 10.1146/annurev-phyto-080615-095944 Dussert, 1997, Variability in storage response within a coffee (Coffea spp.) core collection under slow growth conditions, Plant Cell Rep., 16, 344 Dussert, 2008, Effectiveness of the fatty acid and sterol composition of seeds for the chemotaxonomy of Coffea subgenus Coffea, Phytochemistry, 69, 2950, 10.1016/j.phytochem.2008.09.021 Duyck, 2002, Survival and development of different life stages of three Ceratitis spp. (Diptera: Tephritidae) reared at five constant temperatures, Bull. Entomol. Res., 92, 461, 10.1079/BER2002188 Eira, 2006, Coffee seed physiology, Braz. J. Plant Physiol., 18, 149, 10.1590/S1677-04202006000100011 Feng, 2009, Analysis of a Blumeria graminis-secreted lipase reveals the importance of host epicuticular wax components for fungal adhesion and development, Mol. Plant Microbe Interact., 22, 1601, 10.1094/MPMI-22-12-1601 Gershenzon, 1994, Metabolic costs of terpenoid accumulation in higher plants, J. Chem. Ecol., 20, 1281, 10.1007/BF02059810 Gershenzon, 2007, The function of terpene natural products in the natural world, Nat. Chem. Biol., 3, 408, 10.1038/nchembio.2007.5 Grové, 2017, Indigenous hosts of economically important fruit fly species (Diptera: Tephritidae) in South Africa, J. Appl. Entomol., 141, 817, 10.1111/jen.12381 Gruhnert, 1994, Compartmentation of cyanogenic glucosides and their degrading enzymes, Planta, 195, 36, 10.1007/BF00206289 Heiling, 2021, Specific decorations of 17-hydroxygeranyllinalool diterpene glycosides solve the autotoxicity problem of chemical defense in Nicotiana attenuata, Plant Cell, 33, 1748, 10.1093/plcell/koab048 Joët, 2009, Metabolic pathways in tropical dicotyledonous albuminous seeds: Coffea arabica as a case study, New Phytol., 182, 146, 10.1111/j.1469-8137.2008.02742.x Keeling, 2006, Diterpene resin acids in conifers, Phytochemistry, 67, 2415, 10.1016/j.phytochem.2006.08.019 Kettle, 2015, A γ-lactamase from cereal infecting Fusarium spp. catalyses the first step in the degradation of the benzoxazolinone class of phytoalexins, Fungal Genet. Biol., 83, 1, 10.1016/j.fgb.2015.08.005 Kissen, 2009, The “mustard oil bomb”: not so easy to assemble?! Localization, expression and distribution of the components of the myrosinase enzyme system, Phytochemistry Rev., 8, 69, 10.1007/s11101-008-9109-1 Krischik, 1991, Generalized plant defense: effects on multiple species, Oecologia, 85, 562, 10.1007/BF00323769 Mafu, 2018, Plant diterpenoid metabolism for manufacturing the biopharmaceuticals of tomorrow: prospects and challenges, Phytochemistry Rev., 17, 113, 10.1007/s11101-017-9513-5 Parshikov, 2014, The use of Aspergillus niger cultures for biotransformation of terpenoids, Process Biochem. (Amsterdam, Neth.), 49, 2086 Patui, 2014, Lipase activity and antioxidant capacity in coffee (Coffea arabica L.) seeds during germination, Plant Sci., 219–220, 19, 10.1016/j.plantsci.2013.12.014 Pierman, 2017, Activity of the purified plant ABC transporter NtPDR1 is stimulated by diterpenes and sesquiterpenes involved in constitutive and induced defenses, J. Biol. Chem., 292, 19491, 10.1074/jbc.M117.811935 Radchuk, 2014, Physical, metabolic and developmental functions of the seed coat, Front. Plant Sci., 5, 1, 10.3389/fpls.2014.00510 Rafael, 2010, Evaluation of kahweol and cafestol in coffee tissues and roasted coffee by a new high-performance liquid chromatography methodology, J. Agric. Food Chem., 58, 88, 10.1021/jf9027427 Ren, 2019, Cafestol and kahweol: a review on their bioactivities and pharmacological properties, Int. J. Mol. Sci., 20, 4238, 10.3390/ijms20174238 Schmelz, 2014, Biosynthesis, elicitation and roles of monocot terpenoid phytoalexins, Plant J., 79, 659, 10.1111/tpj.12436 Selmar, 1993, Transport of cyanogenic glucosides: linustatin uptake by Hevea cotyledons, Planta, 191, 191, 10.1007/BF00199749 Shimizu, 2000, A role for trigonelline during imbibition and germination of coffee seeds, Plant Biol., 2, 605, 10.1055/s-2000-16645 Speer, 2006, The lipid fraction of the coffee bean, Braz. J. Plant Physiol., 18, 201, 10.1590/S1677-04202006000100014 Talamond, 2015, Secondary metabolite localization by autofluorescence in living plant cells, Molecules, 20, 5024, 10.3390/molecules20035024 Taniwaki, 2003, The source of ochratoxin A in Brazilian coffee and its formation in relation to processing methods, Int. J. Food Microbiol., 82, 173, 10.1016/S0168-1605(02)00310-0 Tzen, 1997, A new method for seed oil body purification and examination of oil body integrity following germination, J. Biochem., 121, 762, 10.1093/oxfordjournals.jbchem.a021651 Vazquez-Yanes, 1993, Longevity and germination in the tropical rainforest, Annu. Rev. Ecol. Systemat., 24, 69, 10.1146/annurev.es.24.110193.000441 Weidlich, 2015, Secretion of lipases in the digestive tract of the cricket Gryllus bimaculatus, Arch. Insect Biochem. Physiol., 90, 209, 10.1002/arch.21303 Wharton, 2000, Parasitoids of medfly, Ceratitis capitata, and related tephritids in Kenyan coffee: a predominantly koinobiont assemblage, Bull. Entomol. Res., 90, 517, 10.1017/S0007485300000638 Zheng, 2004, Distribution, biosynthesis and function of purine and pyridine alkaloids in Coffea arabica seedlings, Plant Sci., 166, 807, 10.1016/j.plantsci.2003.11.024 Zienkiewicz, 2014, Olive seed protein bodies store degrading enzymes involved in mobilization of oil bodies, J. Exp. Bot., 65, 103, 10.1093/jxb/ert355