Studies on Chemical Constituents of Fritillaria yuminensis

Six compounds were isolated from the bulbs of Fritillaria yuminensis X. Z. Duan. They were elucidated as 5α, 14α-cevanine-3α-hydroxy-6-one ( Ⅰ ), 5α, 14α-cevanine-3-one-6β-O-β-D-glucoside ( Ⅱ ), imperialine ( Ⅲ ), delavinone ( Ⅳ ), tortifolisine ( Ⅴ ) and adenosine( Ⅵ ) by means of spectral analysis and chemical reaction. They all were firstly isolated from this plant. Among them, compound Ⅰ and Ⅱ, named yubeinine and yubeiside respectively, were new compounds.     

Ungeremine effectively targets mammalian as well as bacterial type I and type II topoisomerases

From the methanol extract of the bulbs of Pancratium illyricum L., three phenanthridine type alkaloids, ungeremine (1), (-)-lycorine (2) and (+)-vittatine (3) were isolated. For the evaluation of their anticancer and antibacterial potential, compounds 1-3 were tested against human (I, IIα) and bacterial (IA, IV) topoisomerases. Our data demonstrated that ungeremine impairs the activity of both, human and bacterial topoisomerases. Remarkably, ungeremine was found to largely increments the DNA cleavage promoted by bacterial topoisomerase IA, a new target in antimicrobial chemotherapy.     

Studies of Songbeinone,A New Fritillaria Alkaloid Identified from the Bulb of Fritillaria unibracteata

A compound C was isolated from the dry bulbs of Fritillaria unibracteata Hsiao et K. C: Hsia which belongs to a main resource species of traditional Chinese drug “Chuan Bei-mu” in Chinese Pharmacopoeia (1990 ed.). It was identified as D/E cis(22R, 25S)-20-deoxy-3β-hydroxyl-6-carbonyl-5α, 14α, 17β-cevanine by means of spectroscopic methods. It is a new alkaloid of 5α-cevanine group of isosteroidal alkaloids being attributed to the characteristic constituents of this genus, named as songbeinone.     

长筒石蒜鳞茎中的生物碱类成分(英文)

从长筒石蒜鳞茎的乙醇提取物中分离得到7个生物碱类化合物,经理化方法和波谱分析,分别鉴定为galanthamine(1),lycoramlne(2),6β-hydroxycrinamine(3a),6α-hydroxycrinamine(3b),(-)-amarbellisine(4),tazettine(5),macowine(6).其中化合物3a～6为首次从该植物中分离得到.     

Haemolytic activity and immunological adjuvant effect of a new steroidal saponin from Allium ampeloprasum var. porrum

A new steroidal saponin was isolated from the bulbs of Allium ampeloprasum L. var. porrum. On the basis of chemical evidence, comprehensive spectroscopic analyses, and comparison with known compounds, its structure was established as (3β,5α,6β,25R)-3-{(O-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→2)-O-[O-β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranosyl)oxy}-6-hydroxyspirostan-2-one (1). Results of the present study indicated that 1 exhibited haemolytic activity in the in vitro assays, and immunological adjuvant activity on the cellular immune response against ovalbumin antigen.     

Studies on Chemical Constituents of Fritillaria thunbergii Miq.

In our previous papers, it was reported that peimine, peiminine, eduardine and three new alkaloids, zhebeinine, zhebeirine, zhebeinone, were isolated from the bulbs of Fritillaria thunbergii Miq. In consecutive investigation of the plant, an additional new alkaloidal glucoside, 5α , 14α -cevanine-6α , 20β-dihydroxyl-3β-O-β-D-glucoside, named zhebeininoside (Ⅰ) and aknown picropodophyllotoxin (Ⅱ) were isolated. The structure of zhebeininoside was determined on the basis of spectral analysis and chemical reaction. Picropodophyllotoxin was firstly isolated from Fritillaria plants.     

Homoisoflavonoids and xanthones from the tubers of wild and in vitro regenerated Ledebouria graminifolia and cytotoxic activities of some of the homoisoflavonoids

Eleven homoisoflavonoids and two xanthones were isolated and characterized from the bulbs of Ledebouria graminifolia. Five of the homoisoflavonoids are new compounds and were identified as: 5-hydroxy-7-methoxy-3-(4'-hydroxybenzyl)-4-chromanone, 5-hydroxy-6,7-dimethoxy-3-(4'-hydroxybenzyl)-4-chromanone, 5,7,8-trimethoxy-3-(4'-hydroxybenzyl)-4-chromanone, 5-hydroxy-3',4',7-trimethoxyspiro[2H-1-benzopyran-7'-bicyclo[4.2.0]octa-trien]-4-one, 5,7-dihydroxy-3',4'-dimethoxyspiro[2H-1-benzopyran-7'-bicyclo[4.2.0]octa-trien]-4-one. Structures were elucidated by extensive 1D, and 2D NMR spectroscopy and HRMS. A method for tissue culture was developed and the bulbs of mature plants were found to contain all the compounds isolated from the wild specimens of L. graminifolia.     

Steroidal saponins from the bulbs of Camassia cusickii.

Six new steroidal saponins have been isolated from the fresh bulbs of Camassia cusickii. Their structures were determined by spectroscopic analysis and some chemical transformations to be (25R)-5 alpha-spirostan-3 beta,6 alpha-diol (chlorogenin) 6-O-beta-D-glucopyranoside, chlorogenin 6-O-beta-D-glucopyranosyl-(1----2)-beta-D-glucopyranoside, chlorogenin 6-O-beta-D-glucopyranosyl-(1----3)-beta-D-glucopyranoside, chlorogenin 6-O-beta-D-glucopyranosyl-(1----2)-O-[beta-D-glucopyranosyl-(1----3)]-beta- D-glucopyranoside, (25R)-6 alpha-hydroxy-5 alpha-spirostan-3-one 6-O-beta-D-glucopyranosyl- (1----3)-beta-D-glucopyranoside and (25R)-3,3-dimethoxy-5 alpha-spirostan-6 alpha-ol 6-O-beta-D-glucopyranosyl-(1----3)-beta-D-glucopyranoside. The saponins isolated were shown to contribute to the bitter taste of the bulbs.     

Flavans from Zephyranthes flava

A new optically active flavan aglucone, 7-hydroxy-3′,4′-methylenedioxyflavan, and its 7-glucoside have been isolated from the bulbs of Zephyranthes flava, collected at flowering. Additionally, two known flavans, 7,4′-dihydroxy-3′-methoxyflavan and 7-methoxy-2′-hydroxy-4′,5′-methylenedioxyflavan, have been isolated for the first time from this species. The structures of these flavans have been established by comprehensive analyses (UV, IR, ¹H NMR, ¹³C NMR, mass spectrometry, [α]_D) of the compounds and their acetates, and also by chemical correlation.     

Regio- and enantioselective oxidation of thiaoleic acids by an algal delta 12-desaturase

Five new spirostanol saponins and a new furostanol saponin were isolated from the fresh bulbs of Lilium candidum. Their structures were elucidated on the basis of spectroscopic analysis, including two-dimensional NMR spectroscopic techniques and the result of acid hydrolysis. The isolated saponins contained a branched triglycoside moiety assigned as O-alpha-L-rhamnopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->6)]-beta - D-glucopyranose with the formation of an O-glycosidic linkage to C-3 of the aglycone as the common structural feature. The inhibitory activity of the saponins on Na+/K+ ATPase was evaluated.     

Alkaloids of Crinum pratense

From the bulbs of Crinum pratense, collected at flowering, lycorine, 1,2-diacetyllycorine, ambelline, narcissidine, and three phenanthridone alkaloids, viz. hippadine, pratorinine and anhydrolycorin-7-one, were isolated and characterized on the basis of comprehensive spectral analyses (UV, IR, ¹H NMR, ¹³C NMR, MS, [α]_D) and chemical evidence. Among the phenanthridone alkaloids (1–3, only the natural occurrence of hippadine was previously known. Pratorinine is a new phenanthridone alkaloid and anhydrolycorin-7-one was known before only as a synthetic compound. The physiological significance of hippadine is appraised.     

New class of steroidal alkaloids from Fritillaria imperialis

Two members of a new class of C-nor-D-homo steroidal alkaloids, impranine (1). and dihydroimpranine (2). along with a new pyridyl-pregnane-type steroidal alkaloid, fetisinine (3). and a known base, korsevine (4). were isolated from the bulbs of Fritillaria imperialis. The structures of the compounds were established on the basis of spectroscopic techniques and some chemical transformations. Compounds 1 and 2 form a new class of steroidal alkaloids, named as "impranane."     

Sesquiterpene lactones from Smyrnium cordifolium

In addition to previously obtained furanosesquiterpenes, two new eudesmanolides and a new glechomanolide were isolated from the fruits of Smyrnium cordifolium, while the roots gave two new eudesmanolides. The new compounds from the fruits were 1β-acetoxy-eudesman-4(15), 7(11)-dien-8,12-olide, 1β-acetoxy-8β-hydroxy-eudesman-4(15),7(11)-dien-8,12-olide, 1β,10α;4α,5β-diepoxy-8-hydroxy-glechomanolide, those obtained from the roots were smyrnicordiolide and the corresponding 8β-hydroxy derivative belonging to a new type of oxepine derivative.     

Minor phenolics from Crinum bulbispermum bulbs

From the bulbs of Crinum bulbispermum Milne, four new minor compounds were isolated viz. 4-hydroxy-2',4'-dimethoxydihydrochalcone (1), 4,5-methylenedioxy-4'-hydroxy-2-aldehyde[1,1'-biphenyl] (4), hippacine (6), and 4'-hydroxy-7-methoxyflavan-3-ol (7). In addition, four known compounds were isolated and identified as 2(S),3',4'-dihydroxy-7-methoxy flavan (2), isolarrien (3), isoliquiritigenin (5) and liquiritigenin (8). The structures of the isolated compounds were established by spectral evidence.     

Vavilosides A1/A2–B1/B2, new furostane glycosides from the bulbs of Allium vavilovii with cytotoxic activity

A phytochemical analysis of the bulbs of Allium vavilovii M. Pop. & Vved. was attained for the first time extensively, affording to the isolation of four new furostanol saponins, named vavilosides A1/A2–B1/B2 (1a/b–2a/2b), as two couple of isomers in equilibrium, together with ascalonicoside A1/A2 (3a/3b) and 22-O-methyl ascalonicoside A1/A2 (4a/4b), previously isolated from shallot, Allium ascalonicum. High concentrations of kaempferol, kaempferide, and kaempferol 4^I-glucoside were also isolated. The chemical structures of the new compounds, established through a combination of extensive nuclear magnetic resonance, mass spectrometry and chemical analyses, were identified as (25R)-furost-5(6)-en-1β,3β,22α,26-tetraol 1-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-galactopyranosyl 26-O-α-l-rhamnopyranoside (vaviloside A1), (25R)-furost-5(6)-en-1β,3β,22β,26-tetraol 1-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-galactopyranosyl 26-O-α-l-rhamnopyranoside (vaviloside A2), (25R)-furost-5(6)-en-1β,3β,22α,26-tetraol 1-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-xylopyranosyl 26-O-α-l-rhamnopyranoside (vaviloside B1), (25R)-furost-5(6)-en-1β,3β,22β,26-tetraol 1-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-xylopyranosyl 26-O-α-l-rhamnopyranoside (vaviloside B2). The isolated saponins showed cytotoxic activity on J-774, murine monocyte/macrophage, and WEHI-164, murine fibrosarcoma, cell lines with the following rank: vaviloside B1/B2 > ascalonicoside A1/A2 > vaviloside A1/A2.     

Chemical constituents from bulbs of Fritillaria pallidiflora Schrenk

A new steroidal alkaloid, 5α, 14α, 17β-cevanin-6-oxo-3β, 20β, 24β-triol(1), together with ten known compounds (2–11) were isolated from the bulbs of Fritillaria pallidiflora Schrenk. Their structures were determined on the basis of spectroscopic analysis and by comparison of their spectral data with those reported in the literature. Compounds 8, 9, 10 were obtained from the genus Fritillaria for the first time; Compounds 2, 3, 4 and 11 are isolated from this plant for the first time.     

中国红豆杉中一个新的紫杉烷二萜

从中国红豆杉(Taxus chinensis)枝叶中分离得到4个紫杉烷二萜,通过波谱分析分别确定为：1β-羟基-2α,7β-二去乙酰基巴卡亭I(1),1β-羟基巴卡亭I(2),2α,5α,7β,9α,10β,13α-六乙酰氧基紫杉-4(20),11-二烯(3)和2-去乙酰氧基-5-去肉桂酰taxinine J(4)其中化合物1为新化合物。     

Several 4-Substituted Glutamic Acid Derivatives and Small Peptides in Some Liliaceae Plants

Acidic non-protein amino acids and peptides in five species belonging to the family Liliaceae —Smilax china, Lilium maximowiczii, Tulipa gesneriana, Allium cepa and A. sativum— were surveyed. Two new amino acids —4-hydroxymethyl- and 4-ethyl-4-hydroxyglutamic acid— were isolated from bulbs of T. gesneriana. The first unequivocal identification of 4-ethylglutamic acid was performed from the same plant tissue. A new dipeptide —S-(2-carboxy-n-propyl)cysteinyl glycine— was isolated from A. cepa. Besides the compounds described above, 4-methylene-, 4-methyl- and 4-hydroxy-4-methylglutamic acid were isolated from S. china, L. maximowiczii, and T. gesneriana, but 4-ethylideneglutamic acid was isolated only from T. gesneriana. 4-Methyleneglutamic acid showed no appreciable biological activity, although this aminoacid has an α,β-unsaturated carboxyl group and reacts easily with cysteine in vitro. The most abundant free amino acid in the plant tissues examined in this study is arginine; nevertheless, acidic N_α-acylarginine derivatives which have been found in S. china and L. maximowiczii and published elsewhere could not be detected in bulbs of T. gesneriana, A. cepa, and A. sativum.     

Steroid sapogenins from Tristagma uniflorum

From bulbs of Tristagma uniflorum the known sapogenins tigogenin, neotigogenin and (20S,22R,25S)-5α-spirostan-3β,25-diol, as well as the new (20S,22R,25R)-5α-spirostan-3β,25-diol, (20S,22S,25S)-5α-furostan-22,25-epoxy-3β,26-diol and (20S,22S,25R) -5α-furostan-22,25-epoxy-3β,26-diol, were isolated and characterized by spectroscopic (IR, ¹H NMR, ¹³C NMR, MS) methods.     

朝鲜蓟叶中一个新的倍半萜内酯

从朝鲜蓟（Cynarascolyrnus）叶中分离得到2个倍半萜内酯,其中一个是新化合物,通过波谱学方法确定其结构为3β,8α,11α,13-四羟基-10（14）-愈创木烯-1α,4β,5α,6β氢-6α,12-内酯（1）。