Biodiversity Literature Repository

Submit to community
Liberated Data
Published November 30, 2021 | Version v1
Journal article Restricted

Cembranoids from Boswellia species

Authors/Creators

  • 1. Natural and Medical Sciences Research Center, University of Nizwa, P.O. Box 33, Postal Code 616, Birkat Al Mauz, Nizwa, Oman
  • 2. Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Kurt-Mothes-Str. 2, D-06120, Halle (Saale), Germany

Description

Al-Harrasi, Ahmed, Avula, Satya Kumar, Csuk, René, Das, Biswanath (2021): Cembranoids from Boswellia species. Phytochemistry (112897) 191: 1-17, DOI: 10.1016/j.phytochem.2021.112897, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112897

Files

Restricted

The record is publicly accessible, but files are restricted to users with access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:FFBD216A9F59D627C604FFDBFFF1DB34

Cites
Publication: 10.1055/s-2006-962745 (DOI)
Publication: 10.1016/j.phytochem.2019.01.007 (DOI)
Publication: 10.1016/j.phytochem.2019.04.007 (DOI)
Publication: 10.1002/pca.2743 (DOI)
Publication: 10.1016/j.tetasy.2016.07.007 (DOI)
Publication: 10.1016/j.phytochem.2019.04.020 (DOI)
Publication: 10.36253/jopt-9299 (DOI)
Publication: 10.1002/oms.1210280306 (DOI)
Publication: 10.1002/ffj.992 (DOI)
Publication: 10.1002/anie.201605242 (DOI)
Publication: 10.1074/jbc.M401872200 (DOI)
Publication: 10.1016/S0040-4020(01)82601-6 (DOI)
Publication: 10.1021/ja00869a057 (DOI)
Publication: 10.1016/j.phytochem.2019.04.015 (DOI)
Publication: 10.1016/0040-4020(72) (DOI)
Publication: 10.1055/s-0043-116943 (DOI)
Publication: 10.3389/fchem.2020.00486 (DOI)
Publication: 10.1016/j.phytochem.2005.04.025 (DOI)
Publication: 10.1177/1934578X0700200206 (DOI)
Publication: 10.1080/10412905.2012.742468 (DOI)
Publication: 10.1246/cl.1977.565 (DOI)
Publication: 10.1016/S0040- (DOI)
Publication: 10.1246/bcsj.35.1044 (DOI)
Publication: 10.1007/BF02262464 (DOI)
Publication: 10.1021/acs.orglett.7b03979 (DOI)
Publication: 10.1515/znc-2003-3-416 (DOI)
Publication: 10.1016/j.fct.2011.06.079 (DOI)
Publication: 10.1124/mol.107.038810.LP-1664 (DOI)
Publication: 10.1096/fj.07-101865 (DOI)
Publication: 10.1038/jcbfm.2008.28 (DOI)
Publication: 10.1177/0269881112458729 (DOI)
Publication: 10.1016/S0040-4020(01)96864-4 (DOI)
Publication: 10.1016/S0040-4020(01)93299-5 (DOI)
Publication: 10.1021/acs.jnatprod.6b00141 (DOI)
Publication: 10.1146/annurev.physiol.68.040204.100431 (DOI)
Publication: 10.1039/C7RA07351H (DOI)
Publication: 10.1021/acs.jnatprod.5b00104 (DOI)
Publication: 10.1093/infdis/121.6.597 (DOI)
Publication: 10.1055/s-0030-1250612 (DOI)
Publication: 10.1007/s00894-018-3625-8 (DOI)
Publication: 10.1039/B809437N (DOI)
Publication: 10.1016/0031-9422(82)83057-4 (DOI)
Publication: 10.1039/c9ra09776g (DOI)
Publication: 10.11646/phytotaxa.394.3.3 (DOI)
Publication: 10.1016/j.fitote.2019.104263 (DOI)
Publication: 10.1016/j.phytochem.2020.112425 (DOI)
Publication: 10.1007/978-3-7091-3265-43 (DOI)
Publication: 10.1016/j.phytol.2018.09.010 (DOI)
Publication: 10.1016/j.tet.2018.08.004 (DOI)
Has part
Figure: 10.5281/zenodo.8380750 (DOI)
Dataset: http://table.plazi.org/id/DF52B88C9F58D626C660FC9DFDBAD845 (URL)
Dataset: http://table.plazi.org/id/DF52B88C9F5BD625C660FF4DFE12DBF4 (URL)
Figure: 10.5281/zenodo.8380752 (DOI)
Figure: 10.5281/zenodo.8380754 (DOI)
Figure: 10.5281/zenodo.8380756 (DOI)
Dataset: http://table.plazi.org/id/DF52B88C9F5ED620C660FF4DFD53DBF4 (URL)
Figure: 10.5281/zenodo.8380758 (DOI)
Figure: 10.5281/zenodo.8380760 (DOI)
Figure: 10.5281/zenodo.8380762 (DOI)
Figure: 10.5281/zenodo.8380764 (DOI)
Dataset: http://table.plazi.org/id/DF52B88C9F53D62DC660FF14FD9CDBCC (URL)
Dataset: http://table.plazi.org/id/DF52B88C9F53D62DC660FB10FDFCDFC2 (URL)
Figure: 10.5281/zenodo.8380766 (DOI)

References

  • Abdel Wahab, S.M., Aboutabl, E.A., El-Zalabani, S.M., 1987. The essential oil of olibanum. Planta Med. 53, 382-384. https://doi.org/10.1055/s-2006-962745.
  • Al-Harrasi, Ahmed, Hussain, Hidayat, Csuk, Rene, Khan, Husain Yar, 2018a. Chemistry and Bioactivity of Boswellic Acids and Other Terpenoids of the Genus Boswellia. Elsevier, London.
  • Al-Harrasi, Ahmed, Hussain, Hidayat, Rene Csuk, H.Y.K., 2018b. Chemistry and Bioactivity of Boswellic Acids and Other Terpenoids of the Genus Boswallia. Elsevier, London.
  • Al-Harrasi, A., Csuk, R., Khan, A., Hussain, J., 2019a. Distribution of the anti-inflammatory and anti-depressant compounds: incensole and incensole acetate in genus Boswellia. Phytochemistry 161, 28-40 https://doi.org/https://doi.org/ 10.1016/j.phytochem.2019.01.007.
  • Al-Harrasi, A., Khan, A., Rehman, N.U., Al-Shidhani, S., Karim, N., Khan, I., Halim, S.A., Al-Rawahi, A., Hussain, J., Csuk, R., 2019b. Evidence for the involvement of a GABAergic mechanism in the effectiveness of natural and synthetically modified incensole derivatives in neuropharmacological disorders: a computational and pharmacological approach. Phytochemistry 163, 58-74 https://doi.org/https://doi. org/10.1016/j.phytochem.2019.04.007.
  • Al-Shidhani, S., Rehman, N.U., Mabood, F., Al-Broumi, M., Hussain, H., Hussain, J., Csuk, R., Al-Harrasi, A., 2018. Quantification of incensole in three boswellia species by NIR spectroscopy coupled with PLSR and cross-validation by HPLC. Phytochem. Anal. 29, 300-307 https://doi.org/https://doi.org/10.1002/pca.2743.
  • Ann Bot, Rome, 1907. Boswellia multifoliolata Engl 7, 16.
  • Ann Bot, Rome, 1911. Boswellia pirottae Chiov 9, 53.
  • Ann Bot, Rome, 1915. International Plant Names Index 13, 404.
  • Pescitelli, G., Al-Rawahi, A., Ur Rehman, N., Green, I.R., Al-Harrasi, A., 2016. 5-epi- Incensole: synthesis, X-ray crystal structure and absolute configuration by means of ECD and VCD studies in solution and solid state. Tetrahedron: Asymmetry 27, 829-833 https://doi.org/https://doi.org/10.1016/j.tetasy.2016.07.007.
  • Ayubova, M., Guelleh, Z.O., Guelleh, M.O., Br´evard, H., Baldovini, N., 2019. Analytical investigations on Boswellia occulta essential oils. Phytochemistry 164, 78-85. https://doi.org/10.1016/j.phytochem.2019.04.020.
  • Baldini, R.M., 2020. Mats thulin - the genus boswellia (burseraceae). The frankincense trees. Webbia 75, 133-134. https://doi.org/10.36253/jopt-9299.
  • Barakat, A.O., Rullk¨otter, J., 1993. Gas chromatographic/mass spectrometric analysis of cembrenoid diterpenes in kerogen from a lacustrine sediment. Org. Mass Spectrom. 28, 157-162 https://doi.org/https://doi.org/10.1002/oms.1210280306.
  • Basar, S., Koch, A., K¨onig, W.A., 2001. A verticillane-type diterpene from Boswellia carterii essential oil. Flavour Fragrance J. 16, 315-318 https://doi.org/https://doi. org/10.1002/ffj.992.
  • Boscarelli, A., Giglio, E., Quagliata, C., 1981. Structure and conformation of incensole oxide. Acta Crystallogr. B 37, 744-746 https://doi.org/https://doi.org/10.1107/ S0567740881004160.
  • Bot, J., 1877. African Plant Database 15, 185.
  • Bull, Kew, 1985. Boswellia ogadensis Vollesen 40, 39.
  • Bull, Kew, 2001. Boswellia bullata Thulin 56, 983.
  • Bull Misc Inform Kew, 1910. Boswellia Dalzielli 137.
  • Cerutti-Delasalle, C., Mehiri, M., Cagliero, C., Rubiolo, P., Bicchi, C., Meierhenrich, U.J., Baldovini, N., 2016. The (+)-cis- and (+)-trans-Olibanic acids: key odorants of frankincense. Angew. Chem. Int. Ed. 55, 13719-13723 https://doi.org/https://doi. org/10.1002/anie.201605242.
  • Chung, M.-K., Lee, H., Mizuno, A., Suzuki, M., Caterina, M.J., 2004. TRPV3 and TRPV4 mediate warmth-evoked currents in primary mouse keratinocytes*. J. Biol. Chem. 279, 21569-21575 https://doi.org/https://doi.org/10.1074/jbc.M401872200.
  • Corsano, S., Nicoletti, R., 1967. The structure of incensole. Tetrahedron 23, 1977-1984 https://doi.org/https://doi.org/10.1016/S0040-4020(01)82601-6.
  • Dauben, W.G., Thiessen, W.E., Resnick, P.R., 1962. Cembrene, A 14-membered ring diterpene hydrocarbon. J. Am. Chem. Soc. 84 https://doi.org/10.1021/ ja00869a057, 2015-2016.
  • DeCarlo, A., Johnson, S., Okeke-Agulu, K.I., Dosoky, N.S., Wax, S.J., Owolabi, M.S., Setzer, W.N., 2019. Compositional analysis of the essential oil of Boswellia dalzielii frankincense from West Africa reveals two major chemotypes. Phytochemistry 164, 24-32 https://doi.org/https://doi.org/10.1016/j.phytochem.2019.04.015.
  • Flora, 1843. Boswellia papyrifera (Delile) Hochst 26, 81.
  • Forcellese, M.L., Nicoletti, R., Petrossi, U., 1972. The structure of isoincensole-oxide. Tetrahedron 28, 325-331 https://doi.org/https://doi.org/10.1016/0040-4020(72) 80139-X.
  • Greve, H.L., Kaiser, M., Brun, R., Schmidt, T.J., 2017. Terpenoids from the oleo-gumresin of boswellia serrata and their antiplasmodial effects in vitro. Planta Med. 83, 1214-1226. https://doi.org/10.1055/s-0043-116943.
  • Halim, S.A., Khan, A., Csuk, R., Al-Rawahi, A., Al-Harrasi, A., 2020. Diterpenoids and triterpenoids from frankincense are excellent anti-psoriatic agents: an in silico approach. Frontiers in Chemistry 8. https://doi.org/10.3389/fchem.2020.00486.
  • Hamm, S., Bleton, J., Connan, J., Tchapla, A., 2005. A chemical investigation by headspace SPME and GC-MS of volatile and semi-volatile terpenes in various olibanum samples. Phytochemistry 66, 1499-1514 https://doi.org/https://doi.org/ 10.1016/j.phytochem.2005.04.025.
  • Hanuˇs, L.O., Moussaieff, A., Rezanka ˇ, T., Abu-Lafi, S., Dembitsky, V.M., 2007. Phytochemical analysis and comparison for differentiation of boswellia carterii and B. Serrata. Natural Product Communications 2. https://doi.org/10.1177/ 1934578X0700200206, 1934578X0700200206.
  • Hasegawa, T., Kikuchi, A., Saitoh, H., Yamada, H., 2012. Structure and properties of constituents in hexane extract of frankincense. J. Essent. Oil Res. 24, 593-598. https://doi.org/10.1080/10412905.2012.742468.
  • Hooker' s Icon, Pl, 1971. Boswellia popoviana Hepper 37, 3677.
  • J. Bombay Nat Hist Soc, 1961, No Title 58, 546.
  • Kato, T., Yen, C.C., Uyehara, T., Kitahara, Y., 1977. Cyclization OF polyenes XXIII. Synthesis and stereochemistry OF isoincensole-oxide. Chem. Lett. 6, 565-568. https://doi.org/10.1246/cl.1977.565.
  • Klein, E., Obermann, H., 1978. (S)-1-isopropyl-4,8,12-trimethyl-cyclotetradeca- 3e,7e,11e-trien-1-ol, ein neues cembrenol aus dem ¨atherischen ol ¨von olibanum. Tetrahedron Lett. 19, 349-352 https://doi.org/https://doi.org/10.1016/S0040- 4039(01)85122-4.
  • Kobayashi, H., Akiyoshi, S., 1962. Thunbergene, a macrocyclic diterpene. Bull. Chem. Soc. Jpn. 35, 1044-1045. https://doi.org/10.1246/bcsj.35.1044.
  • Li, F. al, 2010. Macrocyclic diterpenes from boswellia carterii birdwood (frankincense). Chin. J. Org. Chem. 30, 107-111.
  • Li, F., Xu, K., Yuan, S., Yan, D., Liu, R., Tan, J., Zeng, G., Zhou, Y., Tan, G., 2010. Macrocyclic diterpenes from boswellia carterii birdwood (Frankincense). Chin. J. Org. Chem. 30, 107-111.
  • Ma, X., Yu, X., Zheng, Z., Mao, J., 1991. Analytical supercritical fluid extraction of Chinese herbal medicines. Chromatographia 32, 40-44. https://doi.org/10.1007/ BF02262464.
  • Matsuzawa, A., Shiraiwa, J., Kasamatsu, A., Sugita, K., 2018. Enantioselective, protecting-group-free total synthesis of boscartin F. Org. Lett. 20, 1031-1033. https://doi.org/10.1021/acs.orglett.7b03979.
  • McMillan, J.B.M.H., 1999. Isoprenoids Including Carotenoids and Steroids. Comprehensive Natural Products Chemistry, Oxford.
  • Mikhaeil, B.R., Maatooq, G.T., Badria, F.A., Amer, M.M.A., 2003. Chemistry and immunomodulatory activity of frankincense oil. Zeitschrift fur Naturforschung - Section C Journal of Biosciences 58, 230-238. https://doi.org/10.1515/znc-2003-3- 416.
  • Mothana, R.A.A., 2011. Anti-inflammatory, antinociceptive and antioxidant activities of the endemic Soqotraen Boswellia elongata Balf. f. and Jatropha unicostata Balf. f. in different experimental models. Food Chem. Toxicol. 49, 2594-2599 https://doi.org/ https://doi.org/10.1016/j.fct.2011.06.079.
  • Moussaieff, A., Shohami, E., Kashman, Y., Fride, E., Schmitz, M.L., Renner, F., Fiebich, B. L., Munoz, E., Ben-Neriah, Y., Mechoulam, R., 2007. Incensole acetate, a novel anti-inflammatory compound isolated from <em>Boswellia</em> resin, inhibits nuclear factor-κb activation. Mol. Pharmacol. 72 (1657) https://doi.org/10.1124/ mol.107.038810. LP - 1664.
  • Moussaieff, A., Rimmerman, N., Bregman, T., Straiker, A., Felder, C.C., Shoham, S., Kashman, Y., Huang, S.M., Lee, H., Shohami, E., Mackie, K., Caterina, M.J., Walker, J.M., Fride, E., Mechoulam, R., 2008a. Incensole acetate, an incense component, elicits psychoactivity by activating TRPV3 channels in the brain. Faseb. J. 22, 3024-3034 https://doi.org/https://doi.org/10.1096/fj.07-101865.
  • Moussaieff, A., Shein, N.A., Tsenter, J., Grigoriadis, S., Simeonidou, C., Alexandrovich, A. G., Trembovler, V., Ben-Neriah, Y., Schmitz, M.L., Fiebich, B.L., Munoz, E., Mechoulam, R., Shohami, E., 2008b. Incensole acetate: a novel neuroprotective agent isolated from Boswellia carterii. J. Cerebr. Blood Flow Metabol. 28, 1341-1352. https://doi.org/10.1038/jcbfm.2008.28.
  • Moussaieff, A., Gross, M., Nesher, E., Tikhonov, T., Yadid, G., Pinhasov, A., 2012. Incensole acetate reduces depressive-like behavior and modulates hippocampal BDNF and CRF expression of submissive animals. J. Psychopharmacol. 26, 1584-1593. https://doi.org/10.1177/0269881112458729.
  • Nicoletti, R., Forcellese, M.L., 1968. The structure of incensole-oxide. Tetrahedron 24, 6519-6525 https://doi.org/https://doi.org/10.1016/S0040-4020(01)96864-4.
  • Nordic, J. Bot, 2006. Boswellia globosa Thulin 24, 373.
  • Pardhy, R.S., Bhattacharyya, S.C., 1978. Tetracyclic triterpene acids from the resin of Boswellia serrata Roxb. Indian J. Chem. 16B, 174-175.
  • Patil, V.D., Nayak, U.R., Dev, S., 1973. Chemistry of ayurvedic crude drugs-II: guggulu (resin from Commiphora mukul)-2: diterpenoid constituents. Tetrahedron 29, 341-348 https://doi.org/https://doi.org/10.1016/S0040-4020(01)93299-5.
  • Paul, M., 2012. Chemotaxonomic Investigations on Resins of the Frankincense Species Boswellia Papyrifera, Boswellia Serrata and Boswellia Sacra, Respectively. Boswellia carterii.
  • Pharmak, L., 1867. African Plant Database 31.
  • Pollastro, F., Golin, S., Chianese, G., Putra, M.Y., Schiano Moriello, A., De Petrocellis, L., Garcia, V., Munoz, E., Taglialatela-Scafati, O., Appendino, G., 2016. Neuroactive and anti-inflammatory frankincense cembranes: a structure-activity study. J. Nat. Prod. 79, 1762-1768. https://doi.org/10.1021/acs.jnatprod.6b00141.
  • Proc Roy Soc Edinburgh, 1882. Boswellia socotrana Balf.fil. 11, 505.
  • Ramsey, I.S., Delling, M., Clapham, D.E., 2006. AN introduction to trp channels. Annu. Rev. Physiol. 68, 619-647. https://doi.org/10.1146/annurev. physiol.68.040204.100431.
  • Rehman, N.U., Hussain, H., Al-Shidhani, S., Avula, S.K., Abbas, G., Anwar, M.U., Gorecki ´, M., Pescitelli, G., Al-Harrasi, A., 2017. Incensfuran: isolation, X-ray crystal structure and absolute configuration by means of chiroptical studies in solution and solid state. RSC Adv. 7, 42357-42362. https://doi.org/10.1039/C7RA07351H.
  • Qin, H.-L., 2015. Cembranoids from the gum resin of boswellia carterii as potential antiulcerative colitis agents. J. Nat. Prod. 78, 2322-2331. https://doi.org/10.1021/ acs.jnatprod.5b00104.
  • Res, Asiat, 1807. Boswellia serrata. Roxb. ex Colebr. 9, 376.
  • Schmidt, R.M., Rosenkranz, H.S., 1970. Antimicrobial activity of local anesthetics: lidocaine and procaine. J. Infect. Dis. 121, 597-607. https://doi.org/10.1093/ infdis/121.6.597.
  • Schmidt, T.J., Kaiser, M., Brun, R., 2011. Complete structural assignment of serratol, a cembrane-type diterpene from Boswellia serrata, and evaluation of its antiprotozoal activity. Planta Med. 77, 849-850. https://doi.org/10.1055/s-0030-1250612.
  • Setzer, W.N., 2018. Conformational analysis of macrocyclic frankincense (Boswellia) diterpenoids. J. Mol. Model. 24, 74. https://doi.org/10.1007/s00894-018-3625-8.
  • Shah, B.A., Qazi, G.N., Taneja, S.C., 2009. Boswellic acids: a group of medicinally important compounds. Nat. Prod. Rep. 26, 72-89. https://doi.org/10.1039/ B809437N.
  • Strappaghetti, G., Corsano, S., Craveiro, A., Proietti, G., 1982. Constituents of essential oil of Boswellia frereana. Phytochemistry 21, 2114-2115 https://doi.org/https:// doi.org/10.1016/0031-9422(82)83057-4.
  • Sun, X., Geng, Y., Wang, X., Qin, D., Yu, J., 2019. Cembrane-type diterpenoids from the gum resin of Boswellia carterii and their biological activities. RSC Adv. 10, 746-755. https://doi.org/10.1039/c9ra09776g.
  • Thulin, M., Decarlo, A., Johnson, S.P., 2019. Boswellia occulta (Burseraceae), a new species of frankincense tree from Somalia (Somaliland). Phytotaxa 394, 219-224. https://doi.org/10.11646/phytotaxa.394.3.3.
  • Trans Linn Soc London, 1870. B. frereana Birdwood 27, 146.
  • Wang, J., Zhen, B., Hu, J., Shi, M., Wei, C., Wang, X., Sun, H., Ji, T., 2019a. Boscartins L-O: cembrane-type diterpenoids from the gum resin of Boswellia sacra Flueck.
  • Wang, Y. gai, Ren, J., Ma, J., Yang, J. bo, Ji, T., Wang, A. guo, 2019b. Bioactive cembrane-type diterpenoids from the gum-resin of Boswellia carterii. Fitoterapia 137, 104263. https://doi.org/10.1016/j.fitote.2019.104263.
  • Wang, J.-J., Sun, H.-R., Suo, X.-Y., Wang, Xue, Sun, H., Wang, X.-L., Jiang, J.-D., Ji, T.-F., 2020. Ten undescribed cembrane-type diterpenoids from the gum resin of Boswellia sacra and their biological activities. Phytochemistry 177, 112425 https://doi.org/ https://doi.org/10.1016/j.phytochem.2020.112425.
  • Weinheimer, C.W.J., Chang, I., FlamentJ, A., Matson, T., Nishida, G., OhloffF, W., WehrliA, J., 1979. Fortschritte der chemie organischer naturstoffe/progress in the chemistry of organic natural products. Fortschr. Chem. Org. Naturst 36 https://doi. org/https://doi.org/10.1007/978-3-7091-3265-43.
  • Yu, J.-Q., Geng, Y.-L., Wang, D.-J., Zhao, H.-W., Guo, L., Wang, X., 2018a. Terpenes from the gum resin of Boswellia carterii and their NO inhibitory activies. Phytochemistry Letters 28, 59-63 https://doi.org/https://doi.org/10.1016/j.phytol.2018.09.010.
  • Yu, J., Geng, Y., Zhao, H., Wang, X., 2018b. Diterpenoids from the gum resin of Boswellia carterii and their biological activities. Tetrahedron 74, 5858-5866 https://doi.org/ https://doi.org/10.1016/j.tet.2018.08.004.