Byzantionoside B

Bioactive Abietane-Type Diterpenoid Glycosides from Leaves of Clerodendrum infortunatum (Lamiaceae).[Pubmed:34299396]

Molecules. 2021 Jul 6;26(14). pii: molecules26144121.

In this study, two previously undescribed diterpenoids, (5R,10S,16R)-11,16,19-trihydroxy-12-O-beta-d-glucopyranosyl-(1-->2)-beta-d-glucop yranosyl-17(15-->16),18(4-->3)-diabeo-3,8,11,13-abietatetraene-7-one (1) and (5R,10S,16R)-11,16-dihydroxy-12-O-beta-d-glucopyranosyl-(1-->2)-beta-d-glucopyran osyl-17(15-->16),18(4-->3)-diabeo-4-carboxy-3,8,11,13-abietatetraene-7-one (2), and one known compound, the C13-nor-isoprenoid glycoside Byzantionoside B (3), were isolated from the leaves of Clerodendrum infortunatum L. (Lamiaceae). Structures were established based on spectroscopic and spectrometric data and by comparison with literature data. The three terpenoids, along with five phenylpropanoids: 6'-O-caffeoyl-12-glucopyranosyloxyjasmonic acid (4), jionoside C (5), jionoside D (6), brachynoside (7), and incanoside C (8), previously isolated from the same source, were tested for their in vitro antidiabetic (alpha-amylase and alpha-glucosidase), anticancer (Hs578T and MDA-MB-231), and anticholinesterase activities. In an in vitro test against carbohydrate digestion enzymes, compound 6 showed the most potent effect against mammalian alpha-amylase (IC50 3.4 +/- 0.2 muM) compared to the reference standard acarbose (IC50 5.9 +/- 0.1 muM). As yeast alpha-glucosidase inhibitors, compounds 1, 2, 5, and 6 displayed moderate inhibitory activities, ranging from 24.6 to 96.0 muM, compared to acarbose (IC50 665 +/- 42 muM). All of the tested compounds demonstrated negligible anticholinesterase effects. In an anticancer test, compounds 3 and 5 exhibited moderate antiproliferative properties with IC50 of 94.7 +/- 1.3 and 85.3 +/- 2.4 muM, respectively, against Hs578T cell, while the rest of the compounds did not show significant activity (IC50 > 100 muM).

[Terpenoids from leaves of Chinese hawthorn].[Pubmed:34296582]

Zhongguo Zhong Yao Za Zhi. 2021 Jun;46(11):2830-2836.

Fifteen compounds were isolated from the 70% EtOH extract of leaves of Chinese hawthorn(Crataegus pinnatifida var. major) by various purification steps, and their structures were determined as 2alpha,3alpha,12beta,19alpha,-tetrahydroxyursan-13beta,28-olide(1),euscaphic acid(2), tormentic acid(3), ursolic acid(4), pomolic acid(5), corosolic acid(6), maslinic acid(7), linalyl rutinoside(8),(Z)-3-hexenyl beta-D-glucoside(9),(3S, 6S)-cis-linalool-3,7-oxide-beta-D-glucopyranoside(10), pisumionoside(11), icariside B6(12), Byzantionoside B(13),(6R,7E,9R)-9-Hydroxy-4,7-megastigmadien-3-one 9-O-beta-D-glucopyranoside(14) and(6S,7E,9R)-6,9-dihydroxy-4,7-megastigmadien-3-one 9-O-beta-D-glucopyranoside(15) mainly based on the mass spectrum(MS) and nuclear magnetic resonance(NMR) spectroscopic techniques, of which compound 1 was a new pentacyclic triterpene, and compounds 2, 5, 6, 8, 10, 13 and 15 were isolated form this plant for the first time.

Three new C21 steroidal glycosides isolated from Metaplexis japonica and their potential inhibitory effects on tyrosine protein kinases.[Pubmed:33153339]

Nat Prod Res. 2020 Nov 5:1-8.

Three new steroidal glycosides, metapregnoside A-C (II-IV), together with one known compound, Byzantionoside B (I), were isolated from the fresh whole herb of Metaplexis japonica by using high-speed countercurrent chromatography and semi-preparative liquid chromatography. Their structures and relative configurations were elucidated by spectroscopic methods including 1D NMR, 2D NMR and HR-ESI-MS. The potential targets of compound I-IV were identified by virtual screening. And the potential inhibitory effects of these compounds on tyrosine protein kinases were compared by molecular docking. Byzantionoside B (I) was the first isolated compound from Metaplexis genus. The docking score of metapregnoside C (IV) was the highest. And the sugar chain residues at position C-20 in the pregn-4-en-3-one derivatives is the main factor affecting their docking scores on tyrosine protein kinases Fes/Fps.

Bioactive constituents of Lindernia crustacea and its anti-EBV effect via Rta expression inhibition in the viral lytic cycle.[Pubmed:31863859]

J Ethnopharmacol. 2020 Mar 25;250:112493.

ETHNOPHARMACOLOGICAL RELEVANCE: Lindernia crustacea (L.) F.Muell. (Scrophulariaceae) was selected for phytochemical investigation owing to its traditional use against human herpes virus infection and its anti-Epstein-Barr virus (EBV) effect. AIMS OF THE STUDY: The present study focused on the phytochemical investigation of L. crustacea including the isolation and structure determination of its biologically active compounds. Compounds with anti-EBV effects were also investigated. MATERIALS AND METHODS: The EtOH extract of L. crustacea was subsequently partitioned using different solvents. The EtOAc fraction was subjected to several chromatographic methods to obtain pure compounds. The structures of all isolates were established by spectroscopic analysis and compared with previously reported physical data. The anti-EBV effect was evaluated in an EBV-containing Burkitt's lymphoma cell line (P3HR1) to study the expression of EBV lytic proteins. RESULTS: Thirty-three compounds, including one diterpene (1), four anthraquinones (2-5), two ionones (6 and 7), fourteen phenylpropanoid glycosides (8-21), five flavonoids (22-26), one lignan glycoside (27), one phenethyl alcohol glycoside (28), one phenylpropene glycoside (29), one glucosyl glycerol derivative (30), one furanone (31), and two cinnamic acid derivatives (32 and 33), were isolated from the ethanolic extract of the plant. All isolated compounds were obtained for the first time from Lindernia sp. The evaluation of the anti-EBV activity of L. crustacea crude extract, partitioned fractions, and constituents was performed for the first time. Phytol (1), aloe-emodin (2), Byzantionoside B (7), a mixture of trans-martynoside (8) and cis-martynoside (9), a mixture of trans-isomartynoside (10) and cis-isomartynoside (11), luteolin-7-O-beta-D-glucopyranoside (24), and apigenin-7-O-[beta-D-apiofuranosyl (1-->6)-beta-D-glucopyranoside] (25) exhibited significant inhibitory effects on the EBV lytic cycle at 20 mug/mL in the immunoblot analysis. On the other hand, (6R,7E,9R)-3-oxo-alpha-ionol-beta-D-glucopyranoside (6) and a mixture of trans-dolichandroside A (12) and cis-dolichandroside A (13) showed moderate anti-EBV activity at 20 mug/mL. CONCLUSIONS: L. crustacea and its active isolates could be developed as potential candidates against EBV. Our findings provide scientific evidence for the traditional use of L. crustacea for its antiviral effects.

Tirucallane Glycoside from the Leaves of Antidesma bunius and Inhibitory NO Production in BV2 Cells and RAW264.7 Macrophages.[Pubmed:30452166]

Nat Prod Commun. 2016 Jul;11(7):935-937.

One new tirucallane-type triterpene glycoside, antidesoside (1), along with two biflavones, podocarpusflavone A (2) and amentoflavone (3) and two megastigmane glycosides, Byzantionoside B (4), and (6S,9R)-roseoside (5) were isolated from the methanol extract of Antidesma bunius leaves. Their structures were determined by spectroscopic methods and in comparison with the published data. Compounds 1 - 3 were found to show strong inhibitory effect of NO production in BV2.cells and RAW264.7 macrophages LPS-stimulated, with IC(5)(0) values ranging from 8.5 to 26.9 muM.

Stimulation of osteogenic activity in human osteoblast cells by edible Uraria crinita.[Pubmed:24785825]

J Agric Food Chem. 2014 Jun 18;62(24):5581-8.

Uraria crinita is an edible herb used as a natural food for childhood skeletal dysplasia. Ethyl acetate, n-butanol, and aqueous fractions of a 95% ethanol crude extract of U. crinita were obtained and the active ingredients isolated and purified using a bioguided method. In this manner, we isolated and identified a new active flavone glycoside, apigenin 6-C-beta-d-apiofuranosyl(1-->2)-alpha-d-xylopyranoside (3) and 10 known components with stimulatory activity on human osteoblast cells. The new compound 3 at 100 muM significantly increased alkaline phosphatase activity (114.10 +/- 4.41%), mineralization (150.10 +/- 0.80%), as well as osteopontin (1.39 +/- 0.01-fold), bone morphogenetic protein-2 (BMP-2, 1.30 +/- 0.04-fold), and runt-related transcription factor 2 (Runx2, 1.43 +/- 0.10-fold) mRNA expression through the activation of the BMP-2/Runx2 pathway. Two other components, dalbergioidin (1) and Byzantionoside B (9), displayed similar effects. These results show that U. crinita and its active compounds may have the potential to stimulate bone formation and regeneration.

[Chemical constituents from Elephantopus tomentosus].[Pubmed:24010290]

Zhongguo Zhong Yao Za Zhi. 2013 Jun;38(11):1751-6.

OBJECTIVE: To study the chemical constituents of Elephantopus tomentosus. METHOD: The compounds were isolated by repeated HP20 macro porous adsorption resin column combined with Sephadex LH-20, ODS and silica gel chromatographies. The structures were identified on the basis of extensive spectroscopic data analysis and by comparison of their spectral data reported. RESULT: Eighteen compounds were identified as 2-deethoxy-2beta-hydroxyphantomolin (1), 2beta-hydroxy-2-deethoxy-8-O-deacylphantomolin-8-O-tiglinate (2), 2beta-methoxy-2-deethoxyphantomolin (3), 2beta-methoxy-2-deethoxy-8-O-deacylphantomolin-8-O-tiglinate (4), molephantin (5), molephantinin (6), tricin (7), luteolin (8), quercetin (9), 3beta-friedelinol (10), 3beta-hydroxyolean-12-en-28-oic acid (11), 3, 5-di-O-caffeoyl quinic acid (12), 3,4-di-O-caffeoyl quinic acid (13), syringaresinol-4-beta-D-glucopyranoside (14), xylogranatinin (15), Byzantionoside B (16), 2'-hydroxycinnamaldehyde (17), and caffeic acid ethyl ester (18). CONCLUSION: Compounds 9, 11, 14-18 were separated from Elephantopus for the first time.

[Chemical constituents from the seed coat of Juglans regia].[Pubmed:22860453]

Zhongguo Zhong Yao Za Zhi. 2012 May;37(10):1417-21.

Fifteen compounds were isolated from the seed coat of Juglans regia by silica gel, MCI gel and Sephadex LH-20 gel column chromatography, as well as high preparative performance liquid chromatography. Their structures were identified as salidroside (1), (6S, 9S)-roseoside (2), (6S, 9R)-roseoside (3), blumenol C glucoside (4), Byzantionoside B (5), 5-hydroxy-2-methoxy-1, 4-naphthoquinone (6), gallic acid (7), glycerol 1-(9Z-octadecenoate)-2-(9Z, 12Z-octadecadienoate)-3-(9Z, 12Z, 15Z-octadecatrienoate) (8), glycerol 1, 2, 3-tri-(9Z, 12Z-octadecadienoate) (9), glycerol 1, 2, 3-tri-(9Z, 12Z, 15Z-octadecatrienoate) (10), glycerol 1-hexadecanoate-2, 3-di-(9Z, 12Z-octadecadienoate) (11) on the basis of EI-MS, FAB-MS and NMR spectra. Moreover, 35 volatile compounds were identified by GC-MS.

Three new flavonoid glycosides, byzantionoside B 6'-O-sulfate and xyloglucoside of (Z)-hex-3-en-1-ol from Ruellia patula.[Pubmed:21628908]

Chem Pharm Bull (Tokyo). 2011;59(6):725-9.

Three new flavonoid glycosides, demethoxycentaureidin 7-O-beta-D-galacturonopyranoside, pectolinarigenin 7-O-alpha-L-rhamnopyranosyl-(1'''-->4'')-beta-D-glucopyranoside and 7-O-alpha-L-rhamnopyranosyl-(1'''-->4'')-beta-D-glucuronopyranoside, a new megastigmane glucoside, Byzantionoside B 6'-O-sulfate, and a new (Z)-hex-3-en-1-ol O-beta-D-xylopyranosyl-(1''-->2')-beta-D-glucopyranoside, were isolated from leaves of Ruellia patula JACQ., together with 12 known compounds, beta-sitosterol glucoside, vanilloside, bioside (decaffeoyl verbascoside), acteoside (verbascoside), syringin, benzyl alcohol O-beta-D-xylopyranosyl-(1''-->2')-beta-D-glucopyranoside, cistanoside E, roseoside, phenethyl alcohol O-beta-D-xylopyranosyl-(1''-->2')-beta-D-glucopyranoside, (+)-lyoniresinol 3alpha-O-beta-D-glucopyranoside, isoacteoside and 3,4,5-trimethoxyphenol O-alpha-L-rhamnopyranosyl-(1''-->6')-beta-D-glucopyranoside. Their structures were elucidated by means of spectroscopic analyses.

Structural revisions of blumenol C glucoside and byzantionoside B.[Pubmed:20190461]

Chem Pharm Bull (Tokyo). 2010 Mar;58(3):438-41.

The absolute stereochemistry of blumenol C glucoside and Byzantionoside B was revised here as (6R,9S)- and (6R,9R)-9-hydroxymegastigman-4-en-3-one 9-O-beta-D-glucopyranosides, respectively, by modified Mosher's method. The empirical rules of (13)C-NMR chemical shift to determine the absolute stereochemistry of C-9 of 9-hydroxymegastigmane 9-O-beta-D-glucopyranoside were also discussed.

Two new C(13) nor-isoprenoids from the leaves of Casearia sylvestris.[Pubmed:19483351]

Chem Pharm Bull (Tokyo). 2009 Jun;57(6):636-8.

Two new C(13) nor-isoprene glycosides, (6S,9S)-6,9-dihydroxymegastiman-4-en-9-O-beta-D-glucopyranoside (1) and (6S,9S)-6,9-dihydroxymegastiman-4-en-9-O-beta-D-apiofuranosyl-(1-->6)-beta-D-gluc opyranoside (2) were isolated from the leaves of Casearia sylvestris, along with icariside B(5) (3), Byzantionoside B (4), blumenol B (5), blumenol C (6) and loliolide (7). The structures of these compounds were determined on the basis of 1D and 2D NMR, MS and circular dichroism (CD) spectroscopic analyses, chemical methods and comparison with the literature data.

[Chemical constituents from Faeces bombycis].[Pubmed:19149256]

Zhongguo Zhong Yao Za Zhi. 2008 Nov;33(21):2493-6.

OBJECTIVE: To study the chemical constituents from Faeces bombycis. METHOD: Isolation and purification were carried out on silic gel, Sephadex LH-20 and RP-18 column chromatography. The chemical structures of the constituents were elucidated on the basis of physicochemical properties and spectral data. RESULT: Fifteen compounds were identified as 3S, 5R-dihydroxy-6R, 7-megstigmadien-9-one (1), 3S, 5R-dihydroxy-6S, 7-megstigmadien-9-one (2), (6R, 9R)-3-oxo-alpha-ionol-beta-D-glucopyranoside (3), (6R, 9S)-3-oxo-alpha-ionol-beta-D-glucopyranoside (4), blumenol C glucoside (5), Byzantionoside B (6), alangionoside L (7), lutein (8), pipecolic acid (9), betaine (10), alanine (11), glutamic acid (12), phenylalanine (13), leucine (14), isoleucine (15). CONCLUSION: All the compounds were separated from Faeces bombycis for the first time.

New megastigmane glycoside and aromadendrane derivative from the aerial part of Piper elongatum.[Pubmed:12372878]

Chem Pharm Bull (Tokyo). 2002 Oct;50(10):1413-5.

A new megastigmane glycoside, called pipeloside A, and a new aromadendrane type sesquiterpenoid, pipelol A, were isolated from the MeOH extract of the aerial part of Piper elongatum VAHL. along with a known megastigmane glycoside, Byzantionoside B. The structures of these compounds were elucidated on the basis of spectroscopic data and chemical evidence.