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Novel carbazole alkaloid from Murraya koenigii (l.) Spreng

Year 2023, Volume: 10 Issue: 3, 354 - 360, 27.08.2023
https://doi.org/10.21448/ijsm.1193419

Abstract

Background: The plant Murraya koenigii (L.) Spreng.native to Pakistan and India and a part of the Rutaceae family, plays a vital role in the Indian Ayurvedic medicine system. Studies have shown that this plant's bark, roots, and leaves contain many carbazole alkaloids. These alkaloids are known to have substantial therapeutic properties.
Methods:
The crushed and powdered organs of M. koenigii were extracted with several solvents (acetone, chloroform, and methanol). Then, using column chromatography, a dull brown oily substance, MK- 1 (1.05 g), was obtained with chloroform and methanol (7:3).
Result
We have successfully isolated a new carbazole alkaloid, 3-geranyl 8-hydroxy 6, 7-di methoxy 3’, 3’-dimethyl 1, 2-pyranocarbazole, from the seeds of M. koenigii. The structure was further elucidated by cross-referencing our NMR, UV, IR, and MS data with that found in the published literature.
Conclusion:
Comparing the previously published literature data clearly explained that this alkaloid is new to M. koenigii.

References

  • Abeysinghe, D., Alwis, D., Kumara, K., & Chandrika, U. (2021). Nutritive Importance and Therapeutics Uses of Three Different Varieties (Murraya koenigii, Micromelum minutum, and Clausena indica) of Curry Leaves: An Updated Review. Evidence-Based Complementary and Alternative Medicine, 2021, 1 23. https://doi.org/10.1155/2021/5523252
  • Aniqa, A., Kaur, S., & Sadwal, S. (2021). A Review of the Anti-Cancer Potential of Murraya koenigii(Curry Tree) and Its Active Constituents. Nutrition and Cancer, 74(1), 12-26. https://doi.org/10.1080/01635581.2021.1882509
  • Balakrishnan, R., Vijayraja, D., Jo, S.H., Ganesan, P., Su-Kim, I., & Choi, D.K. (2020). Medicinal Profile, Phytochemistry, and Pharmacological Activities of Murraya koenigii and its Primary Bioactive Compounds. Antioxidants (Basel, Switzerland), 9(2), 101. https://doi.org/10.3390/antiox9020101
  • Batool, S., Khera, R., Hanif, M., Ayub, M., & Memon, S. (2020). Curry Leaf. Medicinal Plants Of South Asia, 179-190. https://doi.org/10.1016/b978-0-08-102659-5.00014-8
  • Bhattacharyya, P., & Chakraborty, D. (1987). Carbazole Alkaloids. Fortschritte Der Chemie Organischer Naturstoffe / Progress in The Chemistry of Organic Natural Products, 52, 159-209. https://doi.org/10.1007/978-3-7091-8906-1_4
  • Chakraborty, D., & Roy, S. (1991). Carbazole Alkaloids III. Fortschritte Der Chemie Organischer Naturstoffe / Progress in The Chemistry of Organic Natural Products, 71-152. https://doi.org/10.1007/978-3-7091-9119-4_2
  • Chakraborty, D., & Roy, S. (2003). Carbazole Alkaloids IV. Fortschritte Der Chemie Organischer Naturstoffe / Progress in The Chemistry of Organic Natural Products, 125-230. https://doi.org/10.1007/978-3-7091-6051-0_3
  • Chakraborty, D.P. (1977). Carbazole Alkaloids. In: Herz W., Grisebach H., Kirby G.W. (eds) Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. vol 34. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8476-9_5
  • Chopra, R., Nayar, S., & Chopra, I. (2002). Glossary of Indian medicinal plants. National Institute of Science Communication and Information Resources. New Delhi
  • Gautam, S., Kunwar, L., Dhami, N., Kunwar, R., Bussmann, R., & Paniagua-Zambrana, N. (2020). Murraya koenigii (L.) Spreng. Rutaceae. Ethnobotany of The Himalayas, 1-9. https://doi.org/10.1007/978-3-030-45597-2_155-1
  • Hobani, Y.H. (2022). Cytotoxicity of Mahanimbine from Curry Leaves in Human Breast Cancer Cells (MCF-7) via Mitochondrial Apoptosis and Anti-Angiogenesis. Molecules 27, 971. https://doi.org/10.3390/molecules27030971
  • Kapil, R. (1971). The Carbazole Alkaloids. In: Manske, R., & Holmes, H. (Eds.), Chemistry and Physiology. The Alkaloids, Volume 13, Chapter 6, 273-302. Elsevier Science & Technology
  • Knölker, H., & Reddy, K. (2008). Biological and Pharmacological Activities of Carbazole Alkaloids. The Alkaloids: Chemistry and Biology, 181-193. https://doi.org/10.1016/s1099-4831(07)00004-1
  • Mandal, S. (2016). Curry plant, Murraya koenigii (L.) Spreng: An indigenous spice plant with versatile medicinal property: A minireview. International Journal of Clinical and Experimental Physiology, 3(2), 59. https://doi.org/10.4103/2348-8093.185203
  • Satyavati, G., Gupta, A., Tandon, N., & Seth, S. (1987). Medicinal plants of India. Indian Council of Medical Research. New Delhi
  • Singh, A., Singh, B., & Navneet. (2023). Bioactive compounds in cancer care and prevention. Role of Nutrigenomics in Modern-Day Healthcare and Drug Discovery, 439–468. Elsevier. https://doi.org/10.1016/b978-0-12-824412-8.00007-2
  • Tripathi, Y., Anjum, N., & Rana, A. (2018). Chemical Composition and In vitro Antifungal and Antioxidant Activities of Essential Oil from Murraya koenigii (L.) Spreng. Leaves. Asian Journal of Biomedical and Pharmaceutical Sciences, 8(65). https://doi.org/10.4066/2249-622x.65.18-729

Novel carbazole alkaloid from Murraya koenigii (l.) Spreng

Year 2023, Volume: 10 Issue: 3, 354 - 360, 27.08.2023
https://doi.org/10.21448/ijsm.1193419

Abstract

Background: The plant Murraya koenigii (L.) Spreng.native to Pakistan and India and a part of the Rutaceae family, plays a vital role in the Indian Ayurvedic medicine system. Studies have shown that this plant's bark, roots, and leaves contain many carbazole alkaloids. These alkaloids are known to have substantial therapeutic properties.
Methods:
The crushed and powdered organs of M. koenigii were extracted with several solvents (acetone, chloroform, and methanol). Then, using column chromatography, a dull brown oily substance, MK- 1 (1.05 g), was obtained with chloroform and methanol (7:3).
Result
We have successfully isolated a new carbazole alkaloid, 3-geranyl 8-hydroxy 6, 7-di methoxy 3’, 3’-dimethyl 1, 2-pyranocarbazole, from the seeds of M. koenigii. The structure was further elucidated by cross-referencing our NMR, UV, IR, and MS data with that found in the published literature.
Conclusion:
Comparing the previously published literature data clearly explained that this alkaloid is new to M. koenigii.

References

  • Abeysinghe, D., Alwis, D., Kumara, K., & Chandrika, U. (2021). Nutritive Importance and Therapeutics Uses of Three Different Varieties (Murraya koenigii, Micromelum minutum, and Clausena indica) of Curry Leaves: An Updated Review. Evidence-Based Complementary and Alternative Medicine, 2021, 1 23. https://doi.org/10.1155/2021/5523252
  • Aniqa, A., Kaur, S., & Sadwal, S. (2021). A Review of the Anti-Cancer Potential of Murraya koenigii(Curry Tree) and Its Active Constituents. Nutrition and Cancer, 74(1), 12-26. https://doi.org/10.1080/01635581.2021.1882509
  • Balakrishnan, R., Vijayraja, D., Jo, S.H., Ganesan, P., Su-Kim, I., & Choi, D.K. (2020). Medicinal Profile, Phytochemistry, and Pharmacological Activities of Murraya koenigii and its Primary Bioactive Compounds. Antioxidants (Basel, Switzerland), 9(2), 101. https://doi.org/10.3390/antiox9020101
  • Batool, S., Khera, R., Hanif, M., Ayub, M., & Memon, S. (2020). Curry Leaf. Medicinal Plants Of South Asia, 179-190. https://doi.org/10.1016/b978-0-08-102659-5.00014-8
  • Bhattacharyya, P., & Chakraborty, D. (1987). Carbazole Alkaloids. Fortschritte Der Chemie Organischer Naturstoffe / Progress in The Chemistry of Organic Natural Products, 52, 159-209. https://doi.org/10.1007/978-3-7091-8906-1_4
  • Chakraborty, D., & Roy, S. (1991). Carbazole Alkaloids III. Fortschritte Der Chemie Organischer Naturstoffe / Progress in The Chemistry of Organic Natural Products, 71-152. https://doi.org/10.1007/978-3-7091-9119-4_2
  • Chakraborty, D., & Roy, S. (2003). Carbazole Alkaloids IV. Fortschritte Der Chemie Organischer Naturstoffe / Progress in The Chemistry of Organic Natural Products, 125-230. https://doi.org/10.1007/978-3-7091-6051-0_3
  • Chakraborty, D.P. (1977). Carbazole Alkaloids. In: Herz W., Grisebach H., Kirby G.W. (eds) Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. vol 34. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8476-9_5
  • Chopra, R., Nayar, S., & Chopra, I. (2002). Glossary of Indian medicinal plants. National Institute of Science Communication and Information Resources. New Delhi
  • Gautam, S., Kunwar, L., Dhami, N., Kunwar, R., Bussmann, R., & Paniagua-Zambrana, N. (2020). Murraya koenigii (L.) Spreng. Rutaceae. Ethnobotany of The Himalayas, 1-9. https://doi.org/10.1007/978-3-030-45597-2_155-1
  • Hobani, Y.H. (2022). Cytotoxicity of Mahanimbine from Curry Leaves in Human Breast Cancer Cells (MCF-7) via Mitochondrial Apoptosis and Anti-Angiogenesis. Molecules 27, 971. https://doi.org/10.3390/molecules27030971
  • Kapil, R. (1971). The Carbazole Alkaloids. In: Manske, R., & Holmes, H. (Eds.), Chemistry and Physiology. The Alkaloids, Volume 13, Chapter 6, 273-302. Elsevier Science & Technology
  • Knölker, H., & Reddy, K. (2008). Biological and Pharmacological Activities of Carbazole Alkaloids. The Alkaloids: Chemistry and Biology, 181-193. https://doi.org/10.1016/s1099-4831(07)00004-1
  • Mandal, S. (2016). Curry plant, Murraya koenigii (L.) Spreng: An indigenous spice plant with versatile medicinal property: A minireview. International Journal of Clinical and Experimental Physiology, 3(2), 59. https://doi.org/10.4103/2348-8093.185203
  • Satyavati, G., Gupta, A., Tandon, N., & Seth, S. (1987). Medicinal plants of India. Indian Council of Medical Research. New Delhi
  • Singh, A., Singh, B., & Navneet. (2023). Bioactive compounds in cancer care and prevention. Role of Nutrigenomics in Modern-Day Healthcare and Drug Discovery, 439–468. Elsevier. https://doi.org/10.1016/b978-0-12-824412-8.00007-2
  • Tripathi, Y., Anjum, N., & Rana, A. (2018). Chemical Composition and In vitro Antifungal and Antioxidant Activities of Essential Oil from Murraya koenigii (L.) Spreng. Leaves. Asian Journal of Biomedical and Pharmaceutical Sciences, 8(65). https://doi.org/10.4066/2249-622x.65.18-729
There are 17 citations in total.

Details

Primary Language English
Subjects Plant Biochemistry, Pharmacology and Pharmaceutical Sciences
Journal Section Articles
Authors

Arifa Mehreen 0000-0001-5899-8027

Shagufta Kamal 0000-0003-4073-2583

Sevinc Musayeva 0000-0002-3957-8825

Muhammad Qaisar 0009-0006-1275-5744

Sumia Urainab 0000-0003-1066-9894

Asad Ullah This is me 0009-0000-5783-5242

Early Pub Date July 31, 2023
Publication Date August 27, 2023
Submission Date October 23, 2022
Published in Issue Year 2023 Volume: 10 Issue: 3

Cite

APA Mehreen, A., Kamal, S., Musayeva, S., Qaisar, M., et al. (2023). Novel carbazole alkaloid from Murraya koenigii (l.) Spreng. International Journal of Secondary Metabolite, 10(3), 354-360. https://doi.org/10.21448/ijsm.1193419
International Journal of Secondary Metabolite

e-ISSN: 2148-6905