Secondary metabolites from the leaves of Solanum melongena and their nitric oxide production inhibitory activity

Nguyen Phuc Khanh Nhi, Tran Phuong Ha, Le Tuan Anh, Vu Thi Quynh Chi, Le Canh Viet Cuong
Author affiliations

Authors

  • Nguyen Phuc Khanh Nhi Mientrung Institute for Scientific Rerearch, Vietnam National Museum of Nature,VietnamAcademy of Science and Technology, 321 Huynh Thuc Khang, Hue City, Thua Thien Hue, Viet Nam
  • Tran Phuong Ha Mientrung Institute for Scientific Rerearch, Vietnam National Museum of Nature,VietnamAcademy of Science and Technology, 321 Huynh Thuc Khang, Hue City, Thua Thien Hue, Viet Nam
  • Le Tuan Anh Mientrung Institute for Scientific Rerearch, Vietnam National Museum of Nature,VietnamAcademy of Science and Technology, 321 Huynh Thuc Khang, Hue City, Thua Thien Hue, Viet Nam
  • Vu Thi Quynh Chi The Centre of Marine Environmental Monitoring and Analysis, Duong Kinh, Hai Phong City, Viet Nam
  • Le Canh Viet Cuong Mientrung Institute for Scientific Rerearch, Vietnam National Museum of Nature,VietnamAcademy of Science and Technology, 321 Huynh Thuc Khang, Hue City, Thua Thien Hue, Viet Nam

DOI:

https://doi.org/10.15625/2525-2518/16137

Keywords:

Solanum melogena, quadranoside III, alangilignoside C, torvoside J, N-trans-feruloyloctopamine, NO production

Abstract

Solanum melongena L. var. esculentum Ness. growing widely in Vietnam is a member of the plants family Solanaceae. Fruits and whole plant of S. melongena has been used by traditional medicine to treat various diseases, such as, toothache, turgescence, pruritus, and haemorrhoids. Previous studies indicated that this plant contain of alkaloids, anthocyanins, flavonoids, lignanamides, phenylpropanoid amides, sesquiterpenoids, steroids, steroidal saponins, and triterpenoids and exert diverse biological activities, such as anti-inflammatory, anti-cancer, anti-nociceptive, anti-oxidant, and anti-hypertensive activities. Using various chromatographic separations, four compounds were isolated from the leaves of Solanum melongena L growing in Thua Thien Hue province. Their chemical structures were elucidated to be quadranoside III (1), alangilignoside C (2), torvoside J (3), and N-trans-feruloyloctopamine (4) by 1D-, 2D-NMR spectra and compared with those reported in the literature. This study also reports the anti-inflammatory effect of isolated compounds via their inhibitory activity against the production of nitric oxide (NO) in RAW 264.7 macrophages cells stimulated by lipopolysaccharide. Compounds 1 and 4 showed NO inhibitory effects with IC50 values of 99.67 and 91.80 µM, respectively (posotive control L-NMMA, 32.26 µM), while compounds 2 and 3 were inactive. This is the first time that compound 1 has been reported from Solanum genus.

Downloads

Download data is not yet available.

References

Chi V. V. - Dictionary of Medicinal Plants in Vietnam. Medical Publishing House, Ha Noi, 2012, pp. 278-279.

Vohora S. B., Kumar I., Khan M. S. Y. - Effect of alkaloids of Solanvm melongena on the central nervous system. J.Ethnopharmacol. 11 (1984) 331-336.

Tanchev S. S., Ruskov P. J., Timberlake C. F. - The anthocyanins of bulgarian aubergine (Solanum melongena). Phytochemistry 9 (1970) 1681-1682.

Sun J., Huo H. X., Huang Z., Zhang J., Li J., Tu P. F. - A new γ-alkylated-γ-butyrolactone from the roots of Solanum melongena.Chin. J. Nat. Med. 13 (2015) 699-703.

Sun J., Gu Y. F., Su X. Q., Li M. M., Huo H. X., Zhang J., Zeng K. W., Zhang Q., Zhao Y. F., Li J., Tu P. F. - Anti-inflammatory lignanamides from the roots of Solanum melongena L. Fitoterapia 98 (2014) 110-116.

Yang B. Y., Yin X., Liu Y., Ye H. L., Zhang M. L., Guan W., Kuang H. X. - Bioassay-guided isolation of lignanamides with potential anti-inflammatory effect from the roots of Solanum melongena L.Phytochem. Lett. 30 (2019) 160-164.

Sun J., Huo H. X., Zhang J., Huang Z., Zheng J., Zhang Q., Zhao Y. F., Li J., Tu P. F. - Phenylpropanoid amides from the roots of Solanum melongena L. (Solanaceae). Biochem. Syst. Ecol. 58 (2015) 265-269.

Zhao D. Y., Liu Y., Sun Y. P., Li X. M., Xu Z. P., Pan J., Guan W., Yang B. Y., Kuang H. X. - Sesquiterpenoids with diverse carbon skeletons from the sepals of Solanum melongena L. Fitoterapia 142 (2020) 104517.

Kintia P. K., Shvets S. A. - Melongosides n, o and p: steroidal saponins from seeds of Solanum melongena. Phytochemistry 24 (1985) 1567-1569.

Kintia P. K., Shvets S. A. - Melongoside L and melongoside M, steroidal saponins from Solanum melongena seeds. Phytochemistry 24 (1985) 197-198.

Yang B. Y., Yin X., Liu Y., Zhao D. Y., Kuang H. X. - New steroidal saponins from the roots of Solanum melongena L. Fitoterapia 128 (2018) 12-19.

Chen F. F., Zhou J., Zhang Y. W., Chen Y. P., Wang Y. R., Zhao Y. F., Liu W., Huang X. F. - Five new steroidal saponins from the seeds of Solanum melongena L.Phytochem. Lett. 41 (2021) 21-26.

Han S. W., Tae J., Kim J. A., Kim D. K., Seo G. S., Yun K. J., Choi S. C., Kim T. H., Nah Y. H., Lee Y. M. - The aqueous extract of Solanum melongena inhibits PAR2 agonist-induced inflammation. Clin. Chim. Acta. 328 (2003) 39-44.

Dashti-r M. H., Anvari M., Rezaei-s M. - Antinociceptive effect of Solanum Melongena extract on phasic pain model in male mice. Clin. Biochem. 44 (2011) S335.

Nisha P., Abdul Nazar P., Jayamurthy P. - A comparative study on antioxidant activities of different varieties of Solanum melongena. Food and Chemical Toxicology 47 (2009) 2640-2644.

Sharma H., Chawla N., Dhatt A. S. - Nutraceutical content and free radical scavenging capacity of brinjal (Solanum melongena L.) genotypes. Sci. Hortic. 244 (2019) 294-303.

Yamaguchi S., Matsumoto K., Koyama M., Tian S., Watanabe M., Takahashi A., Miyatake K., Nakamura K. - Antihypertensive effects of orally administered eggplant (Solanum melongena) rich in acetylcholine on spontaneously hypertensive rats. Food Chem. 276 (2019) 376-382.

Nguyen Viet D., Le Ba V., Nguyen Duy T., Pham Thi V. A., Tran Thi H., Le Canh V. C., Bach Long G., Kim Y. H., Tuan Anh H. L. - Bioactive compounds from the aerial parts of Hypericum sampsonii. Nat. Prod. Res. 35 (2021) 646-648.

Adnyana I. K., Tezuka Y., Banskota A. H., Xiong Q., Tran K. Q., Kadota S. - Quadranosides I-V, new triterpene glucosides from the seeds of Combretum quadrangulare. J. Nat. Prod. 63 (2000) 496-500.

Nhiem N. X., Lee H. Y., Kim N. Y., Park S. J., Kim E. S., Han J. E., Yang H., Kim S. H. - Stereochemical assignment of five new lignan glycosides from Viscum album by NMR study combined with CD spectroscopy. Mag. Reson. Chem. 50 (2012) 772-777.

Pinto F. d. C. L., Torres M. d. C. M., Silveira E. R., Pessoa O. D. L., Braz-Filho R., Guedes M. L. d. S. - Constituintes químicos de Solanum buddleifolium Sendtn. Quim. Nova. 36 (2013) 1111-1115.

Challal S., Buenafe O. E., Queiroz E. F., Maljevic S., Marcourt L., Bock M., Kloeti W., Dayrit F. M., Harvey A. L., Lerche H., Esguerra C. V., de Witte P. A., Wolfender J. L., Crawford A. D. - Zebrafish bioassay-guided microfractionation identifies anticonvulsant steroid glycosides from the Philippine medicinal plant Solanum torvum. ACS Chem. Neurosci. 5 (2014) 993-1004.

Agrawal P. K. - 25R/25S stereochemistry of spirostane-type steroidal sapogenins and steroidal saponins via chemical shift of geminal protons of ring-F.Mag. Reson. Chem. 41 (2003) 965-968.

King R. R., Calhoun L. A. - Characterization of cross-linked hydroxycinnamic acid amides isolated from potato common scab lesions. Phytochemistry 66 (2005) 2468-2473.

Downloads

Published

21-06-2022

How to Cite

[1]
N. P. K. . Nhi, T. Phuong Ha, L. Tuan Anh, V. T. Q. Chi, and L. C. V. . Cuong, “Secondary metabolites from the leaves of Solanum melongena and their nitric oxide production inhibitory activity”, Vietnam J. Sci. Technol., vol. 60, no. 3, pp. 362–370, Jun. 2022.

Issue

Section

Natural Products

Most read articles by the same author(s)