17676-33-4

Basic information

• Product Name: NEORUSCOGENIN
• Synonyms: Spirosta-5,25(27)-diene-1,3-diol,(1b,3b)-;SPIROSTA-5,25(27)-DIENE-1B,3B-DIOL;NEORUSCOGENIN;spirosta-5,25(27)-diene-1beta,3beta-diol;Spirosta-5,25(27)-diene-1,3-diol, (1.beta.,3.beta.)-;Spirosta-5,25(27)-diene-1β,3β-diol;Einecs 241-660-1;Neoruscogenin, 98%, from Ophiopogon japonicus (Linn. f.) Ker-Gawl.
• CAS NO: 17676-33-4
• Molecular Formula: C₂₇H₄₀O₄
• Molecular Weight: 428.6
• EINECS: 241-660-1
• Product Categories: Steroids
• Mol File: 17676-33-4.mol

Chemical Properties

• Melting Point: 196～198℃
• Boiling Point: 566.6°Cat760mmHg
• Flash Point: 296.4°C
• Appearance: /
• Density: 1.19±0.1 g/cm3 (20 ºC 760 Torr)
• Solubility: ≤30mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide
• PKA: 14.55±0.70(Predicted)
• CAS DataBase Reference: NEORUSCOGENIN(CAS DataBase Reference)
• NIST Chemistry Reference: NEORUSCOGENIN(17676-33-4)
• EPA Substance Registry System: NEORUSCOGENIN(17676-33-4)

Safety Data

• Hazardous Substances Data: 17676-33-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Neoruscogenin is used as an active pharmaceutical ingredient for the treatment of chronic venous disorders. It is valued for its ability to improve blood circulation and reduce inflammation, making it a beneficial component in the development of medications targeting these conditions.
Used in Traditional Medicine:
Neoruscogenin is also used in traditional medicine, where it has been employed for centuries to address various health issues, including chronic venous disorders. Its natural origin and historical use contribute to its continued relevance in modern herbal remedies and supplements.

Biological Activity

neoruscogenin is a bioavailable, potent, and high-affinity agonist of the nuclear receptor rorα [1]. neoruscogenin is a natural sapogenin extracted from butcher’s broom (rusci rhizoma, ruscus aculeatus, ruscaceae) [2].rar-related orphan receptor alpha (rorα) is a nuclear receptor that participates in the transcriptional regulation of some genes involved incircadian rhythm. genetic studies have revealed that rorα plays an important role in the development of the central nervous system and has been associated with genetic lesions in mice [3].

in vitro

in confluent human microvascular endothelial cells (hmec-1), pre-treatment with neoruscogenin slightly decreased the permeability at concentrations up to 100 μm (71.8%). the ec50 of neoruscogenin against the nuclear receptor rorα was 110 nm [1].

in vivo

in mice, oral administration of neoruscogenin (3 mg/kg/d) for seven days up-regulated the expression of several rorα-inducible genes in the liver [1].

references

[1] helleboid s, haug c, lamottke k, et al. the identification of naturally occurring neoruscogenin as a bioavailable, potent, and high-affinity agonist of the nuclear receptor rorα (nr1f1)[j]. journal of biomolecular screening, 2013: 1087057113497095.[2] barbi m, willer e a, rothenhfer m, et al. spirostanol saponins and esculin from rusci rhizoma reduce the thrombin-induced hyperpermeability of endothelial cells[j]. phytochemistry, 2013, 90: 106-113.[3] giguère v. orphan nuclear receptors: from gene to function 1[j]. endocrine reviews, 1999, 20(5): 689-725.

Upstream product

• 180161-85-7 3β-hydroxyspirosta-5,25(27)-dien-1β-yl-O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-α-L-arabinopyranoside 
• 1009815-93-3 1β-hydroxyspirosta-5,25(27)-dien-3β-yl O-α-L-rhamnopyranosyl-(1->4)-β-D-glucopyranoside 
• 1486510-49-9 neoruscogenin 1-O-α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside 
• 94901-60-7 26-O-β-D-glucopyranosyl 22-hydroxyfurost-5,25(27)-dien-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-α-L-arabinopyranosido-3-O-β-D-glucopyranoside 
• 94921-23-0 neoruscogenin 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-α-L-arabinopyranosido-3-O-β-D-glucopyranoside 

Downstream Products

• 79037-17-5 (20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene 
• 79037-07-3 1β,3β,16β,26-tetrabenzoyloxycholest-5-ene 
• 79037-04-0 1β,3β,16β-tribenzoyloxycholest-5-ene 
• 79037-12-0 C₄₂H₅₆O₇S 
• 79037-13-1 1β,3β-dibenzoyloxycholest-5-ene-16β-ol 
• 472-11-7 (25R)-ruscogenin 

Relevant articles and documents

Four new steroidal saponins from the rhizomes of Helleborus orientalis

A phytochemical analysis has been carried out on theglycoside-enriched fraction of a McOH extract of Helleborus orientalis rhizomes, resulting in the isolation of two new bisdesmosidic furostanol saponins (1 and 2) and two new furospirostanol saponins (3 and 4). The structures of 1-4 were determined on the basis of extensive spectroscopic analysis and acid hydrolysis followed by chromatographic and spectroscopic analysis. Compound (3) showed moderate cytotoxic activity against HSC-2 human squamous cell carcinoma cells with an IC50 value of 16 μg/mL.

Three new neuritogenic steroidal saponins from Ophiopogon japonicus (Thunb.) Ker-Gawl

Three new steroidal saponins (1-3) and a known saponin (4) were isolated from Ophiopogon japonicus (Thunb.) Ker-Gawl. Their structures were determined by spectroscopic analyses and chemical derivatization. The isolated compounds (1-4) were potent inducers of neuritogenesis on PC12 cells. Compound 1 showed the highest neuritogenic activity of 46% at 1 μM. The study of structure-activity relationships suggests that aglycone is important for the neuritogenic activity of the compounds. Specific inhibitor experiments and Western blot analysis suggest that 1-induced neuritogenic activity depends on the activation of mitogen-activated protein kinase kinase (MEK)/extracellular signal regulated kinase (ERK) signaling pathway on PC12 cells.

Steroidal glycosides from the rhizomes of Ruscus hypophyllum

Seven steroidal glycosides, along with one known glycoside, were isolated from the rhizomes of Ruscus hypophyllum (Liliaceae). Comprehensive spectroscopic analysis, including 2D NMR spectroscopy, and the results of acid hydrolysis allowed the chemical structures of the compounds to be assigned as (23S,25R)-23-hydroxyspirost-5-en-3β-yl O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranoside (1), 1β-hydroxyspirosta-5,25(27)-dien-3β-yl O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranoside (2), (22S)-16β,22-dihydroxycholest-5-en-3β-yl O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranoside (3), (22S)-16β-[(β-d-glucopyranosyl)oxy]-22-hydroxycholest-5-en-3β-yl O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranoside (4), (22S)-16β-[(β-d-glucopyranosyl)oxy]-22-hydroxycholest-5-en-3β-yl β-d-glucopyranoside (5), (22S)-16β-[(β-d-glucopyranosyl)oxy]-3β,22-dihydroxycholest-5-en-1β-yl O-α-l-rhamnopyranosyl-(1 → 2)-(3,4-di-O-acetyl-β-d-xylopyranoside) (6), and (22S)-16β-[(β-d-glucopyranosyl)oxy]-3β,22-dihydroxycholest-5-en-1β-yl O-α-l-rhamnopyranosyl-(1 → 2)-O-[β-d-xylopyranosyl-(1 → 3)]-β-d-xylopyranoside (7), respectively. This is the first isolation of a series of cholestane glycosides from a Ruscus species.

Steroidal saponins from Nolina recurvata stems and their inhibitory activity on cyclic AMP phosphodiesterase

Seven steroidal saponins were isolated from the stems of Nolina recurvata, five of which appeared to be new compounds and were assigned as spirosta-5,25(27)-diene-1β,3β-diol (neuruscogenin) 1-O-{O-α-L- rhamnopyranosyl-(1 → 2)-O-[β-D-xylopyranosyl-(1 → 3)-α-L- arabinopyranoside}, (25S)-spirost-5-ene-1β,3β-diol [(25S)-ruscogenin] 1- O-{O-α-L-rhamnopyranosyl-(1 → 2)-O-[β-D-xylopyranosyl-(1 → 3)]-α-L- arabinopyranoside}, neuruscogenin 1-O-{O-α-L-rhamnopyranosyl-(1 → 2)-O- [β-D-xylopyranosyl-(1 → 3)]-β-D-fucopyranoside}, 26-O-β-D- glucopyranosyl-22-O-methylfurosta-5,25(27)-diene-1β,3β,22ζ,26-tetrol 1-O- {-O-α-L-rhamnopyranosyl-(1 → 2)-O-[β-D-xylopyranosyl-(1 → 3)]-α-L- arabinopyranoside} and 26-O-β-D-glucopyranosylfurosta-5,20(22),25(27)- triene-1β,3β,26-triol 1-O-{O-α-L-rhamnopyranosyl-(1 → 2)-α-L- arabinopyranoside}. The isolated saponins were evaluated for their inhibitory activity on cyclic AMP phosphodiesterase to identify new compounds with medicinal potential.

Comparative Studies on the Constituents of Ophiopogonis Tuber and Its Congeners. III. Studies on the Constituents of the Subterranean Part of Ophiopogon ohwii Okuyama and O. jaburan (Kunth) Lodd.

Six steroidal glycosides tentatively named glycosides O-1, O-2 (1), O-3 (2), O-4 (3), O-5 (4) and O-6 (5), were isolated from the subterranean part of Ophiopogon ohwii Okuyama (Liliaceae) and another six steroidal glycosides, tentatively named glycosides J-1, J-2 (6), J-3 (7), J-4 (8), J-5 (9) and J-6 (10), were isolated from the subterranean part of O. jaburan (Kunth) Lodd.Glycosides O-1 and J-1 were identified as so-called β-sitosterol β-D-glucopyranoside.The structures of 1-10 were established as ophiopogonin B (1), Ophiopogonin D (2), ruscogenin 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranoside (3), ruscogenin 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-α-L-arabinopyranoside (=glycoside E of O. planiscapus Nakai) (4), 26-O-β-D-glucopyranosyl 22-hydroxy-25(R)-furost-5-en-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranoside (5), ophiopogonin D (=glycoside O-3 (2)) (6), a mixture of 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranosido-3-O-β-D-glucopyranosides of ruscogenin and neoruscogenin (7), neoruscogenin 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-α-L-arabinopyranosido-3-O-β-D-glucopyranoside (8), a mixture of 26-O-β-D-glucopyranosyl 22-hydroxy-25(R)-furost-5-en-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranosido-3-O-β-D-glucopyranoside and 26-O-β-D-glucopyranosyl 22-hydroxyfurost-5,25(27)-dien-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranosido-3-O-β-D-glucopyranoside (9), and 26-O-β-D-glucopyranosyl 22-hydroxyfurost-5,25(27)-dien-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-α-L-arabinopyranosido-3-O-β-d-glucopyranoside (10).It is interesting that the main saponins, ophiopogonins B and D, found in Ophiopogonis Tuber (obtained from O. japonicus Ker-Gawler) were also found in O. ohwii (Okuyama and the latter saponin was also found in O. jaburan (Kunth) Lodd.Further, several steroidal glycosides carrying sulfate on the sugar moiety were found in Liliaceous plants belonging to the genus Ophiopogon. Keywords - Ophiopogonis Tuber; Ophiopogon ohwii; Ophiopogon jaburan; Liliaceae; spirostanol glycoside; furostanol glycoside; sulfated steroidal glycoside