Boschnaloside

Effects of boschnaloside from Boschniakia rossica on dysglycemia and islet dysfunction in severely diabetic mice through modulating the action of glucagon-like peptide-1.[Pubmed:31102890]

Phytomedicine. 2019 Sep;62:152946.

BACKGROUND: Boschniakia rossica is a well-known traditional Chinese medicine for tonifying kidney and improving impotence. Boschnaloside is the major iridoid glycoside in this herb but therapeutic benefits for diabetes remained to be evaluated. HYPOTHESIS/PURPOSE: The current investigation aims to study the antidiabetic effect and the underlying pharmacological mechanisms. STUDY DESIGN AND METHODS: Receptor binding, cAMP production, Ins secretion, glucagon-like peptide 1 (GLP-1) secretion, and dipeptidyl peptidase-4 activity assays were performed. Therapeutic benefits of orally administrated Boschnaloside (150 and 300mg/kg/day) were evaluated using severely 12-week old female diabetic db/db mice (Hemoglobin A1c >10%). RESULTS: Oral treatment of Boschnaloside for 4 weeks improved diabetic symptoms including fasting blood sugar, hemoglobin A1c, glucose intolerance, and Homeostatic Model Assessment of Ins Resistance, accompanied by circulating GLP-1active and adiponectin levels. In addition, bochnaloside treatment improved islet/beta cell function associated with an alteration of the pancreatic and duodenal homeobox 1 level. It was shown that Boschnaloside interacted with the extracellular domain of GLP-1 receptor and enhanced glucose stimulated Ins secretion. Boschnaloside also augmented the insulinotropic effect of GLP-1. Finally, the presence of Boschnaloside caused a reduction of dipeptidyl peptidase-4 activity while enhanced GLP-1 secretion from STC-1 cells. CONCLUSION: It appears that bochnaloside at oral dosage greater than 150mg/kg/day exerts antidiabetic effects in vivo through modulating the action of GLP-1.

Further iridoid glucosides in the genus Manulea (Scrophulariaceae).[Pubmed:25457503]

Phytochemistry. 2015 Jan;109:43-8.

From Manulea altissima (Scrophulariaceae) were isolated five known secoiridoid glucosides sweroside, eustomoside, eustoside, secoxyloganin and secologanoside as well as the 4''-O-rhamnopyranosyl-feruloyl ester of adoxosidic acid, named altissimoside. Also, the caffeoyl phenylethanoid glycoside verbascoside was isolated. In addition two previously unknown terpenoid esters of 6beta-hydroxy 8-epi-Boschnaloside, named manucoside A and B were isolated from a formerly obtained fraction from the work-up of Manulea corymbosa. The distribution of iridoid glucosides in the Scrophulariaceae is discussed.

Comparative studies for screening of bioactive constituents from various parts of Incarvillea emodi.[Pubmed:24547772]

Nat Prod Res. 2014;28(8):593-6.

A comparative study was performed on various parts (shoots, roots and flowers) of Incarvillea emodi. The alcoholic extracts of different parts were fractionated with solvents of different polarity and studied for the determination of total polyphenol content and total antioxidant potential. Furthermore, we have isolated major iridoid glucosides from the dried flowers of I. emodi followed by the comparative cytotoxicity studies of these iridoids against five different human cancer cell lines. The results have demonstrated that ethyl acetate fraction of all parts have higher phenolic content (167.87-294.31 mg/g as gallic acid equivalent) and higher total antioxidant potential (252.95-384.64 mg/g as trolox equivalent). The results of in vitro cytotoxicity studies have indicated that Boschnaloside (2) possesses promising anticancer potential against three human cancer cell lines, THP-1, A-549 and PC-3, which belong to leukaemia, lung and prostate cancers, respectively, while plantarenaloside (1) expressed relevant cytotoxic activity against THP-1 cell lines of leukaemia.

A proposed biosynthetic pathway of picrosides linked through the detection of biochemical intermediates in the endangered medicinal herb Picrorhiza kurroa.[Pubmed:23696248]

Phytochem Anal. 2013 Nov-Dec;24(6):598-602.

INTRODUCTION: Picrorhiza kurroa Royle ex Benth is an important medicinal herb used in the preparation of several herbal drug formulations due to the presence of picroside-I (P-I) and picroside-II (P-II) along with other iridoid-glucosides derivatives. OBJECTIVE: The endangered status of P. kurroa coupled with lack of information on biosynthesis of P-I and P-II necessitate deciphering the biosynthetic pathway for picrosides. METHODS: LC with electrospray ionisation (ESI) and quadrupole time of flight combined with MS/MS was used to detect intermediates and assemble the picrosides biosynthetic pathway in P. kurroa. RESULTS: The presence of catalpol and aucubin, the major backbone structures of picrosides, along with intermediate metabolites Boschnaloside, bartsioside and mussaenosidic acid, was confirmed in ESI negative mode with pseudomolecular ion peaks, that is, m/z 361, m/z 343, m/z 345, m/z 329 and m/z 375 ions and their fragmentation patterns. CONCLUSION: The picrosides biosynthetic pathway is expected to provide a reliable platform towards understanding the molecular components (genes/enzymes) of P-I and P-II biosynthesis in P. kurroa for their eventual utilisation in various applications.

Isolation of two major iridoid glucosides from Incarvillea emodi.[Pubmed:21644183]

Nat Prod Res. 2011 Jun;25(10):1014-7.

Two major iridoid glucosides, namely plantarenaloside, a neurotrophic compound, and Boschnaloside, an antibacterial iridoid glucoside, have been isolated from the shoots of Incarvillea emodi (a wild ornamental plant). The compounds are characterised by NMR spectral data and ESI mass spectrometery. This is the first ever report on the isolation of iridoid glucosides from I. emodi (Bignoniaceae).

[Study on reproduction biology of Cistanche deserticola--seedling emergence and flowering].[Pubmed:17992986]

Zhongguo Zhong Yao Za Zhi. 2007 Sep;32(17):1729-32.

OBJECTIVE: To study the reproduction characteristic of Cistanche deserticola. METHOD: The reproduction characteristic and growing dynamic in Ningxia plantation were investigated, the contents of Boschnaloside and echinacoside were determined during reproduction period. RESULT: The germination period of C. deserticola was in the first ten days of the month, the duration from the germination to flowering lasted about one month. The contents of Boschnaloside and echinacoside decreased during reproduction period. CONCLUSION: The reproduction period of C. deserticolais lasts about two months, germination period of C. deserticola is the suitable harvest time.

The inhibitory effect of phenylpropanoid glycosides and iridoid glucosides on free radical production and beta2 integrin expression in human leucocytes.[Pubmed:16393473]

J Pharm Pharmacol. 2006 Jan;58(1):129-35.

Rapid production of reactive oxygen species (ROS) and upregulation of beta2 integrin by leucocytes are two important inflammatory responses in human leucocytes. To evaluate whether three phenylpropanoid glycosides (acteoside, crenatoside, and rossicaside B) and two iridoid glucosides (Boschnaloside and 8-epideoxyloganic acid) identified from two medicinal plants with similar indications (Orobanche caerulescens and Boschniakia rossica) exhibited anti-inflammatory activity, their effects on N-formyl-methionyl-leucyl-phenylalanine (fMLP) and phorbol-12-myristate-13-acetate (PMA)-activated peripheral human neutrophils (PMNs) and mononuclear cells were examined. Pretreatment with 1-50 microM phenylpropanoid glycoside concentration-dependently diminished PMA- and fMLP-induced ROS production with IC50 values of approximately 6.8-23.9 and 3.0-8.8 muM, respectively. Iridoid glucoside was less effective than phenylpropanoid glycoside with an IC50 value of approximately 8.9-28.4 microM in PMA-activated PMNs and 19.1-21.1 microM in fMLP-activated mononuclear cells. Phenylpropanoid glycosides also effectively inhibited NADPH oxidase (NOX) and displayed potent free radical-scavenging activity, but did not interfere with pan-protein kinase C (PKC) activity. Furthermore, all compounds, except rossicaside B, significantly inhibited PMA- and fMLP-induced Mac-1 (a beta2 integrin) upregulation at 50 microM but not that of fMLP-induced intracellular calcium mobilization. These drugs had no significant cytotoxicity as compared with the vehicle control. Our data suggested that inhibition of ROS production, possibly through modulation of NOX activity and/or the radical scavenging effect, and beta2 integrin expression in leucocytes indicated that these compounds had the potential to serve as anti-inflammatory agents during oxidative stress.

Aquaticol, a bis-sesquiterpene and iridoid glucosides from Veronica anagallis-aquatica.[Pubmed:10821060]

Planta Med. 2000 Apr;66(3):281-3.

Aquaticol, an unusual bis-sesquiterpene was isolated from the medicinal plant Veronica anagallis-aquatica, in addition to 11 known compounds, aucubin, geniposidic acid, mussaenoside, catalposide, verproside, amphicoside, catalpol, Boschnaloside, shanzhiside methyl ester, sitosterol and beta-stigmast-4-en-6 beta-ol-3-one. The structure of aquaticol was determined by spectroscopic means and by X-ray crystallographic analysis.

Iridoid compounds from Boschniakia rossica.[Pubmed:10071965]

Arch Pharm Res. 1999 Feb;22(1):78-80.

Four iridoid compounds were isolated from methanol extract of Boschniakia rossica by repeated column chromatography. Their structures were determined as Boschnaloside (1), boschnarol (2), bosnarol methylether (3), and 7-deoxy 8-epiloganic acid (4), respectively. Compound 2, 3, and 4 were isolated for the first time from this plant.

8-Epi-iridodial glucoside from Boschniakia rossica.[Pubmed:17396939]

Planta Med. 1982 Sep;46(1):45-7.

Boschnaside, 8-epi-iridodial glucoside a new iridoid glucoside was isolated from Boschniakia rossica Hult., and its absolute structure was determined by chemical correlation of Boschnaloside tetraacetate with boschnaside tetraacetate.