Two new phenolic glycosides from the fruits of <i>Illicium verum</i>

Li, Sainan; Sun, Jinfeng; Wang, Jiaming; Jin, Long; Zong, Tieqiang; Zhou, Wei; Gao, Li

doi:10.1080/10286020.2021.1871606

Cited by 12 publications

(7 citation statements)

References 16 publications

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“…Furthermore, I. verum fruit also contains shikimic acid [1], fatty acids such as linoleic, stearic, and myristic acid [4], and alkylglucoside R-sec-butyl-D-glucopyranoside [1]. The two new, specific phenolic glucosides (E)-4-methoxy-2-(1′-propen-1′-yl)-phenol-1-O-α-L-arabinofuranosyl-(1‴→6″)β-D-glucopyranoside and (E)-4-methoxy-2-(1′-propen-1′-yl)-phenol-1-O-α-Lrhamnopyranosyl-(1″→'6′')-β-D-glucopyranoside were isolated from the I. verum fruit [21].…”

Section: Trans-anetholementioning

confidence: 99%

Illicium verum (Star Anise) and Trans-Anethole as Valuable Raw Materials for Medicinal and Cosmetic Applications

et al. 2022

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Illicium verum Hook f. (star anise) is considered an important species in Traditional Chinese Medicine and is also used in contemporary medicine in East Asian countries. It occurs in natural habitats in southeastern parts of China and Vietnam, and is cultivated in various regions in China. The raw materials - Anisi stellati fructus and Anisi stellati aetheroleum obtained from this species exhibit expectorant and spasmolytic activities. The European Pharmacopoeia (4th edition) indicates that these raw materials have been used in allopathy since 2002. The biological activities of the above-mentioned raw materials are determined by the presence of valuable secondary metabolites such as monoterpenoids, sesquiterpenoids, phenylpropanoids, and flavonoids. Recent pharmacological studies on fruit extracts and the essential oil of this species have confirmed their antibacterial, antifungal, anti-inflammatory, and antioxidant activities and thus their medicinal and cosmetic value. The aim of this review was to examine the progress of phytochemical and pharmacological studies that focused on possible cosmetic applications. In addition to fruit extracts and essential oil, the current consensus on the safety of trans-anethole, which is the main compound of essential oil used in cosmetology, is underlined here.

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Section: Trans-anetholementioning

confidence: 99%

Illicium verum (Star Anise) and Trans-Anethole as Valuable Raw Materials for Medicinal and Cosmetic Applications

et al. 2022

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“…The connectivity of the 2 sugars was mainly based on the HMBC correlations: H-1′ ( δ 5.23, 1H, brs) with C-3 ( δ C 89.4) of the aglycone, H-1″ ( δ H 4.44, 1H, d, J = 7.8 Hz) with C-2′ ( δ C 89.6) ( Figure 1 ). By comparing the chemical shift signals and coupling constants of the sugar moieties from the published literature [ 20 ], the relative configurations of the anomeric centers of the arabinosyl and glucosyl moieties in 1 were determined to be α and β , respectively. The two kinds of sugars, l -arabinofuranose and d -glucose, were identified by GC analysis after derivatization.…”

Section: Resultsmentioning

confidence: 99%

“…In order to determine the absolute configuration of the monosaccharide in triterpenoid saponins, the acid hydrolysis of new compounds were performed. The acid hydrolysis of ardisiacrispin D-F ( 1 – 3 ) (1.0 mg each) was performed according to the previous literatures [ 20 , 25 , 26 ]. The trimethylsilylthiazolidine derivatives from the n -hexane layer were analyzed with GC-MS with a DB-5 capillary column.…”

Section: Methodsmentioning

confidence: 99%

Cytotoxic 13,28 Epoxy Bridged Oleanane-Type Triterpenoid Saponins from the Roots of Ardisia crispa

Yin

Zhou

et al. 2022

Molecules

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Ardisiacrispin D–F (1–3), three new 13,28 epoxy bridged oleanane-type triterpenoid saponins, together with four known analogues (4–7) were isolated from the roots of Ardisia crispa. The structures of 1–7 were elucidated based on 1D and 2D-NMR experiments and by comparing their spectroscopic data with values from the published literatures. Ardisiacrispin D–F (1–3) are first examples that the monosaccharide directly linked to aglycone C-3 of triterpenoid saponins in genus Ardisia are non-arabinopyranose. In the present paper, all compounds are evaluated for the cytotoxicity against three cancer cell lines (HeLa, HepG2 and U87 MG) in vitro. The results show that compounds 1, 4 and 6 exhibited significant cytotoxicity against Hela and U87 MG cells with IC50 values in the range of 2.2 ± 0.6 to 9.5 ± 1.8 µM. The present investigation suggests that roots of A. crispa could be a potential source of natural anti-tumor agents and their triterpenoid saponins might be responsible for cytotoxicity.

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“…There are different secondary metabolites reported form I. verum , such as phenylpropanoids, phenols, organic acids, glycosides, flavonoids, neolignans, mono and sesquiterpeniods. Trans -Anethole is a major constituent of I. verum which is extensively used in food, perfume, and pharmaceutical industries [ 25 , 26 ]. Sharafan et al ., summarized different compounds reported from I. verum , such as phenolic compounds ( Trans -anethole, cis-anethole, estragole, Illiverin A, etc .…”

Section: Discussionmentioning

confidence: 99%

Anti-glycation properties of Illicium verum Hook. f. fruit in-vitro and in a diabetic rat model

Khan

Rasheed

Choudhary

et al. 2022

BMC Complement Med Ther

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Background Chronic hyperglycemic triggers the non-enzymatic glycation of biomolecules, resulting in the production of advanced glycation endproducts, that lead to several micro- and macrovascular complications. Therefore, the discovery of new, effective, and safe anti-glycation agents is an important need. One of the best choices for the management of diabetes is to use complementary and alternative medicinal therapies. Therefore, the present study was designed to evaluate the anti-glycation activity of ethanolic extract of Illicium verum Hook. f. (Star anise, a frequently used spice and medicinally important herb). Methods The anti-glycation activity of ethanolic extract of Illicium verum Hook. f. was determined by using both in-vitro and in-vivo assays. HSA-fructose glycation model was employed to assess the in-vitro inhibition of protein glycation, additionally cross-linked AGEs (formed by incubating lysozyme with fructose) were assessed by SDS polyacrylamide gel electrophoresis. Dual inhibitory mechanisms, i.e., antioxidant and metal chelating activities, were also evaluated by using DPPH, ABTS, and Fe (II)-chelation assays. Acute toxicity of I. verum extract was also performed (by administrating different doses i.e. 2,000, 1,500, 1,000, and 500 mg/kg of body weight). Finally, in-vivo anti-glycation potential was evaluated by 7 weeks of administration of I. verum extract in streptozotocin-induced diabetic rats. Results In HSA-fructose glycation model, extract of I. verum showed a good inhibitory activity with IC50 value of 0.11±0.001 mg/mL, as compared to the standard inhibitor, rutin (IC50 = 0.02±0.01 mg/mL). Extract of I. verum showed inhibitory activity in DPPH, and ABTS radical scavenging assays with IC50 values of 130±1.0, and 57±2.0 μg/mL, respectively, while it was found to be inactive in the Fe+2-chelation assay. The extract was found to be non-toxic, and reduce the elevated blood glucose, urea, lipid, liver function parameters, and renal AGEs levels in streptozotocin-induced diabetic rats. Conclusions These results suggest that I. verum supplementation might help to reduce the burden of AGEs, and may have potential in preventing diabetes-associated complications.

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Two new phenolic glycosides from the fruits of Illicium verum

Cited by 12 publications

References 16 publications

Illicium verum (Star Anise) and Trans-Anethole as Valuable Raw Materials for Medicinal and Cosmetic Applications

Illicium verum (Star Anise) and Trans-Anethole as Valuable Raw Materials for Medicinal and Cosmetic Applications

Cytotoxic 13,28 Epoxy Bridged Oleanane-Type Triterpenoid Saponins from the Roots of Ardisia crispa

Anti-glycation properties of Illicium verum Hook. f. fruit in-vitro and in a diabetic rat model

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