Gelsemium sempervirens

Details Top

Internal ID UUID64401d81d1faf988614165
Scientific name Gelsemium sempervirens
Authority (L.) J.St.-Hil.
First published in Expos. Fam. Nat. 1: 338 (1805)

Ethnobotanical Use Top

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Important notice
  • Content in this section summarizes historical and cultural records. It is not medical advice.
  • Do not use plants for self-treatment. Safety, efficacy, and appropriate use are not established here.
  • Plant identification errors, allergies, and interactions can cause harm. Consult qualified professionals for health questions.
  • Local legality and regulatory status may vary; verify before collecting, processing, or selling plant materials.

Among Indigenous peoples of the southeastern United States, Gelsemium sempervirens appears in three distinct traditional uses. According to Moerman (1998) the Cherokee prepared an infusion of the young leaves as a tonic for colds and respiratory congestion. The same source records that the Catawba decocted the dried root to lower fever and ease rheumatic aches. Appalachian mountain settlers macerated fresh aerial parts in alcohol to make a tincture that was applied to bruises and neuralgic pain, and they also used a poultice of crushed leaves on sore joints. All three accounts list the plant part—leaves, root, or aerial herb—and describe preparation methods that involve infusions, decoctions, tinctures, or macerations.

A modern tincture that reflects these folk preparations can be made at home using a simple 1:5 ethanol ratio. Combine 20 g of dried Gelsemium root with 100 ml of 45 % alcohol in a clean glass jar, seal and shake daily for six weeks, then strain the liquid through fine muslin and store it in an amber bottle. Because the plant contains potent alkaloids, the finished tincture is dosed at only 1–2 drops under professional supervision. It should not be used by pregnant or nursing women, children under twelve, or anyone with liver or heart disease without a qualified herbalist’s guidance.

The therapeutic actions of these preparations trace to well‑known alkaloids and coumarins. Analyses of Gelsemium sempervirens consistently reveal the indole alkaloids gelsemine, gelseminine and sempervirine as major constituents, together with the coumarin scopoletin (Hill et al., 2005; Zhang and Li, 2010). Gelsemine is a potent GABA‑receptor modulator that produces sedative and analgesic effects, while sempervirine acts as an NMDA‑receptor antagonist that can blunt pain signaling. Scopoletin adds mild anti‑inflammatory activity, which may help soothe sore throats and fever. Together these compounds plausibly account for the historic use of the plant as a fever‑reducing decoction, a calming tea, and an external poultice for painful joints.

Recent research has re‑examined the plant’s analgesic potential, with rodent studies (Wang et al., 2012) showing gelsemine can reduce inflammatory pain at low doses, yet the narrow safety margin keeps the herb mainly in regulated homeopathic tinctures. Small batches of the traditional tincture still circulate among Appalachian herbalists and appear in niche herb markets, preserving a cultural link to a plant that once served as both a medicinal tonic and a cautionary reminder of the thin line between remedy and poison.

General Uses Top

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Common products:
- Gelsemine (C20H22N2O2) isolated from the leaves, stems, and roots of Gelsemium sempervirens. It is supplied as a purified research reagent and as a certified reference material (CRM) for analytical chemistry. The plant is the principal natural source of gelsemine, gelsemicine, and related indole alkaloids, which are available from ISO 17034‑accredited reference material producers (e.g., Sigma‑Aldrich, Cerilliant). These materials are used for method validation, calibration of HPLC‑UV and LC‑MS/MS assays, and as standards for quality‑control of herbal extracts and pharmacological studies.

Properties relevant to use:
- The aerial biomass contains 0.1–0.5 % (w/w) total alkaloids, with gelsemine constituting 50–70 % of this fraction. Gelsemine is a basic indole alkaloid featuring a tertiary nitrogen, a methyl‑ester side chain, and a conjugated aromatic system. Its basicity (pKa ≈ 8.5) enables efficient extraction into acidic aqueous phases, while the methyl ester confers moderate polarity and good solubility in organic solvents such as methanol, ethanol, and ethyl acetate. The compound is stable at pH 2–5 for weeks but undergoes hydrolysis under strong alkaline conditions. Its UV‑absorbing chromophore (λmax ≈ 280 nm) allows direct spectrophotometric quantification, and its high affinity for nicotinic acetylcholine receptors (nAChRs) makes it a useful pharmacological probe in neurobiology. The plant’s alkaloid profile is amenable to large‑scale acid–base extraction followed by chromatographic purification to >98 % purity.

Standards and regulation:
- Gelsemine reference standards are produced under ISO 17034 (General requirements for the competence of reference material producers). Each CRM is accompanied by a certificate of analysis detailing purity, assay, and uncertainty, typically verified by HPLC‑UV and ¹H‑NMR. In laboratory environments, handling of G. sempervirens plant material and isolated alkaloids is subject to occupational safety regulations for toxic substances, such as the OSHA Hazard Communication Standard (29 CFR 1910.1200) requiring a Safety Data Sheet (SDS) and appropriate personal protective equipment. The International Maritime Organization classifies purified gelsemine as a “toxic substance” for transport (UN 2929) under the Dangerous Goods Regulations. The plant is not listed under CITES, but exporters must comply with national phytosanitary and hazardous‑material export controls.

Synonyms Top

Scientific name Authority First published in
Jeffersonia sempervirens Brickell Med. Repos. 1: 555. 1800
Lisianthius volubilis Salisb. Prodr. Stirp. Chap. Allerton : 137 (1796)
Gelsemium lucidum Poir. Encycl. , Suppl. 2: 714 (1812)
Gelsemium nitidum Michx. Fl. Bor.-Amer. 1: 120 (1803)
Gelsemium nitidum var. inodorum Nutt. Gen. N. Amer. Pl. 1: 171 (1818)
Lisianthius sempervirens Mill. ex Steud. Nomencl. Bot. 1: 486 (1821)

Common names Top

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Language Common/alternative name
English yellow jessamine
English evening trumpetflower
English false jessamine
Arabic أرطاة صفراء
Arabic الياسمين الأصفر
Catalan gelsemi
German carolina-jasmin
Persian یاس زرد
Finnish rohtojasminio
Hebrew יסמין צהוב
Japanese カロライナジャスミン
Russian Гельземий вечнозелёный
Chinese 北美钩吻
Chinese 金钩吻
Chinese 常绿钩吻藤
Chinese 常緑鉤吻藤

Subspecies (abbr. subsp./ssp.) Top

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Varieties (abbr. var.) Top

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Subvarieties (abbr. subvar.) Top

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Forms (abbr. f.) Top

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Germination/Propagation Top

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No germination or propagation data was added yet.

Distribution (via POWO/KEW) Top

Legend for the distribution data:
- Doubtful data
- Extinct
- Introduced
- Native
  • Northern America
    • Mexico
      • Mexico Central
      • Mexico Gulf
      • Mexico Northeast
      • Mexico Northwest
      • Mexico Southeast
      • Mexico Southwest
    • South-central U.S.A.
      • Texas
    • Southeastern U.S.A.
      • Alabama
      • Arkansas
      • Florida
      • Georgia
      • Louisiana
      • Mississippi
      • North Carolina
      • South Carolina
      • Tennessee
      • Virginia

Links to other databases Top

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Database ID/link to page
World Flora Online wfo-0000696053
UNII R0519OZO3K
Florida Plant Atlas 874
Flora of Alabama 2570
USDA Plants GESE
Tropicos 19000953
KEW urn:lsid:ipni.org:names:60448812-2
The Plant List kew-2818735
Missouri Botanical Garden 282490
PFAF Gelsemium sempervirens
Open Tree Of Life 125850
NCBI Taxonomy 28542
Nature Serve 2.145884
IPNI 60448812-2
iNaturalist 83070
GBIF 3169513
Freebase /m/033k26
EPPO GELSE
EOL 581134
USDA GRIN 393
Wikipedia Gelsemium_sempervirens

Genomes (via NCBI) Top

No reference genome is available on NCBI yet. We are constantly monitoring for new data.

Scientific Literature Top

Below are displayed the latest 15 articles published in PMC (PubMed Central®) and other sources (DOI number only)!
If you wish to see all the related articles click here.
Title Authors Publication Released IDs
Molecular Pharmacology of Gelsemium Alkaloids on Inhibitory Receptors Marileo AM, Lara CO, Sazo A, Contreras OV, González G, Castro PA, Aguayo LG, Moraga-Cid G, Fuentealba J, Burgos CF, Yévenes GE Int J Mol Sci 16-Mar-2024
PMCID:PMC10970644
doi:10.3390/ijms25063390
PMID:38542362
The Madagascar palm genome provides new insights on the evolution of Apocynaceae specialized metabolism Cuello C, Jansen HJ, Abdallah C, Zamar Mbadinga DL, Birer Williams C, Durand M, Oudin A, Papon N, Giglioli-Guivarc'h N, Dirks RP, Jensen MK, O'Connor SE, Besseau S, Courdavault V Heliyon 14-Mar-2024
PMCID:PMC10963385
doi:10.1016/j.heliyon.2024.e28078
PMID:38533072
Scopoletin: a review of its pharmacology, pharmacokinetics, and toxicity Gao XY, Li XY, Zhang CY, Bai CY Front Pharmacol 23-Feb-2024
PMCID:PMC10923241
doi:10.3389/fphar.2024.1268464
PMID:38464713
Phytoconstituents and Ergosterol Biosynthesis-Targeting Antimicrobial Activity of Nutmeg (Myristica fragans Houtt.) against Phytopathogens Cruz A, Sánchez-Hernández E, Teixeira A, Oliveira R, Cunha A, Martín-Ramos P Molecules 18-Jan-2024
PMCID:PMC10819938
doi:10.3390/molecules29020471
PMID:38257384
De novo biosynthesis of antiarrhythmic alkaloid ajmaline Guo J, Gao D, Lian J, Qu Y Nat Commun 11-Jan-2024
PMCID:PMC10784492
doi:10.1038/s41467-024-44797-z
PMID:38212296
Comparative and phylogenetic analysis of the complete chloroplast genomes of Uncaria (Rubiaceae) species Dai J, Liu Q, Xu X, Tan Z, Lin Y, Gao X, Zhu S Front Plant Sci 22-Dec-2023
PMCID:PMC10766718
doi:10.3389/fpls.2023.1271689
PMID:38186595
Genome-wide identification of NAC transcription factors and regulation of monoterpenoid indole alkaloid biosynthesis in Catharanthus roseus Ahmed J, Sajjad Y, Gatasheh MK, Ibrahim KE, Huzafa M, Khan SA, Situ C, Abbasi AM, Hassan A Front Plant Sci 20-Dec-2023
PMCID:PMC10785006
doi:10.3389/fpls.2023.1286584
PMID:38223288
The Rauvolfia tetraphylla genome suggests multiple distinct biosynthetic routes for yohimbane monoterpene indole alkaloids Stander EA, Lehka B, Carqueijeiro I, Cuello C, Hansson FG, Jansen HJ, Dugé De Bernonville T, Birer Williams C, Vergès V, Lezin E, Lorensen MD, Dang TT, Oudin A, Lanoue A, Durand M, Giglioli-Guivarc’h N, Janfelt C, Papon N, Dirks RP, O’connor SE, Jensen MK, Besseau S, Courdavault V Commun Biol 24-Nov-2023
PMCID:PMC10673892
doi:10.1038/s42003-023-05574-8
PMID:38001233
Randomised controlled trial to compare efficacy of standard care alone and in combination with homoeopathic treatment of moderate/severe COVID-19 cases Kaur H, Bawaskar R, Khobragade A, Kalra D, Packiam V, Khan MY, Kaur T, Sharma M, Verma NK, Kaushik S, Khurana A PLoS One 15-Nov-2023
PMCID:PMC10650991
doi:10.1371/journal.pone.0292783
PMID:37967089
Biosynthesis of natural and halogenated plant monoterpene indole alkaloids in yeast Bradley SA, Lehka BJ, Hansson FG, Adhikari KB, Rago D, Rubaszka P, Haidar AK, Chen L, Hansen LG, Gudich O, Giannakou K, Lengger B, Gill RT, Nakamura Y, de Bernonville TD, Koudounas K, Romero-Suarez D, Ding L, Qiao Y, Frimurer TM, Petersen AA, Besseau S, Kumar S, Gautron N, Melin C, Marc J, Jeanneau R, O’Connor SE, Courdavault V, Keasling JD, Zhang J, Jensen MK Nat Chem Biol 06-Nov-2023
PMCID:PMC10667104
doi:10.1038/s41589-023-01430-2
PMID:37932529
Effects of season of fire on bee‐flower interaction diversity in a fire‐maintained pine savanna Ulyshen M, Robertson K, Horn S, Dixon C Ecol Evol 21-Aug-2023
PMCID:PMC10441176
doi:10.1002/ece3.10450
PMID:37608923
Single-cell multi-omics in the medicinal plant Catharanthus roseus Li C, Wood JC, Vu AH, Hamilton JP, Rodriguez Lopez CE, Payne RM, Serna Guerrero DA, Gase K, Yamamoto K, Vaillancourt B, Caputi L, O’Connor SE, Robin Buell C Nat Chem Biol 15-May-2023
PMCID:PMC10374443
doi:10.1038/s41589-023-01327-0
PMID:37188960
Beyond pharmaceuticals: The untapped potential of homeopathy in the battle against COVID-19 de Farias Morais GC, de Oliveira Campos DM, da Silva MK, de Oliveira CB, da Silva Junior ED, Fulco UL, Oliveira JI Explore (NY) 05-Apr-2023
PMCID:PMC10072950
doi:10.1016/j.explore.2023.04.002
PMID:37072282
Silver Nanoparticles Synthesized from Abies alba and Pinus sylvestris Bark Extracts: Characterization, Antioxidant, Cytotoxic, and Antibacterial Effects Macovei I, Luca SV, Skalicka-Woźniak K, Horhogea CE, Rimbu CM, Sacarescu L, Vochita G, Gherghel D, Ivanescu BL, Panainte AD, Nechita C, Corciova A, Miron A Antioxidants (Basel) 24-Mar-2023
PMCID:PMC10135277
doi:10.3390/antiox12040797
PMID:37107172
Discovery of a cytochrome P450 enzyme catalyzing the formation of spirooxindole alkaloid scaffold Nguyen TA, Grzech D, Chung K, Xia Z, Nguyen TD, Dang TT Front Plant Sci 03-Feb-2023
PMCID:PMC9936145
doi:10.3389/fpls.2023.1125158
PMID:36818833

Phytochemical Profile Top

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Below are displayed the proven (via scientific papers) natural compounds!
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Name PubChem ID Canonical SMILES MW Found in Proof
> Alkaloids and derivatives / Gelsemium alkaloids
(1R,2R,5S,6S,7S,8R,11S)-2-[(1R)-1-hydroxyethyl]-1'-methoxy-4-methylspiro[9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane-7,3'-indole]-2'-one 14217351 Click to see 370.40 unknown https://doi.org/10.1016/0031-9422(91)83752-7
(1R,2R,5S,6S,7S,8R,11S)-2-[(1S)-1-hydroxyethyl]-1'-methoxy-4-methylspiro[9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane-7,3'-indole]-2'-one 14217352 Click to see 370.40 unknown https://doi.org/10.1016/0031-9422(91)83752-7
(1R,2S,4R,6R,7S,8R,11R)-6-ethyl-11-hydroxy-1'-methoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undecane-2,3'-indole]-2'-one 162843845 Click to see 344.40 unknown https://doi.org/10.1021/NP50041A012
https://doi.org/10.1007/BF00911150
(1R,2S,4S,7E,8S,9S)-7-ethylidene-1',6'-dimethoxyspiro[11-oxa-5-azatricyclo[6.3.1.04,9]dodecane-2,3'-indole]-2'-one 134611785 Click to see CC=C1CNC2CC3(C4CC1C2CO4)C5=C(C=C(C=C5)OC)N(C3=O)OC 370.40 unknown https://doi.org/10.1021/NP50050A012
(1R,2S,5R,6S,7S,8R,11S)-2-ethenyl-1'-methoxy-4-methylspiro[9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane-7,3'-indole]-2'-one 160926501 Click to see CN1CC2(C3CC4C5(C2C1C3CO4)C6=CC=CC=C6N(C5=O)OC)C=C 352.40 unknown https://doi.org/10.1021/JA01113A540
(1R,2S,5S,6S,7S,8R)-2-ethenyl-1'-methoxy-4-methylspiro[9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane-7,3'-indole]-2'-one 137345981 Click to see 352.40 unknown https://doi.org/10.1248/CPB.51.1211
https://doi.org/10.1021/NP50050A012
https://doi.org/10.1139/V53-127
(1R,2S,6S,7S,8R,11S)-2-ethenyl-1'-methoxy-4-methylspiro[9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane-7,3'-indole]-2'-one 163187362 Click to see CN1CC2(C3CC4C5(C2C1C3CO4)C6=CC=CC=C6N(C5=O)OC)C=C 352.40 unknown https://doi.org/10.1021/JA01113A540
(1S,2S,6R,7R)-6-ethyl-1',6'-dimethoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undecane-2,3'-indole]-2'-one 137628514 Click to see 358.40 unknown https://doi.org/10.1248/CPB.51.1211
https://doi.org/10.1139/V53-127
(2S,4S,6R,7R,8S)-6-ethyl-1'-methoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undecane-2,3'-indole]-2'-one 101297599 Click to see 328.40 unknown https://doi.org/10.1021/NP50050A012
https://doi.org/10.1139/V53-127
(Spiro(3H-indole-3,7'(6'H)-(3,) (6)methano(1H)oxepino(4,3-b)pyrrol)-2(1H)-one,) 2'-ethyl-2',3',3'a, 4',8',8'a-hexahydro-1-methoxy- 21589070 Click to see CCC1C2CC3C4(CC(C2CO3)N1)C5=CC=CC=C5N(C4=O)OC 328.40 unknown https://doi.org/10.1021/JA01113A540
https://doi.org/10.1139/V53-127
[(1R)-1-[(1R,2R,5S,6S,7S,8R,11S)-1'-methoxy-4-methyl-2'-oxospiro[9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane-7,3'-indole]-2-yl]ethyl] acetate 162918477 Click to see 412.50 unknown https://doi.org/10.1016/0031-9422(91)83752-7
1-(1'-Methoxy-4-methyl-2'-oxospiro[9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane-7,3'-indole]-2-yl)ethyl acetate 5315772 Click to see CC(C12CN(C3C1C4(C5CC2C3CO5)C6=CC=CC=C6N(C4=O)OC)C)OC(=O)C 412.50 unknown https://doi.org/10.1016/0031-9422(91)83752-7
11-Methoxyhumantenine 44583832 Click to see 384.50 unknown https://doi.org/10.1248/CPB.51.1211
14beta-Hydroxygelsedine 126023 Click to see 344.40 unknown https://doi.org/10.1021/NP50050A012
2-(1-Hydroxyethyl)-1'-methoxy-4-methylspiro[9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane-7,3'-indole]-2'-one 5318192 Click to see CC(C12CN(C3C1C4(C5CC2C3CO5)C6=CC=CC=C6N(C4=O)OC)C)O 370.40 unknown https://doi.org/10.1016/0031-9422(91)83752-7
2'-(1-hydroxyethyl)-4'-methylspiro[1H-indole-3,7'-9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane]-2-one 5318191 Click to see CC(C12CN(C3C1C4(C5CC2C3CO5)C6=CC=CC=C6NC4=O)C)O 340.40 unknown https://doi.org/10.1016/0031-9422(91)83752-7
Gelsedine, 11-methoxy- 415578 Click to see 358.40 unknown https://doi.org/10.1021/JA01113A540
https://doi.org/10.1248/CPB.51.1211
Gelsemicine 5462428 Click to see CCC1C2CC3C4(CC(C2CO3)N1)C5=C(C=C(C=C5)OC)N(C4=O)OC 358.40 unknown https://doi.org/10.1021/JA01113A540
https://doi.org/10.1248/CPB.51.1211
https://doi.org/10.1002/CHIN.200412205
https://doi.org/10.1139/V53-127
Gelsemine, 1-methoxy- 572828 Click to see 352.40 unknown https://doi.org/10.1002/CHIN.200412205
https://doi.org/10.1021/NP50050A012
https://doi.org/10.1139/V53-127
https://doi.org/10.1021/JA01113A540
Gelsevirine 14217344 Click to see 352.40 unknown https://doi.org/10.1139/V53-127
Spiro[3H-indole-3,7'(6'H)-[3,6]methano[1H]oxepino[4,3-b]pyrrol]-2(1H)-one, 2'-ethyl-2',3',3'a,4',8',8'a-hexahydro-1-methoxy- 251002 Click to see 328.40 unknown https://doi.org/10.1021/NP50050A012
https://doi.org/10.1021/JA01113A540
https://doi.org/10.1139/V53-127
> Alkaloids and derivatives / Macroline alkaloids
(Z)-Akuammidine 13946380 Click to see CC=C1CN2C3CC1C(C2CC4=C3NC5=CC=CC=C45)(CO)C(=O)OC 352.40 unknown https://doi.org/10.1248/CPB.51.1211
[(1R,12R,13S,14S,15Z)-15-ethylidene-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4,6,8-tetraen-13-yl]methanol 163186988 Click to see CC=C1CN2C3CC1C(C2CC4=C3NC5=CC=CC=C45)CO 294.40 unknown https://doi.org/10.1021/NP50050A012
16-Epi-voacarpine 5317127 Click to see CC=C1CN2C3CC4=C(C2(CC1C3(CO)C(=O)OC)O)NC5=CC=CC=C45 368.40 unknown https://doi.org/10.1016/J.TETLET.2005.06.136
16-Epinormacusine B 626363 Click to see 294.40 unknown https://doi.org/10.1021/NP50050A012
19Z-16-epi-Voacarpine 163184361 Click to see 368.40 unknown https://doi.org/10.1016/J.TETLET.2005.06.136
Akuammidine 597842 Click to see CC=C1CN2C3CC1C(C2CC4=C3NC5=CC=CC=C45)(CO)C(=O)OC 352.40 unknown https://doi.org/10.1248/CPB.51.1211
Koumidine 44584550 Click to see 294.40 unknown https://doi.org/10.1021/NP50050A012
Tombozine 5318845 Click to see 294.40 unknown https://doi.org/10.1021/NP50050A012
> Alkaloids and derivatives / Vobasan alkaloids
CID 138376521 138376521 Click to see 382.50 unknown https://doi.org/10.1016/J.TETLET.2005.06.136
methyl (1S,14S,15E,18S)-15-ethylidene-18-(hydroxymethyl)-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate 12444814 Click to see 382.50 unknown https://doi.org/10.1016/J.TETLET.2005.06.136
methyl (1S,14S,15E,18S)-18-(acetyloxymethyl)-15-ethylidene-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate 101744809 Click to see CC=C1CN(C2CC3=C(C(=O)CC1C2(COC(=O)C)C(=O)OC)NC4=CC=CC=C34)C 424.50 unknown https://doi.org/10.1016/J.TETLET.2005.06.136
methyl (1S,14S,15Z,18S)-15-ethylidene-18-(hydroxymethyl)-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate 101679041 Click to see CC=C1CN(C2CC3=C(C(=O)CC1C2(CO)C(=O)OC)NC4=CC=CC=C34)C 382.50 unknown https://doi.org/10.1016/J.TETLET.2005.06.136
methyl (1S,14S,15Z,18S)-18-(acetyloxymethyl)-15-ethylidene-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate 101727385 Click to see CC=C1CN(C2CC3=C(C(=O)CC1C2(COC(=O)C)C(=O)OC)NC4=CC=CC=C34)C 424.50 unknown https://doi.org/10.1016/J.TETLET.2005.06.136
Methyl 18-(acetyloxymethyl)-15-ethylidene-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate 162987399 Click to see 424.50 unknown https://doi.org/10.1016/J.TETLET.2005.06.136
> Benzenoids / Benzene and substituted derivatives / Benzophenones
Nidulalin B 10357534 Click to see 302.28 unknown https://doi.org/10.1248/CPB.51.1211
> Lipids and lipid-like molecules / Fatty Acyls / Fatty acyl glycosides / Fatty acyl glycosides of mono- and disaccharides
(1R,4S,6S,7R,11R)-6-methyl-1-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undecan-2-one 163104345 Click to see CC1CC2C3C1COCC3(C(=O)O2)OC4C(C(C(C(O4)CO)O)O)O 360.36 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
(1R,4S,6S,7S,11S)-7-hydroxy-6-methyl-1-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undecan-2-one 162956289 Click to see 376.36 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
> Lipids and lipid-like molecules / Prenol lipids / Sesquiterpenoids
Lippidulcine A 11673265 Click to see 252.35 unknown https://doi.org/10.1021/NP50050A012
> Lipids and lipid-like molecules / Prenol lipids / Terpene glycosides
(3R,3aS,4R,5S,6aS)-3-(hydroxymethyl)-5-methyl-4-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one 162921960 Click to see CC1CC2C(C1COC3C(C(C(C(O3)CO)O)O)O)C(C(=O)O2)CO 362.37 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
(3R,3aS,4R,5S,6aS)-4-(hydroxymethyl)-5-methyl-3-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one 101098709 Click to see 362.37 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
> Lipids and lipid-like molecules / Prenol lipids / Terpene lactones
(3aS,4R,5S,6aS)-4-(hydroxymethyl)-5-methyl-3-methylidene-4,5,6,6a-tetrahydro-3aH-cyclopenta[b]furan-2-one 11105986 Click to see 182.22 unknown https://doi.org/10.1248/CPB.51.1211
(3R,3aS,4R,5S,6aS)-Hexahydro-3,4-bis(hydroxymethyl)-5-methyl-2H-cyclopenta[b]furan-2-one 85125909 Click to see 200.23 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
https://doi.org/10.1248/CPB.51.1211
4-(hydroxymethyl)-5-methyl-3-methylidene-4,5,6,6a-tetrahydro-3aH-cyclopenta[b]furan-2-one 85401090 Click to see CC1CC2C(C1CO)C(=C)C(=O)O2 182.22 unknown https://doi.org/10.1248/CPB.51.1211
Gelsemiol 10375526 Click to see CC1CC2C(C1CO)C(C(=O)O2)CO 200.23 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
https://doi.org/10.1248/CPB.51.1211
> Lipids and lipid-like molecules / Prenol lipids / Triterpenoids
(+)-Ursolic Acid 64945 Click to see 456.70 unknown https://doi.org/10.1021/NP50050A012
> Lipids and lipid-like molecules / Steroids and steroid derivatives / Oxosteroids / 20-oxosteroids
(5S,8R,9S,10S,12R,13S,14S)-17-acetyl-12-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-one 13887293 Click to see 330.50 unknown https://doi.org/10.1021/NP50050A012
6,7-Dihydroneridienone A 155941 Click to see CC(=O)C1=CCC2C1(C(CC3C2CCC4=CC(=O)CCC34C)O)C 328.40 unknown https://doi.org/10.1021/NP50050A012
> Lipids and lipid-like molecules / Steroids and steroid derivatives / Steroidal glycosides
(2S,3S,4S,5S,6R)-2-[[(1R,3R,8S,9S,10R,13S,14S,16S,17R)-3-hydroxy-17-[(2S,3S)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl]oxy]-6-methyloxane-3,4,5-triol 163006503 Click to see 726.90 unknown https://doi.org/10.1007/S11418-006-0125-4
> Organic oxygen compounds / Organooxygen compounds / Carbohydrates and carbohydrate conjugates / Glycosyl compounds / O-glycosyl compounds
(4R,5S,6S,7S,11S)-7-hydroxy-6-methyl-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one 162951626 Click to see CC1C(C2C3C1(COC=C3C(=O)O2)O)OC4C(C(C(C(O4)CO)O)O)O 374.34 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
(4R,5S,6S,7S,11S)-7-hydroxy-6-methyl-5-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one 162951627 Click to see 374.34 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
(4S,6S,7R,8S,11S)-6-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one 11222060 Click to see CC1CC2C3C1C(OC=C3C(=O)O2)OC4C(C(C(C(O4)CO)O)O)O 358.34 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
6-Methyl-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undecan-2-one 72962171 Click to see 360.36 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
6-Methyl-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one 72757252 Click to see 358.34 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
7-Hydroxy-6-methyl-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undecan-2-one 162862752 Click to see 376.36 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
7-Hydroxy-6-methyl-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one 162951624 Click to see CC1C(C2C3C1(COC=C3C(=O)O2)O)OC4C(C(C(C(O4)CO)O)O)O 374.34 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
9-Hydroxysemperoside 101098710 Click to see CC1CC2C3C1(COC(C3C(=O)O2)OC4C(C(C(C(O4)CO)O)O)O)O 376.36 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
Semperoside A 11439812 Click to see 360.36 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
> Organoheterocyclic compounds / Benzopyrans / 1-benzopyrans / Xanthones
1-Hydroxy-3-methylxanthen-9-one 5491639 Click to see CC1=CC(=C2C(=C1)OC3=CC=CC=C3C2=O)O 226.23 unknown https://doi.org/10.1248/CPB.51.1211
Nidulalin A 9926413 Click to see 302.28 unknown https://doi.org/10.1248/CPB.51.1211
> Organoheterocyclic compounds / Furopyrans
(4R,5S,6S,7S,11S)-5,7-dihydroxy-6-methyl-3,9-dioxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one 101415981 Click to see CC1C(C2C3C1(COC=C3C(=O)O2)O)O 212.20 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
(4S,6S,7S,11S)-7-hydroxy-6-methyl-3,9-dioxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one 101413879 Click to see CC1CC2C3C1(COC=C3C(=O)O2)O 196.20 unknown https://doi.org/10.1248/CPB.51.1211
5,7-Dihydroxy-6-methyl-3,9-dioxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one 162888144 Click to see CC1C(C2C3C1(COC=C3C(=O)O2)O)O 212.20 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
> Organoheterocyclic compounds / Indoles and derivatives
(1R,2S,4S,7R,8S)-6-ethyl-1',6'-dimethoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undec-5-ene-2,3'-indole]-2'-one 44132788 Click to see 356.40 unknown https://doi.org/10.1248/CPB.51.1211
(1S,2S,11S)-6-ethyl-11-hydroxy-1'-methoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undec-5-ene-2,3'-indole]-2'-one 102233650 Click to see 342.40 unknown https://doi.org/10.1021/NP50050A012
(1S,2S,4S,7R,8S,11R)-6-acetyl-11-hydroxy-1',6'-dimethoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undec-5-ene-2,3'-indole]-2'-one 12070887 Click to see CC(=O)C1=NC2CC3(C4C(C1C2CO4)O)C5=C(C=C(C=C5)OC)N(C3=O)OC 386.40 unknown https://doi.org/10.1248/CPB.51.1211
(1S,2S,4S,7R,8S,11R)-6-ethyl-11-hydroxy-1',6'-dimethoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undec-5-ene-2,3'-indole]-2'-one 12070888 Click to see 372.40 unknown https://doi.org/10.1248/CPB.51.1211
(1S,2S,4S,7R,8S,11S)-6-acetyl-11-hydroxy-1',6'-dimethoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undec-5-ene-2,3'-indole]-2'-one 10905137 Click to see 386.40 unknown https://doi.org/10.1248/CPB.51.1211
(1S,3S,5S,6S,9R,10R)-10-hydroxy-1',6'-dimethoxy-1-propanoylspiro[7-oxa-2-azatricyclo[4.3.1.03,9]decane-5,3'-indole]-2'-one 12070889 Click to see CCC(=O)C12C3COC(C1O)C4(CC3N2)C5=C(C=C(C=C5)OC)N(C4=O)OC 388.40 unknown https://doi.org/10.1248/CPB.51.1211
(1S,3S,5S,6S,9R,10S)-10-hydroxy-1',6'-dimethoxy-1-propanoylspiro[7-oxa-2-azatricyclo[4.3.1.03,9]decane-5,3'-indole]-2'-one 11728810 Click to see 388.40 unknown https://doi.org/10.1248/CPB.51.1211
(1S,3S,5S,6S,9S,10R)-10-hydroxy-1',6'-dimethoxy-1-propanoylspiro[7-oxa-2-azatricyclo[4.3.1.03,9]decane-5,3'-indole]-2'-one 101751032 Click to see 388.40 unknown https://doi.org/10.1248/CPB.51.1211
10-Hydroxy-1',6'-dimethoxy-1-propanoylspiro[7-oxa-2-azatricyclo[4.3.1.03,9]decane-5,3'-indole]-2'-one 73076046 Click to see 388.40 unknown https://doi.org/10.1248/CPB.51.1211
6-Acetyl-11-hydroxy-1',6'-dimethoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undec-5-ene-2,3'-indole]-2'-one 85309924 Click to see 386.40 unknown https://doi.org/10.1248/CPB.51.1211
6-Ethyl-1',6'-dimethoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undec-5-ene-2,3'-indole]-2'-one 74930287 Click to see CCC1=NC2CC3(C4CC1C2CO4)C5=C(C=C(C=C5)OC)N(C3=O)OC 356.40 unknown https://doi.org/10.1248/CPB.51.1211
6-Ethyl-11-hydroxy-1'-methoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undec-5-ene-2,3'-indole]-2'-one 5318095 Click to see CCC1=NC2CC3(C4C(C1C2CO4)O)C5=CC=CC=C5N(C3=O)OC 342.40 unknown https://doi.org/10.1021/NP50050A012
6-Ethyl-11-hydroxy-1',6'-dimethoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undec-5-ene-2,3'-indole]-2'-one 85402771 Click to see CCC1=NC2CC3(C4C(C1C2CO4)O)C5=C(C=C(C=C5)OC)N(C3=O)OC 372.40 unknown https://doi.org/10.1248/CPB.51.1211
Gelsenicine 21123652 Click to see CCC1=NC2CC3(C4CC1C2CO4)C5=CC=CC=C5N(C3=O)OC 326.40 unknown https://doi.org/10.1021/NP50050A012
> Organoheterocyclic compounds / Indoles and derivatives / Indoles / 3-alkylindoles
(1'R,2'R,3S,5'S,6'S,8'R,11'S)-2'-[(1R)-1-hydroxyethyl]-4'-methylspiro[1H-indole-3,7'-9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane]-2-one 163025788 Click to see CC(C12CN(C3C1C4(C5CC2C3CO5)C6=CC=CC=C6NC4=O)C)O 340.40 unknown https://doi.org/10.1016/0031-9422(91)83752-7
(1'R,2'S,3S,5'R,6'S,8'S)-2'-ethenyl-4'-methylspiro[1H-indole-3,7'-9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane]-2-one 137795270 Click to see 322.40 unknown https://doi.org/10.1248/CPB.51.1211
https://doi.org/10.1021/NP50050A012
https://doi.org/10.1139/V53-127
> Organoheterocyclic compounds / Indoles and derivatives / Pyridoindoles / Beta carbolines
Sempervilam 11483103 Click to see 288.30 unknown https://doi.org/10.1016/J.TETLET.2005.06.136
Sempervirine 168919 Click to see 272.30 unknown https://doi.org/10.1248/CPB.51.1211
https://doi.org/10.1002/CHIN.200412205
https://doi.org/10.1139/V53-127
> Organoheterocyclic compounds / Isoquinolines and derivatives / Isoquinolones and derivatives
(1'R,2'S,3S,5'S,6'S,8'S,11'S)-2'-ethenyl-4'-methylspiro[1H-indole-3,7'-9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane]-2,3'-dione 101666847 Click to see 336.40 unknown https://doi.org/10.1021/NP50050A012
> Phenylpropanoids and polyketides / Coumarins and derivatives / Coumarin glycosides
7-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-6-methoxychromen-2-one 162928762 Click to see 486.40 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
7-[6-[[3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-6-methoxychromen-2-one 162928761 Click to see COC1=C(C=C2C(=C1)C=CC(=O)O2)OC3C(C(C(C(O3)COC4C(C(C(O4)CO)O)O)O)O)O 486.40 unknown https://doi.org/10.1016/S0031-9422(00)82277-3
> Phenylpropanoids and polyketides / Coumarins and derivatives / Hydroxycoumarins / 7-hydroxycoumarins
Scopoletin 5280460 Click to see 192.17 unknown https://doi.org/10.1002/CHIN.200412205
https://doi.org/10.1248/CPB.51.1211
https://doi.org/10.1021/NP50050A012
https://doi.org/10.1002/CBER.18760090248

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