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

Abstract

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

Effect of <i>Veratrum maackii</i> on Testosterone Propionate-Induced Benign Prostatic Hyperplasia in Rats

“…17) However, VM has long been applied as the Chinese traditional medicine, "Lilu," which is used to treat apoplexy-associated aphasia, wind-type dysentery, jaundice, headache, scabies, chronic malaria, and other disorders. [14][15][16][17] In the present work, rats treated with VM showed lower body weights compared to the control group (Table 1). However, previous studies showed that daily injection of testosterone propionate can reduce body weight gain 45) and we did not find any significant difference between the VM-treated group and those treated with other versions of testosterone propionate (the BPH and FINA groups).…”

“…7) However, 5α-reductase inhibitors may have serious side-effects, such as loss of libido, ejaculatory or erectile disorders, and dizziness. 12,13) Therefore, there is increasing interest in the use of phytotherapies for BPH, because plantderived compounds may have fewer adverse effects.…”

“…These compounds have been proven to be effective against several disorders (coughs, wounds, epilepsy, and aphasia), making it popular among Americans, Europeans, and Asians. 14) In addition, the dried roots and rhizomes of several Veratrum species, including V. nigrum and V. maackii, have traditionally been used to treat apoplexy-related aphasia, wind-type dysentery, jaundice, headache, scabies, and chronic malaria. 15,16) Recent studies of several species in this genus have documented anti-hypertensive, anti-cholinergic, cAMP phosphodiesterase inhibitory, anti-asthmatic, anti-tussive, antifungal, anti-melanogenesis, and anti-tumor activities.…”

One New Veratramine-Type Alkaloid From Veratrum maackii var. japonicum and Antioxidative Activities of Isolated Compounds

“…japonicum (Baker) T. Shimizu is a traditional medicinal herb belonging to the family Melanthiaceae which comprises about 40 species. [1][2][3] It is widely distributed in Korea, China, and America. Previous chemical investigations of Veratrum sp.…”

“…revealed the existence of various types of steroidal alkaloids such as jervanine, veratramine, cevanine, and verazine 4 with anti-inflammatory, 5 anti-hypotensive, 6 antioxidative, 7 and anti-fungal activities. 8 In our continuous investigation of anti-oxidative constituents from herbal plants, we isolated one new steroidal alkaloid (1), along with four known compounds (2)(3)(4)(5) from the roots of V. maackii var. japonicum.…”