CREATED USING THE RSC ARTICLE TEMPLATE (VER. 3.0) - SEE WWW.RSC.ORG/ELECTRONICFILES FOR DETAILS
Organic & Biomolecular Chemistry
Page 4 of 4
ARTICLE TYPE
10. P. B. Murti and T. R. Seshadri, Proc. Indian Natl. Sci. Acad., A,
1945, 20, 279-291.
11. L. M. Al Muqarrabun, N. Ahmat, S. A. Ruzaina, N. H. Ismail and I.
Sahidin, J. Ethnopharmacol., 2013, 150, 395-420.
DOI: 10.1039/C5OB01802A
12. S. Rangaswami and T. R. Seshadri, Proc. Indian Acad. Sci., 1942, 15,
417-423.
65 13. M. M. Saha, U. K. Mallik and A. K. Mallik, Phytochemistry, 1991,
30, 3834-3836.
14. A. K. Tamrakar, P. P. Yadav, P. Tiwari, R. Maurya and A. K.
Srivastava, J. Ethnopharmacol., 2008, 118, 435-439.
of pongamol (1a, 100 mg, 1 equiv.) in DMF was added K2CO3
(94 mg, 2 equiv.) and reaction mixture was stirred at 60 oC for 12
h. After completion of the reaction, reaction mixture was
partitioned between water and dichloromethane. The organic
layer was collected, evaporated in vacuo and the crude product
was purified using silica gel column chromatography to get
lanceolatin (3ab, 85%). Ovalitenone (2a) was converted to
pongaglabrone (4ab) using similar method.
60
5
15. S. S. Rangaswami, Rama.V.B., Curr. Sci., 1955, 24, 15.
70 16. A. F. Magalhães, A. M. Tozzi, E. G. Magalhães, M. A. Nogueira and
S. C. Queiroz, Phytochemistry, 2000, 55, 787-792.
17. J. Li, Z. Jiang, X. Li, Y. Hou, F. Liu, N. Li, X. Liu, L. Yang and G.
Chen, Bioorg. Med. Chem. Lett., 2015, 25, 53–58.
18. X. Huo, L. Zhang, L. Gao, Y. Guo, L. Zhang, L. Li, J. Si and L. Cao,
Lanceolatin B (3ab). Yellowish white solid; 60 mg; yield: 85%;
ο
10 m.p. 126-128 C; IR (CHCl3): νmax 3418, 2922, 2851, 2080,
1650, 1605,1530, 1494, 1458, 1449, 1404, 1360, 1282, 1216 cm-
1
1; H NMR (400 MHz, CDCl3):
δ (ppm) 8.19 (d, J = 8 Hz , 1H,
CH-5), 7.98 (m, 2H, Ar-2'- 6' ), 7.79 (d, J = 4 Hz 1H, OCH=CH),
7.56-7.56 (m, 4H, Ar-3',4',5', CH-6), 7.22 (d, J = 4Hz, 1H,
15 OCH=CH), 6.90 (s, 1H,COCH=CPh); 13C NMR (100 MHz,
75
80
85
Biol. Pharm. Bull., 2015, 38, 1328-1336.
19. Y. R. Lee and A. T. Morehead Jr, Tetrahedron, 1995, 51, 4909-4922.
20. M. C. Pirrung and Y. R. Lee, Tetrahedron Lett., 1994, 35, 6231-6234.
21. Y. R. Lee and K. Y. Kang, Lett. Org. Chem, 2007, 4, 440-444.
22. G. W. Kabalka and A. R. Mereddy, Tetrahedron Lett., 2005, 46,
6315–6317.
23. G. P. Romanelli, E. G. Virla, P. R. Duchowicz, A. L. Gaddi, D. M.
Ruiz, D. O. Bennardi, E. Del Valle Ortiz and J. C. Autino, J. Agric.
Food Chem., 2010, 58, 6290-6295.
24. S. K. Jain, A. S. Pathania, S. Meena, R. Sharma, A. Sharma, B.
Singh, B. D. Gupta, S. Bhushan, S. B. Bharate and R. A.
Vishwakarma, J. Nat. Prod., 2013, 76, 1724−1730.
25. J. A. Seijas, M. P. Vazquez-Tato and R. Carballido-Reboredo, J. Org.
Chem., 2005, 70, 2855-2858.
26. B. Kosmrlj and B. Sket, Org. Lett., 2007, 9, 3993-3996.
CDCl3):
δ (ppm) 178.3 (C=O), 162.6, 158.3, 150.8, 145.8
(OCH=CH), 131.7, 131.6, 129.6, 126.2, 121.7, 119.3, 117.1,
110.2, 108.0 (OCH=CH), 104.2 (COCH=CPh); HR-ESIMS: m/z
263.0694 [M+H]+ calcd for C17H10O3+ H+ (263.0703).
20 Pongaglabrone (4ab). White brown cystals; 65 mg; m.p. 132-134
°C; IR (CHCl3): νmax 3584, 3356, 2993, 2920, 2852, 1642, 1607,
1584, 1528, 1504, 1482, 1404, 1374, 1331, 1295, 1239, 1211 cm-
1
1; H NMR (400 MHz, CDCl3):
δ (ppm) 8.18 (d, J = 8 Hz, 1H,
CH-5), 7.78 (d, 1H, OCH=CH), 7.56 (m, 2H, CH), 7.41 (d, J = 4
25 Hz, 1H ), 7.21 (d, 1H, OCH=CH), 6.97 (d, 1H, CH), 6.78 (s, 1H,
COCH=CPh), 6.11 (s, 2H, OCH2O); 13C NMR (100 MHz,
90 27. J. Zhao, Y. Zhao and H. Fu, Angew. Chem. Int. Ed., 2011, 50, 3769-
3773.
28. H. Xu, B. Yu, H. Zhang, Y. Zhao, Z. Yang, J. Xu, B. Han and Z. Liu,
Chem. Commun., 2015, 51, 12212-12215.
29. S. K. Talapatra, A. K. Mallik and B. Talapatra, Phytochemistry, 1980,
CDCl3):
δ (ppm) 178.2 (C=O), 162.3, 158.3, 150.7, 150.6, 148.5,
145.8 (OCH=CH), 125.7, 121.7, 121.3, 119.2, 117.0, 110.1,
108.0, 107.0, 106.2 (OCH=CH), 104.2 (COCH=CPh), 101.9;
30 HR-ESIMS: m/z 307.0596 [M+H]+ calcd for C18H10O5+ H+
(307.0601).
95
19, 1199-1202.
30. B.J. Harborne, The Flavonoids Advances in Research Since 1986,1st
ed., Chapman & Hall/CRC, London, U.K, 1994, pp. 398.
31. F. Gomez-Garibay, O. Tellez-Valdez, G. Moreno-Torres and J. S.
Calderon, Z. Naturforsch. 2002, 57c, 579-583.
100 32. Compounds 5 and 6 are synthetic chalcones prepared via reaction of
corresponding acetophenones with aryl aldehydes using a routine
base-mediated chalcone synthesis procedure.
Acknowledgements
RS is thankful to CSIR, New Delhi for the award of senior
35 research fellowship. This research was supported by a grant from
the CSIR 12th FYP project (BSC-0205).
Notes and references
1. A. Krishnamurthi, In: The Wealth of India; Publication and
40
Information, Directorate, CSIR: New Delhi, India,, 1969, Vol. VIII.
2. P. K. Warrier, V. P. K. Nambiar and C. Ramankutty, Indian
Medicinal Plants: A Compendium of 500 Species, Orient Longman,
1993.
3. G. R. Rout, D. P. Sahoo and S. Aparajita, Crop. Breed. Appl. Biot.,
2009, 9, 268-273.
45
4. H. Pavithra, M. Shivanna, K. Chandrika, K. Prasanna and B. Gowda,
Tree Genet. Genomes, 2014, 10, 173-188.
5. M. Bala, T. N. Nag, S. Kumar, M. Vyas, A. Kumar and N. S. Bhogal,
J. Am. Oil. Chem. Soc., 2011, 88, 559-562.
50 6. K. R. Kritikar, B. D. Basu and L. M. Basu, Indian Medicinal Plants,
2nd ed.; Allahabad, India, 1956, Vol. 1, pp. 830-832.
7. R. Ranga Rao, A. K. Tiwari, P. Prabhakar Reddy, K. Suresh Babu, A.
Z. Ali, K. Madhusudana and J. Madhusudana Rao, Bioorg. Med.
Chem., 2009, 17, 5170-5175.
55 8. C. Muthu, M. Ayyanar, N. Raja and S. Ignacimuthu, J. Ethnobiol.
Ethnomed., 2006, 2, 43-43.
9. G. Bhatia, A. Puri, R. Maurya, P. PrakashYadav, M. Khan, A.
Khanna and J. Saxena, Med. Chem. Res., 2008, 17, 618-620.
4
|Journal Name, [year], [vol], 00–00
This journal is © The Royal Society of Chemistry [year]