Abstract
A number of foods, vegetables, fruits, and beverages (tea, coffee, and liqueur) contain many kinds of diterpenoids (mainly abietanes, cembranes, clerodanes, cyatanes, dolabellanes, fusicoccanes, kauranes, labdanes, pimaranes, taxanes, trachilobanes, totaranes) and their related compounds. This chapter summarizes the distribution of diterpenoids in dietary foods, vegetables, fruits, beverages, and processed foods, and their biological and pharmacological activity, effects, and application to our health, as well as metabolic pathways of several diterpenoids, which are widely distributed in dietary foods, by microorganisms and mammals.
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References
Abad MJ, Bermejo P (2007) Baccharis (composite): a review update. ARKIVOC 7:76–96
Abe M, Ozawa Y, Uda Y, Yamada F, Morimitsu Y, Nakamura Y, Osawa T (2004) Antimicrobial activities of diterpene dialdehydes, constituents from Myoga (Zingiber mioga roscoe), and their quantitative analysis. Biosci Biotechnol Biochem 68(7):1601–1604
Al Haidari RA (2018) A review of traditional uses, phytochemical and bioactivities of the genus Hypoestes. Afr Tradit Complement Altern Med 15(3):1–17. https://doi.org/10.21010/ajtcam.v15i3.1
Aminimoghadamfarouj N, Nematollahi A (2017) Propolis diterpenes as remarkable bio-source for drug discovery development: a review. Int J Mol Sci 18(6):1290–1306. https://doi.org/10.3390/ijms18061290
Anis M, Ahmed S, Hasan MM (2017) Algae as nutrition, medicinal and cosmetic: the forgotten history, present status and future trends. World J Pharm Pharmaceut Sci 6(6):1934–1959. https://doi.org/10.20959/wjpps20176-9447
Appendino G (1995) The phytochemistry of the yew tree. Nat Prod Rep 12:349–360
Appendino G (2016) Ingenane diterpenoids. In: Kinghorn AD, Falk H, Gibbons S, Kobayashi J (eds) Progress in the chemistry of organic natural products, vol 102. Springer, Vienna, pp 1–90
Arruda C, Mejia JAA, Ribeiro VP, Borges CHG, Marins CHG, Veneziani CS, Ambrosio SR, Rastos JK (2019) Occurrence, chemical composition, biological activities and analytical methods on Copaifera genus-a review. Biomed Phamacother 109:1–20. https://doi.org/10.1016/j.biopha.2018.10.030
Asakawa Y (1982) Chemical constituents of Hepaticae. In: Herz W, Grisebach H, Kirby GW (eds) Progress in the chemistry of organic natural products, vol 42. Springer, Vienna, pp 1–285
Asakawa Y (1995) Chemical constituents of bryophytes. In: Herz W, Grisebach H, Kirby GW, Moore RE, Steglich W, Tamm C (eds) Progress in the chemistry of organic natural products, vol 65. Springer, Vienna, pp 1–618
Asakawa Y (2021) Dietary Monoterpenoids. In: Xiao J, Sarker SD, Asakawa Y (eds) Handbook of dietary phytochemicals. Springer, Singapore. https://doi.org/10.1007/978-981-13-1745-3_17-2
Asakawa Y, Noma Y (2010) Biotransformation of di- and triterpenoids, steroids, and miscellaneous synthetic substances. In: Mander L, Liu HW (eds) Comprehensive natural products II, Chemistry and biology, vol 3. Elsevier, Oxford, pp 893–914
Asakawa Y, Noma Y (2020) Biotransformation of sesquiterpenoids, ionones, damascones, adamantanes, and aromatic compounds by green algae, fungi, and mammals. In: Baser HC, Buchbauer G (eds) Handbook of essential oils. Science, technology, and application, 3rd edn. CRC Press, Boca Raton, pp 769–871
Asakawa Y, Ludwiczuk A, Nagashima F (2013) Chemical constituents of bryophytes. Bio- and chemical diversity, biological activity, and chemosystematics. In: Kinghorn AD, Falk H, Kobayashi J (eds) Progress in the chemistry of organic natural products, vol 95. Springer, Vienna, pp 1–796
Baskaran XR, Vigila AG, Zhang SZ, Feng SX, Liao WB (2018) A review of the use of pteridophytes for treating human ailments. J Zhejian Univ Sci B 19(2):85–119. https://doi.org/10.1631/jzus.B1600344
Bhatti HN, Khera RA (2014) Biotransformation of diterpenoids and triterpenoids: a review. J Asian Nat Prod Res 16(1):70–104. https://doi.org/10.1080/10286020.2013.846908
Bowen L, Li C, Bin L, Ying T, Shijun L, Junzing D (2020) Chemical constituents, cytotoxic and antioxidant activities of extract from the rhizomes of Osmunda japonica Thunb. Nat Prod Res 34(6):847–850. https://doi.org/10.1080/14786419.2018.1501629
Burgos EG, Carretero ME, Gomez SMP (2011) Sideritis spp: uses, chemical composition and pharmacological activities-a review. J Ethnopharmcol 235(2):209–225
Cao H, Chai TT, Wang X, Morais-Braga MFB, Yan JH, Wong FC, Wang R, Yan H, Cao J, Cornara L, Burland B, Wang Y, Xiao J, Coutinho HDM (2017) Phytochemicals from fern species: potential for medicine applications. Phytochem Rev 16:379–440. https://doi.org/10.1007/s1101-016-9488-7
Carovic-Stanko K, Peket M, Grdisa M, Pntar J, Bedekovic D, Custic MH, Satovic Z (2016) Medicinal plants of the family Lamiaceae as functional foods- a review. Czech J Food Sci 34(5):377–390. https://doi.org/10.17331/504/2015-CJFS
Chakraborty K, Lipton A, Raj RP, Vijayan KK (2010) Antibacterial labdane diterpenoids of Ulva fasciata Delile from southwestern coast of the Indian peninsula. Food Chem 119(4):1399–1408
Chen J, Zhao Z, Xia X, Li B, Zhang J, Yan X (2018) Diterpenoids from the marine algae of the genus Dictyota. Mar Drugs 16(5):159. https://doi.org/10.3390/md.16050159
Chen YY, Ma CYM, Wang ML, Lu JH, Hu P, Chen JW (2020) Five new ent-kaurane diterpenes from Annona squamosal L. pericarps. Nat Prod Res 34(15):2243–2247
Choudhary MI, Mohammad MY, Musharraf SG, Onajobi I, Mohammad A, Anis I, Shah MR, Rahman AU (2013) Biotransformation of clerodane diterpenoids by Rhizopus stolonifera and antimicrobial activity of resulting metabolites. Phytochemistry 90:56–61. https://doi.org/10.1016/j.phytochem.2013.02.007
Coll J, Tandron YA (2008) Neo-Clerodane diterpenoids from Ajuga: structural elucidation and biological activity. Phytochem Rev 7:25–49. https://doi.org/10.1007/s1110-006-9023-3
Connolly JD, Hill RA (1991) Dictionary of Terpenoids. Vol. 3. Di- and higher terpenoids. Chapman and Hall, London, pp 655–1095
Custodio DL, Veiga VF Jr (2012) True and common balsam. Braz J Pharmacogn 22(6):1372–1383. https://doi.org/10.1590/S0102-695X20120050000097
De Sousa IP, Teixeira MVS, Futado NAJC (2018) An overview of biotransformation and toxicity of diterpenoids. Molecules 23(6):1386. https://doi.org/10.3390/molecules23061387
Decorzant R, Vial C, Naf F, Whitesides GM (1987) A short synthesis of Ambrox® from sclareol. Tetrahedron 43(8):1871–1879
Duru ME, Cayan GT (2015) Biologically active terpenoids from mushroom origin: a review. Res Nat Prod 9(4):456–483
El Gemal AA (2010) Biological importance of marine algae. Saudi Pharm J 18(1):1–25. https://doi.org/10.1016/j.jsps.2009.12.001
Fahlbusch KG, Hammerschmidt FJ, Panten J, Pickenhagen W, Schatkowski D, Bauer K, Surburg H (2007) Flavors and fragrances. Ullmann’s encyclopedia of industrial chemistry, 7th edn. Wiley, Weinheim, p 72. https://doi.org/10.1002/14356007.a11141
Fan M, Luo D, Peng LY, Li XN, Wu ZD, Zhao QS (2019) Neoclerodane diterpenoids from the aerial parts of Salvia hispania L. and their cardioprotective effects. Phytochemistry 166:112065. https://doi.org/10.1016/j.phytochem.2019.112065
Fan M, Luo D, Peng LY, Wu ZD, Zhao QS (2020) Rearranged neoclerodane diterpenoids from the aerial parts of Salvia hispania. Fitoterapia 149:104672. https://doi.org/10.1016/j.fitote.2020.104672
Frij LMT, Frade RFM, Afonso CAM (2011) Isolation, chemical, and biotransformation routes of labdane-type diterpenoids. Chem Rev 111:4418–4452. https://doi.org/10.1021/cr100258k
Ge X, Ye G, Li P, Tang WJ, Gao JL, Zhao WM (2008) Cytotoxic diterpenoids and sesquiterpenoids from Pteris multifida. J Nat Prod 71:227–231. https://doi.org/10.1021/mp0706421
Geuns JMC, Buyse J, Vankeirsbilck A, Temme EHM, Compernollle F, Toppet S (2006) Identification of steviol glucuronide in human urine. J Agr Food Chem 54(7):2794–2798. https://doi.org/10.1021/jf052693e
Ghorbani A, Esmaeilizadeh M (2017) Pharmacological properties of Salvia officinalis and its components. J Tradit Complement Med 7(4):433–440. https://doi.org/10.1016/j.jtcme.2016.12.014
Goyal SK, Samsher, Goyal RK (2010) Stevia (Stevia rebaudiana) a bio-sweeten: a review. Int J Food Sci Nutr 61(1):1–10. https://doi.org/10.3109/09637480903193049
Gross G, Jaccaud E, Huggett AC (1997) Analysis of the content of the diterpenes cafestol and kahweol in coffee brews. Food Chem Toxicol 35(6):547–554
Hanson J, Nichols I, Mukhrish Y, Bagley M (2017) Diterpenoids of terrestrial origin. Nat Prod Rep 34:1233–1243
Higdon JV, Frei B (2007) Coffee and health: a review of recent human research. Crit Rev Food Sci Nutr 46:101–123. https://doi.org/10.1080/10408390500400009
Hu GL, Gao Y, Peng XR, Liu JH, Su HG, Huang YJ, Qiu MH (2020) Lactam ent-kaurane diterpene: a new class of diterpenoids in roasted beans of Coffea arabica. J Agr Food Chem 68(22):6112–6121. https://doi.org/10.1021/acs/jafc.9b08149
Huang Q, Iwamoto Y, Aoki S, Tanaka N, Tajima K, Yamahara J, Takaishi Y, Yoshida M, Tomimatsu T, Tamai Y (1991) Anti-5-hydroxytryptamine 3 effect of galanolactone, diterpenoids isolated from ginger. Chem Pharm Bull 39(2):397–399. https://doi.org/10.1248/cpb.39.397
Huneck S, Yoshimura I (1996) Identification of lichen substances. Springer, Berlin, pp 1–493
Inoue M, Yoshimi I, Sobue T, Tsugane S (2005) Influence of coffee drinking on subsequent risk of hepatocellular carcinoma: a prospective study in Japan. J Natl Cancer Inst 97:293–300. https://doi.org/10.1093/jnci/dji040
Islam MT, Mata AMOF, Aguiar RPS, Paz MFCJ, Alencar MVOB, Ferreira PMP, Melo-Cavalcante AA (2016) Therapeutic potential of essential oils focusing on diterpenoids. Phytother Res 30:1420–1444
Jiang Z, Gao W, Huang L (2019) Tanshinones, critical pharmacological components in Salvia miltiorrhiza. Front Pharmacol 10:202. https://doi.org/10.3389/fphar.2019.00202
Jin YZ, Shi LL, Zhang DP, Wei HY, Si Y, Ma GZ, Zhang J (2019) A review on daphnane-type diterpenoids and their bioactive studies. Molecules 24:1842. https://doi.org/10.3990/molecules24091842
Jones WP, Kinghorn AD (2008) Biologically active natural of the genus Callicarpa. Curr Bioact Compds 4:15–32
Kavitha C, Rajamani K, Vadivel E (2010) Coleus forskohlii: a comprehensive review on morphology, phytochemistry and pharmacological aspects. J Med Plants Res 4(4):278–285
Kawagishi H, Shimada A, Shirai R, Okamoto K, Ojima F, Sakamoto H, Ishiguro Y, Furukawa S (1994) Erinacines a, band C, strong stimulators of nerve growth factor (NGF)-synthesis, from the mycelia of Hericium erinaceum. Tetrahedron Lett 35:1569–1572
Kawagishi H, Simada A, Shizuki K, Mori H, Sakamoto H, Furukawa S (1996a) Erinacine D. a stimulator of NGF-synthesis from the mycelia of Hericium erinaceum. Heterocycl Comm 2:51–54
Kawagishi H, Simada A, Shizuki K, Mori H, Sakamoto H, Furukawa S (1996b) Erinacines E, F, and G, stimulators of nerve growth factor (NGF)-synthesis, from the mycelia of Hericium erinaceum. Tetrahedron Lett 41:7399–7402
Kawagishi H, Masui A, Tokuyama S, Nakamura T (2006) Erinacines J and K from the mycelia of Hericium erinaceum. Tetrahedron 62:8463–8466
Kenmoku H, Sassa T, Kato N (2000) Isolation of erinacine P, a new parental metabolite of cyathane-xylosides, from Hericium erinaceum and its biomimetic conversion into erinacines a and B. Tetrahedron Lett 41:4389–4393
Kenmoku H, Kato N, Shimada M, Omoto M, Mori A, Mituhashi W, Sassa T (2001) Isolation of (−)-cyatha-3, 12-diene, a common biosynthetic intermediate of cyathane diterpenoids, from an erinacine-producing basidiomycete, Hericium erinaceum. Tetrahedron Lett 42:7439–7422
Kenmoku H, Shima T, Toyomasu T, Kato N, Sassa T (2002) Erinacine Q, a new erinacine from Hericium erinaceum, and its biosynthetic route to erinacine C in the basidiomycete. Biosci Biotechnol Biochem 66(3):571–575
Kenmoku H, Tanaka K, Okada K, Kato N, Sassa T (2004) Erinacol (cyatha-3,12-dien-14β-ol) and 11-O-acetylcyathin A3, new cyathane metabolites from an erinacine Q-producing Hericium erinaceum. Biosci Biotechnol Biochem 68:1786–1789
Kinghorn AD, Chin YW, Pan L, Jia Z (2010) Natural products as sweeteners and sweetness modifiers. In: Lin HW, Mander L (eds) Comprehensive natural products II. Chemistry and biology, vol 3. Elsevier, Oxford, pp 269–315
Kingston DGI, Molinero AA, Rimoldi JM (1993) The taxane diterpenoids. In: Herz W, Grisebach H, Kirby GW, Moore RE, Steglich W, Tamm C (eds) Progress in the chemistry of organic natural products, vol 61. Springer, Vienna, pp 1–206
Kurzrock T, Speer K (2001) Diterpenes and diterpene esters in coffee. Food Rev Int 17(4):433–450
Leandro LM, Vargas FS, Barbosa PCS, Neves JKO, Silva JA, Veiga VF Jr (2012) Chemistry and biological activities of terpenoids from copaiba (Copaifera spp.) oleoresins. Molecules 17:3866–3889. https://doi.org/10.3390/molecules17043866
Li ZL, Yang LM, Zhao Y, Wang RR, Zu G, Zheng YT, Peng LY, Cheng X, Zhao QS (2007) Tetranorclerodanes and clerodane-type diterpene glycosides from Dicranopteris dichotoma. J Nat Prod 70:265–268
Li R, Morrris-Natschke S, Lee KH (2016) Review Clerodane diterpenes: sources, structures, and biological activities. Nat Prod Rep 33:1166–1226
Liu M, Wang WG, Sun HD, Pu JX (2017) Diterpenoids from Isodon species: an update. Nat Prod Rep 34:1090–1140. https://doi.org/10.1039/c7np00027h
Lukhoba CW, Simmonds MSJ, Paton AJ (2006) Plectranthus: a review of ethnobotanical uses. J Ethnopharmcol 103:1–24. https://doi.org/10.1016/j.jep.2005.09.011
Ma BJ, Shen JW, Yu HY, Ruan Y, Wu TT, Zhao W, Ting-Ting W, Zhao X (2010) Hericenones and erinacines: stimulators of nerve growth factor (NGF) biosynthesis in Hericium erinaceus. Mycology 1(2):92–98. https://doi.org/10.1080/21501201003735556
Mafu S, Zerbe P (2018) Plant metabolism for manufacturing the biopharmaceuticals of tomorrow: prospects and challenges. Phytochem Rev 17:113–130. https://doi.org/10.1007/s11101-017-9513-5
Malek SNA, Lee GS, Hong SL, Yaacob H, Wahab NB, Weber JFF, Shah SAA (2011) Phytochemical and cytotoxic investigations of Curcuma mangga rhizomes. Molecules 16(6):4539–4548
Martinez MR, Medina FG, Marrero JG, Robles SO (2014) Biotransformation of diterpenes. RSC Adv 4:10627. https://doi.org/10.1039/c3ra45146a
Monteiro AF, Seidl C, Severino VGP, Cardoso CL, Castro-Gamboa I (2017) Biotransformation of labdane and halimane diterpenoids by two filamentous fungi strains. R Soc Open Soc 4:170854. https://doi.org/10.1098/rsos.170854
Nakanishi K (2005) Terpene trilactones from Ginkgo biloba: from ancient times to the 21st century. Bioorg Med Chem 13:4987–5000. https://doi.org/10.1016/j.bmc.2005.06.014
Ndoile MM (2020) Isodon diterpenoids, derivatives and their pharmacological potentials-a review. Tanz J Sci 46(1):171–189
Noma Y, Asakawa Y (2020) Biotransformation of monoterpenoids by microorganisms, insects, and mammals. In: Baser HC, Buchbauer G (eds) Handbook of essential oils. Science, technology, and application, 3rd edn. CRC Press, Boca Raton, pp 613–767
Novaes FJM (2018) Coffee diterpenes: before harvesting the bean to you cup. Nutri Food Sci Int J 7(2):555706. https://doi.org/10.19080/NFSIJ.2018.07.555706
Palmeira SF Jr, Conserva LM, Filho MB (2006) Clerodane diterpenes from Croton species: distribution and a compilation of their 13C NMR spectral data. Nat Prod Commun 1(4):319–336
Quang DN, Hashimoto T, Asakawa Y (2006) Inedible mushrooms, a good source of biologically active compounds. J Chem Rec 6:77–99
Rajabalian S (2008) Methanolic extract of Teucrium polium L. potentiates cytotoxic and apoptotic effects of cancer drugs of vincristine and vinblastine and doxorubicin against a panel of cancerous cell lines. Exp Oncol 30:133–138
Rajamanikyam M, Vadlapudi V, Upadhyayula SM (2017) Aspergillus mediated biotransformation: a review. Res J Pharm Biol Chem Sci 8(2):828–840
Rajkumari S, Sanatombi K (2017) Nutritional value, phytochemical composition, and biological activities of edible Curcuma species: a review. Int J Food Prop 20(Suppl 3):S-2668–S-2687. https://doi.org/10.1080/10942912,2017.1387556
Remy S, Litaudon M (2019) Macrocyclic diterpenoids from Euphorbiacae as a source of potent and selective inhibitors of Chikungunya virus replication. Molecules 24:2336. https://doi.org/10.3390/molecules24/22236
Ren Y, Wang C, Xu J, Wang S (2019) Cafestol and kahweol: a review on their bioactivities and pharmacological properties. Int J Mol Sci 20(17):4238. https://doi.org/10.3390/ijms20174238
Rivera D, Obon C (1995) The ethnopharmacology of Madeira and Porto Santo Islands, a review. J Ethnopharmacol 46:73–93
Roos B, Weg G, Urgert R, Bovenkamp P, Charrier A, Katan MB (1997) Levels of cafestol, kahweol, and related diterpenoids in wild species of the coffee plant Coffea. J Agr Food Chem 45:3065–3069
Roos B, Caslake MJ, Stalenhoef AFH, Bedford D, Demacker PNM, Katan MB, Packard CJ (2001) The coffee diterpene cafestol increases plasma triacyl glycerol increasing the production rate of large VLDL apolipoprotein B in healthy normolipidemic subjects. Am J Clinic Nutr 73:45–52. https://doi.org/10.1093/ajcn/73.1.45
Suffness M (1995) In: Saffness M (ed) Taxol® science and applications. CRC Press, Boca Raton, pp 1–426
Salatino AS, Salatino MLF, Negri G (2007) Traditional uses, chemistry and pharmacology of Croton species (Euphorbiaceae). J Braz Chem Soc 18(1). https://doi.org/10.1590/S0103-50532007000100002
Shigemori H, Kobayashi J (2004) Biological activity and chemistry of toxoids from the Japanese yew, Taxus cuspidata. J Nat Prod 67:245–256. https://doi.org/10.1021/np030346y
Silva EO, Furtado NAJC, Aleu J, Collado IG (2013) Terpenoid biotransformations by Mucor species. Phytohem Rev 12:857–876. https://doi.org/10.10007/s1101-013-9313-5
Socolsky C, Asakawa Y, Bardon A (2007) Diterpenoids glycosides from bitter fens Gleichenia quadripartite. J Nat Prod 70(12):1837–1845
Strømgaard K, Nakanishi K (2004) Chemistry and biology of terpene trilactones from Ginkgo biloba. Angew Chem Int Ed 43:1640–1658. https://doi.org/10.1002/anie.200300601
Sultana N, Saify ZS (2012) Enzymatic biotransformation of terpenes as bioactive agents. J Enzym Inhibit Med Chem 28(6):1113–1128. https://doi.org/10.3109/14756366.2012.727411
Sun HD, Huang SX, Han QB (2006) Diterpenoids from Isodon species and their biological activities. Nat Prod Rep 23(5):673–698. https://doi.org/10.1039/b604174d
Trindade R, Silva JA, Setzer WN (2018) Copaifer of neotropics: a review of the phytochemistry and pharmacology. Int J Mol Sci 19:1511. https://doi.org/10.3390/ijms1901511
Trinh K, Andrews L, Krause J, Hanak T, Lee D, Gelb M, Pallanck L (2010) Decaffeinated coffee and nicotine-free tobacco provide neuroprotection in Drosphila models of Parkinson’s disease through an NRF2-dependent mechanism. J Neurosci 30(16):5525–5532. https://doi.org/10.1523/NEUROSCI4777-09.2010
Urgert R, Katan MB (1997) The cholesterol-raising factor from coffee beans. Ann Rev Nutri 17:305–324. https://doi.org/10.1146/annurev.nutr.17.1.305
Van Cruchten STJ, van Waart DR, Kunne C, Hooiveld GJE, Boekschoten MV, Katan MB, Oude Elferink RPJ, Witkamp RF (2010) Absorption, distribution, and biliary excretion of cafestol, a potent cholesterol-elevating compounds in unfiltered coffees, in mice. Am Soc Pharmacol Exper Therap 38(4):638–640
Vanitha V, Umadevi KJ, Vijayalakshmi K (2011) Determination of bioactive components of Annona squamosal L leaf by GC-MS analysis. Int J Pharm Sci Drug Res 3(4):309–321
Vargas FS, Almeida PDO, Arahha ESP, Boleti APA, Newton P, Vasconcellos MC, Veirgas VF Jr, Lima ES (2015) Biological activities and cytotoxicity of diterpenes from Copaifera spp. Oleoresins Molecules 20:6194–6210. https://doi.org/10.3390/molcules20046194
Vasas A, Hohman J (2014) Euphorbia diterpenes: isolation, structures, biological activity, and syntheses (2008–2012). Chem Rev 114(17):8579–8612
Vieira-Junior GM, Dutra LA, Ferreira PM, Moraes MOD, Lotufo LVC, Pessoa CDO, Torres RB, Boralle N, Bolzani VDS, Cavalheiro AJ (2011) Cytotoxic clerodane diterpenes from Casearia rupestris. J Nat Prod 74:776–781
Wang DI, Liang Y, Chen WD, Xie L, Wang GJ, Liu XD (2008) Identification of ginkgolide B metabolites in urine and rat liver cytochrome P450 enzymes responsible for their formation in vitro. Acta Pharmacol Sin 29(3):376–384. https://doi.org/10.1111/j.1745-7254.2008.00758.x
Wang YF, Shi QW, Dong N, Kiyota H, Gu YC, Cong B (2011) Natural Taxanes: developments since 1828. Chem Rev 111:7652–7709. https://doi.org/10.1021/cr100147u
Wani MC, Taylor HL, Wall ME, Coggon P, McPhall AT (1971) Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 93(9):2325–2327
Widyowati R, Agil M (2018) Chemical constituents of bioactivities of several Indonesian plants typically used in Jamu. Chem Pharm Bull 66(5):506–518. https://doi.org/10.1111/j.1745-7254.2008.00758.x/cpb.c17-00983
Wu YC, Hung YC, Chang FR, Cosentino M, Wang HK, Lee KS (1996) Identification of ent-16b,17-dihydroxykauran-19-oic acid as an anti-HIV principle and isolation of the new diterpenoids annosquamosins a and B from Annona squamosa. J Nat Prod 59:635–637
Wu YB, Ni ZY, Shi QW, Dong M, Kiyota H, Gu YC, Cong B (2012) Constituents from Salvia species and their biological activities. Chem Rev 112:5967–6026
Xia X, Li B, Hou Y, Zhang J, Yan X (2020) Diterpenes from the marine brown algae of the genus Dilophus. Nat Prod Commun 15(2):1–14. https://doi.org/10.1177/1934578X20907786
Xiang Z, Liu X, Li X (2015) Chemical constituents of Rabdosia japonica var. glaucocalyx. Pharm Chem J 48(12):806–816. https://doi.org/10.1007/s11094-015-1200-5
Xu WH, Liu WY, Liang Q (2018) Chemical constituents from Croton species and their biological activities. Molecules 23(9):2333. https://doi.org/10.3390/molecules23092333
Yilmaz A, Boga M, Topcu G (2016) Novel terpenoids with potential anti-Alzheimer activity from Nepeta obtusicrena. Rec Nat Prod 10(5):530–541
Yoshikawa K, Kudo N, Tanaka M, Nakano T, Sibata H, Aragaki N, Higuchi T, Hashimoto T (2008) Novel abietane diterpenoids and aromatic compounds from Cladonia ragiferina and their antimicrobial activity against antibiotics resistant bacteria. Chem Pharm Bull 56(1):89–92
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Asakawa, Y., Kenmoku, H. (2021). Dietary Diterpenoids. In: Xiao, J., Sarker, S.D., Asakawa, Y. (eds) Handbook of Dietary Phytochemicals. Springer, Singapore. https://doi.org/10.1007/978-981-13-1745-3_18-1
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