Name | sarsasapogenin |
Synonyms | PARIGENIN Sarsagenin PARIGENIN SARSAGENIN Sarsasapogein spirostan-3-ol sarsasapogenin SARSASAPOGENIN Sarsasapogenin baqia Spirostan-3-ol, (3b,5b,25S)- Spirostan-3-ol, (3β,5β,25S)- (3beta,5beta,25S)-spirostan-3-ol (25S)-5-beta-spirostan-3-beta-ol |
CAS | 126-19-2 82597-74-8 |
EINECS | 204-776-3 |
InChI | InChI=1/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17+,18-,19-,20+,21+,22+,23-,24-,25-,26-,27-/m0/s1 |
Molecular Formula | C27H44O3 |
Molar Mass | 416.64 |
Density | 1.0362 (rough estimate) |
Melting Point | 194°C |
Boling Point | 474.91°C (rough estimate) |
Specific Rotation(α) | D25 -75°; 25546 -89° (c = 0.5 in CHCl3) |
Flash Point | 266.2°C |
Solubility | Ethanol : 1 mg/mL (2.40 mM; Need ultrasonic) |
Vapor Presure | 7.83E-13mmHg at 25°C |
Appearance | Colorless long needle crystal |
Merck | 13,8456 |
pKa | 15.14±0.70(Predicted) |
Storage Condition | 2-8°C |
Refractive Index | 1.4700 (estimate) |
MDL | MFCD00270414 |
Physical and Chemical Properties | Brown to dark brown tea liquid, with special odor. It has good foaming performance, low proportion, stable foam, and the pH value of 2~10 can be used. The main component of Sapona saponin (Sarsa-sapoge-nin), melting point of 194~195 ℃, some of the mold, yeast antibacterial. |
In vitro study | The treatment of Sarsasapogenin can increase the number of S-phase Hela cells, resulting in the accumulation of G2/M phase cells. It can induce apoptosis of HeLa cells by inducing the mitochondrial apoptosis pathway dependent on caspase. Sarsasapogenin induces the activation of endoplasmic reticulum stress response signaling pathway, and induces toxicity to human cervical cancer cells through cell cycle arrest, ROS-mediated mitochondrial pathway and endoplasmic reticulum stress response pathway. Sarsasapogenin also induces early activation of UPR, activating CHOP, which may promote lineal membrane permeabilization by dephosphorylating Akt, thus transmitting apoptotic signals from the endoplasmic reticulum to mitochondria. Sarsasapogenin effectively inhibited the activation of NF-κB and MAPK, and inhibited the phosphorylation of IRAK1, TAK1, and IκBα in macrophages stimulated by LPS. Sarsasapogenin also inhibits the binding of LPS to TLR4 receptors in macrophages and inhibits the polarization of M2 to M1 macrophages. |
In vivo study | Oral administration of sarsasapogenin in mice can inhibit the colon shortening and myeloperoxidase activity induced by TNBS, reduce the activation of NF-κB and the levels of IL-1β, TNF-α, IL-6, and enhance the expression level of IL-10. In colonic lamina propria, sarsasapogenin inhibited Th17 cell differentiation and induced Treg cell differentiation. In Vivo, Sarsasapogenin effectively inhibits the inflammatory response. |
WGK Germany | 3 |
Reference Show more | 1. Wang Fang, Ma Shufeng, Li Hanchen, et al. Immunoregulation of Asparagus Alcohol Extract [J]. Journal of Food and Biotechnology, 2013, 032(003):324-329. 2. Liu, Mengshun, et al. "Folding fan mode counter-current chromatography offers fast blind screening for drug discovery. Case study: finding anti-enterovirus 71 agents from Anemarrhena asphodeloides." Journal of Chromatography A 1368 (2014): 116-124.https:// 3. [IF = 4.759] Mengshun Liu et al. "Folding fan mode counter-current chromatography offers fast blind screening for drug discovery. Case study: Finding anti-enterovirus 71 agents from Anemarrhena asphodeloides." J Chromatogr A.2014 Nov;1368:116 4. [IF = 4.142] Wang Chenxi et al. "Systematic quality evaluation of Peiyuan Tongnao capsule by offline two-dimensional liquid chromatography/quadrupole-Orbitrap mass spectrometry and adjusted parallel reaction monitoring of quality markers." Anal Bioanal Chem. 2019 Nov;4 5. [IF = 2.289] Zhou Shun et al. "Anthelmintic efficacy of natural saponins against Gyrodactylus kobayashii in goldfish (Carassius auratus) and their 3D-QSAR analysis." Parasitol Res. 2021 Mar;120(3):1143-1150 |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
use limit | FEMA: non-alcoholic beverage 150 mg/kg. |
biological activity | Sarsasapogenin (SAR, Parigenin) is a steroidal saponin, which can induce ROS production and activate unfolded protein response (UPR) signaling pathway. SAR can effectively inhibit the activation of NF-κB and MAPK, and inhibit the phosphorylation of IRAK1, TAK1 and IκBα in macrophages stimulated by LPS. |
Target | Value |
use | emulsifier; Foaming agent; Preservative. Mainly used for refreshing drinks, foaming sweets, mixed wines, etc. GB 2760-2000 specifies spices for food that are allowed to be used. |
Production method | The whole plant of Yucca arborescens and Yucca schidirera, which are produced in the deserts of Mexico and Central and South America, is extracted with hot water or mild-temperature aqueous ethanol or aqueous isopropyl alcohol after cutting. |