A review of 13C NMR spectra of drimane sesquiterpenes

Trends in Phytochemical Research

مقاله 8، دوره 3، شماره 3، آذر 2019، صفحه 147-180   

نوع مقاله: Review article

نویسنده

Sylvia Awino Opiyo^*

Department of Physical and Biological Sciences, Murang’a University of Technology, P. O. Box 75-10200, Murang’a, Kenya

چکیده

Drimane sesquiterpenes are important group of phytochemicals with a wide range of medicinal properties including antibacterial, antifungal, anti-inflammatory, antioxidant, antiplasmodial, antileishmanial, molluscicidal, antifeedant and insecticidal features. Due to their wide range of medicinal activities, scientists are prompted to continuously search for novel drimane sesquiterpenes since most of the currently available anti-infective agents have drawbacks such as drug resistance and side effects. Structure determination of new compounds relies on accurate interpretation of spectroscopic data which is quite challenging but can be simplified by comparison with the data of known related compounds from the reliable databases. A large number of drimane sesquiterpenes have been examined by 13C NMR spectroscopy but such data are scattered in the literature making it hard for researchers to use them. This paper provides a review on previously reported drimane sesquiterpenes and a compilation of their 13C NMR data. It also provides a brief discussion on the substituent effect on the 13C shielding of the drimane sesquiterpenes.

کلیدواژه‌ها

Chemical shift؛ 13C NMR data؛ Drimane sesquiterpenes؛ Shielding؛ Structure determination

مراجع

Aasen, A.J., Nishida, J., Enzell, C.D., Appel, H.H., 1977. The structure of (11xi, 12xi)-11,12-di (7-drimen11-oxy)-11,12-epoxy-7-drimene. Acta Chem. Scand. 31B, 51-55.

Appendino, G., Ozen, H.C., Tagliapietra, S., Cisero, M., 1992. Coumarins from Heptaptera anisoptera. Phytochemistry 31(9), 3211-3213.

Aranda, G., Moreno, L., Cortes, M., Prange, T., Maurs, M., Azerad, D., 2001.A new example of 1α-hydroxylation of drimanic terpenes through combined microbial and chemical processes. Tetrahedron57, 6051-6056.

Ayer, W.A., Craw, P.A., 1989. Metabolites of the fairy ring fungus, Marasmius oreades. Part 2.Norsesquiterpenes, further sesquiterpenes, and agrocybin. Can. J. Chem. 67,1371-1380.

Barrero, A.F., Manzaneda, E.A., Altearejos, J., Salido, S., Ramos, J.M., Simmonds, M.S.J., Blaney, W.M., 1995. Synthesis of biologically active drimanes and homodrimanes from (-)-sclareol. Tetrahedron 51, 7435-7450.

Barrero, F., Cortés, M., Manzaneda, E.A., Cabrera, E., Chahboun, R., Lara, M., Rivas, A.R., 1999. Synthesis of 11,12-epoxydrim-8,12-en-11-ol, 11,12-diacetoxydrimane, and warburganal from (−) -sclareol. J. Nat. Prod. 62, 1488-1491.

Bastos, J.K., Kaplan, M.A.C., Gottlieb, O.R., 1999. Drimane-type sesquiterpenoids as chemosystematic markers of Canellaceae. J. Braz. Chem. Soc. 10, 136-139.

Benites, J., Preite, M.D., Cortes, M., 2001.Conversion of (+)-confertifolin into 11,12-bisnordriman-9-one and (+)-8αH,9αH-11,12-dacetoxydriname. Synth. Commun. 31, 1347-1354.

Butler, M.S., Capon, R.J., 1993. Beyond polygodial: New drimane sesquiterpenes from a Southern Australian marine sponge, Dysidea sp. Aust. J. Chem. 46, 1255-1267.

Chaudhary, S., Thomas,V., Todaro, L., Le Gendre, O., Pecic, S., Harding W.W., 2008. New drimane sesquiterpenoids from Tidestromiao blongifolia. Nat. Prod. Commun. 3, 1747-1750.

Chen, Z., Dong, Z., Wen, J., Feng, T., Liu J.A., 2016. New sesquiterpene from the endophytic fungus Nigrospora sphaerica. Rec. Nat. Prod.10, 307-310.

Claudino, V.D.,da Silva, K.C., Filho, V.C., Yunes, R.A., Monache, F.D.,Giménez, A.,Salamanca, E.,Gutierrez-Yapu, D., Malheiros, A., 2013. Drimanes from Drimys brasiliensis with leishmanicidal and antimalarial activity. Mem. Inst. Oswaldo Cruz 108(2), 140-144.

Cuellar, M., Moreno, L., Preite, M., 2003. Regioselective oxidative fragmentation of drimanic terpene alcohols: a short, easy and efficient access to natural and synthetic 11-nordrimane terpene derivatives. ARKIVOC 10, 169-177.

Cunha, F., Fröde, T., Mendes, G., Malheiros, A., Filho, V.C., Yunes, R.A., Calixto, J.B., 2001. Additional evidence for the anti-inflammatory and anti-allergic properties of the sesquiterpene polygodial. Life Sci. 70, 159-169.

Dacunto, M., 2012. Total Synthesis of Terpenoidic Unsatured Dialdehydes and Evaluation of their activity towards TRP Receptors. Ph.D. Thesis, Università Degli Studi di Salerno, Salerno, Italy.

De Bernardi, M., Mellerio, G., Vidari, G., Vita-Finzi, P., Fronza, G., 1980. Fungal metabolites. Part 5. Uvidins, new drimane sesquiterpenes from Lactarius uvidus Fries. J. Chem. Soc. Perkin Transactions. 1, 221-226.

Delgado, V., Armstrong, V., Cortésa, M., Barrero, A.F., 2008. Synthesis of racemic and chiral albicanol, albicanyl acetate and cyclozonarone: Cytotoxic activity of ent-cyclozonarone. Braz. Chem. Soc. 19, 1258-1263.

Derita, M., Montenegro, I., Garibotto, F., Enriz, R., Cuellar, M., Zacchino, S., 2013.Structural requirements for the antifungal activities of natural drimane sesquiterpenes and analogues, supported by conformational and electronic studies. Molecules 18, 2029-2051.

Ding, J.H., Ding, Z.G., Chunyu, W.X., Zhao, J.Y., Wang, H.B., Liu, S.W., Wang, F., 2016. Three new drimane sesquiterpenoids from cultures of the fungus Penicillium sp. J. Asian Nat. Prod. Res. 19, 780-785.

Echeverri, F., Luis, J.G., Torres, F., Quinones, W., Alzate, F., Cardona, G., Archbold, R., Roldan, J., Lahlou, E.H., 1997.Danilol, a new drimane sesquiterpene from Polygonum punctatum leaves. Nat. Prod. Lett. 10, 295-301.

Felix, S., Sandjo, L.P., Opatz, T., Erel, G., 2014.Anti-inflammatory drimane sesquiterpene lactones from an Aspergillus species. Bioorg. Med. Chem. 22, 2912-291.

Fukuyama, Y., Sato, T., Miura, I., Asakawa, Y., 1985. Drimane-type sesqui- and norsesquirterpenoids from Polygonum hydropiper. Phytochemistry 24, 1521-1524.

Gaspar, H., Cutignano, A., Ferreira, T., Calado, G., Cimino, G., Fontana, A., 2008. Biosynthetic evidence supporting the generation of terpene chemodiversity in marine mollusks of the genus Doriopsilla.J. Nat. Prod. 71(12), 2053-2056.

Gören, N., Ulubelen, A., 1988. A sesquiterpene-coumarin ether and an acetylenic compound from Tanacetum heterotomum. Phytochemistry 27(5), 1527-1529.

Grabley, S., Thiericke, R., Zerlin, M., Goert, A., Phillips, S., Zeeck, A., 1996.New albrassitriols from Aspergillus sp. (FH-A 6357). J. Antibiot. 49, 593-595.

 Grace, M.H., Lategan, C.A., Mbeunkui, F., Graziose, R.T., Smith, P.J., Raskin, I., Lila, M.A., 2010. Antiplasmodial and cytotoxic activities of drimane sesquiterpenes from Canella winterana. Nat. Prod. Commun. 5(12), 1869-1872.

Harinantenaina, L., Matsunami, K., Otsuka, H., Kawahata, M., Yamaguchi, K., Asakawa, Y., 2008.Secondary metabolities of Cinnamosma madagascariensis and their α-glucosidase inhibitory properties. J. Nat. Prod. 71, 123-126.

Hashimoto, T., Tori, M., Asakawa, Y., 1989. Drimane-type sesquiterpenoids from the liverwort Makinoa crispate. Phytochemistry 28(12), 3377-3381.

He, D., Slebodnick, C., Rakotondraibe, L.H., 2017. Bioactive drimane sesquiterpenoids and aromatic glycosides from Cinnamosma fragrans. Bioorg. Med. Chem. Lett. 27(8), 1754-1759.

He, J.B., Feng, T., Xhang, S., Dong, Z.J., Li, Z.H., Zhu, H.J., Liu, J.K., 2014.Seven new drimane-type sesquiterpenoids from cultures of fungus Phellius tuberculosis. Nat. Prod. Bioprospect. 4, 21-25.

He, J.B., Tao, J., Miao, X.S., Bu,W., Zang, S., Dong, Z.J., Li, Z.H., Feng, T., 2015. Seven new drimane-type sesquiterpenoids from cultures of fungus Laetiporus sulphureus. Fitoterapia 102, 1-6.

Hlubucel, J.R, Aasen A.J., Almqvist, S.O., Enzell, C.R., 1974. Tobacco Chemistry 25. Two new drimane sesquiterpene alcohols from Greek Nicotiana tabacum L. Acta Chem. Scand. B28, 289.

Inocente, E.A., Shaya, M., Acosta, N., Rakotondraibe, L.H., Piermarini, P.M., 2018.A natural agonist of mosquito TRPA1 from the medicinal plant Cinnamosma fragrans that is toxic, antifeedant, and repellent to the yellow fever mosquito Aedes aegypti. PLoS Negl. Trop. Dis. 12, e0006265.

Iranshahi, M., Barthomeuf, C., Bayet-Robert, M., Chollet, P., Davoodi, D., Piacente, S., Rezaee, R., Sahebkar, A., 2014. Drimane-type sesquiterpene coumarins from Ferula gummosa fruits enhance doxorubicin uptake in doxorubicin-resistant human breast cancer cell line. J. Tradit. Complement. Med. 4(2), 118-125.

Jacobsson, U., Muddathir A., 1992. Four biologically active sesquiterpenes of the drimane type isolated from Polygonum glabrum. Phytochemistry 31(12), 4207-4211.

Jansen, B.J.M., 1993. Total synthesis of insect antifeedant drimane sesquiterpenes, Ph.D. Thesis, Agricultural University, Wageningen.

Jansen, B.J.M., de Groot, A., 2004.Occurrence, biological activity and synthesis of drimane sesquiterpenoids. Nat. Prod. Rep. 21, 449-477.

Jeruto, P., Arama, P., Anyango, B., Nyunja, R., Taracha, C.,Opiyo S., 2017. Morphometric study of Senna didymobotrya (Fresen.) H. S. Irwin and Barneby in Kenya. J. Nat. Sci. Res. 7(6), 54-69.

Justicia, J., Oltra, J.E., Barrero, A.F., Guadano, A., Gonzalez-Coloma A., Cuerva, J.M., 2005. Total synthesis of 3-hydroxydrimanes mediated by titanocene (III)- evaluation of their antifeedant activity. Eur. J. Org. Chem.2005, 712-718.

Kinoshita, M., Ohtsuka, M., Nakamura, D., Akita, H., 2002. First synthesis of (+)-α - and (+)-γ -polypodatetraenes. Chem. Pharm. Bull. 50, 930-934.

Kioy, D., Gray, A.I., Waterman, P.G., 1989.Further drimane sesquiterpenes from the stem bark of Canella winterana. J. Prod. Nat. 52, 174-177.

Kioy, D., Gray, A.I., Waterman, P.G., 1990. A comparative study of the stem-bark drimane sesquiterpenes and leaf volatile oils of Warburgia ugandensis and W. stuhlmannii. Phytochemistry 29, 3535-3538.

Kisiel, W., Stojakowska, A., 2002. A sesquiterpene coumarin ether from transformed roots of Tanacetum parthenium. Phytochemistry 46(3), 515-516.

Kuang, C., Jing, S.X., Liu, Y., Luo, S.H., Li, S.H., 2016.Drimane sesquiterpenoids and isochromone derivative from the endophytic fungi Pestalotiopsis sp. M-23. Nat. Prod. Bioprospect. 6, 155-160.

Kubo, I., Matsumoto, T., Kakooko, A.B., Mubiru, N.K., 1983. Structure of mukaadial, a molluscicide from Warburgia plants. Chem. Lett. 7, 979-980.

Kubo, I., 1995.Antifungal sesquiterpene dialdehydes from the Warburgia plants and their synergists. In: Atta-ur-Rahman, Ed. Studies in Natural Products Chemistry: Structure and Chemistry (part D). Amsterdam: Elsevier Science, pp. 233-249.

Kubo, I., Nakanishi, K., 1977.Insect Antifeedants and Repellents from African Plants. In: Host Plant Resistance to Pest. Hedin P.A., Ed., ACS Symposium Series 62. American Chemical Society, Washington DC. pp. 165-178.

Kuchkova, K.I., Aryku A.N., Dragalin I.P., Vlad P.F., 2005. Synthesis of drim-9 (11)-en-8α-and-8β-ols from drimenol. Chem. Nat. Compd. 41, 190-193.

Lagnel, B.M.F., Morin, C., De Groot, A., 2000.Synthesis of drimanes from (+)-larixol. Synthesis 13, 1907-1916.

Lee, C.L., Chiang, L.C., Cheng, L.H., Liaw, C.C., El-Razek, M.H.A., Chang, F.R., Wu, Y.C., 2009. Influenza A (H₁N₁) antiviral and cytotoxic agents from Ferula assa-foetida. J. Nat. Prod. 72(9), 1568-1572.

Liu, M.S., Liu, C., Zhang, X.P., Sheng, L., Zhang, J.Q., Kang, S.L., 2010.Two new drimane sesquiterpenoids from compound changweikang and their inhibitory activity against nitric oxide production. Chem. Pharm. Bull. 58, 1224-1226.

Lu, Z., Wang, Y., Miao, C., Liu, P., Hong, K., Zhu, W., 2009.Sesquiterpenoids and benzofuranoids from the marine-derived fungus Aspergillus ustus 094102. J. Nat. Prod. 72, 1761-1767.

Ludwiczuka, A., Gradsteinb, S.B., Nagashima, F., Asakawa, Y., 2011. Chemosystematics of Porella (Marchantiophyta, Porellaceae). Nat. Prod. Commun. 6(3), 315-321.

Madikane, V.E., Bhakta, S., Russell, A.J., Campbell, W.E., Claridge, T.D.W., Elisha, G., Davies, S.G.D., Smith, P., Sim, E., 2007. Inhibition of mycobacterial arylamine N-acetyltransferase contributes to anti-mycobacterial activity of Warburgia salutaris. Bioorg. Med. Chem.15, 3579-3586.

Mahato, S.B., Kundu, A.P. 1994.¹³C NMR spectra of pentacyclic triterpenoids - a compilation and some salient features. Phytochemistry 37, 1517-1575.

Mahmoud, I.I., Kinghorn, A.D., Cordell, G.A., Farnsworth, N.R., 1980. Potential anticancer agents XVI. Isolation of bicyclofarnesane sesquiterpenoids from Capsicodndron dinisii. J. Nat. Prod. 43, 365-371.

Mashimbye, M.J., Maumela, M.C., Drewes, S.E., 1999.A drimane sesquiterpenoid lactone from Warburgia salutaris. Phytochemistry 51, 435-438.

Mathie, K., Lainer, J., Spreng, S., Dawid, C., Andersson, D.A., Bevan, S., Hofmann, T., 2017. Structure-pungency relationships and TRP channel activation of drimane sesquiterpenes in Tasmanian pepper (Tasmannia lanceolata). J. Agric. Food Chem. 65(28), 5700-5712.

Meng, J., Li, Y.Y., Ou, Y.X., Song, L.F., Lu, C.H., Shen Y.M., 2011. New sesquiterpenes from Marasmius cladophyllus. Mycology 2, 30-36.

 Mohammadhosseini, M., 2017. The ethnobotanical, phytochemical and pharmacological properties and medicinal applications of essential oils and extracts of different Ziziphora species. Ind. Crops Prod. 105, 164-192.

Mohammadhosseini, M., Sarker, S.D., Akbarzadeh, A., 2017. Chemical composition of the essential oils and extracts of Achillea species and their biological activities: A review. J. Ethnopharmacol. 199, 257-315.

Mohammadhosseini, M., Venditti, A., Sarker, S.D., Nahar, L., Akbarzadeh, A., 2019. The genus Ferula: Ethnobotany, phytochemistry and bioactivities - A review. Ind. Crops Prod. 129, 350-394.

Montagnac, A., Martin, M.T., Debitus, C., Païs, M., 1996.Drimane sesquiterpenes from the sponge Dysìdea fusca. J. Nat. Prod.59, 866-868.

Montenegro, I., Corral, S.D., Napal, G.N.D., Carpinella, M.C., Mellado, M., Madrid, A.M., Villena, J., Palaciosa, S.M., Cuellar M.A., 2018a. Antifeedant effect of polygodial and drimenol derivatives against Spodoptera frugiperda and Epilachna paenulata and quantitative structure-activity. Pest Manag. Sci. 74, 1623-1629.

Montenegro, I., Madrid, A.., Cuellar, M., Seeger, M. , Alfaro , J.F., Besoain, X. , Martínez J.P., Ingrid Ramirez, I., Olguín, Y., Miryam Valenzuela, M., 2018b. Biopesticide activity from drimanic compounds to control tomato pathogens. Molecules 23, 2053, doi:10.3390/molecules23082053

Montenegro, I., Pino, L., Werner, E., Madrid, A., Espinoza, L., Moreno, L., Villena, J., Cuellar, M., 2013.Comparative study on the larvicidal activity of drimane sesquiterpenes and nordrimane compounds against Drosophila melanogaster til-til. Molecules 18, 4192-4208.

Montenegro, I., Tomasoni, G., Bosio, C., Quiñones, N., Madrid, A., Carrasco, H., Olea, A., Martinez, R., Cuellar, M., Villena, J., 2014.Study on the cytotoxic activity of drimane sesquiterpenes and nordrimane compounds against cancer cell lines. Molecules 19, 18993-19006.

Muñoz, O., Gutierrez, M., Gonzalez, R., Hammann, S., Vetter, W., 2015.Antifungal and insecticidal properties of the phytoconstituents of Drimys winteri (Winteraceae) growing in Chiloe Island (Chile). Nat. Prod. Chem. Res. 3, 4-9.

Nakanishi, K., Kubo, I., 1978.Studies on warburganal, muzigadal and related compounds. J. Chem.16, 28-31.

Nyaba, Z.N., Murambiwa, P., Opoku, A.R., Mukaratirwa, S., Shode, F.O., Simelane, M.B.C., 2018.Isolation, characterization, and biological evaluation of a potent anti-malarial drimane sesquiterpene from Warburgia salutaris stem bark. Malar. J. 17, 296-303.

Ochieng, C.O., Ishola, I.,Opiyo, S.A., Manguro, L.O.A., Owuor, P.O., Wong, K.C. 2013. Phytoecdysteroids from the stem bark of Vitex doniana and their anti-inflammatory effects. Plant Medica. 79, 52-59.

Ochieng, C.O., Opiyo, S.A., Mureka, E.W., Ishola, I., 2017. Cyclooxygenase inhibitory compounds from Gymnosporia heterophylla aerial parts. Fitoterapia 119, 168-174.

Ochung’, A.A., Manguro, L.O.A., Owuor, P.O., Jondiko, J.I.O., Nyunja, R.A., Akala, H., Mwinzi, P., Opiyo, S.A., 2015. Bioactive carbazole alkaloids from Alysicarpus Ovalifolius (Schumach). J. Korean. Soc. Appl. Biol. Chem., 58(6), 839-846.

Ochung’, A.A., Owuor, P.O., Manguro, L.O.A., Ishola, I.O., Nyunja, R.A., Ochieng, C.O., Opiyo, S.A., 2018. Analgesics from Lonchocarpus eriocalyx Harms. Trends Phytochem. Res. 2(4), 253-260.

Odyek, O., Olila, D., Albrecht, C., Dagne, E., 1993. Muzigadial, a cytotoxic sesquiterpine from Warburgia ugandensis. Proceedings of the 5^th NAPRECA Symposium on Natural Products, September19 - 23, 1993, Antananarivo Madagascar, p. 160.

Ohloff, G., Giersch, W., 1985.Structure-activity relationships in odor perception of drimane derivatives, CCACAA, 58, 491-509.

Opiyo, S.A., Manguro, L.A.O., Owuor, P.O., Ateka, E.M., 2017. Triterpenes from Elaeodendron schweinfurthianum and their antimicrobial activities against crop pathogens. Am. J. Chem. 7(3), 97-104.

Opiyo, S.A., 2011.Development of a Multiplex PCR Technique for Simultaneous Detection of Sweet Potato Viruses and Evaluation of Traditional Medicinal Plant Extracts for Antimicrobial Activity Against the Crop Pathogens. Ph.D. Thesis, Maseno University, Kenya.

Opiyo, S.A., Manguro, L.O.A., Okoth, D.A., Ochung, A.A., Ochieng, C.O., 2015.Biopesticidal extractives and compounds from Warburgia ugandensis against maize weevil (Sitophilus zeamais). Nat. Prod. J. 5, 236-243.

Opiyo, S.A., Manguro, L.O.A., Owuor P.O., Ateka, E.M., Lemmen, P., 2011. 7α-Acetylugandensolide and antimicrobial properties of Warburgia ugandensis extracts and isolates against sweet potato pathogens. Phytochem Lett. 4, 161-165.

Panasenko A., Gorincioi E.C., Aricu A.N., Barcari E.A., Deleanu K., Vlad PF., 2004. ¹H and ¹³C NMR spectra of some drimanic sesquiterpenoids. Russ. Chem. Bull. Int. Ed. 53, 2700-2705.

Paul, V.J., Seo, Y., Cho, K.W., Rho, J.R., Shin, J., Bergguist, P.R.J., 1997.Sesquiterpenoids of the drimane class from a sponge of the genus Dysidea. J. Nat. Prod. 60, 1115-1120.

Pittayakhajonwut, P., Dramae, A., Intaraudom, C., Boonyuen, N., Nithithanasilp, S., Rachtawee, P., Laksanacharoen, P., 2011.Two new drimane sesquiterpenes, fudecadiones A and B, from the soil fungus Penicillium sp. BCC 17468. Planta Med. 77, 74-76.

Rajab, M.S., Ndegwa, J.S.,2000.11α-Hydroxy muzigadiolide, a novel drimane sesquiterpenes from the stem bark of Warburgia ugandensis. Ethiopia Chem. Soc. Bull. 14, 45-49.

Ramirez, H.E., Cortes, M.M., Agosin, E., 1993.Bioconversion of drimenol into 3β-hydroxydrimanes by Aspergillus niger. effect of culture additives. J. Nat. Prod. 56, 762-764.

Reddy, P.P., Tiwari, A.K., Rao, R.R., Madhusudhana, K., Rao, V.R.S., Ali, A.Z., Babu, K.S., Rao, J.M., 2009. New labdane diterpenes as intestinal α-glucosidase inhibitor from antihyperglycemic extract of Hedychium spicatum (Ham. Ex Smith) rhizomes. Bioorg. Med. Chem. Lett. 19(9), 2562-2565.

Rodríguez, B., Zapata, N., Medina, P., Viñuela, E., 2005.A complete ¹H and ¹³C-NMR data assignment for four drimane sesquiterpenoids isolated from Drimys winteri. Magn. Reson. Chem. 43, 82-84.

Rukachaisirikul, V., Khamthong, N., Sukpondma, Y., Phongpaichit, S., Hutadilok-Towatana, N., Graidist, P., Sakayaroj, J., Kirtikara, K., 2010.Cyclohexene, diketopiperazine, lactone and phenol derivatives from the sea fan-derived fungi Nigrospora sp. PSU-F11 and PSU-F12. Arch.Pharm. Res. 33, 375-380.

Sakio, Y., Hirano, Y.J., Hayashi, M., Komiyama, K., Ishibashi, M., 2001. Dendocarbins A-N, new drimane sequiterpenes from the nudibranch Dendrodoris carbunculosa. J. Nat. Prod. 64, 726-731.

Santoso, B.B., Hernandez, H.P., Rodriguez, E.B., Dalmacio, I.F., 2018.Two antimicrobial compounds drimane sesquiterpene polygodial and 11-hydroxydrim-8-en-7-one from the stem bark of Drimys arfakensis Gibbs. (Winteraceae). Mal. J. Fund. Appl. Sci. 1, 150-154.

Seeram, N.P., Francis, L.S., Needham, O.L., Jacobs, H., McLean, S., Reynolds, W.F., 2003. Drimane and bisabolane sesquiterpenoids from Cinnamodendron corticosum (Canellaceae). Biochem. Syst. Ecol. 31, 637-640.

Shiono, Y., Hiramatsu, F., Murayama, T., Koseki, T., Funakoshi, T., Ueda, K., Yasuda, H., 2007.Two drimane-type sesquiterpenes, strobilactones A and B, from the liquid culture of the edible mushroom strobilurus ohshimae. Z. Naturforsch. 62, 1585-1589.

Skiredj, A., Beniddir, M.A., Evanno, L., Poupon, E., 2016. Mimicking the main events of the biosynthesis of drimentines: synthesis of Δ8’-isodrimentine A and related compounds. Eur. J. Org. Chem.2016, 2954-2958.

Sultana, R., Hossain, R., Adhikari, A., Ali, Z., Yousuf, S., Choudhary, M.I., Ali, M.Y., Zaman, M.S., 2011.Drimane-type sesquiterpenes from Polygonum hydropiper. Planta Med. 77, 1848-1851.

Toshima, H., Oikawa, H., Toyomasu, T., Sassa, T., 2001. Total synthesis of (+)-albicanol and (+)-albicanyl acetate. Biosci. Biotechnol. Biochem. 65, 1244-1247.

Tosun, F., Beutler, J.A., Ransom, T.T., Miski, M., 2019. Anatolicin, a highly potent and selective cytotoxic sesquiterpene coumarin from the root extract of Heptaptera anatolica. Molecules 24, 1153-1160.

Toyota, M., Ooiso, Y., Kusuyama, T., Asakawa, Y., 1994. Drimane-type sesquiterpenoids from the liverwort Diplophyllum serrulatum. Phytochemistry 35(5), 1263-1265.

Vieira, D.R., Amaral, F.M., Maciel, M.C, Nascimento, F.R., Libério, S.A., Rodrigues, V.P., 2014. Plant species used in dental diseases: ethnopharmacology aspects and antimicrobial activity evaluation. J. Ethnopharmacol. 155(3), 1441-1449.

Vlad, P.F., Coltsa, M.N., Aricu, A.N., Ciocarlan, A.G., Gorincioi, E.C., Edu, C.G., Deleanu, C., 2006.Photooxidative dehydrogenation of Δ⁸-drimen-and Δ⁸-11-homodrimen-7-ones into α,α′-dienones. Russ. Chem. Bull. 55, 703-707.

Vlad, P.F., Gorincioi, E.C., Coltsa, M.N., Deleanu, C., 2000. Synthesis of isodrimenin from drim-8-en-7-one. Russ. Chem. Bull. 49(3), 546-548.

Wahlberg, I., Eklund, A.M., Nishida, T., Enzell, C.R., 1981. Tobacco chemistry. Two new nor-drimanes from Greek tobacco. Acta Chem. Scand. B. 35, 307-310.

Wansi, J.D., Sewald, N., Nahar, L., Martin, C., Sarker, S.D., 2019. Bioactive essential oils from the Cameroonian rain forest: A review - Part II. Trends Phytochem. Res. 3(1), 3-52.

Wansi, J.D., Sewald, N., Nahar, L., Martin, C., Sarker, S.D., 2018. Bioactive essential oils from the Cameroonian rain forest: A review - Part I. Trends Phytochem. Res. 2(4), 187-234.

Wayman, K.A., de Lange, P.J., Larsen. L., Sansom, C.E., Perry, N.B., 2010. Chemotaxonomy of Pseudowintera: sesquiterpene dialdehyde variants are species markers. Phytochemistry 71(7), 766-72.

World Health Organization, WHO, 2014. Traditional Medicine Strategy 2014-2023, 2014. DOI: http:llapps.who.int7irislbitstream710665l92455l1l9789241506090eng.pdf?ua=1.

Wube, A.A., Franz, B., Gibbons, S., Asres, K., 2005.Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity. Phytochemistry 66, 2309-2315.

Wube, A.A., Bucar, F., Gibbons S, Asres, K., Rattreay, L., Croft, S.L., 2010.Antiprotozoal activity of drimane and coloratane sesquiterpenes towards Trypanosoma brucei rhodesiense and Plasmodium falciparum in vitro. Phytother.Res. 24, 1468-1472.

Xiao, J., Lin, L., Hu, J., Jiao, F., Duan, D., Zhang, Q., Tang, H., Gao, J., Wang, X., 2017.Highly oxygenated caryophyllene-type and drimane-type sesquiterpenes from Pestalotiopsisadusta, an endophytic fungus of Sinopodophyllum hexandrum. RSC Adv. 7, 29071-29079.

Xu, D., Sheng, Y., Zhou, Z.Y., Liu, R., Leng, Y., Liu, J.K., 2009a. Sesquiterpenes from cultures of the basidiomycete Clitocybe conglobata and their 11b-hydroxysteroid dehydrogenase inhibitory activity. Chem. Pharm. Bull., 57, 433-435.

Xu, M., Litaudon, M., Krief, S., Martin, M.T., Kasenene, J., Kiremire, B., Dumontet, V., Guéritte, F., 2009b. A new drimane-type sesquiterpenoid from Warburgia ugandensis. Molecules 14, 3844-3850.

Yang, X.Y., Feng, T., Ding, J.H., Li, Z.H.,Li, Y., Fan, Q.Y., Liu, J.K., 2013.Two new drimane sesquiterpenoids from cultures of the basidiomycete Trichaptum biforme. Nat. Prod. Bioprospect. 3, 154-157.

Yonemura, Y., Ohyama, T., Hoshino, T., 2012. Chemo-enzymatic syntheses of drimane-type sesquiterpenes and the fundamental core of hongoquercin meroterpenoid by recombinant squalene-hopene cyclase. Org. Biomol. Chem. 10, 440-446.

Zhao, Z.Z., Chen, H.P., Feng, T., Li, Z.H., Liu, J.K., 2014. Four new sesquiterpenoids from cultures of the fungus Phellinidium sulphurascens. Nat. Prod. Bioprospect. 5, 23-28.