Sesquiterpenoids from the Resinous Exudates of Commiphora myrrha and Their Neuroprotective Effects

Abstract

Ten new furanosesquiterpenoids, myrrhterpenoids A–J (1–10), together with eight known analogues (11–18), were isolated from the resinous exudates of Commiphora myrrha. Their structures and relative configurations were elucidated by spectroscopic methods (IR, ESIMS, HRESIMS, 1D and 2D NMR) and by the ChemDraw 3D modeling using MM2. All isolated furanosesquiterpenes showed neuroprotective effects against MPP⁺-induced neuronal cell death in SH-SY5Y cells.

Key words

Commiphora myrrha - Burseraceae - furanosesquiterpene - neuroprotective effect

References

• 1 Hedberg I, Edwards S editors.. Flora of Ethiopia. vol. 3 Addis Ababa: Addis Ababa University Press; 1989: 442-478
• 2 Habtemariam S. Cytotoxic and cytostatic activity of erlangerins from Commiphora erlangeriana.  Toxicon. 2003;  41 723-727
• 3 Shoemaker M, Hamilton B, Dairkee S H, Cohen I, Campbell M J. In vitro anticancer activity of twelve Chinese medicinal herbs.  Phytother Res. 2005;  19 649-651
• 4 Shen T, Wan W, Yuan H, Kong F, Guo H, Fan P, Lou H. Secondary metabolites from Commiphora opobalsamum and their antiproliferative effect on human prostate cancer cells.  Phytochemistry. 2007;  68 1331-1337
• 5 Dolara P, Luceri C, Ghelardini C, Monserrat C, Aiolli S, Luceri F, Lodovici M, Menichetti S, Romanelli M N. Analgesic effects of myrrh.  Nature. 1996;  379 29
• 6 Meselhy M R. Inhibition of LPS-induced NO production by the oleogum resin of Commiphora wightii and its constituents.  Phytochemistry. 2003;  62 213-218
• 7 Francis J A, Raja S N, Nair M G. Bioactive terpenoids and guggulusteroids from Commiphora mukul gum resin of potential anti-inflammatory interest.  Chem Biodivers. 2004;  1 1842-1853
• 8 Matsuda H, Morikawa T, Ando S, Oominami H, Murakami T, Kimura I, Yoshikawa M. Absolute stereostructures of polypodane- and octanordammarane-type triterpenes with nitric oxide production inhibitory activity from guggul-gum resins.  Bioorg Med Chem. 2004;  12 3037-3046
• 9 Saeed M A, Sabir A W. Antibacterial activities of some constituents from oleo-gum-resin of Commiphora mukul.  Fitoterapia. 2004;  75 204-208
• 10 Dolara P, Corte B, Ghelardini C, Pugliese A M, Cerbai E, Menichetti S, Lo Nostro A. Local anaesthetic, antibacterial and antifungal properties of sesquiterpenes from myrrh.  Planta Med. 2000;  66 356-358
• 11 Meeker H G, Linke H A. The antibacterial action of eugenol, thyme oil, and related essential oils used in dentistry.  Compend Contin Educ Dent. 1988;  9 32-35
• 12 Zhu N, Kikuzaki H, Sheng S, Sang S, Rafi M M, Wang M, Nakatani N, DiPaola R S, Rosen R T, Ho C T. Furanosesquiterpenoids of Commiphora myrrha.  J Nat Prod. 2001;  64 1460-1462
• 13 Zhu N, Sheng S, Sang S, Rosen R T, Ho C T. Isolation and characterization of several aromatic sesquiterpenes from Commiphora myrrha.  Flav Fragr J. 2003;  18 282-285
• 14 Shen T, Wan W Z, Wang X N, Yuan H Q, Ji M, Lou H X. A triterpenoid and sesquiterpenoids from the resinous exudates of Commiphora myrrha.  Helv Chim Acta. 2009;  92 645-652
• 15 Su S L, Duan J A, Tang Y P, Zhang X, Yu L, Jiang F R, Zhou W, Luo D, Ding A W. Isolation and biological activities of neomyrrhaol and other terpenes from the resin of Commiphora myrrha.  Planta Med. 2009;  75 351-355
• 16 Ubillas R P, Mendez C D, Jolad S D, Luo J, King S R, Carlson T J, Fort D M. Antihyperglycemic furanosesquiterpenes from Commiphora myrrha.  Planta Med. 1999;  65 778-779
• 17 Fatope M O, Al-Burtomani S K S, Ochei J O, Abdulnour A O, Al-Kindy S M Z, Takeda Y. Muscanone: a 3-O-1″,8″,14″-trimethylhexadecanylnaringenin from Commiphora wightii.  Phytochemistry. 2003;  62 1251-1255
• 18 Zhu N, Rafi M M, DiPaola R S, Xin J, Chin C K, Badmaev V, Ghai G, Rosen R T, Ho C T. Bioactive constituents from gum guggul Commiphora wightii.  Phytochemistry. 2001;  56 723-727
• 19 Fourie T G, Snyckers F O. A pentacyclic triterpene with anti-inflammatory and analgesic activity from the roots of Commiphora merkeri.  J Nat Prod. 1989;  52 1129-1131
• 20 Provan G J, Waterman P G. Chemistry of the Burseraceae. Part 10. Major triterpenes from the resins of Commiphora incisa and C. kua and their potential chemotaxonomic significance.  Phytochemistry. 1988;  27 3841-3843
• 21 Dekebo A, Dagne E, Hansen L K, Gautun O R, Aasen A J. Two octanordammarane triterpenes from Commiphora kua.  Phytochemistry. 2002;  59 399-403
• 22 Brieskorn C H, Noble P. Three new furanogermacrenes from myrrh.  Tetrahedron Lett. 1980;  21 1511-1514
• 23 Dekebo A, Lang M, Polborn K, Dagne E, Steglich W. Four lignans from Commiphora erlangeriana.  J Nat Prod. 2002;  65 1252-1257
• 24 Waterman P G, Ampofo S. Chemistry of the Burseraceae. Part 2. Dammarane triterpenes from the stem bark of Commiphora dalzielii.  Phytochemistry. 1985;  24 2925-2928
• 25 Shen T, Wan W Z, Wang X N, Sun L M, Yuan H Q, Wang X L, Ji M, Lou H X. Sesquiterpenoids from the resinous exudates of Commiphora opobalsamum (Burseraceae).  Helv Chim Acta. 2008;  91 881-887
• 26 Shen T, Yuan H Q, Wan W Z, Wang X L, Wang X N, Ji M, Lou H X. Cycloartane-type triterpenoids from the resinous exudates of Commiphora opobalsamum.  J Nat Prod. 2008;  71 81-86
• 27 Dawson T M, Dawson V L. Molecular pathways of neurodegeneration in Parkinson's disease.  Science. 2003;  302 819-822
• 28 Shen T, Lou H X. Bioactive constituents of myrrh and frankincense, two simultaneously prescribed gum resins in Chinese traditional medicine.  Chem Biodivers. 2008;  5 540-553
• 29 Lange G L, Lee M. Carbon-13 NMR determination of the configuration of methyl-substituted double bonds in medium- and large-ring terpenoids.  Magn Reson Chem. 1986;  24 656-658
• 30 Yuan T, Zhang C R, Yang S P, Yin S, Wu W B, Dong L, Yue J M. Sesquiterpenoids and phenylpropanoids from Chloranthus serratus.  J Nat Prod. 2008;  71 2021-2025
• 31 Zhang S, Su Z S, Yang S P, Yue J M. Four sesquiterpenoids from Chloranthus multistachys.  J Asian Nat Prod Res. 2010;  12 522-528
• 32 Hikino H, Sakurai Y, Takemoto T. Sesquiterpenoids. XX. Structure and absolute configuration of curcolone.  Chem Pharm Bull. 1967;  15 1065-1066
• 33 Xu J, Liu C, Guo P, Guo Y, Jin D Q, Song X, Sun Z, Gui L, Ma Y. Neuroprotective labdane diterpenes from Fritillaria ebeiensis.  Fitoterapia. 2011;  82 772-776
• 34 Pettifer K M, Jiang S, Bau C, Ballerini P, D'Alimonte I, Werstiuk E S, Rathbone M P. MPP⁺-induced cytotoxicity in neuroblastoma cells: antagonism and reversal by guanosine.  Purinergic Signal. 2007;  3 399-409