Steroids of the furostan and spirostan series from Nolina microcarpa II. structures of nolinospiroside D and nolinofurosides D,E, and F

In addition to the know steroid sapogenin (25S)-ruscogenin (I), three new glycosides have been isolated from the leaves ofNolina microcarpa S. Wats. (family Dracaenacea), and the following structures are suggested for them: (25S)-spirost-5-ene-1β,3β-diol 1-O-β-D-fucopyranoside (nolinospiroside C, II), (25S)-furost-5-ene-1β,3β,22α,26-tetraol 1-O-β-D-fucopyranoside (nolinofuroside A, III), and (25S)-furost-5-ene-1β, 3β, 22α, 26-tetraol 1-O-β-D-fucopyranoside 26-O-β-D-glucopyranoside (nolinofuroside C, V). M. V. Frunze Simferopol' State University. Institute of Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 672–678, September–October, 1991.     

Two new steroidal glucosides from Ophiopogon.japonicus （L.f.） Ker-Gawl

Two new steroidal glucosides, 26-O-β-D-glucopyranosyl （25S）-furost-5-ene-1β,3β,22α,26-tetraol l-O-β-D-xylopyranosyl- （1 → 3）-[α-h-rhamnopyranosyl-（1 → 2）]-[β-D-fueopyranoside and （25R） spirost-5-ene-3β,14α-diol-3-β-O-β-L-rhanmopyranosyl- （1 → 2）-[β-D-xylopyranosyl（1 → 4）]-[-β-D-glucopyranoside, were isolated from the Ophiopogon japonicus （L.f.） Ker-Gaw. Their structures were elucidated by spectroscopic methods.     

Steroids of the spirostan and furostan series from Nolina microcarpa I. Structures of nolinospiroside C and nolinofurosides A and C

In addition to the know steroid sapogenin (25S)-ruscogenin (I), three new glycosides have been isolated from the leaves ofNolina microcarpa S. Wats. (family Dracaenacea), and the following structures are suggested for them: (25S)-spirost-5-ene-1,3-diol 1-O--D-fucopyranoside (nolinospiroside C, II), (25S)-furost-5-ene-1,3,22,26-tetraol 1-O--D-fucopyranoside (nolinofuroside A, III), and (25S)-furost-5-ene-1, 3, 22, 26-tetraol 1-O--D-fucopyranoside 26-O--D-glucopyranoside (nolinofuroside C, V).M. V. Frunze Simferopol' State University. Institute of Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 672–678, September–October, 1991.     

Medicinal foodstuffs. XVII. Fenugreek seed. (3): structures of new furostanol-type steroid saponins, trigoneosides Xa, Xb, XIb, XIIa, XIIb, and XIIIa, from the seeds of Egyptian Trigonellafoenum-graecum L

Six new furostanol-type steroid saponins called trigoneosides Xa, Xb, XIb, XIIa, XIIb, and XIIIa were isolated from the seeds of Egyptian Trigonella foenum-graecum L. (Leguminosae) together with six known furostanol-type steroid saponins: trigoneosides Ia, Ib, and Va, glycoside D, trigonelloside C, and compound C. The structures of trigoneosides Xa, Xb, Xlb, XIIa, Xllb, and XIIIa were determined on the basis of chemical and physicochemical evidence as 26-O-beta-D-glucopyranosyl-(25S)-5alpha-furostane-2alpha+ ++,3beta,22xi,26-tetraol 3-O-alpha-L-rhamnopyranosyl(1-->2)-,beta-D-glucopyranoside, 26-O-beta-D-glucopyranosyl-(25R)-5alpha-furostane-2 alpha,beta,22xi,26tetraol 3-O-alpha-L-rhamnopyranosyl(l -->2)-beta-D-glucopyranoside, 26-O-beta-D-glucopyranosyl-(25R)-5alpha-furostane2alpha++ +,beta,22xi,26-tetraol 3-O-beta-D-xylopyranosyl(l -->4)-beta-D-glucopyranoside, 26-O-beta-D-glucopyranosyl-(25S)-furost-4-ene-3beta,22xi,26- triol 3-O-Ca-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranoside, 26-O-beta-D-glucopyranosyl-(25R)-furost-4-ene-3beta,22xi+ ++,26-triol 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranoside, and 26-O-beta-D-glucopyranosyl(25S)-furost-5-ene-3beta,22xi,26-t riol 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl (1-->3)-beta-D-glucopyranosyl(1--4)]-beta-D-glucopyranoside, respectively.     

Steroids of the furostan and spirostan series from Nolina microcarpa II. structures of nolinospiroside D and nolinofurosides D, E, and F

Proofs are given of the structures of two new glycosides of the furostan series isolated from the leaves of the plantNolina microscarpa S. Wats. (family Dracaenaceae). Nolinofuroside D is (25S)-furost-5-ene-1,3,22,26-tetraol 1-O--D-galactopyranoside 26-O--D-glucopyranoside (I), and nolinofuroside F is (25S)-furost-5-ene-1,3,22,26-tetraol 1-O--D-fucopyranoside 26-O--D-glucopyranoside 3-O--L-rhamnopyranoside (VII). The latter was characterized as its 22-O-methyl ether (VIII). Nolinofuroside E (IV) has the structure of (25S)-furost-5-ene-1,3,22,26-tetraol 26-O--glucopyranoside 1-O-[O--L-rhamnopyranosyl-(12)--D-fucopyranoside], which followed from the structure of the fermentation product (VI). The products of the fermentation of the above-named compounds were present in the plant in only trace amounts. Only one of them — nolinospiroside D (III) — has not been described previously. This monoside of the spirostan series is (25S)-spirost-5-ene-1,3-diol 1-O--D-galactopyranoside.M. V. Frunze Simferopol' State University. Institute of Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 678–686, September–October, 1991.     

A New Enolate Furostanoside from Asparagus Filicinus

The roots of Asparagus filicinus Buch.-Ham are used to treat lung diseases such asbronchitis, pneumonities and cough in folk medicinel. Some steroidal glycosides havebeen isolated and characterized from the roots of this plant by several research groups'-'.In this paper, we report the isolation of a new unusual furostanol glycoside possessing anenolate moiety, whose strUcture was determined by I D and ZD NMR methods, FABMS,and hydrolysis. Bioassay results showed that the compound exhibit…     

Triterpene glycosides of Astragalus and their genins XLIV. Structure of cyclocarposides A and C

The structures of two new cycloartane glycosides — cyclocarposides A and C, isolated from the herbAstragalus coluteocarpus Boiss. — have been established on the basis of spectral characteristics and chemical transformations. Cyclocarposides A and C are: 204R,24S-epoxycycloartane-3β,6α,17β,25-tetraol 3-O-(2-O-acetyl-β-D-xylopyranoside)6-O-(2-O-acetyl-α-L-rhamnopyranoside) and 20R,24S-epoxycyloartane-3β,6α,16β,25-tetraol 3-O-(2-O-acetyl-β-D-xylopyranoside) 6-O-α-L-rhamnopyranoside, respectively.     

黑叶菝葜中呋甾烷甙

百合科菝葜属(SmilaxL.)植物在我国品种较多,且许多为民间药用,继前文我们又对黑叶菝葜(S.NigrescensWangetTang)的化学成分进行了研究,从其根部的乙醇提取物中得到4种呋甾烷甙,其中一种为新化合物,本文报道它们的结构鉴定。     

Total synthesis of methyl protodioscin: a potent agent with antitumor activity

Methyl protodioscin (1), otherwise known as 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-d-glucopyranosyl]-26-O-[beta-D-glucopyranosyl]-22-methoxy-25(R)-furost-5-ene-3 beta,26-diol, has been synthesized for the first time from diosgenin through nine steps in an overall yield of 7.8%.     

Steroid saponins and sapogenins ofAllium. XVI. Turoside C fromAllium turcomanicum

From a methanolic extract of the bulbs ofAllium turcomanicum Rgl. we have isolated a new furostanol glycoside, turoside C (I). An acid hydrolysate was found to contain the aglycone — neoagigenin (II) — and the sugars D-xylose, D-glucose, and D-galactose in a ratio of 1:4:1. The structure of the furostanol (I) has been established by methylation, enzymatic hydrolysis, and oxidative cleavage, and also by the oxidative cleavage of (II), as (25S)-5α-furostan-2α,3β,6β,22α,26-pentaol 26-O-β-D-glucopyranoside 3-O-{[O-β-D-xylopyranosyl-(1→3)]-[O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)]-O-β-D-glucopyranosyl-(1→4)-β-D-galacto-pyranoside}.     

Steroid glycosides ofNicotiana tabacum seeds I. The structures of nicotianosides A,B, and E

Two steroid glycosides of the spirostan series — nicotianosides A and B — and one glycoside of the furostan series — nicotianoside E — have been isolated from the seeds ofNicotiana tabacum L. Nicotianoside A is (25S)-5α-spirostan-3β-ol 3-O-β-D-glucopyranoside, nicotianoside B is (25S)-5β-spirostan-3β-ol 3-O-[O-α-L-rhamnopyranosyl-(1→2)-gb-D-glucopyranoside], and nicotianoside E is (25S)-5α-furostan-3β,22α,26-triol 26-O-β-glucopyranoside 3-O-[O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside].     

蒺藜果化学成分的分离和鉴定

分离鉴定了2个六糖呋甾皂苷, 其中化合物1为新化合物.     

Tomatoside a from the seeds ofLycopersicum esculentum

Results are given which confirm the structure of the furostanol glycoside from tomato seeds forming wastes of the preserving industry. From a butanolic extract of the seeds ofLycopersicum esculentum Mill. we have isolated the furostanol glycoside tomatoside A (I) the structure of which has been established as 25(S)-5α-furostan-3β,22α,26-triol 26-O-β-D-glucopyranoside 3-O-[O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside]. At the same time, by enzymatic and chemical transformations three new spirostanol glycosides of neotigogenin have been obtained: tomatoside B (III), which is 25(S)-5α-spirostan-3β-ol 3-O-[O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranoside], 25(S)-5α-spirostan-3β-ol 3-O-[O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside] (V), and 25(S)-5α-spirostan-3β-ol 3-O-β-D-galactopyranoside (IV).     

Studies on Balanites aegyptiaca fruits, an antidiabetic Egyptian folk medicine

An aqueous extract of mesocarps of the fruits of Balanites aegyptiaca exhibited a prominent antidiabetic activity by oral administration in streptozotocin induced diabetic mice. From one of the active fractions of this extract, two new steroidal saponins were isolated, and their structures were determined as 26-O-beta-D-glucopyranosyl-(25R)-furost-5-ene-3 beta,22,26-triol 3-O-[alpha-L-rhamnopyranosyl-(1----2)]-[beta-D-xylopyranosyl-(1---- 3)]-[alpha-L-rhamnopyranosyl-(1----4)]-beta-D-glucopyranoside and its 22-methyl ether. In addition, two known saponins, 26-O-beta-D-glucopyranosyl-(25R)-furost-5-ene-3 beta,22,26-triol 3-O-(2,4-di-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside and its methyl ether were isolated and identified. It was revealed that the individual saponins did not show antidiabetic activity, while the recombination of these saponins resulted in significant activity. From an ethanolic extract of the epicarps, two known flavonol glycosides, isorhamnetin-3-O-robinobioside and isorhamnetin-3-O-rutinoside were isolated and identified.     

Steroids of the spirostan and furostan series of plants of the Allium genus. XXIII. Structure of cepagenin and of alliospirosides C and D from Allium cepa

Two new steroid glycosides of the spirostan series have been isolated from the fruit ofAllium cepa L. (family Liliaceae): alliospirosides C and D. On the basis of chemical transformations and spectral characteristics it has been established that the aglycon of both glycosides is a new steroid sapogenin — cepagenin — having the structure of (24S,25R)-spirost-5-ene-1β,3β,24-triol. Alliospirosides C and D are cepagenin 1-O-[O-α-L-rhamnopyranosyl-(1→2)α-L-arabinopyranoside] and 1-O-[O-α-L-rhamnopyranosyl-(1→2)-O-β-D-galactopyranoside], respectively.     

Triterpenoids from the leaves of far eastern species of the shrubby birchesBetula ovalifolia andB. middendorfii

From the unsaponifiable fraction of an ethereal extract of the leaves ofBetula ovalifolia have been isolated the new triterpene 20(S),24(R)-epoxydammarane-3α,17α,25-triol (V) and the corresponding monoketone at C³ (VI). The leaves ofB. middendorfii have yielded the triterpene (IX) and (X), identified as, respectively, dammar-23-ene-3α,12β,20(S),25-tetraol and damman-25-ene-3α,12β,20-(S),24-tetraol, which have been obtained previously from the leaves ofBetula platyphylla Sukatchev var.japonica.     

九子参中三个糖链上带乙酰基的新三萜皂苷-九子参苷B,C, D

从石竹科植物九子参(Silene rubicunda)根中得到四个糖链上带乙酰基的新的三萜皂苷-九子参苷A, B, C, D(rubicunosides A~D, 1~4)。前文已详细报道了九子参苷A的结构研究, 本文报道九子参苷B, C, D的结构。通过FAB-MS和NMR,分别确定九子参苷B, C, D为糖链上带单乙酰基的三萜九糖苷、七糖苷和糖链上带双乙酰基的三萜八糖苷, 分别命名为皂树酸-3-O-β-D-吡喃半乳糖-(1→2)-[β-D-吡喃木糖-(1→3)]-β-D-吡喃葡萄糖醛酸-28-O-β-D-吡喃木糖-(1→3)-β-D-吡喃木糖-(1→4)-α-L-吡喃鼠李糖-(1→4)-[β-D-吡喃葡萄糖-(1→4')-β-D-吡喃鸡纳糖-(1→2)]-[3'-O-乙酰基]-β-D-吡喃夫糖苷(九子参苷B, 2), 皂树酸-3-O-β-D-吡喃半乳糖-(1→2)-[β-D-吡喃木糖-(1→3)]-β-D-吡喃萄淘糖醛酸-28-O-β-D-吡喃木糖-(1→4)-α-L-吡喃鼠李糖-(1→4)-[4"-O-乙酰基-β-D-吡喃葡萄糖-(1→2)]-β-D-吡喃夫糖苷(九子参苷C, 3), 皂树酸-3-O-β-D－吡喃半乳糖-(1→2)-[β-D-吡喃半乳糖-(1→2)-[β-D-吡喃木糖-(1→3)]-[6'-O-正丁基]-β-D-吡喃葡萄糖醛酸-28-O-β-D-吡喃木糖-(1→3)-β-D-吡喃木糖-(1→4)-α-L-吡喃鼠李糖-(1→4)-[2"-O-乙酰基-β-D-吡喃鸡纳糖-(3'-O-乙酰基]-β-D-吡喃夫糖苷(九子参苷D, 4)。     

Steroids of the spirostan and furostan series from nolina microcarpa III. Structure of nolinofurosides G and H

Two new glycosides which have been called nolinofurosides G(I) and H(III), have been isolated from the leaves ofNolina microcarpa. Nolinofuroside G is the sodium salt of 26-β-D-glucofuranosyloxy-(25S)-furost-5,20(22)-diene-1β, 3β-diol 1-sulfate, and nolinofuroside H is the sodium salt of 1-β-D-fucopyranosyloxy-26-β-D-glucopyranosyloxy-(25S)-furost-5,20(22)-dinen-1β-3β-ol 3-sulfate. M. V. Frunze Simferopol' State University. Institute of the Chemistry of Plant Substances, Uzbek. Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 801–806, November–December, 1991.     

海枫藤中C21甾体苷的分离和结构测定

从萝摩科植物海枫藤[Marsdenia officinalis Tsiang et P.T.Li.]的藤茎中分离得到四个C21甾体去氧糖苷(1)～(4). 通过化学降解和波谱技术, 确定它们的化学结构依次为: 12-O-桂皮酰基-20-O-乙酰基(20S)-孕甾烷-6-烯-3β,5α,8β,12β,14β, 17β,20-庚醇 3-O-甲基-6-去氧-β-D-阿洛吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(1), 12-O-桂皮酰基-20-O-乙酰基(20S)-孕甾烷-6-烯-3β,5α,8β,12β,14β,17β,20-庚醇3-O-β-D-葡萄吡喃糖基-(1→4)-3-O-甲基-6-去氧-β-D-阿洛吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(2), 12-O-桂皮酰基-20-O-乙酰基(20S)-孕甾烷-6- 烯-3β,5α,8β,12β,14β,17β,20-庚醇3-O-β-D-黄夹吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(3), 12-O-烟酰基-肉珊瑚苷元3-O-β-D-葡萄吡喃糖基-(1→4)-3-O-甲基-6-去氧-β-D-阿洛吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基- (1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(4). 其中1和2为新化合物, 分别命名为haifengtenoside A, haifengtenoside B, 3和4分别为已知化合物mucronatoside H 和 hainaneosides A, 系首次从该植物中分离得到.     

Two new polyhydroxylated triterpenoids from Salvia urmiensis and their cytotoxic activity

Two new polyhydroxylated triterpenoids were isolated from the acetone extract of the aerial parts of Salvia urmiensis Bunge. Their structures were elucidated by 1D and 2D NMR and HR-ESI-MS analyses as olean-12-ene-1β,3β,11α,22α-tetraol (1) and urs-12-ene-1β,3β,11β,22α-tetraol (2). The effect of these compounds on cell viability of MCF-7 cells was investigated by the MTT assay. Compounds 1 and 2 showed weak cytotoxicity with IC₅₀ values of 110.23 ± 0.12 and 88.35 ± 0.09 μM, respectively.