Skip to main content
Erschienen in: Journal of Natural Medicines 1/2017

17.08.2016 | Note

Constituents from Vitex negundo var. heterophylla and their inhibition of nitric oxide production

verfasst von: Chongyue Qiu, Liang Tong, Ting Yuan, Fei Wang, Feng Zhao, Lixia Chen

Erschienen in: Journal of Natural Medicines | Ausgabe 1/2017

Einloggen, um Zugang zu erhalten

Abstract

An iridoid glucoside, 10-p-hydroxybenzoyl-6β-hydroxyiridoid 1-O-β-d-(6′-O-p-hydroxybenzoyl)-glucopyranoside (1), and a phenol glucoside, 4-hydroxyphenethanol 3-O-β-d-(6′-O-p-hydroxybenzoyl)-glucopyranoside (2), along with nine known compounds (311) were isolated from the dried leaves of Vitex negundo var. heterophylla. Their structures were elucidated by extensive analysis of NMR spectra. All of the isolated compounds were evaluated for their inhibitory effects on nitric oxide production in RAW 264.7 macrophages. Compounds 2 and 3 exhibited obvious inhibitory effects on NO production with IC50 values of 30.76 and 49.89 μM, respectively. Molecular docking studies of compounds 2 and 3 with nitric oxide synthase (NOS) further confirmed the above results.
Anhänge
Nur mit Berechtigung zugänglich
Literatur
1.
Zurück zum Zitat Hu P, Li DH, Wang KB, Wang H, Wang ZH, Li ZL, Hua HM (2015) New phenolic compounds from Vitex negundo var. heterophylla and their antioxidant and NO inhibitory activities. J Funct Foods 19:174–181CrossRef Hu P, Li DH, Wang KB, Wang H, Wang ZH, Li ZL, Hua HM (2015) New phenolic compounds from Vitex negundo var. heterophylla and their antioxidant and NO inhibitory activities. J Funct Foods 19:174–181CrossRef
2.
Zurück zum Zitat Chawla AS, Sharma AK, Handa SS, Dhar KL (1992) Chemical investigation and anti-inflammatory activity of Vitex negundo seeds. J Nat Prod 55:163–167CrossRefPubMed Chawla AS, Sharma AK, Handa SS, Dhar KL (1992) Chemical investigation and anti-inflammatory activity of Vitex negundo seeds. J Nat Prod 55:163–167CrossRefPubMed
3.
Zurück zum Zitat Li SH, Zhang HJ, Qiu SX, Niu XM, Santarsiero BD, Mesecar AD, Fong HHS, Farnsworth NR, Sun HD (2002) Vitexlactam A, a novel labdane diterpene lactam from the fruits of Vitex agnus-castus. Tetrahedron Lett 43:5131–5134CrossRef Li SH, Zhang HJ, Qiu SX, Niu XM, Santarsiero BD, Mesecar AD, Fong HHS, Farnsworth NR, Sun HD (2002) Vitexlactam A, a novel labdane diterpene lactam from the fruits of Vitex agnus-castus. Tetrahedron Lett 43:5131–5134CrossRef
4.
Zurück zum Zitat Ono M, Sawamura H, Ito Y, Mizuki K, Nohara T (2000) Diterpenoids from the fruits of Vitex trifolia. Phytochemistry 55:873–877CrossRefPubMed Ono M, Sawamura H, Ito Y, Mizuki K, Nohara T (2000) Diterpenoids from the fruits of Vitex trifolia. Phytochemistry 55:873–877CrossRefPubMed
5.
Zurück zum Zitat Prasanna K, Karthikeyan V (2015) Preliminary phytochemical, total phenolics and flavonoid content analysis of Vitex negundo and Calatropis gigantea leaf ethanolic extracts. J Chem Pharm Res 7:282–285 Prasanna K, Karthikeyan V (2015) Preliminary phytochemical, total phenolics and flavonoid content analysis of Vitex negundo and Calatropis gigantea leaf ethanolic extracts. J Chem Pharm Res 7:282–285
6.
Zurück zum Zitat Leitao SG, Monache FD (1998) 2″-O-caffeoylorientin from Vitex polygama. Phytochemistry 49:2167–2169CrossRef Leitao SG, Monache FD (1998) 2″-O-caffeoylorientin from Vitex polygama. Phytochemistry 49:2167–2169CrossRef
7.
Zurück zum Zitat Kawazoe K, Yutani A, Takaishi Y (1999) Arylnaphthalenes norlignans from Vitex rotundifolia. Phytochemistry 52:1657–1659CrossRef Kawazoe K, Yutani A, Takaishi Y (1999) Arylnaphthalenes norlignans from Vitex rotundifolia. Phytochemistry 52:1657–1659CrossRef
8.
Zurück zum Zitat Yamasaki T, Kawabata T, Masuoka C, Kinjo J, Ikeda T, Nohara T, Ono M (2008) Two new lignan glucosides from the fruit of Vitex cannabifolia. J Nat Med 62:47–51CrossRefPubMed Yamasaki T, Kawabata T, Masuoka C, Kinjo J, Ikeda T, Nohara T, Ono M (2008) Two new lignan glucosides from the fruit of Vitex cannabifolia. J Nat Med 62:47–51CrossRefPubMed
9.
Zurück zum Zitat Dos Santos TC, Schripsema J, Monache FD, Suzana GL (2001) Iridoids from Vitex cymosa. J Br Chem Soc 12:763–766 Dos Santos TC, Schripsema J, Monache FD, Suzana GL (2001) Iridoids from Vitex cymosa. J Br Chem Soc 12:763–766
10.
Zurück zum Zitat Rabanes HR, Guidote AM Jr, Quirino JP (2014) Micellar electrokinetic chromatography of the constituents in Philippine lagundi (Vitex negundo) herbal products. Microchem J 112:153–158CrossRef Rabanes HR, Guidote AM Jr, Quirino JP (2014) Micellar electrokinetic chromatography of the constituents in Philippine lagundi (Vitex negundo) herbal products. Microchem J 112:153–158CrossRef
11.
Zurück zum Zitat Sundaram R, Naresh R, Shanthi P, Sachdanandam P (2012) Antihyperglycemic effect of iridoid glucoside, isolated from the leaves of Vitex negundo in streptozotocin-induced diabetic rats with special reference to glycoprotein components. Phytomedicine 19:211–216CrossRefPubMed Sundaram R, Naresh R, Shanthi P, Sachdanandam P (2012) Antihyperglycemic effect of iridoid glucoside, isolated from the leaves of Vitex negundo in streptozotocin-induced diabetic rats with special reference to glycoprotein components. Phytomedicine 19:211–216CrossRefPubMed
12.
Zurück zum Zitat Jangwan JS, Aquino RP, Mencherini T, Picerno P, Singh R (2015) Chemical constituents of ethanol extract and free radical scavenging activity of Vitex trifolia linn. Acta Chim Pharm Indica 5:1–7 Jangwan JS, Aquino RP, Mencherini T, Picerno P, Singh R (2015) Chemical constituents of ethanol extract and free radical scavenging activity of Vitex trifolia linn. Acta Chim Pharm Indica 5:1–7
13.
Zurück zum Zitat Zheng CJ, Huang BK, Han T, Zhang QY, Zhang H, Rahman K, Qin LP (2009) Nitric oxide scavenging lignans from Vitex negundo seeds. J Nat Prod 72:1627–1630CrossRefPubMed Zheng CJ, Huang BK, Han T, Zhang QY, Zhang H, Rahman K, Qin LP (2009) Nitric oxide scavenging lignans from Vitex negundo seeds. J Nat Prod 72:1627–1630CrossRefPubMed
14.
Zurück zum Zitat Rosa SIG, Rios-Santos F, Balogun SO, Martins D (2016) Vitexin reduces neutrophil migration to inflammatory focus by down-regulating pro-inflammatory mediators via inhibition of p38, ERK1/2 and JNK pathway. Phytomedicine 23:9–17CrossRefPubMed Rosa SIG, Rios-Santos F, Balogun SO, Martins D (2016) Vitexin reduces neutrophil migration to inflammatory focus by down-regulating pro-inflammatory mediators via inhibition of p38, ERK1/2 and JNK pathway. Phytomedicine 23:9–17CrossRefPubMed
15.
Zurück zum Zitat Lee H, Jung KH, Lee H, Park S, Choi W, Bae H (2015) Casticin, an active compound isolated from Vitex fructus, ameliorates the cigarette smoke-induced acute lung inflammatory response in a murine model. Int Immunopharmacol 28:1097–1101CrossRefPubMed Lee H, Jung KH, Lee H, Park S, Choi W, Bae H (2015) Casticin, an active compound isolated from Vitex fructus, ameliorates the cigarette smoke-induced acute lung inflammatory response in a murine model. Int Immunopharmacol 28:1097–1101CrossRefPubMed
16.
Zurück zum Zitat Huang HC, Chang TY, Chang LZ, Wang HF, Yih KH, Hsieh WY, Chang TM (2012) Inhibition of melanogenesis versus antioxidant properties of essential oil extracted from leaves of Vitex negundo Linn and chemical composition analysis by GC-MS. Molecules 17:3902–3916CrossRefPubMed Huang HC, Chang TY, Chang LZ, Wang HF, Yih KH, Hsieh WY, Chang TM (2012) Inhibition of melanogenesis versus antioxidant properties of essential oil extracted from leaves of Vitex negundo Linn and chemical composition analysis by GC-MS. Molecules 17:3902–3916CrossRefPubMed
17.
Zurück zum Zitat Zheng CJ, Huang BK, Han T, Zhang QY, Zhang H, Rahman K, Qin LP (2010) Antinociceptive activities of the liposoluble fraction from Vitex negundo seeds. Pharm Biol 48:651–658CrossRefPubMed Zheng CJ, Huang BK, Han T, Zhang QY, Zhang H, Rahman K, Qin LP (2010) Antinociceptive activities of the liposoluble fraction from Vitex negundo seeds. Pharm Biol 48:651–658CrossRefPubMed
18.
Zurück zum Zitat Kulkarni LA (2011) Pharmacological review on Vitex trifolia Linn. (Verbaeaceae). Pharmacologyonline 3:858–863 Kulkarni LA (2011) Pharmacological review on Vitex trifolia Linn. (Verbaeaceae). Pharmacologyonline 3:858–863
20.
Zurück zum Zitat Ling TJ, Ling WW, Chen YJ, Wan XC, Xia T, Du XF, Zhang ZZ (2010) Antiseptic activity and phenolic constituents of the aerial parts of Vitex negundo var. cannabifolia. Molecules 15:8469–8477CrossRefPubMed Ling TJ, Ling WW, Chen YJ, Wan XC, Xia T, Du XF, Zhang ZZ (2010) Antiseptic activity and phenolic constituents of the aerial parts of Vitex negundo var. cannabifolia. Molecules 15:8469–8477CrossRefPubMed
21.
Zurück zum Zitat Ono M, Eguchi K, Konoshita M, Furusawa C, Sakamoto J (2011) A new diterpenoid glucoside and two new diterpenoids from the fruit of Vitex agnus-castus. Chem Pharm Bull 59:392–396CrossRefPubMed Ono M, Eguchi K, Konoshita M, Furusawa C, Sakamoto J (2011) A new diterpenoid glucoside and two new diterpenoids from the fruit of Vitex agnus-castus. Chem Pharm Bull 59:392–396CrossRefPubMed
22.
Zurück zum Zitat Ono M, Yamamoto M, Yanaka T, Ito Y, Nohara T (2001) Ten new labdane-type diterpenes from the fruit of Vitex rotundifolia. Chem Pharm Bull 49:82–86CrossRefPubMed Ono M, Yamamoto M, Yanaka T, Ito Y, Nohara T (2001) Ten new labdane-type diterpenes from the fruit of Vitex rotundifolia. Chem Pharm Bull 49:82–86CrossRefPubMed
23.
Zurück zum Zitat Zheng CJ, Huang BK, Wang Y, Ye Q, Han T, Zhang QY, Zhang H, Qin LP (2010) Anti-inflammatory diterpenes from the seeds of Vitex negundo. Bioorg Med Chem 18:175–181CrossRefPubMed Zheng CJ, Huang BK, Wang Y, Ye Q, Han T, Zhang QY, Zhang H, Qin LP (2010) Anti-inflammatory diterpenes from the seeds of Vitex negundo. Bioorg Med Chem 18:175–181CrossRefPubMed
24.
Zurück zum Zitat Jiang B, Han WL, Zhang QW, Zhang XQ, Ye WC (2012) Chemical constituents from the aerial roots of Ficus microcarpa. J Chin Med Mater 35:904–908 Jiang B, Han WL, Zhang QW, Zhang XQ, Ye WC (2012) Chemical constituents from the aerial roots of Ficus microcarpa. J Chin Med Mater 35:904–908
25.
Zurück zum Zitat Xiao Y, Wang LB, Jin G, Sun R, Hu X, Yang CJ (2012) Studies on phenolic acid constituents of Acanthopanax sessiliflorus fruits. Chin J Med Chem 22:223–226 Xiao Y, Wang LB, Jin G, Sun R, Hu X, Yang CJ (2012) Studies on phenolic acid constituents of Acanthopanax sessiliflorus fruits. Chin J Med Chem 22:223–226
26.
Zurück zum Zitat Peng DQ, Gao J, Guo XM, Wang JL, Zhang SJ (2014) Chemical constituents from roots of Taraxacum mongolicum. Chin Tradit Patent Med 36:1462–1466 Peng DQ, Gao J, Guo XM, Wang JL, Zhang SJ (2014) Chemical constituents from roots of Taraxacum mongolicum. Chin Tradit Patent Med 36:1462–1466
27.
Zurück zum Zitat Zhang SJ, Wang D, Xu C, Wang JL, Zhao M (2014) Chemical constituents from roots of Ixeris chinensis. Chin J Chin Mater Med 39:3089–3093 Zhang SJ, Wang D, Xu C, Wang JL, Zhao M (2014) Chemical constituents from roots of Ixeris chinensis. Chin J Chin Mater Med 39:3089–3093
28.
Zurück zum Zitat Zhao Y, Liang GX, Wang CF, He L (2012) Chemical constituents from Sibiraea angustata. J Beijing Normal Univ 48:621–625 Zhao Y, Liang GX, Wang CF, He L (2012) Chemical constituents from Sibiraea angustata. J Beijing Normal Univ 48:621–625
29.
Zurück zum Zitat Dutta PK, Chowdhury US, Chakravarty AK, Achari B, Pakrashi SC (1983) Studies on Indian medicinal plants-part LXXV. Nishindaside, a novel iridoid glycoside from Vitex negundo (Rehd.) Hand. –Mazz. Tetrahedron 39:3067–3072CrossRef Dutta PK, Chowdhury US, Chakravarty AK, Achari B, Pakrashi SC (1983) Studies on Indian medicinal plants-part LXXV. Nishindaside, a novel iridoid glycoside from Vitex negundo (Rehd.) Hand. –Mazz. Tetrahedron 39:3067–3072CrossRef
30.
Zurück zum Zitat Ahmad I, Afza N, Anis I, Malik A, Tareen RB (2004) Iridoid galactosides and a benzofuran type sesquiterpene from Buddleja crispa. Heterocycles 63:1875–1881CrossRef Ahmad I, Afza N, Anis I, Malik A, Tareen RB (2004) Iridoid galactosides and a benzofuran type sesquiterpene from Buddleja crispa. Heterocycles 63:1875–1881CrossRef
31.
Zurück zum Zitat Klimek B (1996) Hydroxycinnamoyl ester glycosides and saponins from flowers of Verbascum Phlomoides. Phytochemistry 43:1281–1284CrossRefPubMed Klimek B (1996) Hydroxycinnamoyl ester glycosides and saponins from flowers of Verbascum Phlomoides. Phytochemistry 43:1281–1284CrossRefPubMed
32.
Zurück zum Zitat Kim DK (2009) Antioxidative constituents from the twigs of Vitex rotundifolia. Biomol Ther 17:412–417CrossRef Kim DK (2009) Antioxidative constituents from the twigs of Vitex rotundifolia. Biomol Ther 17:412–417CrossRef
33.
Zurück zum Zitat Piaz FD, Vassallo A, Temraz A, Cotugno R, Belisario MA, Bifulco G, Chini MG, Pisano C, Tommasi ND, Braca A (2013) A chemical-biological study reveals C9-type iridoids as novel heat shock protein 90 (Hsp90) inhibitors. J Med Chem 56:1583–1595CrossRef Piaz FD, Vassallo A, Temraz A, Cotugno R, Belisario MA, Bifulco G, Chini MG, Pisano C, Tommasi ND, Braca A (2013) A chemical-biological study reveals C9-type iridoids as novel heat shock protein 90 (Hsp90) inhibitors. J Med Chem 56:1583–1595CrossRef
Metadaten
Titel
Constituents from Vitex negundo var. heterophylla and their inhibition of nitric oxide production
verfasst von
Chongyue Qiu
Liang Tong
Ting Yuan
Fei Wang
Feng Zhao
Lixia Chen
Publikationsdatum
17.08.2016
Verlag
Springer Japan
Erschienen in
Journal of Natural Medicines / Ausgabe 1/2017
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-016-1032-y

Weitere Artikel der Ausgabe 1/2017

Journal of Natural Medicines 1/2017 Zur Ausgabe