Agarwood (Oud) Oil (Aquilaria Malaccensis) 100% Natural Undiluted Frangrance Therapeutic Grade Essential Oil For Aromatherapy 0.33 fl. oz

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Chhipa, H.; Chowdhary, K.; Kaushik, N. Artificial production of agarwood oil in Aquilaria sp. by fungi: A review. Phytochem. Rev. 2017, 16, 835–860. [ Google Scholar] [ CrossRef] Van Thanh, L.; Van Do, T.; Son, N.H.; Sato, T.; Kozan, O. Impacts of biological, chemical and mechanical treatments on sesquiterpene content in stems of planted Aquilaria crassna trees. Agrofor. Syst. 2015, 89, 973–981. [ Google Scholar] [ CrossRef] The composition of agarwood oil is exceedingly complex with more than 150 chemical compounds identified. [7] At least 70 of these are terpenoids which come in the form of sesquiterpenes and chromones; no monoterpenes have been detected at all. Other common classes of compounds include agarofurans, cadinanes, eudesmanes, valencanes and eremophilanes, guaianes, prezizanes, vetispiranes, simple volatile aromatic compounds as well as a range of miscellaneous compounds. [7] The exact balance of these materials will vary depending on the age and species of tree as well as the exact details of the oil extraction process.

Hiruy, M.; Bisrat, D.; Mazumder, A.; Asres, K. Two chromones with antimicrobial activity from the leaf latex of Aloe monticola Reynolds. Nat. Prod. Res. 2019, 35, 1052–1056. [ Google Scholar] [ CrossRef] Chen, X.; Sui, C.; Liu, Y.; Yang, Y.; Liu, P.; Zhang, Z.; Wei, J. Agarwood Formation Induced by Fermentation Liquid of Lasiodiplodia theobromae, the Dominating Fungus in Wounded Wood of Aquilaria sinensis. Curr Microbiol. 2017, 74, 460–468. [ Google Scholar] [ CrossRef] Li, W.; Cai, C.-H.; Guo, Z.-K.; Wang, H.; Zuo, W.-J.; Dong, W.-H.; Mei, W.-L.; Dai, H.-F. Five new eudesmane-type sesquiterpenoids from Chinese agarwood induced by artificial holing. Fitoterapia 2015, 100, 44–49. [ Google Scholar] [ CrossRef] Azren, P.D.; Lee, S.Y.; Emang, D.; Mohamed, R. History and perspectives of induction technology for agarwood production from cultivated Aquilaria in Asia: A review. J. For. Res. 2018, 30, 1–11. [ Google Scholar] [ CrossRef]Subasinghe, S.M.C.U.P.; Hitihamu, H.I.D.; Fernando, K.M.E.P. Use of two fungal species to induce agarwood resin formation in Gyrinops walla. J. For. Res. 2018, 30, 721–726. [ Google Scholar] [ CrossRef] Faizal, A.; Esyanti, R.R.; Aulianisa, E.N.; Santoso, E.; Turjaman, M. Formation of agarwood from Aquilaria malaccensis in response to inoculation of local strains of Fusarium solani. Trees 2017, 31, 189–197. [ Google Scholar] [ CrossRef] Tamuli, P.; Boruah, P.; Nath, S.C.; Samanta, R. Fungi from disease agarwood tree (Aquilaria agallocha Roxb): Two new records. Adv. For. Res. India 2000, 22, 182–187. [ Google Scholar]

The types and derivatives of major compounds in agarwood are extremely wide and diverse, indicating the miscellaneous fragrance properties of agarwood from different species and regional sources. The better insight of agarwood metabolites will definitely facilitate the identification of universally accepted biomarkers for agarwood grading. Since the publication of the comprehensive review of Naef (2011) regarding the major constituents of agarwood, new compounds continue to be discovered in the later studies ( Wu et al., 2012a; Yang et al., 2014b; Wang et al., 2015). The number of discovered compounds in agarwood will certainly be further increased in the future. The Biosynthesis Pathways of Agarwood Constituents Ueda, J.Y.; Imamura, L.; Tezuka, Y.; Tran, Q.L.; Tsudab, M.; Kadotaa, S. New sesquiterpene from Vietnamese agarwood and its induction effect on brain-derived neurotrophic factor mRNA expression in vitro. Bioorg. Med. Chem. 2006, 14, 3571–3574. [ Google Scholar] [ CrossRef] Zhang, Z.; Han, X.M.; Wei, J.H.; Xue, J.; Yang, Y.; Liang, L.; Li, X.J.; Guo, Q.M.; Xu, Y.H.; Gao, Z.H. Compositions and antifungal activities of essential oils from agarwood of Aquilaria sinensis (Lour.) Gilg induced by Lasiodiplodia theobromae (Pat.) Griffon. Maubl. J. Braz. Chem. Soc. 2014, 25, 20–26. [ Google Scholar] Kuroda, M.; Uchida, S.; Watanabe, K.; Mimaki, Y. Chromones from the tubers of Eranthis cilicica and their antioxidant activity. Phytochemistry 2009, 70, 288–293. [ Google Scholar] [ CrossRef]Salehi, B.; Armstrong, L.; Rescigno, A.; Yeskaliyeva, B.; Seitimova, G.; Beyatli, A.; Sharmeen, J.; Mahomoodally, M.F.; Sharopov, F.; Durazzo, A.; et al. Lamium Plants—A Comprehensive Review on Health Benefits and Biological Activities. Molecules 2019, 24, 1913. [ Google Scholar] [ CrossRef][ Green Version] Yagura, T.; Ito, M.; Kiuchi, F.; Honda, G.; Shimada, Y. Four New 2-(2-Phenylethyl)chromone Derivatives from Withered Wood of Aquilaria sinensis. Chem. Pharm. Bull. 2003, 51, 560–564. [ Google Scholar] [ CrossRef][ Green Version] Yang, D.L.; Li, W.; Dong, W.H.; Wang, J.; Mei, W.L.; Dai, H.F. Five new 5,11-epoxyguaiane sesquiterpenes in agarwood “qi-nan” from Aquilaria sinensis. Fitoterapia 2016, 112, 191–196. [ Google Scholar] [ CrossRef]

Sen, S.; Dehingia, M.; Talukdar, N.C.; Khan, M. Chemometric analysis reveals links in the formation of fragrant bio-molecules during agarwood (Aquilaria malaccensis) and fungal interactions. Sci. Rep. 2017, 7, 44406. [ Google Scholar] [ CrossRef][ Green Version]

Data Availability Statement

On the other hand, chromones are a large group of secondary metabolites with wide-ranging potential therapeutic indications toward immunomodulation, inflammation, cancer, diabetes, neurological conditions, bacterial and viral infections ( Khadem and Marles, 2011; Yang et al., 2012; Tawfik et al., 2014). Chromone is derived from a polycyclic organic compound namely benzopyran ring, with a keto group substitution on its oxime ring. It is generally believed that derivations of chromones take place as a consequence of the convergence of multiple secondary metabolite biosynthetic pathways involving pentaketide pathway, shikimic acid pathway and the addition of nitrogenous moiety from amino acids or other sources ( Khadem and Marles, 2011). Owing to the extensive pharmacological properties associated with its bicyclic ring structure, chromones have been used as the privileged scaffold in the development of new drugs ( Reis et al., 2017). The PECs are small class of chromones, which hold a phenylethyl substituent at the C 2 of benzopyran ring of the chromone that happened to be structurally unique in the family ( Ibrahim and Mohamed, 2015). Until now, the PECs have only been found to be present in a few species of plants for example Bothriochloa ischaemum ( Wang et al., 2001), Imperata cylindrical ( Liu X. et al., 2013), Cucumis melo L. ( Ibrahim, 2014), Gyrinops salicifolia ( Shao et al., 2016), and Aquilaria species ( Wu et al., 2012b; Yang et al., 2014a). Recently, a hypothetical scheme for the biosynthetic pathway of PECs was proposed by Liao et al. (2018) based on in-dept analysis of agarwood chemical constituents using GC-EL-MS and UPLC-ESI-MS/MS methods. In their study, the PECs was found to be the major agarwood resin constituents, which is comprised mostly of flindersia-type 2-(2-phenylethyl) chromones (FTPECs). The formation of FTPECs is further elucidated to be possibly catalyzed by type III polyketide synthase (PKs) through condensation of dihydro-cinnamoyl-CoA analogs and malonyl-CoA with 2-hydroxy-benzoyl-CoA to produce PEC scaffold that will subsequently be catalyzed by hydroxylases or O-methyltransferases (OMTs) to form structurally diverse FTPECs ( Liao et al., 2018). Recent study showed that salinity stress could induce the biosynthesis of PECs in A. sinensis calli ( Wang et al., 2016). Transcriptomic analysis of these salt-induced A. sinensis calli have identified several upregulated candidate genes potentially involved in the biosynthesis of PECs, including three OMT-encoding genes (flavonol-OMT 1, flavonol-3-OMT and caffeoyl-CoA-OMT) and a type III polyketide synthase gene encodes for chalcone synthase 1 (AsCHS1). Gu, L.P.; Zheng, K.; Liu, Y.R.; Ma, H.F.; Xiao, Z.Y. Effects of two fungi on xylem tissue structure of white wood incense. West. For. Sci. 2018, 47, 141–144. (In Chinese) [ Google Scholar] Chen, X.; Liu, Y.; Yang, Y.; Feng, J.; Liu, P.; Sui, C.; Wei, J. Trunk surface agarwood-inducing technique with Rigidoporus vinctus: An efficient novel method for agarwood production. PLoS ONE 2018, 13, e0198111. [ Google Scholar] [ CrossRef] Kim, Y.A.; Kong, C.-S.; Park, H.H.; Lee, E.; Jang, M.-S.; Nam, K.-H.; Seo, Y. Anti-Inflammatory Activity of Heterocarpin from the Salt Marsh Plant Corydalis heterocarpa in LPS-Induced RAW 264. 7 Macrophage Cells. Molecules 2015, 20, 14474–14486. [ Google Scholar] [ CrossRef][ Green Version]