Chemistry, bioactivity and geographical diversity of steroidal alkaloids from the Liliaceae family

Li, Huijun; Jiang, Yan; Li, Ping

doi:10.1039/b609306j

Cited by 182 publications

(90 citation statements)

References 66 publications

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“…4). The resonances of CH 2 -7 {d H 2.72 and 1.92 (each 1H, m); d C 17.6} suggested that CH 2 -6 and CH-8 were connected through an sp 3 methylene (CH 2 -7), which was confirmed by 1 H-1 H COSY cross-peaks of H 2 -6/H 2 -7 and H 2 -7/H-8. Detailed analysis of the NOESY spectrum disclosed the cis/trans/cis/trans/trans junctions of A to F rings and the b-orientations for 16-OH, 20-OH, and 27-Me (Fig.…”

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confidence: 54%

Veramadines A and B, New Steroidal Alkaloids from Veratrum maackii var. japonicum

Tanaka

Suto

Kobayashi

2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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NoteThe plants belonging to the genus Veratrum (family Liliaceae) were used medicinally by Native Americans, preindustrial Europeans, and Chinese to treat various type of disorders (e.g. coughs, wounds, mania and epilepsy, aphasia arising from apoplexy, jaundice, scabies, and bacterial infections).1) These plants are known to contain steroidal alkaloids, which have been categorized according to the carbon framework into cevanine, veratramine, jervine, solanidine, and verazine types.1) In our continuing search for structurally interesting compounds from plants, [2][3][4] two new cevaninetype steroidal alkaloids, veramadines A (1) and B (2), were isolated from the aerial parts of Veratrum maackii var. japonicum. In this paper, we describe the isolation and structure elucidation of 1 and 2.The aerial parts of Veratrum maackii var. japonicum were extracted with MeOH, and the extracts were partitioned between EtOAc and 3% tartaric acid. The water-soluble materials were adjusted pH 10 with saturated Na 2 CO 3 , which were extracted with CHCl 3 . The CHCl 3 -soluble materials were subjected to a silica gel and an amino silica gel column chromatographies, and then purified by C 18 HPLC to afford veramadines A (1, 0.0008%) and B (2, 0.0004%) together with known steroidal alkaloids, neogermine (3), 5) 3-veratroylgermine (4), 6) 3-veratroylzygadenine (5), 7) 3-angeloylzygadenine (6), 7) and veramarine (7). 3) were ascribed to those bearing a nitrogen atom. The presence of a veratroyl group (3,4-dimethoxybenzoyl group) was implied by heteronuclear multiple bond correlation (HMBC) crosspeaks of H-2Ј and H-6Ј to C-7Ј and nuclear Overhauser effect spectroscopy (NOESY) correlations for 3Ј-OMe/H-2Ј and 4Ј-OMe/H-5Ј (Fig. 1). From these data, 1 was presumed to be a steroidal alkaloid having a veratroyl group. The gross structure of 1 was assigned based on the analysis of the 2D-NMR data as follows. The 1 H-1 H correlation spectroscopy (COSY) spectrum disclosed the existence of four partial structures a (C-1-C-3), b (C-5-C-8), c (C-11-C-13, C-13-C-17, C-13-C-18, C-15-C-17), and d (C-22-C-26, C-25-C-27) as shown in Fig. 1. Connectivities among C-3, C-5, and 4-OH through C-4 were implied by HMBC correlations for H-5 to C-4 and 4-OH to C-3 and C-4. HMBC correlations for H 2 -11 to C-9, H-8 to C-9, and H 3 -19 to C-1, C-5, C-9, and C-10 suggested the connectivities of C-1 to C-5, C- Two new steroidal alkaloids possessing a cevanine-type skeleton, veramadines A (1) and B (2), were isolated from the aerial parts of Veratrum maackii var. japonicum. The structures of 1 and 2 were elucidated on the basis of their spectroscopic data. Veramadines

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confidence: 54%

Veramadines A and B, New Steroidal Alkaloids from Veratrum maackii var. japonicum

Tanaka

Suto

Kobayashi

2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The male-predominant expression and activity of CYP3A were verified to be the major reasons for the gender-dependent pharmacokinetics of indinavir in rats (78). Steroidal alkaloids of Liliaceae mainly possess a C 27 cholestane carbon skeleton with four or five carbocyclic and one heterocyclic rings (3,79). Among the Liliaceae family, genus Veratrum and Fritillaria, two most important steroidal alkaloids containing herbs, were widely used as folk remedies *p < 0.05, significant difference; **p < 0.01, highly significant difference (vs. the same metabolite for male rats).…”

Section: Discussionmentioning

confidence: 99%

“…Genus Veratrum of Liliaceae, commonly known as American Hellebore or Black False Hellebore and which have a variety of Veratrum alkaloids as active components, has been used for medicinal purposes to treat hypertension, epilepsy, stroke, excessive phlegm, jaundice, scabies, chronic malaria, and wounds in European and Asian countries (1)(2)(3)(4)(5). Veratramine ( Fig.…”

Section: Introductionmentioning

confidence: 99%

“…In the clinic, the alternative and complementary medicines, such as "Ji Ming Zi Pills," primarily containing Veratrum alkaloids, were used for the treatment of breast tumor in China. Veratrum alkaloids have also been used clinically for the treatment of hypertension in Chinese hospitals and used medically by Native Americans and Europeans (3)(4)(5)11,(21)(22)(23). Moreover, the marketed veratramine containing medicine "San Qi Xue Shang Ning Capsule" is listed in the Chinese Pharmacopeia (China, 2010) for the treatment of relieving symptoms of blood congestion.…”

Section: Introductionmentioning

confidence: 99%

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Gender-Dependent Pharmacokinetics of Veratramine in Rats: In Vivo and In Vitro Evidence

Lyu

Zhang

Zhou

et al. 2016

AAPS J

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ABSTRACT. Veratramine, a major alkaloid from Veratrum nigrum L., has distinct anti-tumor and antihypertension effects. Our previous study indicated that veratramine had severe toxicity toward male rats. In order to elucidate the underling mechanism, in vivo pharmacokinetic experiments and in vitro mechanistic studies have been conducted. Veratramine was administrated to male and female rats intravenously via the jugular vein at a dose of 50 μg/kg or orally via gavage at 20 mg/kg. As a result, significant pharmacokinetic differences were observed between male and female rats after oral administration with much lower concentrations of veratramine and 7-hydroxyl-veratramine and higher concentrations of veratramine-3-O-sulfate found in the plasma and urine of female rats. The absolute bioavailability of veratramine was 0.9% in female rats and 22.5% in male rats. Further experiments of veratramine on Caco-2 cell monolayer model and in vitro incubation with GI content or rat intestinal subcellular fractions demonstrated that its efficient passive diffusion mediated absorption with minimal intestinal metabolism, suggesting no gender-related difference during its absorption process. When veratramine was incubated with male or female rat liver microsomes/cytosols, significant malepredominant formation of 7-hydroxyl-veratramine and female-predominant formation of veratramine-3-O-sulfate were observed. In conclusion, the significant gender-dependent hepatic metabolism of veratramine could be the major contributor to its gender-dependent pharmacokinetics.

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“…Steroidal compounds display a variety of biological [1][2][3] functions and play a very important role in life [4][5][6], and attracted profound attention for development of potent pharmacological agents for treatments of various diseases [7] including: cardiovascular disease [8], adrenal insufficiencies [9], autoimmune disorders [10], fungal and microbial infections [11,12]. Furthermore, different steroidal derivatives have been considered as potent anti-cancer agents for the treatment of leukemia [7], breast cancer [13][14][15], prostate cancer [16] and brain tumors [17].…”

Section: Introductionmentioning

confidence: 99%

Exploration of new 3α-pregnenolone ester analogues via Mitsunobu reaction, their anti-HIV activity and molecular modeling study

2015

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A new series of (5-pregnen-20-on-3α-yl)-substituted-benzoate analogues (10-13), (5-pregnene-20-on-3α-yl)-3-(substituted)acrylate derivatives (17-19) as well as the (17-(2-acetoxyacetyl)pregen-3α-yl)-3,4,5-trihydroxybenzoate (21) were synthesized from the β-pregenenolone scaffolds, by applying Mitsunobu reaction. All new compounds were characterized by 1 H, 13 C and 2D NMR spectroscopy. The inversion in configuration at C-3 during the formation of α-ester analogues was confirmed by NOESY NMR spectroscopy. The new compounds were evaluated for their in vitro antiviral activity against the replication of HIV-1 and HIV-2 in MT-4 cells. Compounds 18 showed an EC50 value of >1.95 mg/mL. In addition, preliminary structure-activity relationship and molecular modeling of compound 18 has been studied.

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Chemistry, bioactivity and geographical diversity of steroidal alkaloids from the Liliaceae family

Cited by 182 publications

References 66 publications

Veramadines A and B, New Steroidal Alkaloids from Veratrum maackii var. japonicum

Veramadines A and B, New Steroidal Alkaloids from Veratrum maackii var. japonicum

Gender-Dependent Pharmacokinetics of Veratramine in Rats: In Vivo and In Vitro Evidence

Exploration of new 3α-pregnenolone ester analogues via Mitsunobu reaction, their anti-HIV activity and molecular modeling study

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