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(12) Patent Application Publication (10) Pub. No.: US 2014/0079834 A1 Maurya Et Al US 20140079834A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0079834 A1 Maurya et al. (43) Pub. Date: Mar. 20, 2014 (54) BIOACTIVE FRACTIONS AND COMPOUNDS Publication Classification FROM DALBERGIASISSOO FOR THE PREVENTION OR TREATMENT OF (51) Int. Cl. OSTEO-HEALTH RELATED DISORDERS A613 L/7048 (2006.01) A613 L/352 (2006.01) (75) Inventors: Rakesh Maurya, Lucknow (IN); Preety A61E36/48 (2006.01) Dixit, Lucknow (IN); Ritu Trivedi, (52) U.S. Cl. Lucknow (IN); Vikram Khedgikar, CPC ............. A6 IK3I/7048 (2013.01); A61K 36/48 Lucknow (IN); Jyoti Gautam, Lucknow (2013.01); A61 K3I/352 (2013.01) (IN): Avinash Kumar, Lucknow (IN); USPC ............. 424/757:536/18.1: 514/27: 514/456 Divya Singh, Lucknow (IN); Sheelendra Pratap Singh, Lucknow (IN); (none) Wahajuddin, Lucknow (57) ABSTRACT (IN); Girish Kumar Jain, Lucknow (IN); Naibedya Chattopadhyay, The present invention relates to bioactive fractions and com Lucknow (IN) pounds from Dalbergia Sissoo for the prevention or treatment of osteo-health related disorders. The present invention (73) Assignee: COUNCIL OF SCIENTIFIC & relates in the field of pharmaceutical composition that pro INDUSTRIAL RESEARCH, New vides new plant extracts, their fractions and pure compound Delhi (IN) isolated from natural sources that are useful for the prevention and/or treatment of various medical indications associated (21) Appl. No.: 14/113,561 with estrogen dependent or independent diseases or syn dromes or disorders preferably in the prevention or treatment (22) PCT Filed: Apr. 25, 2012 of estrogen dependent or independent diseases or syndromes or disorders caused in humans and animals, and achievement (86). PCT No.: PCT/IN12/00301 of peak bone mass during skeletal growth and health in S371 (c)(1), humans and animals. Particularly the present invention fur (2), (4) Date: Oct. 23, 2013 ther relates to the processes for the preparation of biologically active extracts, fractions, and isolation of pure compounds, (30) Foreign Application Priority Data from Dalbergia Sissoo plant from the family Fabaceae their pharmaceutically acceptable salts and compositions of the Apr. 25, 2011 (IN) ........................... 1206/DELA2O11 principal aspect of the present invention. Patent Application Publication Mar. 20, 2014 Sheet 1 of 8 US 2014/0079834 A1 Triturated with hexane and - chloroform succecively r-Hexane Chloroform insoluble (FOO2) (F003) fraction (1) Suspended in distilled water (II) Extracted with n-butanol 7-Butanol (FOO4) Isolation of compound using chromatography techniques compound 1-13 Figure 1 Patent Application Publication Mar. 20, 2014 Sheet 2 of 8 US 2014/0079834 A1 Figure 2 Patent Application Publication Mar. 20, 2014 Sheet 3 of 8 US 2014/0079834 A1 Serum Osteocalcin 160 CTX 140 120 OOOOO !ds 2468O O Sham OVX OVX-50. Ox100 o:EST Sham Ox Ox50mgow 100mg 0xEST Figure 3 Patent Application Publication Mar. 20, 2014 Sheet 4 of 8 US 2014/0079834 A1 (A) (B). (C) 0.16 Mineralization 0.14 is 0.12 c O.08 c. 0.06 O 0.04 0.02 Sham Ow Ox+50 Ow-100 Ow-EST Figure 4 Patent Application Publication Mar. 20, 2014 Sheet 5 of 8 US 2014/0079834 A1 ov:50 mg/kg ovxt 100 mg/kg ov. EST Shar OW . body weight body weight Sham -- OVX -- OVX -- OVx - OVx + Vehicle Vehicle 50 mg/kg 100mg/kg EST MAR (um/day) 1.13+ 0.03 ** 0.55+ 0.04 1.03 0.070 * 0.98 003 ** 0.880.06*** (um/um/day)BFR 1.09 + 0.04 * 0.54 + 0.04 0.98: 0.06' 0.96+0.03" 0.92+0.07" Each parameter represents pooled data from 10 rats/group and values are expressed as mean-i-S.E.M. " P < 0.05, " P-30.01 and" P< 0.001 compared with OV x + vehicle group. There was no significant difference in MAR and BFR between the two doses (50 mg/kg bodyweight and 100 mg/kg body weight). Figure 5 Patent Application Publication Mar. 20, 2014 Sheet 6 of 8 US 2014/0079834 A1 O.16 0.14 O.2 0.1 0.08 0.06 0.04 0.02 Control Compound 1 Compound 3 Compound 4 OnM OnM OM O. Control Compound 6 Compound 10 Compound 10 1pM 10pM 1pM Figure 6 Patent Application Publication Mar. 20, 2014 Sheet 7 of 8 US 2014/0079834 A1 22 O5 1 5 1 O 5 Control Compound 4 Compound 10 Figure 7 Patent Application Publication Mar. 20, 2014 Sheet 8 of 8 US 2014/0079834 A1 0.3 Compound 4 0.25 Compound 6 Y0.2 0.15 0.25 a 0.1 5 0.2 O 9.05. 0.5 O Control. 1 pt 100pM 10nM 1M g 1. 0.05 0.3 Compound 1 '... 0.25 Control 1 p 100pM 10nM 1M 5 0.2 0.15 Compound 10 O3 is 0,1 0.05 Control 1pM 100pm OnM 1M 0.3 Compound 3 0.25 Control 1pM 100pM 10nM 1M O. 2 0.15 0.1 s 0.05 Control 1pm 100pM 10nM ful Figure 8 US 2014/0079834 A1 Mar. 20, 2014 BOACTIVE FRACTIONS AND COMPOUNDS poorly absorbed and may cause gastrointestinal irritation, FROM DALBERGIASISSOO FOR THE diarrhea and constipation. Raloxifene has been reported to PREVENTION OR TREATMENT OF increase incidence of hot flashes, deep vein thrombosis, pull OSTEO-HEALTH RELATED DISORDERS monary embolism and leg cramps Clemett, D.; Spencer, C. M. Drugs 60,380-409 (2000). FIELD OF THE INVENTION 0006. In view of the use of these therapies and their asso 0001. The present invention relates to bioactive fractions ciated side effects indicate a need for the alternative options in and compounds from Dalbergia Sissoo for the prevention or the prevention and treatment of osteoporosis. treatment of osteo-health related disorders. The present 0007 Traditional medicine is an ancient medical practice invention relates in the field of pharmaceutical composition that existed in human Societies before the application of mod that provides new plant extracts, their fractions and pure ern science to health. The importance of traditional medicine compound isolated from natural sources that are useful for the as a source of primary health care was first officially recog prevention and/or treatment of various medical indications nized by the World Health Organization (WHO) in 1976 by associated with estrogen dependent or independent diseases globally addressing its Traditional Medicine Programme. In or syndromes or disorders preferably in the prevention or traditional medicine, there are many natural crude drugs that treatment of estrogen dependent or independent diseases or have the potential to treat bone diseases. However, not much syndromes or disorders caused in humans and animals, and laboratory work has been reported evaluating their possible achievement of peak bone mass during skeletal growth and development and use, except ipriflavone, a natural product health in humans and animals. Particularly the present inven derivative, which has been used clinically for such indications tion further relates to the processes for the preparation of Fujita, T.; Yoshikawa, S.; Ono, K.; Inoue, T.; Orimo, H. J. biologically active extracts, fractions, and isolation of pure Clin. Exp. Med 138, 113-141 (1986), Passeri, M.: Biondi, compounds, from Dalbergia Sissoo plant from the family M.; Costi, D.; Bufalino, L. Castiglione, g. N.; DiPeppe, C.; Fabaceae their pharmaceutically acceptable salts and compo Abate, G. Bone Miner. 19 (Suppl. 1), S57-62 (1992). It is sitions of the principal aspect of the present invention. believed that herbal medicines are easily available, less expensive, and safer than chemically synthesized drugs. In BACKGROUND OF THE INVENTION India Ayurvedic medicine emerged during the rise of the philosophies of the Upanishads, Buddhism, and other schools 0002 Osteoporosis, which has been defined as a “state of of thought in India. Herbs played an important role in low bone mass” is one of the major aging problems of the Ayurvedic medicine. In our program search for natural osteo society. Osteoporosis is a metabolic disorder characterized by genic plant, n-butanol soluble fraction of ethanol extract of microarchitectural deterioration of bone tissue leading to Dalbergia Sissoo aerial part which is renewable source exhib enhanced bone fragility and consequent increase in fracture ited osteogenic activity in our test model. Thus, the plant risk in older members of the population. Osteoporosis frac extract might possess bioactive ingredients that could pro tures occur most commonly in the spine, hip, distal radius and mote bone formation. The effects on osteoporosis and total ribs. The risk is high in women as compared to men and osteo-health and related disorders and has not been explored. increases sharply after 50 years of age. Factors predisposing 0008. There is a well-recognized link between the preva towards osteoporosis include family history, genetic factors, lence of low peak bone mass (PBM) attainment and hormonal factors, inadequate nutrition, and intake of certain osteoporosis among South Asian women Adami, S.; medications, immobility and disease. The quality of life is Osteoporos Int, Suppl 1, S27-30, (1994). PBM is defined as greatly impaired in persons with sever osteoporosis. It is the highest level of bone mass achieved as a result of normal known to affect >50% of women and 30% men over the age of growth. Adolescence is the most critical period across the life 50 years. In women, there is also an accelerated rate of bone span for bone health because more than half of PBM is accu loss immediately and for variable number of years following mulated during the teenage years. During these early years of menopause. life, bone formation is greater than bone resorption and the 0003 Most of the pharmacological agents available for bone mass increases. PBM attained in early adult life is an clinical use such as calcium, Vitamin D and its analogue, important determinant of skeletal fragility at least until the calcitonin, bisphosphonates, raloxifene, hormone replace age of 70 years (Ref).
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