Top

Published in:

01-07-2016 | Original Paper

Chemical structures of constituents from the whole plant of Bacopa monniera

Authors: Tomoe Ohta, Seikou Nakamura, Souichi Nakashima, Yoshimi Oda, Takahiro Matsumoto, Masashi Fukaya, Mamiko Yano, Masayuki Yoshikawa, Hisashi Matsuda

Published in: Journal of Natural Medicines | Issue 3/2016

Abstract

Two new dammarane-type triterpene oligoglycosides, bacomosaponins A and B, and three new phenylethanoid glycosides, bacomosides A, B₁, and B₂, were isolated from the whole plant of Bacopa monniera Wettst. The chemical structures of the new constituents were characterized on the basis of chemical and physicochemical evidence. In the present study, bacomosaponins A and B with acyl groups were obtained from the whole plant of B. monniera. This is the first report of acylated dammarane-type triterpene oligoglycosides isolated from B. monniera. In addition, dammarane-type triterpene saponins significantly inhibited the aggregation of 42-mer amyloid β-protein.

Mukherjee GD, Dey CD (1966) Clinical trial on Brahmi. I. J Exp Med Sci 10:5–11PubMed

Holcomb LA, Dhanasekaran M, Hitt AR, Young KA, Riggs M, Manyam BV (2006) Bacopa monniera extract reduces amyloid levels in PSAPP mice. J Alzheimers Dis 9:243–251PubMed

Limpeanchob N, Jaipan S, Rattanakaruna S, Phrompittayarat W, Ingkaninan K (2008) Neuroprotective effect of Bacopa monnieri on beta-amyloid-induced cell death in primary cortical culture. J Ethnopharmacol 120:112–117CrossRefPubMed

Uabundit N, Wattanathorn J, Mucimapura S, Ingkaninan K (2010) Cognitive enhancement and neuroprotective effects of Bacopa monnieri in Alzheimer’s disease model. J Ethnopharmacol 127:26–31CrossRefPubMed

Saini N, Singh D, Sandhir R (2012) Neuroprotective effects of Bacopa monnieri in experimental model of dementia. Neurochem Res 37:1928–1937CrossRefPubMed

Nakamura S, Moriura T, Park S, Fujimoto K, Matsumoto T, Ohta T, Matsuda H, Yoshikawa M (2012) Melanogenesis inhibitory and fibroblast proliferation accelerating effects of noroleanane- and oleanane-type triterpene oligoglycosides from the flower buds of Camellia japonica. J Nat Prod 75:1425–1430CrossRefPubMed

Ohta T, Nakamura S, Nakashima S, Matsumoto T, Ogawa K, Fujimoto K, Fukaya M, Yoshikawa M, Matsuda H (2015) Acylated oleanane-type triterpene oligoglycosides from the flower buds of Camellia sinensis var. assamica. Tetrahedron 71:846–851CrossRef

Matsumoto T, Nakamura S, Ohta T, Fujimoto K, Yoshikawa M, Ogawa K, Matsuda H (2014) A rare glutamine derivative from the flower buds of daylily. Org Lett 16:3076–3078CrossRefPubMed

Matsumoto T, Nakamura S, Nakashima S, Fujimoto K, Yoshikawa M, Ohta T, Ogawa K, Matsuda H (2014) Lignan dicarboxylates and terpenoids from the flower buds of Cananga odorata and their inhibitory effects on melanogenesis. J Nat Prod 77:990–999CrossRefPubMed

10.

Nakamura S, Fujimoto K, Matsumoto T, Nakashima S, Ohta T, Ogawa K, Matsuda H, Yoshikawa M (2013) Acylated sucroses and acylated quinic acids analogs from the flower buds of Prunus mume and their inhibitory effect on melanogenesis. Phytochemistry 92:128–136CrossRefPubMed

11.

Nakamura S, Nakashima S, Oda Y, Yokota N, Fujimoto K, Matsumoto T, Ohta T, Ogawa K, Maeda S, Nishida S, Matsuda H, Yoshikawa M (2013) Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B. Bioorg Med Chem 21:1043–1049CrossRefPubMed

12.

Matsumoto T, Nakamura S, Nakashima S, Yoshikawa M, Fujimoto K, Ohta T, Morita A, Yasui R, Kashiwazaki E, Matsuda H (2013) Diarylheptanoids with inhibitory effects on melanogenesis from the rhizomes of Curcuma comosa in B16 melanoma cells. Bioorg Med Chem Lett 23:5178–5181CrossRefPubMed

13.

Rastogi S, Pal R, Kulshreshtha DK (1994) Bacoside A₃–A triterpenoid saponin from Bacopa monniera. Phytochemistry 36:133–137CrossRefPubMed

14.

Zhou Y, Shen YH, Zhang C, Su J, Liu RH, Zhang WD (2007) Triterpene saponins from Bacopa monnieri and their antidepressant effects in two mice models. J Nat Prod 70:652–655CrossRefPubMed

15.

Chakravarty AK, Sarkar T, Masuda K, Shiojima K, Nakane T, Kawahara N (2001) Bacopaside I and II: two pseudojujubogenin glycosides from Bacopa monniera. Phytochemistry 58:553–556CrossRefPubMed

16.

Garai S, Mahato SB, Ohtani K, Yamasaki K (1996) Dammarane-type triterpenoid saponins from Bacopa monniera. Phytochemistry 42:815–820CrossRefPubMed

17.

Chakaravarty AK, Sarkar T, Takahisa N, Kawahara N, Masuda K (2002) New phenylethanoid glycosides from Bacopa monnieri. Chem Pharm Bull 50:1616–1618CrossRef

18.

Yoshikawa M, Morikawa T, Kobayashi H, Nakamura A, Matsuhira K, Nakamura S, Matsuda H (2007) Bioactive saponins and glycosides. XXVII. Structures of new cucurbitane-type triterpene glycosides and antiallergic constituents from Citrullus colocynthis. Chem Pharm Bull (Tokyo) 55:428–434CrossRef

19.

Velde VV, Lavie D (1983) ¹³C NMR spectroscopy of cucurbitacins. Tetrahedron 39:317–321CrossRef

20.

Hatam NAR, Whiting DA, Yousif NJ (1989) Cucurbitacin glycosides from Citrullus colocynthis. Phytochemistry 28:1268–1271CrossRef

21.

Mahato SB, Garai S, Chakravarty AK (2000) Bacopasaponins E and F: two jujubogenin bisdesmosides from Bacopa monniera. Phytochemistry 53:711–714CrossRefPubMed

22.

Tanaka T, Nakashima T, Ueda T, Tomii K, Kouno I (2007) Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem Pharm Bull (Tokyo) 55:899–901CrossRef

23.

Miyamae Y, Kurisu M, Murakami K, Han J, Isoda H, Irie K, Shigemori H (2012) Protective effects of caffeoylquinic acids on the aggregation and neurotoxicity of the 42-residue amyloid β-protein. Bioorg Med Chem 20:5844–5849CrossRefPubMed

Title: Chemical structures of constituents from the whole plant of Bacopa monniera
Authors: Tomoe Ohta
Seikou Nakamura
Souichi Nakashima
Yoshimi Oda
Takahiro Matsumoto
Masashi Fukaya
Mamiko Yano
Masayuki Yoshikawa
Hisashi Matsuda
Publication date: 01-07-2016
Publisher: Springer Japan
Published in: Journal of Natural Medicines / Issue 3/2016
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-016-0986-0

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Chemical structures of constituents from the whole plant of Bacopa monniera

Abstract

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 3/2016

In vivo anti-inflammatory activities of the essential oil from Radix Angelicae dahuricae

Euphorins A–H: bioactive diterpenoids from Euphorbia fischeriana

Amentoflavone enhances osteogenesis of human mesenchymal stem cells through JNK and p38 MAPK pathways

Hypolipidemic and antioxidant activity of the aqueous extract from the uneaten pulp of the fruit from Cordia dichotoma in healthy and hyperlipidemic Wistar albino rats

Synthesis and stereochemical determination of an antiparasitic pseudo-aminal type monoterpene indole alkaloid

In vivo efficacy of trans-cinnamaldehyde, carvacrol, and thymol in attenuating Listeria monocytogenes infection in a Galleria mellonella model