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Siamenoside I

$493

  • Brand : BIOFRON

  • Catalogue Number : BD-P0774

  • Specification : 98.5%(HPLC)

  • CAS number : 126105-12-2

  • PUBCHEM ID : 71307460

  • Volume : 25mg

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Catalogue Number

BD-P0774

Analysis Method

HPLC,NMR,MS

Specification

98.5%(HPLC)

Storage

-20℃

Molecular Weight

Appearance

White crystalline powder

Botanical Source

Siraitia grosvenorii/Siraitiae fructus

Structure Type

Triterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(CCC(C(C)(C)O)OC1C(C(C(C(O1)COC2C(C(C(C(O2)CO)O)O)O)O)O)OC3C(C(C(C(O3)CO)O)O)O)C4CCC5(C4(CC(C6(C5CC=C7C6CCC(C7(C)C)OC8C(C(C(C(O8)CO)O)O)O)C)O)C)C

Synonyms

β-D-Glucopyranoside, (1R,4R)-4-[(3β,8α,9β,10α,11α,17β)-3-(β-D-glucopyranosyloxy)-11-hydroxy-4,4,9,14-tetramethylestr-5-en-17-yl]-1-(1-hydroxy-1-methylethyl)pentyl O-β-D-g lucopyranosyl-(1->2)-O-[β-D-glucopyranosyl-(1->6)]-/β-D-glucopyranoside, (1R,4R)-4-[(3β,8α,9β,10α,11α,17β)-3-(β-D-glucopyranosyloxy)-11-hydroxy-4,4,9,14-tetramethylestr-5-en-17-yl]-1-(1-hydroxy-1-methylethyl)pentyl O-β-D-glucopyranosyl-(1->;2)-O-[β-D-glucopyranosyl-(1->6)]-/(1S,4R,8β,9β,11α,24R)-1-(β-D-Glucopyranosyloxy)-11,25-dihydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholest-5-en-24-yl β-D-glucopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->6)]-β-D- glucopyranoside/Siamenoside I/(1S,4R,8β,9β,11α,24R)-1-(β-D-Glucopyranosyloxy)-11,25-dihydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholest-5-en-24-yl β-D-glucopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->6)]-β-D-glucopyranoside/SiamenosideI

IUPAC Name

(2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[(3R,6R)-2-hydroxy-6-[(3S,8S,9R,10R,11R,13R,14S,17R)-11-hydroxy-4,4,9,13,14-pentamethyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptan-3-yl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Applications

Siamenoside I is one of the mogrosides that has several kinds of bioactivities.

Density

1.5±0.1 g/cm3

Solubility

Methanol; Water; DMSO

Flash Point

667.0±34.3 °C

Boiling Point

1179.3±65.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C54H92O24/c1-22(23-15-16-52(6)30-12-10-24-25(54(30,8)31(58)17-53(23,52)7)11-14-32(50(24,2)3)76-47-43(68)39(64)35(60)27(19-56)73-47)9-13-33(51(4,5)70)77-49-45(78-48-44(69)40(65)36(61)28(20-57)74-48)41(66)37(62)29(75-49)21-71-46-42(67)38(63)34(59)26(18-55)72-46/h10,22-23,25-49,55-70H,9,11-21H2,1-8H3/t22-,23-,25-,26-,27-,28-,29-,30+,31-,32+,33-,34-,35-,36-,37-,38+,39+,40+,41+,42-,43-,44-,45-,46-,47+,48+,49+,52+,53-,54+/m1/s1

InChl Key

XJIPREFALCDWRQ-UYQGGQRHSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:126105-12-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

30754652

Abstract

Mogrosides, the main bioactive compounds isolated from the fruits of Siraitia grosvenorii, are a group of cucurbitane-type triterpenoid glycosides that exhibit a wide range of notable biological activities and are commercially available worldwide as natural sweeteners. However, the extraction cost is high due to their relatively low contents in plants. Therefore, molecular breeding needs to be achieved when conventional plant breeding can hardly improve the quality so far. In this study, the levels of 21 active mogrosides and two precursors in 15 S. grosvenorii varieties were determined by HPLC-MS/MS and GC-MS, respectively. The results showed that the variations in mogroside V content may be caused by the accumulation of cucurbitadienol. Furthermore, a total of four wild-type cucurbitadienol synthase protein variants (50R573L, 50C573L, 50R573Q, and 50C573Q) based on two missense mutation single nucleotide polymorphism (SNP) sites were discovered. An in vitro enzyme reaction analysis indicated that 50R573L had the highest activity, with a specific activity of 10.24 nmol min−1 mg−1. In addition, a site-directed mutant, namely, 50K573L, showed a 33% enhancement of catalytic efficiency compared to wild-type 50R573L. Our findings identify a novel cucurbitadienol synthase allele correlates with high catalytic efficiency. These results are valuable for the molecular breeding of luohanguo.

KEYWORDS

Siraitia grosvenorii, molecular breeding, site-directed mutant, mogrosides, cucurbitadienol synthase, single nucleotide polymorphism (SNP)

Title

Identification of a Novel Specific Cucurbitadienol Synthase Allele in Siraitia grosvenorii Correlates with High Catalytic Efficiency

Author

Jing Qiao,1 Zuliang Luo,1 Zhe Gu,1 Yanling Zhang,2 Xindan Zhang,2 and Xiaojun Ma1,*

Publish date

2019 Feb;

PMID

30409616

Abstract

In response to growing concerns about the consumption of artificial sweeteners, the demand for natural sweeteners has recently increased. Mogroside V is a common natural sweetener extracted from the fruit of Siraitia grosvenorii, but its taste should be improved for marketability. Here, we screened various microbes for the ability to perform selective hydrolysis of glycosidic bonds in mogroside V, converting it to siamenoside I, which has a higher sweetening power and better taste than other mogrosides. Dekkera bruxellensis showed the most promising results in the screen, and the Exg1 gene (coding for a β-glucosidase) of D. bruxellensis was cloned and purified. We then used HPLC-MS/MS to assess the β-glucosidase activity of purified enzymes on p-nitrophenyl β-glucoside and mogroside V. The results demonstrated that D. bruxellensis had a unique enzyme that can selectively hydrolyze mogrol glycosides and promote the conversion of the natural sweetener mogroside V to siamenoside I.

Copyright © 2018 Elsevier Ltd. All rights reserved.

KEYWORDS

Dekkera bruxellensis; Mogrosides; Natural sweetener; Siamenoside I; β-Glucosidase

Title

Dekkera bruxellensis, a beer yeast that specifically bioconverts mogroside extracts into the intense natural sweetener siamenoside I.

Author

Wang R1, Chen YC1, Lai YJ1, Lu TJ2, Huang ST3, Lo YC4.

Publish date

2019 Mar 15;

PMID

26840289

Abstract

Siamenoside I is the sweetest mogroside that has several kinds of bioactivities, and it is also a constituent of Siraitiae Fructus, a fruit and herb in China. Hitherto the metabolism of siamenoside I in human or animals remains unclear. To reveal its metabolic pathways, a high-performance liquid chromatography-electrospray ionization-ion trap-time of flight-multistage mass spectrometry (HPLC-ESI-IT-TOF-MS(n)) method was used to profile and identify its metabolites in rats. Altogether, 86 new metabolites were identified or tentatively identified, and 23 of them were also new metabolites of mogrosides. In rats, siamenoside I was found to undergo deglycosylation, hydroxylation, dehydrogenation, deoxygenation, isomerization, and glycosylation reactions. Among them, deoxygenation, pentahydroxylation, and didehydrogenation were novel metabolic reactions of mogrosides. The distributions of siamenoside I and its 86 metabolites in rat organs were firstly reported, and they were mainly distributed to intestine, stomach, kidney, and brain. The most widely distributed metabolite was mogroside IIIE. In addition, eight metabolites were bioactive according to literature. These findings would help to understand the metabolism and effective forms of siamenoside I and other mogrosides in vivo.

KEYWORDS

LC-IT-TOF-MSn; Siraitia grosvenorii; cucurbitanes; distribution; metabolism; mogrosides; natural sweeteners; saponins; siamenoside I

Title

Metabolites of Siamenoside I and Their Distributions in Rats.

Author

Yang XR1, Xu F2, Li DP3, Lu FL4, Liu GX5, Wang L6, Shang MY7, Huang YL8, Cai SQ9.

Publish date

2016 Jan 30;