Nevadensin: Isolation, chemistry and bioactivity
DOI:
https://doi.org/10.22377/ijgp.v4i4.150Abstract
Nevadensin (5,7-dihydroxy-6,8,4'-trimethoxyflavone) has already established itself as a promising natural bioactive substance that bears the potential to become a novel “natural lead†in drug discovery programmes. The bioflavonoid exhibited a wide range of significant biological activities including hypotensive, anti-tubercular, antimicrobial, anti-inflammatory, anti-tumour and anti-cancer activities. This review deals with natural sources, isolation, chemistry and biological activities of the flavonoid in detail. The present resume is aimed to boost the ongoing researches on pharmaceutically potential natural “lead molecules†in drug discovery programmes.Key words: Bioactivity, chemistry, isolation, natural sources, nevadensin
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References
Brahmachari G. Prospects of natural products research in the 21st
century: A sketch. In: Brahmachari G, editor. Chemistry of Natural
Products: Recent Trends and Developments. 1st ed. Trivandrum:
Research Signpost; 2006. p. 1-22
Brahmachari G. Mother nature: An inexhaustible source of
drugs and lead molecules. In: Brahmachari G, editor. Chemistry,
Biochemistry and Pharmacology. 1st ed. New Delhi: Narosa
Publishing House Pvt. Ltd.; 2009. p. 1-20.
Brahmachari G, Gorai D. Progress in the research of naturally
occurring flavones and flavonols: An overview. Curr Org Chem
;10:873-98.
Brahmachari G, Gorai D. Progress in the research of natural
flavonoids: An overview. In: Brahmachari G, editor. Chemistry
of Natural Products: Recent Trends and Developments. 1st ed.
Trivandrum: Research Signpost; 2006. p. 78-168.
Brahmachari G. Naturally occurring flavanones: An overview. Nat
Prod Commun 2008;3:1337-54.
Ravindranath MH, Muthugounder S, Presser N, Viswanathan S.
Anticancer therapeutic potential of soy isofavone, Genistein. Adv
Exp Med Biol 2004;546:121-65.
Cazarolli LH, Zanatta L, Alberton EH, Figueiredo MS, Folador P,
Damazio RG, et al. Flavonoids: Prospective drug candidates. Mini
Rev Med Chem 2008;8:1429-40.
Sharma D, Gupta VK, Brahmachari G, Mondal S, Gangopadhyay
A. X-ray study of weak interactions in two flavonoids. Bull Mater
Sci 2007;30:469-75.
Farkas L, Nogradi M, Sudarsanam V, Herz W. Constituents of
Iva species. V. Isolation, structure, and synthesis of nevadensin, a
new flavone from Iva nevadensis M.E. Jones and Iva acerosa (Nutt.)
Jackson. J Org Chem 1966;31:3228-32.
Du J, Gao L. Chemical constituents of the leaves of Acanthopanax
trifoliatus (Linn) Merr. Zhongguo Zhong Yao Za Zhi 1992;17:356-7.
Chidiak S, Guada M, Buitrago D, Morales A. Flavonoids isolate
from specie Baccharis nitida (Ruiz et Pavon Pers). Ciencia
;15:361-5.
Feresin GE, Tapia A, Gimenez A, Ravelo AG, Zacchino S, Sortino
M, et al. Constituents of the Argentinian medicinal plant Baccharis
grisebachii and their antimicrobial activity. J Ethnopharmacol
;89:73-80.
Greenham J, Vassiliades DD, Harborne JB, Williams CA, Eagles
J, Grayer RJ, et al. A distinctive flavonoid chemistry for the
anomalous genus Biebersteinia. Phytochemistry 2001;56:87-91.
Barros-Filho BA, Nunes FM, Oliveira MD, Andrade-Neto M,
Mattos MC, Barbosa FG, et al. Secondary metabolites from
Esenbeckia almawillia Kaastra (Rutaceae). QuÃm Nova 2007;30:1589-
Rieseberg LH, Soltis DE, Arnold D. Variation and localization of
flavonoid aglycones in Helianthus annuus (Compositae). Am J
Bot 1987;74:224-33.
Mullin CA, Alfatafta AA, Harman JL, Everett SL, Serino AA.
Feeding and toxic effects of floral sesquiterpene lactones,
diterpenes, and phenolics from sunflower (Helianthus annuus L.)
on western corn rootworm. J Agric Food Chem 1991;39:2293-9.
Herz W, De Groote R. Desacetyleupaserrin and nevadensin from
Helianthus pumilus. Phytochemistry 1977;16:1307-8.
Pereda-Miranda R, Delgado G. Triterpenoids and flavonoids from
Hyptis albida. J Nat Prod 1990;53:182-5.
Bui ML, Grayer RJ, Veitch NC, Kite GC, Tran H, Nguyen QK.
Uncommon 8-oxygenated flavonoids from Limnophila aromatica
(Scrophulariaceae). Biochem Syst Ecol 2004;32:943-7.
Kukongviriyapan U, Luangaram S, Leekhaosoong K,
Kukongviriyapan V, Preeprame S. Antioxidant and vascular
protective activities of Cratoxylum formosum, Syzygium gratum and
Limnophila aromatica. Biol Pharm Bull 2007;30:661-6.
Suksamrarn A, Poomsing P, Aroonrerk N, Punjanon T, Suksamrarn
S, Kongkun S. Antimycobacterial and antioxidant flavones from
Limnophila geoffrayi. Arch Pharm Res 2003;26:816-20.
Liu MC, Chen ZS, Chung LC, Yang MS, Ho ST, Chen MT. Studies
on hypotensive constituents of Limnophila rugosa. Chung-hua Yao
Hsueh Tsa Chih 1991;43:35-40.
Brahmachari G, Mondal S, Jash SK, Mandal KS, Chattopadhyay S,
Gangopadhyay A. Naturally occurring bioactive O-heterocycles:
A quest for new sources. Nat Prod Indian J 2006;2:74-7.
Liu Y, Wagner H, Bauer R. Phenylpropanoids and flavonoid
glycosides from Lysionotus pauciflorus. Phytochemistry 1998;
:339-43.
Liu Y, Wagner H, Bauer R. Nevadensin glycosides from Lysionotus
pauciflorus. Phytochemistry 1996;42:1203-5.
Xu Y, Hu ZB, Feng SC, Fan GJ. Studies on the anti-tuberculosis
principles from Lysionotus pauciflora Maxim. Yao Xue Xue Bao
;14:447-8.
Wang SY, Zhou GM, Huang C. RP-HPLC determination of
nevadensin in Lysionotus pauciflorus Maxim. Chinese J Pharm
Analysis 2006;26:1617-9.
Grayer RJ, Veitch NC, Kite GC, Price AM, Kokubun T. Distribution
of 8-oxygenated leaf-surface flavones in the genus Ocimum.
Phytochemistry 2001;56:559-67.
Xaasan CC, Ciilmi CS, Faarax MX, Passannanti S, Paternostro
MP. Unusual flavones from Ocimum Canum. Phytochemistry
;19:2229-30.
Xaasan CC, Cabdulraxvaan AD, Passannanti S, Prozzi F, Schmid
JP. Constituents of the essential oil of Ocimum canum. J Nat Prod
;44:752-3.
Vieira RE, Grayer RJ, Paton AJ. Chemical profiling of Ocimum
americanum using external flavonoids. Phytochemistry 2003;
:555-67.
Grayer RJ, Bryan SE, Veitch NC, Goldston FJ, Paton A, Wollenweber
E. External flavones in sweet basil, Ocimum basilicum, and related
taxa. Phytochemistry 1996;43:1041-7.
Wollenweber E, Dörr M, Rivera D, Roitman JN. Externally
accumulated flavonoids in three mediterranean Ononis species.
Z Naturforsch 2003;58:771-5.
Barrero AF, Sanchez JF, Rodrı´guez I. N-Δ13-Docosenoylanthranilic
acid and alkylresorcinols from Ononis natrix subsp. hispanica.
Phytochemistry 1990;29:1967-9.
Wollenweber E. On the distribution of exudate flavonoids among
angiosperms. Rev Latinoamer Quim 1990;21:115-21.
Tamayo-Castillo G, Jakupovic J, Bohlmann F, King RM, Boldt
PE. Germacranolides and diterpenes from Viguiera species. Rev
Latinoamer Quim 1990;21:.67-9.
Bohm BA, Stuessy TF. Flavonoids of the sunflower family
(Asteraceae). New York: Springer-Wien; 2001. p. 299.
Brahmachari G. Limnophila (Scrophulariaceae): Chemical and
pharmaceutical aspects. Open Nat Prod J 2008;1:34-43.
Talapatra SK, Mallik AK, Talapatra B. Pongaglabol, a new
hydroxyfuranoflavone, and aurantiamide acetate, a dipeptide from the flowers of Pongamia glabra. Phytochemistry 1980;19:1199-202.
Mabry TJ, Markham KR, Thomas MR. The systematic identification
of flavonoids. New York: Springer; 1970. p. 48.
Verykokidoce-Vitsaropoulou E, Vijias C. Methylated flavones from
Teucrium polium. Planta Med 1986;52:401-2.
Vyas AV, Mulchandani NB. Polyoxygenated flavones from
Ageratum conyzoides. Phytochemistry 1986;25:2625-7.
Brahmachari G, Gorai D, Chatterjee D, Mondal S, Mistri B.
,8-Dihydroxy-6,7,4'-trimethoxyflavone, a novel flavonoid
constituent of Limnophila indica. Indian J Chem 2004;43B:219-22.
Mukherjee KS, Brahmachari G, Manna TK, Mukherjee P. A
methylenedioxy flavone from Limnophila indica. Phytochemistry
;49:2533-4.
Rabjohn N, Rosenberg DW. Preparation of some simple structural
analogs of Khellin. J Org Chem 1959;24:1192-7.
Song JY, He XZ, Chen XF, Hu JY, Luo GY, Mo YZ. Hypotensive
effect of nevadensin. Acta Pharmacol Sin 1985;6:99-102.
Reddy GB, Melkhani AB, Kalyani GA, Rao JV, Shirwaikar A, Kotian
M, et al. Chemical and pharmacological investigation of Limnophila
conferta and Limnophila heterophylla. Int J Pharmacog 1991;29:145-53.
Harborne JB, Baxter H, Moss GP,. Phytochemical Dictionary: A
Handbook of Bioactive Compounds from Plants. 2nd ed. New York:
Talyor and Francis, CRC Press; 1999, p447.
Yang JL, Shen ZM, Sun YF, Han JX, Xu B. Cultured human
hepatoma cell (BEL-7404) for anticancer drugs screening. Acta
Pharmacol Sin 1985;6:144-8.
Dong XP, Che CT, Farnsworth NR. Cytotoxic flavonols from
Gutierrezia microcephala. J Nat Prod 1987;50:337-8.
Chung CJ, Geahlen RL. Protein-tyrosine kinase inhibition:
Mexchanism-based discovery of antitumor agents. J Nat Prod
;55:1529-60.
Alhusainy W, Paini A, Punt A, Louisse J, Spenkelink A, Vervoort
J, et al. Identification of nevadensin as an important herb-based
constituent inhibiting estragole bioactivation and physiologybased
biokinetic modeling of its possible in vivo effect. Toxicol
Appl Pharmacol 2010;245:179-90.
Brahmachari G, Mandal NC, Jash SK, Ghosh PP, Roy R, Mandal
LC, et al. Evaluation of antimicrobial potentiality of two flavonoids
from Limnophila plants. Chem Biodivers 2010 [In Press].
Brahmachari G, Jash SK, Mandal LC, Mondal A, Roy R.
Cyclooxygenase (COX)-inhibitory flavonoid from Limnophila
hterophylla. Rasayan J Chem 2008;1:288-91.
Ganpaty S, Chandrasekhar VM, Chitme HR, Narsu ML. Free
radical scavenging activity of gossypin and nevadensin: An
in vitro evaluation. Indian J Pharmacol 2007;39:281-3.
Yoshimura K, Toibana A, Nakahama K. Human lysozyme:
Sequencing of a cDNA, and expression and secretion by
Saccharomyces cerevisiae. Biochem Biophys Res Commun
;150:794-801.
Peters CW, Kruse U, Pollwein R, Grzeschik KH, Sippel AE. The
human lysozyme gene. Sequence organization and chromosomal
localization. Eur J Biochem 1989;182:507-16.
Daojin L, Jingfeng Z, Jing J. Spectrophotometric studies on the
interaction between nevadensin and lysozyme. J Photochem
Photobiol 2007;189:114-20.
Han GZ, Su CY, Zhang Y. Determination of nevadensin in
biological specimens and its pharmacokinetic study. Acta
Pharmacol Sin 1981;2:182-5.
Han GZ, Su CY, Zhang Y. The absorption, distribution and
elimination of nevadensin in the rat, and the relationship between
plasma concentration of the drug and its hypotensive effect. Yao
Xue Xue Bao 1982;17:572-8.