Alkaline phosphatase activity-guided isolation of active compounds and new dammarane-type triterpenes from Cissus quadrangularis hexane extract

Journal of Ethnopharmacology

Volumn 160, Issue , 2015, Pages 52-60

  Pathomwichaiwat, Thanika ^a   Ochareon, Pannee ^a   Soonthornchareonnon, Noppamas ^a   Ali, Zulfiqar ^b   Khan, Ikhlas A ^b,c   Prathanturarug, Sompop ^a  

^a MAHIDOL UNIVERSITY   (Thailand)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Dammarane; Osteoporosis; Synergy; Triterpenoids; Vitaceae

Indexed keywords

24 METHYL DAMMARA 2,20,25 TRIENE 1 ONE; 24 METHYL DAMMARA 20,25 DIENE 3 ONE; 24 METHYL DAMMARA 20,25 DIENE 3BETA YL ACETATE; 24 METHYL DAMMARA 20,25 DIENE 3BETA YL PALMITATE; 9 OCTADECENOIC ACID METHYL ESTER; 9,12 OCTADECADIENOIC ACID METHYL ESTER; 9,12,15 OCTADECATRIENOIC ACID METHYL ESTER; ACETIC ACID ETHYL ESTER; ALKALINE PHOSPHATASE; BENZENE; BETA SITOSTEROL 3,5,6 TRIOL; CEREBROSIDE; CISSUS QUADRANGULARIS EXTRACT; CISSUS QUADRANGULARIS HEXANE EXTRACT; DAMMARANE DERIVATIVE; DICHLOROMETHANE; ESTER; FATTY ACID ESTER; LUPENONE; LUPEOL 3 ACETATE; METHANOL; METHYL DAMMARA 20,25 DIENE 3BETA YL STEARATE; PHYTOL LINOLEOATE; PHYTOL OLEATE; PHYTOL PALMITATE; SITOSTEROL OLEATE; SQUALENE; STEROID; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; DAMMARANE; HEXANE; N-HEXANE; PLANT EXTRACT; TRITERPENE;

ANIMAL CELL; ANTIOSTEOPOROTIC ACTIVITY; ARTICLE; BIOASSAY; BONE DIFFERENTIATION; CELL DIFFERENTIATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG POTENTIATION; DRUG STRUCTURE; ENZYME ACTIVITY; FEMALE; IN VITRO STUDY; MC3T3 E1 CELL; MOUSE; MUSCULOSKELETAL SYSTEM PARAMETERS; NONHUMAN; OSSIFICATION; OSTEOBLAST; OSTEOPOROSIS; QUALITY CONTROL; SPECTROSCOPY; VITACEAE; BONE DEVELOPMENT; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; CISSUS; DRUG EFFECTS; ENZYMOLOGY; ISOLATION AND PURIFICATION; METABOLISM; PLANT STEM;

CISSUS QUADRANGULARIS; VITACEAE;

ALKALINE PHOSPHATASE; BIOLOGICAL ASSAY; CELLS, CULTURED; CISSUS; DRUG SYNERGISM; HEXANES; MOLECULAR STRUCTURE; OSTEOBLASTS; OSTEOGENESIS; PLANT EXTRACTS; PLANT STEMS; TRITERPENES;

EID: 84916622934     PISSN: 03788741     EISSN: 18727573     Source Type: Journal    
DOI: 10.1016/j.jep.2014.11.026     Document Type: Article

References (54)

1. Aswar, U.M., Bhaskaran, S., Mohan, V., Bodhankar, S.L., 2010. Estrogenic activity of friedelin rich fraction (IND-HE) separated from Cissus quadrangularis and its effect on female sexual function. Pharmacognosy Research 2, 138-145.
2. Aswar, U.M., Mohan, V., Bodhankar, S.L., 2012. Antiosteoporotic activity of phytoestrogen-rich fraction separated from ethanol extract of aerial parts of Cissus quadrangularis in ovariectomized rats. Indian Journal of Pharmacology 44, 345-350.
3. Baron, R., Hesse, E., 2012. Update on bone anabolics in osteoporosis treatment: rationale, current status, and perspectives. The Journal of Clinical Endocrinology and Metabolism 97, 311-325.
4. Chadwick, L.R., Nikolic, D., Burdette, J.E., Overk, C.R., Bolton, J.L., Breemen, R.B.v., Fröhlich, R., Fong, H.H.S., Farnsworth, N.R., Pauli, G.F., 2004. Estrogens and congeners from spent hops (Humulus lupulus). Journal of Natural Products 67, S1-S76.
5. Chen, X., Garner, S.C., Quarles, L.D., Anderson, J.J.B., 2003. Effects of genistein on expression of bone markers during MC3T3-E1 osteoblastic cell differentiation. Journal of Nutritional Biochemistry 14, 342-349.
6. Chung, C.Y., Iida-Klein, A., Wyatt, L.E., Rudkin, G.H., Ishida, K., Yamaguchi, D.T., Miller, T.A., 1999. Serial passage of MC3T3-E1 cells alters osteoblastic function and responsiveness to transforming growth factor- β1 and bone morphogenetic protein-2. Biochemical and Biophysical Research Communications 265, 246-251.
7. Deng, Z.L., Sharff, K.A., Tang, N., Song, W.X., Luo, J., Luo, X., Chen, J., Bennett, E., Reid, R., Manning, D., Xue, A., Montag, A.G., Luu, H.H., Haydon, R.C., He, T.C., 2008. Regulation of osteogenic differentiation during skeletal development. Frontiers in Bioscience 13, 2001-2021.
8. Desmaële, D., Gref, R., Couvreur, P., 2012. Squalenoylation: a generic platform for nanoparticular drug delivery. Journal of Controlled Release 161, 609-618.
9. Dewick, P.M., 2009. The mevalonate and methylerythritol phosphate pathways: terpenoids and steroids. In: Dewick, P.M. (Ed.), Medicinal natural products: a biosynthetic approach, third ed. John Wiley & Sons, Ltd, pp. 187-310.
10. Gao, Z., Ali, Z., Khan, I.A., 2008. Glycerogalactolipids from the fruit of Lycium barbarum. Phytochemistry 69, 2856-2861.
11. García-Pérez, M.A., 2006. Physiological regulation of bone metabolism and estrogen agonism. In: Cano, A., Calaf, i, Alsina, J., Dueñas-Díez, J.L. (Eds.), Selective estrogen receptor modulators. Springer, Berlin Heidelberg, pp. 161-186.
12. Harris, S.A., Enger, R.J., Riggs, B.L., Spelsberg, T.C., 1995. Development and characterization of a conditionally immortalized human fetal osteoblastic cell line. Journal of Bone and Mineral Research 10, 178-186.
13. Hawse, J.R., Subramaniam, M., Ingle, J.N., Oursler, M.J., Rajamannan, N.M., Spelsberg, T.C., 2008. Estrogen-TGFβ cross-talk in bone and other cell types: role of TIEG, Runx2, and other transcription factors. Journal of Cellular Biochemistry 103, 383-392.
14. Hoemann, C.D., El-Gabalawy, H., McKee, M.D., 2009. In vitro osteogenesis assays: influence of the primary cell source on alkaline phosphatase activity and mineralization. Pathologie Biologie 57, 318-323.
15. Inoue, T., Sakurai, N., Nagai, S., Nagai, M., 1992. Studies on the constituents of Aceraceae plants (X): isolation of flavonoid glycosides and a cerebroside from the leaves of Acer negundo. Shoyakugaku Zasshi 46, 261-264.
16. Itoh, D., Kawano, K., Nabeta, K., 2003. Biosynthesis of chloroplastidic and extrachloroplastidic terpenoids in liverwort cultured cells: 13C serine as a probe of terpene biosynthesis via mevalonate and non-mevalonate pathways. Journal of Natural Products 66, 332-336.
17. Jung, J.H., Lee, C.O., Kim, Y.C., Kang, S.S., 1996. New bioactive cerebrosides from Arisaema amurense. Journal of Natural Products 59, 319-322.
18. Kanno, S., Hirano, S., Kayama, F., 2004. Effects of phytoestrogens and environmental estrogens on osteoblastic differentiation in MC3T3-E1 cells. Toxicology 196, 137-145.
19. Kartsogiannis, V., Ng, K.W., 2004. Cell lines and primary cell cultures in the study of bone cell biology. Molecular and Cellular Endocrinology 228, 79-102.
20. Khosla, S., Melton, L.J., Riggs, B.L., 2011. The unitary model for estrogen deficiency and the pathogenesis of osteoporosis: is a revision needed? Journal of Bone and Mineral Research 26, 441-451.
21. Khosla, S., Oursler, M.J., Monroe, D.G., 2012. Estrogen and the skeleton. Trends in Endocrinology and Metabolism 23, 576-581.
22. Kim, K.H., Choi, S.U., Kim, C.S., Lee, K.R., 2012. Cytotoxic steroids from the trunk of Berberis koreana. Bioscience, Biotechnology, and Biochemistry 76, 825-827.
23. Kumar, M., Rawat, P., Dixit, P., Mishra, D., Gautam, A.K., Pandey, R., Singh, D., Chattopadhyay, N., Maurya, R., 2010. Anti-osteoporotic constituents from Indian medicinal plants. Phytomedicine 17, 993-999.
24. Kumar, T.S., Anandan, A., Jegadeesan, M., 2012. Identification of chemical compounds in Cissus quadrangularis L. variant-I of different sample using GC-MS analysis. Archives of Applied Science Research 4, 1782-1787.
25. Ma, X.H., Zheng, C.J., Han, L.Y., Xie, B., Jia, J., Cao, Z.W., Li, Y.X., Chen, Y.Z., 2009. Synergistic therapeutic actions of herbal ingredients and their mechanisms from molecular interaction and network perspectives. Drug Discovery Today 14, 579-588.
26. Marcus, T., Majumder, S., 2001. The nature of osteoporosis. In: Marcus, R., Feldman, D., Kelsey, J. (Eds.), Osteoporosis, second ed. Academic Press, San Diego, pp. 3-17.
27. Mata, R., Macías, M.L., Rojas, I.S., Lotina-Hennsen, B., Toscano, R.A., Anaya, A.L., 1998. Phytotoxic compounds from Esenbeckia yaxhoob. Phytochemistry 49, 441-449.
28. Maurya, R., Singh, G., Yadav, P.P., 2008. Antiosteoporotic agents from natural sources. In: Rahman, A.U. (Ed.), Studies in Natural Products Chemistry. Elsevier, pp. 517-548.
29. McCarthy, F.O., Chopra, J., Ford, A., Hogan, S.A., Kerry, J.P., O'Brien, N.M., Ryan, E., Maguire, A.R., 2005. Synthesis, isolation and characterisation of β-sitosterol and β-sitosterol oxide derivatives. Organic & Biomolecular Chemistry 3, 3059-3065.
30. Medina-Franco, J.L., Giulianotti, M.A., Welmaker, G.S., Houghten, R.A., 2013. Shifting from the single to the multitarget paradigm in drug discovery. Drug Discovery Today 18, 495-501.
31. Muthusami, S., Ramachandran, I., Krishnamoorthy, S., Govindan, R., Narasimhan, S., 2011a. Cissus quadrangularis augments IGF system components in human osteoblast like SaOS-2 cells. Growth Hormone & IGF Research 21, 343-348.
32. Muthusami, S., Senthilkumar, K., Vignesh, C., Ilangovan, R., Stanley, J., Selvamurugan, N., Srinivasan, N., 2011b. Effects of Cissus quadrangularis on the proliferation, differentiation and matrix mineralization of human osteoblast like SaOS-2 cells. Journal of Cellular Biochemistry 112, 1035-1045.
33. Notaro, G., Piccialli, V., Sica, D., Corriero, G., 1991. 3β,5α,6β-trihydroxylated sterols with a saturated nucleus from two populations of the marine sponge Cliona copiosa. Journal of Natural Products 54, 1570-1575.
34. Owen, T.A., Pan, L.C., 2008. Isolation and culture of rodent osteoprogenitor cells. In: Westendorf, J.J. (Ed.), Osteoporosis: Methods and Protocols. Humana Press, Totowa, pp. 3-18.
35. Parisuthiman, D., Singhatanadgit, W., Dechatiwongse, T., Koontongkaew, S., 2009. Cissus quadrangularis extract enhances biomineralization through upregulation of MAPK-dependent alkaline phosphatase activity in osteoblasts. In Vitro Cellular & Developmental Biology - Animal 45, 194-200.
36. Pathomwichaiwat, T., Suvitayavat, W., Sailasuta, A., Piyachaturawat, P., Soonthornchareonnon, N., Prathanturarug, S., 2012. Antiosteoporotic effect of sequential extracts and freeze-dried juice of Cissus quadrangularis L. in ovariectomized mice. Asian Biomedicine 6, 377-384.
37. Pluemjai, T., Saifah, E., 1986. Constituents of Cissus quadrangularis Linn. Thai Journal of Pharmaceutical Science 11, 205-211.
38. Pullela, S.V., Choi, Y.W., Khan, S.I., Khan, I.A., 2005. New acylated clionasterol glycosides from Valeriana officinalis. Planta Medica 71, 960-961.
39. Sacchi, R., Addeo, F., Paolillo, L., 1997. 1 H and 13C NMR of virgin olive oil. An overview. Magnetic Resonance in Chemistry 35, S133-S145.
40. Shinozaki, J., Nakane, T., Onodera, N., Takano, A., Masuda, K., 2011. Composite constituent: lactucenyl acetate, a novel migrated lupane triterpenoid from Lactuca indica revision of structure of tarolupenyl acetate. Chemical and Pharmaceutical Bulletin 59, 767-769.
41. 13C nuclear magnetic resonance of lupane-type triterpenes, lupeol, betulin and betulinic acid. Chemical and Pharmaceutical Bulletin 28, 1006-1008.
42. Sims, N.A., Gooi, J.H., 2008. Bone remodeling: multiple cellular interactions required for coupling of bone formation and resorption. Seminars in Cell & Developmental Biology 19, 444-451.
43. Singh, G., Rawat, P., Maurya, R., 2007. Constituents of Cissus quadrangularis. Natural Product Research 21, 522-528.
44. 3 in 17β-estradial induced-proliferation and differentiation of osteoblastic MC3T3-E1 cells. European Journal of Pharmacology 659, 273-280.
45. Spanova, M., Daum, G., 2011. Squalene-biochemistry, molecular biology, process biotechnology, and applications. European Journal of Lipid Science and Technology 113, 1299-1320.
46. Stohs, S.J., Ray, S.D., 2013. A review and evaluation of the efficacy and safety of Cissus quadrangularis extracts. Phytotherapy Research 27, 1107-1114.
47. Tomosaka, H., Koshino, H., Tajika, T., Omata, S., 2001. Lupeol esters from the twig bark of Japanese pear (Pyrus serotina Rehd.) cv. Shinko. Bioscience. Biotechnology, and Biochemistry 65, 1198-1201.
48. Tsai, P.W., De Castro-Cruz, K.A., Shen, C.C., Ragasa, C.Y., 2012. Chemical constituents of Broussonetia luzonicus. Pharmacognosy Journal 4, 1-4.
49. Wang, D., Christensen, K., Chawla, K., Xiao, G., Krebsbach, P.H., Franceschi, R.T., 1999. Isolation and characterization of MC3T3-E1 preosteoblast subclones with distinct in vitro and in vivo differentiation/mineralization potential. Journal of Bone and Mineral Research 14, 893-903.
50. Williamson, E.M., 2001. Synergy and other interactions in phytomedicines. Phytomedicine 8, 401-409.
51. Williamson, E.M., 2002. Major Herbs of Ayuraveda. Churchill Livingstone, London.
52. Wu, Y.B., Lin, X.H., Wu, J.G., Yi, J., Zheng, Y.Z., Wu, J.Z., 2011. Volatile components of fruits of Ligustrum lucidum Ait stimulate proliferation and differentiation of rat calvarial osteoblasts. African Journal of Biotechnology 10, 8662-8668.
53. Yan, X.Z., Yang, W., Yang, F., Kersten-Niessen, M., Jansen, J.A., Both, S.K., 2014. Effects of continuous passaging on mineralization of MC3T3-E1 cells with improved osteogenic culture protocol. Tissue Engineering Part C: Methods 20, 198-204.
54. Yang, Y., Zhang, Z., Li, S., Ye, X., Li, X., He, K., 2014. Synergy effects of herb extracts: pharmacokinetics and pharmacodynamic basis. Fitoterapia 92, 133-147.