Subscribe to RSS
DOI: 10.1055/s-0028-1112214
© Georg Thieme Verlag KG Stuttgart · New York
Isolation and Biological Activities of Neomyrrhaol and Other Terpenes from the Resin of Commiphora myrrha
Publication History
Received: August 6, 2008
Revised: November 4, 2008
Accepted: November 7, 2008
Publication Date:
19 December 2008 (online)
Abstract
A new cycloartane-type triterpene named cycloartane-1α,2α,3β,25-tetraol (neomyrrhaol) (1), along with four known terpenes, sandaracopimaric acid (2), abietic acid (3), 2-methoxy-5-acetoxyfruranogermacr-1(10)-en-6-one (4), and dehydroabietic acid (5) have been isolated from the resin of Commiphora myrrha. Their structures were elucidated by means of 1D, 2 D NMR and HR-mass spectroscopy. Compounds 2 – 5 are known compounds but not previously isolated from the resin of C. myrrha. Compounds 4 and 5 exhibited significant aromatase inhibiting activity with IC50 values at 0.2 μM and 0.3 μM, respectively. As shown in the MTT assay, 2, 3, 4, and 5 had inhibitory effects on HUVEC growth with IC50 values of 0.122 μM (2), 0.125 μM (3), 0.069 μM (5). Compounds 1 – 5 did not inhibit contraction of the isolated uterine and did not protect HUVEC from damage induced by H2O2 at the tested concentration.
Key words
Commiphora myrrha - Burseraceae - resin - terpenes - aromatase inhibitory activity - effects on HUVEC growth
- Supporting Information for this article is available online at
- Supporting Information .
References
- 1 Vollesen K. Flora of Ethiopia. Addis Ababa; Addis Ababa University Press 1989: 442-78
- 2 Elashry E SH, Rashed N, Salama O M, Sleh A. Components, therapeutic value and uses of myrrh. Pharmazie. 2003; 58 163-8
- 3 Shen T, Lou H X. Chemical constituents from resin of Commiphora species and their biological activities. Nat Prod Res Dev. 2008; 20 360-6
- 4 Massoud A. Preliminary study of therapeutic efficacy of a new fasciolicidal drug derived from Commiphora molmol (myrrh). Am J Trop Med Hyg. 2001; 65 96-9
- 5 Zhu N Q, Sheng S Q, Sang S M. Isolation and characterization of several aromatic sesquiterpenes from Commiphora myrrha. . Flavour Fragr J. 2003; 18 282-5
- 6 Lukas A H, Christoph G, Michael V T, Friedrich N. Role of the vaginally administered aromatase inhibitor anastrozole in women with rectovaginal endometriosis: A pilot study. Fertil Steril. 2005; 84 1033-6
- 7 Su S L, Hua Y Q, Duan J A, Shang E X, Tang Y P, Bao X J. Hypothesis of active components in volatile oil from a Chinese herbs formulation, ‘Shao-Fu-Zhu-Yu decoction’, using GC-MS and chemometrics. J Sep Sci. 2008; 31 85-91
- 8 Su S L, Yu L, Hua Y Q, Duan J A, Deng H S, Tang Y P. Screening and analysis of potential bioactive components from Shaofu Zhuyu decoction, using human umbilical vein endothelial cell extract and high performance liquid chromatography coupled with Q-TOF/MS spectrometry. Biomed Chromatogr. 2008; 22 1385-92
- 9 Su S L, Bao X J, Duan J A, Hua Y Q, Tang Y P, Ding A W. Evaluating bioactivity of myrrh oil from Commiphora myrrha and analyzing the volatile components by GC-MS. J Nanjing Univ Trad Chin Med. 2008; 24 109-15
- 10 Altunyurt S, Gol M, Altunyurt S, Sezer O, Demir N. Primary dysmenorrhea and uterine blood flow: a color Doppler study. J Reprod Med. 2005; 50 251-5
- 11 Kadohama N, Yarborough C, Zhou D, Chen S, Osawa Y. Kinetic properties of aromatase mutants Pro308Phe, Asp309Asn, and Asp309Ala, and their interactions with aromatase inhibitors. J Steroid Biochem Mol Biol. 1992; 43 693-701
- 12 Baiba J G, Elizabeth T E, Kao Y C, Shiuan C. White button mushroom phytochemicals inhibit aromatase activity and breast cancer cell proliferation. J Nutr. 2001; 131 3288-93
- 13 Lee D, Bhat K P, Fong H H. Aromatase inhibitors from Broussonetia papyrifera. . J Nat Prod. 2001; 64 1286-93
- 14 Jaffe E A, Nachman R L, Becker C G. Culture of human endothelial cells derived from umbilical veins. Identification by morphologic and immunologic criteria. J Clin Investig. 1973; 52 2745-56
- 15 Sophie F, Hugues M, Carole C, Christine D, Robert D, Thierry G. Characterization of TNP-470-induced modifications to cell functions in HUVEC and cancer cells. J Pharmacol Toxicol Methods. 2000; 43 15-24
- 16 Bruggisser R, von Daeniken K, Jundt G, Schaffner W, Tullberg-Reinert H. Interference of plant extracts, phytoestrogens and antioxidants with the MTT tetrazolium assay. Planta Med. 2002; 68 445-8
- 17 Matthew A, Kupittayanant S, Burdyga T. Characterization of contractile activity and intracellular Ca2+ signalling in mouse myometrium. J Soc Gynecol Investig. 2004; 11 207-12
- 18 Cantillo-Ciau Z, Brito-Loeza W, Quijano L. Triterpenoids from Tillandsia fasciculate. . J Nat Prod. 2001; 64 953-5
- 19 Hossain C F, Jacob M R, Clark A M, Walker L A, Nagle D G. Genipatriol, a new cycloartane triterpene from Genipa spruceana. . J Nat Prod. 2003; 66 398-400
- 20 Nes W D, Koike K, Jia Z H, Sakamoto Y, Satou T, Nikaido T. 9,19-Cyclosterol analysis by 1H and 13C NMR. Crystallogr Observations Mol Mechanism Calc. 1998; 120 5970-80
- 21 Shen T, Wan W Z, Yuan H Q. Secondary metabolites from Commiphora opobalsamum and their antiproliferative effect on human prostate cancer cells. Phytochemistry. 2007; 68 1331-7
- 22 Luan J L, Jiang R S, Lin Y W, Ding W P. Studies on chemical constituents of Sagittaria sagittifolia L. China J Chin Mater Med. 1993; 18 100-1
- 23 Yang X, Ding Y, Zhang D M, Sun Z H. Studies on chemical constituents from pine cone of Pinus armandii. . China J Chin Mater Med. 2005; 30 518-20
- 24 Fang J M, Tsai W Y, Chebg Y S. Serratene triterpenes from Pinus armandii bark. Phytochemistry. 1991; 30 1333-8
- 25 Shen T, Yuan H Q, Wan W Z, Wang X L, Wang X N, Ji M. et al . Cycloartane-type triterpenoids from the resinous exudates of Commiphora opobalsamum. . J Nat Prod. 2008; 71 81-6
- 26 Brieskorn C H, Noble P. Three new furanogermacrene from myrrh (Commiphorra molmol Engler.). Tetrahedron Lett. 1980; 21 1511-4
- 27 Yan B Z, Li W X, Jiao S K. The NMR study on the isostructure of disproportioned resin. Chin J Magn Reson. 1999; 16 449-53
- 28 Franich R, Tavendale M, Wilkins A. Synthesis of 6,6-d 2-dehydroabietic acid. Synth Commun. 1998; 28 3081-90
- 29 Bulun S E, Imir G, Utsunomiya H, Thung S, Gurates B, Tamura M. . J Steroid Biochem Mol Biol. 2005; 95 57-62
- 30 Alberto d ‘O, Alberto G. The response to antiangiogenic anticancer drugs that inhibit endothelial cell proliferation. Applied Math Comput. 2006; 181 1155-62
Prof. Dr. Jin-ao Duan
Jiangsu Key Laboratory for TCM Formulae Research
Nanjing University of Chinese Medicine
Nanjing 210046
People’s Republic of China
Phone: +86-25-8581-1116
Fax: +86-25-8581-1116
Email: dja@njutcm.edu.cn
- www.thieme-connect.de/ejournals/toc/plantamedica