- 7-Deoxyloganin 7-hydroxylase in Lonicera japonica cell cultures
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The activity of 7-deoxyloganin 7-hydroxylase, an enzyme catalyzing the conversion of 7-deoxyloganin into loganin, was detected in a microsomal preparation from the cell suspension cultures of Lonicera japonica. It was dependent on NADPH and molecular oxyg
- Katano, Nobuyuki,Yamamoto, Hirobumi,Iio, Reiko,Inoue, Kenichiro
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- New iridoids from Asperula maximowiczii
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Three new dimeric iridoid glucosides, named asperuloides A (1), B (2), and C (3), were isolated from Asperula maximowiczii, along with the known compound picconioside II. The structures of the new compounds were determined by spectroscopic and chemical methods and by the single-crystal X-ray diffraction analysis of 1.
- Park, Aeri,Ja Kim, Hyoung,Lee, Ji Sun,Woo, Eun-Rhan,Park, Hokoon,Lee, Yong Sup
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- An iridoid glucoside from Jasminum hemsleyi
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A new iridoid glucoside, jashemsloside E, was isolated from the leaves of Jasminum hemsleyi. Its structure was elucidated on the basis of chemical and spectral data.
- Tanahashi, Takao,Shimada, Atsuko,Kai, Mayumi,Nagakura, Naotaka,Inoue, Kenichiro,Chen, Cheng-Chang
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- Absolute structure assignment of an iridoid-monoterpenoid indole alkaloid hybrid from Dipsacus asper
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Iridoid-monoterpenoid indole alkaloid hybrids (IMIAHs)represent a rare class of natural products reported from only several plants of Rubiaceae and Dipsacaceae families, while their structural assignments remain a very challenging work due to complexity and flexibility. In the current study, a new IMIAH (1)was isolated from the roots of Dipsacus asper and its structure with absolute configuration was unambiguously established by a combination of spectroscopic analyses, chemical degradation and ECD calculation. A new oleanane-type triterpenoid saponin (2)and 15 known co-metabolites were also obtained and structurally characterized. Our biological evaluations showed that compound 2 exhibited moderate inhibition against acetylcholine esterase (AChE)with an IC50 value of 15.8 ± 0.56 μM, and compound 15 displayed potent cytotoxicity selectively against human A549 and H157 lung cancer cells with IC50 values of 6.94 ± 0.24 and 9.06 ± 0.12 μM, respectively.
- Yu, Zhi-Pu,Wang, Yin-Yin,Yu, Shu-Juan,Bao, Jie,Yu, Jin-Hai,Zhang, Hua
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- IRIDOID GLUCOSIDES FROM MELAMPYRUM
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Melampyrum arvense and M. cristatum contain, besides aucubin, 8-epiloganin and melampyroside, a new natural iridoid glucoside: gardoside methyl ester.In addition, M. arvense contains mussaenoside and M. cristatum mussaenosidic acid, another novel iridoid glucoside. - Key Word Index: Melampyrum arvense; M. cristatum; Scrophulariaceae; iridoid glucosides; gardoside methyl ester; mussaenosidic acid; aucubin; 8-epiloganin; mussaenoside; melampyroside.
- Damtoft, Soeren,Hansen, Soeren Brun,Jacobsen, Birthe,Jensen, Soeren Rosendal,Nielsen, Bent Juhl
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- Synthesis of LoganVir, a new carbocyclic nucleoside analogue
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Starting from a natural cyclopentanoid monoterpene belonging to the class of iridoid glucosides called loganin, we performed the synthesis of a new carbocyclic nucleoside, allowing the preparation of a new lead compound, with a potential HIV antiviral activity as an reverse transcriptase competitive inhibitor that we named LoganVir. The stereocontrol of the coupling reaction was completed utilizing the procedure described by Mitsunobu with a purinic base.
- Ornano, Luigi,Bianco, Armandodoriano
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- Ligustrinoside, a new bisiridoid glucoside from Strychnos ligustrina
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A new bisiridoid glucoside, ligustrinoside (1), along with three known iridoids, loganin, loganetin and loganic acid was isolated from the wood of Strychnos ligustrina Bl. (Loganiaceae), collected in Indonesia. The structure of ligustrinoside (1) has been determined as an ester dimmer of loganin and loganic acid between C-7 and C-11.
- Mitsunaga,Koike,Fukuda,Ishii,Ohmoto
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- Iridoids from Symphoricarpos albus
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Twelve compounds including secologanin, loganin, the aglycon of loganin, and a new iridoid called glucologanin were isolated from fruit of common snowberry Symphoricarpos albus (L.) Blake. The structure of glucologanin was confirmed using PMR and mass spe
- Makarevich,Kovalenko,Gusarova,Gubin
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experimental part
p. 40 - 44
(2009/06/20)
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- Structure elucidation of six acylated iridoid glucosides from Jasminum hemsleyi
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Six new iridoid glucosides, jashemslosides A-D (2-5), 6'-O-trans-p-coumaroylloganin (6) and 6'-O-cis-p-coumaroylloganin (7), were isolated from the leaves of Jasminum hemsleyi, together with the known glycosides, loganin, 7-dehydrologanin, jasminoside, 10-hydroxyoleoside dimethyl ester and lariciresinol-4-O-β-D-glucoside. The structures of the new glucosides 2-7, which contain a menthiafolic acid unit or p-coumaroyl group in addition to the loganin moiety, were elucidated by spectroscopic and chemical studies. Chirospecific HPLC analysis of the monoterpenic acid derivatives prepared from 2 and 3 revealed that each of the new compounds was a mixture of two inseparable diastereoisomers.
- Tanahashi,Shimada,Nagakura,Inoue,Ono,Fujita,Chen
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p. 729 - 733
(2007/10/02)
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- Iridoids, XXII. - Glucosidation of Hemiacetals. - Highly Stereoselective Synthesis of Iridoid Glucosides
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Reaction of the racemic iridoid aglucone acetates 9d-12d with the trimethylsilyl β-glucopyranoside 4a in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate (7) in acetonitrile or liquid sulfur dioxide at -30 deg C and -50 deg C, respectively, followed by solvolysis gives in excellent yields nearly exclusively the β-glucosides 9g and 11g.Glucosidation of the enantiomerically pure acetates 9d/10d affords the β-glucoside 9g.In a similar way, the biosynthetical key intermediate loganin (1) is obtained from 16a in 60 percent yield.
- Tietze, Lutz F.,Fischer, Roland,Remberg, Gerd
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p. 971 - 976
(2007/10/02)
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- Investigations of the Biosynthesis of Indole Alkaloids. Feeding Experiments with Synthetic Radioactively Labelled Monoterpene Aldehydes
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Oxidation of citral (8a/8b) with selenium oxide using different reaction conditions gave the hydroxy aldehydes 4a/4b and the dialdehydes 5a/b.Reduction of 5a/b with potassium borohydride in the presence of LiCl led to the hydroxy aldehyes 4c/d.Feeding experiments with the corresponding tritiated compounds 4a - d and 5a/b to Catharanthus roseus G.Don indicate that 4a/b, 4c/d, and 5a/b are biogenetic precursors of secologanin (3) and the indole alkaloids of the Corynanthe, Aspidosperma, and Iboga type.
- Battersby, Alan R.,Thompson, Mervyn,Gluesenkamp, Karl-Heinz,Tietze, Lutz-F.
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p. 3430 - 3438
(2007/10/02)
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