The Absolute Configuration at C(7) of Voacangine Hydroxyindolenine

Madinaveitia, Alberto; Fuente, Gabriel de la; González, Antonio G.

doi:10.1002/(sici)1522-2675(19980909)81:9<1645::aid-hlca1645>3.0.co;2-p

Cited by 13 publications

(22 citation statements)

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“…As in the case of known compound 19,20-dihydrotabernamine ( 8 ), the NMR data suggested similar configurations at C-3 (α-substitution), C-16, and C-20 of the vobasinyl unit and at C-14′, C-16′, C-20′, and C-21′ of the iboga unit (Figure ). The α-orientation of 7′-OH was determined based on the biosynthetic pathway, since the C-7 configuration of 7-hydroxyindolenine of ibogaine has been previously established . Thus, the structure of 3 was established to be 10′-demethoxy-19,20-dihydrovobatensine D as shown (Figure ).…”

Section: Results and Discussionmentioning

confidence: 99%

“…The α-orientation of 7′-OH was determined based on the biosynthetic pathway, since the C-7 configuration of 7-hydroxyindolenine of ibogaine has been previously established. 28 Thus, the structure of 3 was established to be 10′-demethoxy-19,20-dihydrovobatensine D as shown (Figure 1). Compound 4 was isolated as a light yellowish solid with the molecular formula C 45 H 54 N 4 O 5 , determined by the HR-ESIMS ion ([M + H] + at m/z = 731.4173).…”

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confidence: 99%

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Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata

et al. 2018

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Four new monoterpenoid bisindole alkaloids, flabellipparicine (1), 19,20-dihydrovobparicine (2), 10'-demethoxy-19,20-dihydrovobatensine D (3), and 3'-(2-oxopropyl)ervahanine A (4), and 10 known monoterpenoid indole alkaloids were isolated from the stems of Tabernaemontana divaricata. All structures were elucidated based on spectroscopic methods, and the absolute configuration of 1 was established using conformational analysis and TDDFT-ECD calculation of selected stereoisomers. Compound 1 represents the first flabelliformide-apparicine-type bisindole alkaloid, in which the flabelliformide-like unit connects to the apparicine-like unit with a C-3-C-22' bond and an N-1-C-16' bond to form an uncommon five-membered ring between the two monomers. All alkaloids were evaluated for their cytotoxicity against two human cancer cell lines, MCF-7 and A-549. Compounds 2, 4, and 14 exhibited cytotoxicity against MCF-7 and A-549 with IC values in the range of 2 nM to 8 μM.

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Section: Results and Discussionmentioning

confidence: 99%

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confidence: 99%

Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata

et al. 2018

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“…Six Iboga-type compounds: ervataine ( 304 ) [ 151 ], ibogaine ( 305 ) [ 154 ], coronaridine ( 306 ) [ 49 ], heyneanine ( 307 ) [ 155 ], voacangine hydroxyindolenine ( 308 ) [ 156 , 157 ] and coronaridine hydroxyindolenine ( 309 ) [ 158 , 159 ] ( Figure 25 ), were obtained from the Chinese Ervatamia yunnanensis [ 151 ].…”

Section: Ervatamiamentioning

confidence: 99%

“…Seven new iboga-type derivatives: ervaoffines A–D ( 319 – 322 ), (7 S )-3-oxoibogaine hydroxyindolenine ( 323 ), ibogaine-5,6-dione ( 324 ), and 19- epi -5-oxovoacristine ( 325 ), along with ten compounds, 305 , 307 , 311 , iboluteine ( 326 ) [ 168 ], (7 S )- ibogaine hydroxyindolenine ( 327 ) [ 157 ], ibogaline ( 328 ) [ 169 ], conopharyngine ( 329 ) [ 170 ], voacristine ( 330 ) [ 171 ], 19 S -hydroxyibogamine ( 331 ) [ 172 ], and ibogaine N 4 -oxide ( 332 ) [ 173 , 174 ] ( Figure 26 ), were isolated from the twigs and leaves of E. officinalis .…”

Section: Ervatamiamentioning

confidence: 99%

Chemical Diversity and Bioactivities of Monoterpene Indole Alkaloids (MIAs) from Six Apocynaceae Genera

et al. 2021

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By the end of the twentieth century, the interest in natural compounds as probable sources of drugs has declined and was replaced by other strategies such as molecular target-based drug discovery. However, in the recent times, natural compounds regained their position as extremely important source drug leads. Indole-containing compounds are under clinical use which includes vinblastine and vincristine (anticancer), atevirdine (anti-HIV), yohimbine (erectile dysfunction), reserpine (antihypertension), ajmalicine (vascular disorders), ajmaline (anti-arrhythmic), vincamine (vasodilator), etc. Monoterpene Indole Alkaloids (MIAs) deserve the curiosity and attention of researchers due to their chemical diversity and biological activities. These compounds were considered as an impending source of drug-lead. In this review 444 compounds, were identified from six genera belonging to the family Apocynaceae, will be discussed. These genera (Alstonia, Rauvolfia, Kopsia, Ervatamia, and Tabernaemontana, and Rhazya) consist of 400 members and represent 20% of Apocynaceae species. Only 30 (7.5%) species were investigated, whereas the rest are promising to be investigated. Eleven bioactivities, including antibacterial, antifungal, anti-inflammatory and immunosuppressant activities, were reported. Whereas cytotoxic effect represents 47% of the reported activities. Convincingly, the genera selected in this review are a wealthy source for future anticancer drug lead.

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“…The spectroscopic data of all compounds were in good agreement with the literature data [4][5][6][7][8][9][10][11][12][13][14]. All these structures are isolated from E. flabellformia for the first time.…”

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Indole alkaloids from Ervatamia flabellformia

Liang

Chen

et al. 2008

Chem Nat Compd

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Ervatamia flabellformia Tsiang (Apocynaceae) [1] is a common plant cultivated in Yunnan and Guanxi provinces of China, and its chemical constituents have not been reported yet. As a part of our continuous research on anti-addictive constituents from the genus Ervatamia [2, 3], thirteen indole alkaloids were isolated from the stems of Ervatamia flabellformia.The stems of E. flabellformia were collected in October 2002 in Xishuangbanna, Yunnan province and identified by senior engineer Wang Hong, Xishuangbanna Tropical Botanic Garden of the Chinese Academy of Science. A voucher specimen (No. 200210-1) has been deposited in the Herbarium of the School of Pharmacy, Second Military Medical University, Shanghai.The air-dried and powdered stems (12 kg) were extracted with 95% EtOH (50 L) under reflux. After removal of EtOH by evaporation under reduced pressure, the residues were extracted with 2% HCl. The aqueous layer was basified with NH 4 OH and partitioned with CHCl 3 . The CHCl 3 layer was dried over Na 2 SO 4 and evaporated under reduced pressure to give 45 g of crude alkaloid fraction, which was submitted to repeated column chromatography over silica gel and Sephadex LH20 (MeOH) to yield 13 indole alkaloids.All compounds were identified by spectroscopic methods, including NMR and mass spectrometry (NMR spectra were acquired on a Bruker DRX-500 spectrometer with TMS as internal standard, operating at 500 MHz for 1 H and 13 C; ESIMS data were obtained on a Q-Tof micro mass spectrometer; silica gel H (10-40 μm) for column chromatography and HPTLC plates precoated with silica gel HF 254 (5-7 μm) were supplied by Zhifu Huangwu Silica Gel D & R Plant, Yantai, China; Sephadex LH-20 and ODS were purchased from Pharmacia and Merck, respectively. The spectroscopic data of all compounds were in good agreement with the literature data [4][5][6][7][8][9][10][11][12][13][14]. All these structures are isolated from E. flabellformia for the first time.Dihydroperivine (1), colorless cubic crystal (methyl acetate), C 20 H 24 N 2 O 3 . 1 H and 13 C NMR data are shown in Tables 1 and 3 [4].3-(R)-Hydroxyvoacangine (2), white powder, C 22 H 28 N 2 O 4 . EI-MS m/z (%): 368

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The Absolute Configuration at C(7) of Voacangine Hydroxyindolenine

Cited by 13 publications

References 3 publications

Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata

Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata

Chemical Diversity and Bioactivities of Monoterpene Indole Alkaloids (MIAs) from Six Apocynaceae Genera

Indole alkaloids from Ervatamia flabellformia

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