Scientific name	Authority	First published in
Silybum marianum var. albiflorum	Eig	Bull. Inst. Agric. Nat. Hist. Tel-Aviv 6: 44 (1927)
Centaurea dalmatica	Fraas	Syn. Pl. Fl. Class. : 204 (1845)
Mariacantha maculosa	Bubani	Fl. Pyren. 2: 150 (1899)
Carduus mariae	Crantz	Inst. Rei Herb. 1: 248 (1766)
Silybum mariae	Gray	Nat. Arr. Brit. Pl. 2: 436 (1821 publ. 1822)
Carduus lactifolius	Stokes	Bot. Mat. Med. 4: 141 (1812)
Silybum maculatum	Moench	Meth. 2: 555 (1794)
Mariana mariana	Hill	Hort. Kew. : 61
Carduus marianus	L.	Sp. Pl. : 823 (1753)
Silybum leucanthum	Jord. & Fourr.	Brev. Pl. Nov. ii. 83 (1868)
Silybum marianum var. marianum	(L.) Gaertn.
Silybum intermedium	Willk.	Index Seminum (TU, Dorpatensis) (1869) 6.
Carduus versicolor	Salisb.	Prodr. Stirp. Chap. Allerton : 185 (1796)
Silybum pygmaeum	Cass.	Dict. Sci. Nat. , ed. 2, 50: 469 (1827)
Mariana lactea	Hill.	Herb. Brit. 1: 75 (1769)
Cirsium maculatum	Scop.	Fl. Carniol. , ed. 2, 2: 130 (1772)
Carthamus maculatus	Lam.	Encycl. 1: 638 (1785)

Common names Top

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Filter by language:

Language	Common/alternative name
English	blessed milkthistle
English	milk thistle
English	blessed thistle
English	carduus marianus
English	holy thistle
English	marian thistle
English	mariana mariana
English	mary thistle
English	mediterranean milk thistle
English	milkthistle
English	saint mary's thistle
English	scotch thistle
English	st. mary's thistle
English	variegated thistle
Spanish	silybum maculatum
Spanish	bedegar
Spanish	cardanchos
Spanish	cardinchas
Spanish	cardo borde
Spanish	cardo de maria
Spanish	cardo pelotero
Spanish	cardos alcachoferos
Spanish	carduncho
Spanish	carduus lactifolius
Spanish	carduus mariae
Spanish	cartamo mariano
Spanish	cártamo mariano
Spanish	centaurea dalmatica
Spanish	escarciles
Spanish	escardancha
Spanish	mariana lactea
Arabic	سلبين مريمي
Azerbaijani	carduus marianus
Azerbaijani	mariana mariana
Azerbaijani	adi alaqanqal
azb	عادی آلاقانقال
Belarusian	Растаропша плямістая
Bulgarian	бял трън
Catalan	card marià
Czech	ostropestřec mariánský
Welsh	ysgallen fair
German	gewöhnliche mariendistel
German	carduus marianus
German	christi krone
German	donnerdistel
German	fieberdistel
German	frauendistel
German	heilandsdistel
German	marienkörner
German	stechkörner
German	mariendistel
Greek	Γαϊδουράγκαθο
Esperanto	lakta kardo
Estonian	harilik maarjaohakas
Basque	astalikardu
Persian	خار علیص
Persian	خار مریم
Finnish	maarianohdake
French	chardon-marie
Galician	cardo de maría
Galician	cardo leiteiro
Hebrew	carduus marianus
Hebrew	mariana mariana
Hebrew	גדילן מצוי
Croatian	marijin oslobod
Hungarian	máriatövis
Armenian	Կաթնափուշ բծավոր
Italian	carciofi selvatici
Italian	carciofo selvatico
Italian	cardi mariani
Italian	cardo mariano
Japanese	オオアザミ
Japanese	ミルクシスル
Japanese	マリアアザミ
Georgian	carduus marianus
Georgian	mariana mariana
Georgian	ბაყაყურა
Kabyle	asennan n weɣyul
Kazakh	Алатікен
ku	givzonik
Cornish	askall mogh
Lithuanian	tikrasis margainis
Macedonian	Млечен трн
mn	Мэригийн чонын өргөс
mwl	silybum
Norwegian Bokmål	mariatistel
Dutch	mariadistel
Dutch	silymarin
oc	cardet marian
oc	cardon de maria
Polish	ostropest plamisty
pms	sylibum marianum
Punjab	لے
Pashto	مريم څڅ
Romanian	armurariu
Russian	carduus marianus
Russian	mariana mariana
Russian	марьин чертополох
Russian	остро-пёстро
Russian	расторопша пятнистая
Slovak	pestrec mariánsky
Slovenian	pegasti badelj
Serbian	Гујина трава
Swedish	mariatistlar
Swedish	mariatistelsläktet
tg	Хори каррок
Ukrainian	Розторопша плямиста
Urdu	مریم گوکھرد
Uzbek	sutli qushqo'nmas
Walloon	tcherdon notru-dame
Chinese	水飞蓟
Chinese	奶蓟
Chinese	水飞雉
Chinese	老鼠筋
Chinese	乳薊
Chinese	乳蓟

Subspecies (abbr. subsp./ssp.) Top

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No subspecies added yet.

Varieties (abbr. var.) Top

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No variety added yet.

Subvarieties (abbr. subvar.) Top

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No subvariety added yet.

Forms (abbr. f.) Top

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No forms added yet.

Germination/Propagation Top

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Sow seeds at 20°C, expecting germination within 3 months without further temperature treatment.

Distribution (via POWO/KEW) Top

No distribution data was extracted from POWO/KEW yet. We are constantly monitoring for new data.

Links to other databases Top

Suggest others/fix!

Database	ID/link to page
World Flora Online	wfo-0000014591
UNII	JLK089424F
Flora of Alabama	971
Canadensys	3434
USDA Plants	SIMA3
Tropicos	2711064
INPN	123705
Flora of Italy	5927
KEW	urn:lsid:ipni.org:names:249211-1
The Plant List	gcc-114114
Missouri Botanical Garden	277472
Open Tree Of Life	650188
Observations.org	7468
NCBI Taxonomy	92921
NBN Atlas	NHMSYS0000463605
Nature Serve	2.143221
IUCN Red List	202991
IPNI	91418-3
iNaturalist	52586
GBIF	3145214
Freebase	/m/073ynx
EPPO	SLYMA
EOL	509366
Elurikkus	7280
Calflora (Californian flora)	7622
US Library of Congress	sh97008688
USDA GRIN	33952
Wikipedia	Silybum_marianum
CMAUP	NPO5645

Genomes (via NCBI) Top

Below is displayed the reference genome only!
If you wish to browse all genomes for this plant click here.

Accession	Assembly
Accession	Name	Level	Submitter	Released	Coverage	Size
GCA_036898165.1	MJU_Smar_1.0	Chromosome	Myongji University	2024-02-28	187.1x	662.20 Mb

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

Review on anti-alzheimer drug development: approaches, challenges and perspectives

Abdallah AE

RSC Adv

05-Apr-2024

PMCID:	PMC10995770
doi:	10.1039/d3ra08333k
PMID:	38586442

Mechanism of action of microRNA166 on nitric oxide in alfalfa (Medicago sativa L.) under drought stress

Wei B, Wang Y, Ruan Q, Zhu X, Wang X, Wang T, Zhao Y, Wei X

BMC Genomics

28-Mar-2024

PMCID:	PMC10976769
doi:	10.1186/s12864-024-10095-7
PMID:	38549050

Mitigation of haemato-genotoxic and stress response effects in Cyprinus carpio via silymarin dietary supplementation following deltamethrin exposure

Jindal R, Sharma R, Kaur P, Kaur S, Multisanti CR, Faggio C

Heliyon

27-Mar-2024

PMCID:	PMC10999925
doi:	10.1016/j.heliyon.2024.e28419
PMID:	38590886

Impact of Heavy Metal Pollution in the Environment on the Metabolic Profile of Medicinal Plants and Their Therapeutic Potential

Asiminicesei DM, Fertu DI, Gavrilescu M

Plants (Basel)

21-Mar-2024

PMCID:	PMC10976221
doi:	10.3390/plants13060913
PMID:	38592933

The first Neolithic boats in the Mediterranean: The settlement of La Marmotta (Anguillara Sabazia, Lazio, Italy)

Gibaja JF, Mineo M, Santos FJ, Morell B, Caruso-Fermé L, Remolins G, Masclans A, Mazzucco N

PLoS One

20-Mar-2024

PMCID:	PMC10954169
doi:	10.1371/journal.pone.0299765
PMID:	38507432

Climate and soil factors co-derive the functional traits variations in naturalized downy thorn apple (Datura innoxia Mill.) along the altitudinal gradient in the semi-arid environment

Khan N, Ullah R, Okla MK, Abdel-Maksoud MA, Saleh IA, Abu-Harirah HA, AlRamadneh TN, AbdElgawad H

Heliyon

14-Mar-2024

PMCID:	PMC10957434
doi:	10.1016/j.heliyon.2024.e27811
PMID:	38524627

Long-Term Monitoring of the Traditional Knowledge of Plant Species Used for Culinary Purposes in the Valencia Region, South-Eastern Spain

Belda A, Jordán-Nuñez J, Micó-Vicent B, López-Rodríguez D

Plants (Basel)

08-Mar-2024

PMCID:	PMC10975046
doi:	10.3390/plants13060775
PMID:	38592810

Developing Chinese herbal-based functional biomaterials for tissue engineering

Ge W, Gao Y, He L, Jiang Z, Zeng Y, Yu Y, Xie X, Zhou F

Heliyon

07-Mar-2024

PMCID:	PMC10944231
doi:	10.1016/j.heliyon.2024.e27451
PMID:	38496844

Higher Plant-Derived Biostimulants: Mechanisms of Action and Their Role in Mitigating Plant Abiotic Stress

Martínez-Lorente SE, Martí-Guillén JM, Pedreño MÁ, Almagro L, Sabater-Jara AB

Antioxidants (Basel)

06-Mar-2024

PMCID:	PMC10967762
doi:	10.3390/antiox13030318
PMID:	38539851

A decade of advances in the study of buckwheat for organic farming and agroecology (2013-2023)

Vieites-Álvarez Y, Reigosa MJ, Sánchez-Moreiras AM

Front Plant Sci

06-Mar-2024

PMCID:	PMC10950947
doi:	10.3389/fpls.2024.1354672
PMID:	38510443

Silybin Alleviated Hepatic Injury by Regulating Redox Balance, Inflammatory Response, and Mitochondrial Function in Weaned Piglets under Paraquat-Induced Oxidative Stress

Cai L, Ming D, Chen W, Zhao Y, Li Y, Sun W, Pi Y, Jiang X, Li X

Antioxidants (Basel)

06-Mar-2024

PMCID:	PMC10967606
doi:	10.3390/antiox13030324
PMID:	38539857

Clinically Effective Molecules of Natural Origin for Obesity Prevention or Treatment

Hidalgo-Lozada GM, Villarruel-López A, Nuño K, García-García A, Sánchez-Nuño YA, Ramos-García CO

Int J Mol Sci

25-Feb-2024

PMCID:	PMC10931663
doi:	10.3390/ijms25052671
PMID:	38473918

Formulation of Folate Receptor-Targeted Silibinin-Loaded Inhalable Chitosan Nanoparticles by the QbD Approach for Lung Cancer Targeted Delivery

Patel P, Raval M, Airao V, Ali N, Shazly GA, Khan R, Prajapati B

ACS Omega

24-Feb-2024

PMCID:	PMC10918659
doi:	10.1021/acsomega.3c07954
PMID:	38463259

A Comprehensive Review of Various Therapeutic Strategies for the Management of Skin Cancer

Dachani SR, Kaleem M, Mujtaba MA, Mahajan N, Ali SA, Almutairy AF, Mahmood D, Anwer MK, Ali MD, Kumar S

ACS Omega

22-Feb-2024

PMCID:	PMC10918819
doi:	10.1021/acsomega.3c09780
PMID:	38463249

Synergistic interactions of assorted ameliorating agents to enhance the potential of heavy metal phytoremediation

Sanjana S, Jazeel K, Janeeshma E, Nair SG, Shackira AM

Stress Biol

16-Feb-2024

PMCID:	PMC10873264
doi:	10.1007/s44154-024-00153-1
PMID:	38363436

Phytochemical Profile Top

Add a new one!

Below are displayed the proven (via scientific papers) natural compounds!
You can also contribute to this by clicking here.

Name	PubChem ID	Canonical SMILES	MW	Found in	Proof
> Benzenoids / Benzene and substituted derivatives / Cyclohexylphenols
(3R)-9-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-one	42608131	Click to see COC1=C(C=CC(=C1)C2C3COC4(C3C=C(C2C4=O)C5CC(=O)C6=C(C=C(C=C6O5)O)O)O)O	466.40	unknown	via CMAUP database
> Benzenoids / Benzene and substituted derivatives / Phenethylamines
4-(2-Aminoethyl)phenol;hydron	67458472	Click to see [H+].C1=CC(=CC=C1CCN)O	138.19	unknown	via CMAUP database
Tyramine	5610	Click to see C1=CC(=CC=C1CCN)O	137.18	unknown	via CMAUP database
> Benzenoids / Phenols / Tyrosols and derivatives / Tyrosols
2,6-Dideuterio-4-(2-hydroxyethyl)phenol	10773058	Click to see C1=CC(=CC=C1CCO)O	140.18	unknown	via CMAUP database
> Lignans, neolignans and related compounds / Flavonolignans
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-2-(3-hydroxy-4-methoxy-phenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one	46186856	Click to see COC1=C(C=C(C=C1)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	via CMAUP database
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-2-(3-hydroxy-5-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one	162867851	Click to see COC1=CC(=CC(=C1)O)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO	482.40	unknown	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2910627/
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one	44584758	Click to see COC1=C(C=C(C=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1039/C39790000696
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-[4-hydroxy-3-(hydroxymethyl)phenyl]-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one	29927688	Click to see C1=CC(=C(C=C1C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)CO)O	482.40	unknown	via CMAUP database
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one	26339692	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1021/NP070136B
(2R,3R)-3,5,7-trihydroxy-2-[(2S,3S)-2-(3-hydroxy-4-methoxy-phenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one	46186857	Click to see COC1=C(C=C(C=C1)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	via CMAUP database
(2R,3R)-3,5,7-trihydroxy-2-[(2S,3S)-2-(3-hydroxy-5-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one	162867852	Click to see COC1=CC(=CC(=C1)O)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO	482.40	unknown	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2910627/
(2R,3S)-3,5,7-trihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one	26339689	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1039/C39790000696 https://doi.org/10.1021/NP070136B
(2R,3S)-3,5,7-trihydroxy-2-[(2R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one	45358153	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	via CMAUP database
(2S,3S)-2-[(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)(2H,3H-benzo [e]1,4-dioxin-6-yl)]-3,5,7-trihydroxychroman-4-one	16211710	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	via CMAUP database
(2S,3S)-3,5,7-trihydroxy-2-[(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one	98047181	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	via CMAUP database
(2S,3S)-3,5,7-trihydroxy-2-[(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one	1549163	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	via CMAUP database
(2S)-2alpha-[(2S,3R)-2-(Hydroxymethyl)-3-(3-methoxy-4-hydroxyphenyl)-2,3-dihydro-1,4-benzodioxin-7-yl]-5,7-dihydroxy-2,3-dihydro-4H-1-benzopyran-4-one	93022855	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4CC(=O)C5=C(C=C(C=C5O4)O)O)CO)O	466.40	unknown	via CMAUP database
(3R)-3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one	45039613	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	via CMAUP database
(3S)-3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one	131632597	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1081/JLC-120014271 https://doi.org/10.1300/J044V01N04_04 https://doi.org/10.1016/S0731-7085(01)00364-8 https://doi.org/10.1016/S0731-7085(98)00231-3 https://doi.org/10.1016/S0367-326X(00)00134-9 https://doi.org/10.1055/S-2006-962330
2-Hydroxy-2,2-diphenylaceticacid	4481258	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4CC(=O)C5=C(C=C(C=C5O4)O)O)CO)O	466.40	unknown	https://doi.org/10.1093/CHROMSCI/46.2.93
2,3-Dehydrosilybin	5467200	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4=C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	480.40	unknown	https://doi.org/10.1007/978-3-540-71095-0_9380
3,5,7-Trihydroxy-2-[3-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one	67120654	Click to see COC1=C(C=C(C=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1039/C39790000696
CID 21723007	21723007	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	via CMAUP database
Flavobion	24832061	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1055/S-2006-957999 https://doi.org/10.1055/S-2006-960009 https://doi.org/10.1016/J.LFS.2005.01.011 https://doi.org/10.1300/J044V01N04_04 https://doi.org/10.1016/B978-1-4377-2333-5.00123-1
Isosilybin	3085830	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1021/NP030163B https://doi.org/10.1039/C39790000696 https://doi.org/10.1158/0008-5472.CAN-04-4662 https://doi.org/10.1039/B300099K https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2910627/ https://doi.org/10.1021/NP070136B https://doi.org/10.1055/S-2007-990239 https://doi.org/10.1021/NP400955Q
Isosilybin A	11059920	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1021/NP030163B https://doi.org/10.1177/1534735407301825 https://doi.org/10.1002/PTR.2650070122 https://doi.org/10.1039/B300099K https://doi.org/10.1021/NP070136B https://doi.org/10.1055/S-2007-990239 https://doi.org/10.1021/NP030414G https://doi.org/10.1002/CHIN.200338195 https://doi.org/10.1055/S-2005-864187
Isosilybin B	10885340	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1021/NP030163B https://doi.org/10.1177/1534735407301825 https://doi.org/10.1002/PTR.2650070122 https://doi.org/10.1039/B300099K https://doi.org/10.1021/NP070136B https://doi.org/10.1055/S-2007-990239 https://doi.org/10.1021/NP030414G https://doi.org/10.1002/CHIN.200338195 https://doi.org/10.1055/S-2005-864187
Silandrin	441663	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4CC(=O)C5=C(C=C(C=C5O4)O)O)CO)O	466.40	unknown	https://doi.org/10.1093/CHROMSCI/46.2.93
Silibinin	31553	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	fruit, unknown	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6150307/ https://doi.org/10.1039/B300099K https://doi.org/10.1055/S-2008-1074893 https://doi.org/10.1081/JLC-120014271 https://doi.org/10.1300/J044V01N04_04 https://doi.org/10.1016/S0731-7085(01)00364-8 https://doi.org/10.1016/S0367-326X(00)00134-9 https://doi.org/10.1055/S-2006-962330 https://doi.org/10.1055/S-2005-864187 https://doi.org/10.1021/NP070136B https://doi.org/10.1021/NP030414G https://doi.org/10.1016/J.LFS.2005.01.011 https://doi.org/10.1002/PTR.2650070122 https://doi.org/10.1007/978-3-540-71095-0_9380 https://doi.org/10.1055/S-2006-957999 https://doi.org/10.1055/S-2007-990239 https://doi.org/10.1021/NP030163B https://doi.org/10.1158/0008-5472.CAN-06-2601 https://doi.org/10.1016/S0731-7085(98)00231-3 https://doi.org/10.1016/J.JDERMSCI.2007.06.008 https://doi.org/10.4268/CJCMM20160915 https://doi.org/10.1002/CHIN.200338195 https://doi.org/10.1080/11263508209428058 https://doi.org/10.1016/S0021-9673(01)87884-5 https://doi.org/10.1016/S0021-9673(99)00071-0 https://doi.org/10.1093/MUTAGE/GEP064 https://doi.org/10.1177/1534735407301825
Silibinin B	1548994	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1021/NP030163B https://doi.org/10.1177/1534735407301825 https://doi.org/10.1002/PTR.2650070122 https://doi.org/10.1039/B300099K https://doi.org/10.1021/NP070136B https://doi.org/10.1055/S-2007-990239 https://doi.org/10.1021/NP030414G https://doi.org/10.1002/CHIN.200338195 https://doi.org/10.1055/S-2005-864187
Silybin	3086637	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	via CMAUP database
Silybin [22888-70-6]	45933924	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	via CMAUP database
Silymarin	5213	Click to see COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1021/NP400955Q https://doi.org/10.1039/B300099K https://doi.org/10.1055/S-2006-960009 https://doi.org/10.1300/J044V01N04_04 https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2910627/ https://doi.org/10.1016/B978-1-4377-2333-5.00123-1 https://doi.org/10.1021/NP070136B https://doi.org/10.1016/J.LFS.2005.01.011 https://doi.org/10.1055/S-2006-957999 https://doi.org/10.1055/S-2007-990239 https://doi.org/10.1021/NP030163B https://doi.org/10.1158/0008-5472.CAN-06-2601 https://doi.org/10.1016/J.JDERMSCI.2007.06.008 https://doi.org/10.1158/0008-5472.CAN-04-4662 https://doi.org/10.1093/CARCIN/BGL032 https://doi.org/10.1021/JF063156C https://doi.org/10.1093/MUTAGE/GEP064
> Lignans, neolignans and related compounds / Furanoid lignans / Tetrahydrofuran lignans / 7,7-epoxylignans
2beta-(3,4,5-Trimethoxyphenyl)-3beta,4alpha-dimethyl-5beta-(3,5-dimethoxy-4-hydroxyphenyl)tetrahydrofuran	24796592	Click to see CC1C(C(OC1C2=CC(=C(C(=C2)OC)O)OC)C3=CC(=C(C(=C3)OC)OC)OC)C	418.50	unknown	via CMAUP database
> Lipids and lipid-like molecules / Fatty Acyls / Fatty acid esters
Ethylene glycol monostearate	24762	Click to see CCCCCCCCCCCCCCCCCC(=O)OCCO	328.50	unknown	via CMAUP database
> Lipids and lipid-like molecules / Fatty Acyls / Fatty acids and conjugates / Long-chain fatty acids
Arachidate	5461017	Click to see CCCCCCCCCCCCCCCCCCCC(=O)[O-]	311.50	unknown	via CMAUP database
Arachidic Acid	10467	Click to see CCCCCCCCCCCCCCCCCCCC(=O)O	312.50	unknown	via CMAUP database
Arachidonic Acid	444899	Click to see CCCCCC=CCC=CCC=CCC=CCCCC(=O)O	304.50	unknown	via CMAUP database
Myristic Acid	11005	Click to see CCCCCCCCCCCCCC(=O)O	228.37	unknown	https://doi.org/10.1007/978-3-540-71095-0_9380
Oleic Acid	445639	Click to see CCCCCCCCC=CCCCCCCCC(=O)O	282.50	unknown	https://doi.org/10.1007/978-3-540-71095-0_9380
Palmitic Acid	985	Click to see CCCCCCCCCCCCCCCC(=O)O	256.42	unknown	https://doi.org/10.1007/978-3-540-71095-0_9380
Stearic Acid	5281	Click to see CCCCCCCCCCCCCCCCCC(=O)O	284.50	unknown	https://doi.org/10.1007/978-3-540-71095-0_9380
> Lipids and lipid-like molecules / Fatty Acyls / Fatty acids and conjugates / Medium-chain fatty acids
(3E,9E)-undeca-3,9-dienoic acid	52914864	Click to see CC=CCCCCC=CCC(=O)O	182.26	unknown	via CMAUP database
> Lipids and lipid-like molecules / Fatty Acyls / Fatty acids and conjugates / Very long-chain fatty acids
Behenic Acid	8215	Click to see CCCCCCCCCCCCCCCCCCCCCC(=O)O	340.60	unknown	via CMAUP database
Docosenoic acid	6433893	Click to see CCCCCCCCCCCCCCCCCCCC=CC(=O)O	338.60	unknown	via CMAUP database
> Lipids and lipid-like molecules / Fatty Acyls / Lineolic acids and derivatives
9,12-Octadecadienoate	5867807	Click to see CCCCCC=CCC=CCCCCCCCC(=O)[O-]	279.40	unknown	via CMAUP database
Linoleic Acid	5280450	Click to see CCCCCC=CCC=CCCCCCCCC(=O)O	280.40	unknown	via CMAUP database
Linolenic Acid	5280934	Click to see CCC=CCC=CCC=CCCCCCCCC(=O)O	278.40	unknown	via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Diterpenoids / Tigliane and ingenane diterpenoids / Phorbol esters
Phorbol 12-myristate 13-acetate	27924	Click to see CCCCCCCCCCCCCC(=O)OC1C(C2(C(C=C(CC3(C2C=C(C3=O)C)O)CO)C4C1(C4(C)C)OC(=O)C)O)C	616.80	unknown	via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Quinone and hydroquinone lipids / Vitamin E compounds / Tocopherols
(2R)-2,5,7,8-Tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-ol	12359166	Click to see CC1=C(C2=C(CCC(O2)(C)CCCC(C)CCCC(C)CCCC(C)C)C(=C1O)C)C	430.70	unknown	https://doi.org/10.1016/S0308-8146(01)00152-2
Alpha-Tocopherol	14985	Click to see CC1=C(C2=C(CCC(O2)(C)CCCC(C)CCCC(C)CCCC(C)C)C(=C1O)C)C	430.70	unknown	https://doi.org/10.1016/S0308-8146(01)00152-2
Tocopherols	14986	Click to see CC1=C(C=C2CCC(OC2=C1C)(C)CCCC(C)CCCC(C)CCCC(C)C)O	416.70	unknown	https://doi.org/10.1515/ZNC-1998-9-1001
> Lipids and lipid-like molecules / Prenol lipids / Terpene lactones / Quassinoids
[(1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-en-3-yl] (2S)-2-methylbutanoate	53320678	Click to see CCC(C)C(=O)OC1C2C3(C(C(C4C2(CO3)C(CC5C4(C(C(=O)C=C5C)O)C)OC1=O)O)O)C	478.50	unknown	via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Triterpenoids
(1S,3S,4aR,6aR,6aR,6bR,8aR,10S,12aS,14bS)-3,10-dihydroxy-1,6a,6b,9,9,12a-hexamethyl-2-methylidene-7-oxo-3,4,5,6,6a,8,8a,10,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid	162928281	Click to see CC1C2C3=CCC4C5(CCC(C(C5CC(=O)C4(C3(CCC2(CC(C1=C)O)C(=O)O)C)C)(C)C)O)C	484.70	unknown	https://doi.org/10.1002/MRC.1881
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(3S,4R,5R,10R,13R,14R,17R)-4-(hydroxymethyl)-17-[(2R)-6-hydroxy-6-methyl-5-methylideneheptan-2-yl]-4,10,13,14-tetramethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-3,4,5-triol	162822179	Click to see CC(CCC(=C)C(C)(C)O)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)CO)OC5C(C(C(C(O5)CO)O)O)O)C)C)C	634.90	unknown	https://doi.org/10.1248/CPB.54.103
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(3S,5S,10R,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-3,4,5-triol	163010558	Click to see CC(C)C(=C)CCC(C)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)O)C)C)C	602.90	unknown	https://doi.org/10.1248/CPB.54.103
(3S,4aR,6aR,6aR,6bR,8aR,10S,12aS,14bS)-3,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-7-oxo-3,4,5,6,6a,8,8a,10,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid	163019701	Click to see CC1(CC2C3=CCC4C5(CCC(C(C5CC(=O)C4(C3(CCC2(CC1O)C(=O)O)C)C)(C)C)O)C)C	486.70	unknown	https://doi.org/10.1002/MRC.1881
(3S,4R,5R,10S,13R,14R,17R)-4-(hydroxymethyl)-17-[(2R)-6-hydroxy-6-methyl-5-methylideneheptan-2-yl]-4,10,13,14-tetramethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,5,6,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-7-one	163194865	Click to see CC(CCC(=C)C(C)(C)O)C1CCC2(C1(CCC3=C2C(=O)CC4C3(CCC(C4(C)CO)OC5C(C(C(C(O5)CO)O)O)O)C)C)C	648.90	unknown	https://doi.org/10.1248/CPB.54.103
2-(hydroxymethyl)-6-[[4,4,10,13,14-pentamethyl-17-(6-methyl-5-methylideneheptan-2-yl)-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-3,4,5-triol	73049179	Click to see CC(C)C(=C)CCC(C)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)O)C)C)C	602.90	unknown	https://doi.org/10.1248/CPB.54.103
3-Hydroxy-17-(6-hydroxy-6-methyl-5-methylideneheptan-2-yl)-4,4,10,13,14-pentamethyl-1,2,3,5,6,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-7-one	73007605	Click to see CC(CCC(=C)C(C)(C)O)C1CCC2(C1(CCC3=C2C(=O)CC4C3(CCC(C4(C)C)O)C)C)C	470.70	unknown	https://doi.org/10.1248/CPB.54.103
3,10-dihydroxy-1,6a,6b,9,9,12a-hexamethyl-2-methylidene-7-oxo-3,4,5,6,6a,8,8a,10,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid	162928280	Click to see CC1C2C3=CCC4C5(CCC(C(C5CC(=O)C4(C3(CCC2(CC(C1=C)O)C(=O)O)C)C)(C)C)O)C	484.70	unknown	https://doi.org/10.1002/MRC.1881
3,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-7-oxo-3,4,5,6,6a,8,8a,10,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid	163019699	Click to see CC1(CC2C3=CCC4C5(CCC(C(C5CC(=O)C4(C3(CCC2(CC1O)C(=O)O)C)C)(C)C)O)C)C	486.70	unknown	https://doi.org/10.1002/MRC.1881
4-(Hydroxymethyl)-17-(6-hydroxy-6-methyl-5-methylideneheptan-2-yl)-4,10,13,14-tetramethyl-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,5,6,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-7-one	163046537	Click to see CC(CCC(=C)C(C)(C)O)C1CCC2(C1(CCC3=C2C(=O)CC4C3(CCC(C4(C)CO)OC5C(C(C(C(O5)CO)O)O)O)C)C)C	648.90	unknown	https://doi.org/10.1248/CPB.54.103
Marianine	11569021	Click to see CC(CCC(=C)C(C)(C)O)C1CCC2(C1(CCC3=C2C(=O)CC4C3(CCC(C4(C)C)O)C)C)C	470.70	unknown	https://doi.org/10.1248/CPB.54.103 https://doi.org/10.1002/CHIN.200632217
Marianoside A	11671819	Click to see CC(CCC(=C)C(C)(C)O)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)CO)OC5C(C(C(C(O5)CO)O)O)O)C)C)C	634.90	unknown	https://doi.org/10.1002/CHIN.200632217
Marianoside B	11671631	Click to see CC(C)C(=C)CCC(C)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)O)C)C)C	602.90	unknown	https://doi.org/10.1248/CPB.54.103 https://doi.org/10.1002/CHIN.200632217
> Lipids and lipid-like molecules / Steroids and steroid derivatives / Cholestane steroids / Cholesterols and derivatives
Cholesterol	5997	Click to see CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C	386.70	unknown	via CMAUP database
> Lipids and lipid-like molecules / Steroids and steroid derivatives / Ergostane steroids / Ergosterols and derivatives
(5R,8R,9S,10S,13R,14S,17R)-17-[(2R,5R)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol	99565629	Click to see CC(C)C(C)CCC(C)C1CCC2C1(CCC3C2CCC4C3(CC=C(C4)O)C)C	400.70	unknown	via CMAUP database
24-Methylenelophenol	5283640	Click to see CC1C(CCC2(C1CC=C3C2CCC4(C3CCC4C(C)CCC(=C)C(C)C)C)C)O	412.70	unknown	via CMAUP database
> Lipids and lipid-like molecules / Steroids and steroid derivatives / Stigmastanes and derivatives
17-(5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol	86821	Click to see CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C	414.70	unknown	https://doi.org/10.1007/978-3-540-71095-0_9380
Stigmasterol	5280794	Click to see CCC(C=CC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C	412.70	unknown	via CMAUP database
> Organic acids and derivatives / Carbothioic S-acids
Pentadecanethioic acid	18413781	Click to see CCCCCCCCCCCCCCC(=O)S	258.50	unknown	via CMAUP database
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Alpha amino acids and derivatives / Alpha amino acids
2-Azaniumylacetate	5257127	Click to see C(C(=O)[O-])[NH3+]	75.07	unknown	via CMAUP database
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Alpha amino acids and derivatives / Alpha amino acids / D-alpha-amino acids
(R)-2-Aminobutanoate	6971251	Click to see CCC(C(=O)[O-])[NH3+]	103.12	unknown	via CMAUP database
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Alpha amino acids and derivatives / Alpha amino acids / L-alpha-amino acids
(2S)-2-azaniumylbutanoate	6971252	Click to see CCC(C(=O)[O-])[NH3+]	103.12	unknown	via CMAUP database
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Alpha amino acids and derivatives / Glutamic acid and derivatives
(2S)-2-amino-5-hydroxy-5-oxopentanoate;hydron	88747398	Click to see [H+].C(CC(=O)O)C(C(=O)[O-])N	147.13	unknown	via CMAUP database
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Alpha amino acids and derivatives / Leucine and derivatives
N-Benzyloxycarbonyl-L-leucine	74840	Click to see CC(C)CC(C(=O)O)NC(=O)OCC1=CC=CC=C1	265.30	unknown	via CMAUP database
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Cysteine and derivatives
(2R)-2-ammonio-3-mercaptopropanoate	6419722	Click to see C(C(C(=O)[O-])[NH3+])S	121.16	unknown	via CMAUP database
> Organic oxygen compounds / Organooxygen compounds / Alcohols and polyols / Tertiary alcohols
(2S,3S,9S)-2,6,10,10-tetramethyltricyclo[7.2.1.01,6]dodecane-2,3-diol	5316758	Click to see CC1(CC23CC1CCC2(CCC(C3(C)O)O)C)C	252.39	unknown	via CMAUP database
> Organoheterocyclic compounds / Benzodioxoles
(3R)-3alpha-Methyl-4alpha-[(S)-alpha-(7-methoxy-1,3-benzodioxole-5-yl)-3,4,5-trimethoxybenzyl]tetrahydrofuran-2-one	57522109	Click to see CC1C(COC1=O)C(C2=CC3=C(C(=C2)OC)OCO3)C4=CC(=C(C(=C4)OC)OC)OC	430.40	unknown	via CMAUP database
(3R)-3alpha-Methyl-4alpha-[bis(7-methoxy-1,3-benzodioxole-5-yl)methyl]tetrahydrofuran-2-one	101577343	Click to see CC1C(COC1=O)C(C2=CC3=C(C(=C2)OC)OCO3)C4=CC5=C(C(=C4)OC)OCO5	414.40	unknown	via CMAUP database
(3S)-3beta-Methyl-4alpha-[(S)-alpha-(7-methoxy-1,3-benzodioxole-5-yl)-3,4,5-trimethoxybenzyl]tetrahydrofuran-2-one	14541875	Click to see CC1C(COC1=O)C(C2=CC3=C(C(=C2)OC)OCO3)C4=CC(=C(C(=C4)OC)OC)OC	430.40	unknown	via CMAUP database
> Organoheterocyclic compounds / Benzopyrans / 1-benzopyrans
Blandachromene I	101396971	Click to see CC1=C(C=C2C=CC(OC2=C1O)(C)CCC=C(C)C)C=O	286.40	unknown	via CMAUP database
Blandachromene II	101396972	Click to see CC1=CC2=C(C=CC(O2)(C)CCC=C(C)C)C(=C1C=O)O	286.40	unknown	via CMAUP database
> Organoheterocyclic compounds / Benzopyrans / 1-benzopyrans / Chromones
5,7-Dihydroxychromone	5281343	Click to see C1=COC2=CC(=CC(=C2C1=O)O)O	178.14	unknown	via CMAUP database
> Phenylpropanoids and polyketides / 2-arylbenzofuran flavonoids
(2R,3R)-3,5,7-trihydroxy-2-[(2S,3R)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-4-yl]-2,3-dihydrochromen-4-one	162895260	Click to see COC1=C(C=CC(=C1)C2C(C3=C(C=CC(=C3O2)O)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1515/ZNB-1981-0225
(2R)-5,7-dihydroxy-2-[(2S,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-4-yl]-2,3-dihydrochromen-4-one	154497082	Click to see COC1=C(C=CC(=C1)C2C(C3=C(C=CC(=C3O2)O)C4CC(=O)C5=C(C=C(C=C5O4)O)O)CO)O	466.40	unknown	https://doi.org/10.1055/S-2007-969717
(2S)-5,7-dihydroxy-2-[(2R,3R)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-4-yl]-2,3-dihydrochromen-4-one	162997693	Click to see COC1=C(C=CC(=C1)C2C(C3=C(C=CC(=C3O2)O)C4CC(=O)C5=C(C=C(C=C5O4)O)O)CO)O	466.40	unknown	https://doi.org/10.1055/S-2007-969717
(7-(Acetyloxy)-2-[4-(acetyloxy)-3-methoxyphenyl]-5-[3,5,7-tris(acetyloxy)-4-oxo-3,4-dihydro-2H-chromen-2-yl]-2,3-dihydro-1-benzofuran-3-yl)methyl acetate	592854	Click to see CC(=O)OCC1C(OC2=C1C=C(C=C2OC(=O)C)C3C(C(=O)C4=C(O3)C=C(C=C4OC(=O)C)OC(=O)C)OC(=O)C)C5=CC(=C(C=C5)OC(=O)C)OC	734.70	unknown	https://doi.org/10.1158/0008-5472.CAN-04-4662
3,5,7-Trihydroxy-2-[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzouran-4-yl]-2,3-dihydrochromen-4-one	14849116	Click to see COC1=C(C=CC(=C1)C2C(C3=C(C=CC(=C3O2)O)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1177/1534735407301825 https://doi.org/10.1002/CHIN.200338195 https://doi.org/10.1039/B300099K https://doi.org/10.1515/ZNB-1981-0225
Isosilychristin	21589839	Click to see COC1=C(C=CC(=C1)C2C(C3=C(C=CC(=C3O2)O)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1039/B300099K
Neosilyhermin B	42607998	Click to see COC1=C(C=CC(=C1)C2C(C3=C(C=CC(=C3O2)O)C4CC(=O)C5=C(C=C(C=C5O4)O)O)CO)O	466.40	unknown	via CMAUP database
Silicristin	441764	Click to see COC1=C(C=CC(=C1)C2C(C3=C(O2)C(=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1080/11263508209428058 https://doi.org/10.1177/1534735407301825 https://doi.org/10.1055/S-2006-962330 https://doi.org/10.1007/978-3-540-71095-0_9380 https://doi.org/10.1016/S0367-326X(00)00134-9 https://doi.org/10.1002/PTR.2650070122 https://doi.org/10.4268/CJCMM20160915 https://doi.org/10.1039/B300099K https://doi.org/10.1021/NP070136B https://doi.org/10.1016/S0731-7085(01)00364-8 https://doi.org/10.1055/S-2006-957999 https://doi.org/10.1300/J044V01N04_04 https://doi.org/10.1016/S0731-7085(98)00231-3 https://doi.org/10.1002/CHIN.200338195 https://doi.org/10.1081/JLC-120014271
Silychristin B	12442785	Click to see COC1=C(C=CC(=C1)C2C(C3=C(O2)C(=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1055/S-2005-864187 https://doi.org/10.1021/NP070136B
Silychrystin	4481797	Click to see COC1=C(C=CC(=C1)C2C(C3=C(O2)C(=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)O)CO)O	482.40	unknown	https://doi.org/10.1039/B300099K https://doi.org/10.1021/NP070136B
Silyhermin	10389806	Click to see COC1=C(C=CC(=C1)C2C(C3=C(O2)C(=CC(=C3)C4CC(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	466.40	unknown	via CMAUP database
Silyhermin B	121232947	Click to see COC1=C(C=CC(=C1)C2C(C3=C(O2)C(=CC(=C3)C4CC(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O	466.40	unknown	https://doi.org/10.1055/S-2007-969717
> Phenylpropanoids and polyketides / Flavonoids / Flavans / Flavanones
(1R,3R,6R,7R,10R)-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-8-[(2R)-3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-one	3033957	Click to see COC1=C(C=CC(=C1)C2C3COC4(C3C(=CC2C4=O)C5C(C(=O)C6=C(C=C(C=C6O5)O)O)O)O)O	482.40	unknown	https://doi.org/10.1080/11263508209428058 https://doi.org/10.1177/1534735407301825 https://doi.org/10.1055/S-2006-962330 https://doi.org/10.1016/J.LFS.2005.01.011 https://doi.org/10.1016/S0367-326X(00)00134-9 https://doi.org/10.1158/0008-5472.CAN-04-4662 https://doi.org/10.1002/PTR.2650070122 https://doi.org/10.1021/NP070136B https://doi.org/10.1016/S0731-7085(01)00364-8 https://doi.org/10.1055/S-2006-957999 https://doi.org/10.1016/S0731-7085(98)00231-3 https://doi.org/10.1002/CHIN.200338195 https://doi.org/10.1081/JLC-120014271
(1R,3R,6R,7R,10S)-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-8-[(2R,3R)-3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-one	5321311	Click to see COC1=C(C=CC(=C1)C2C3COC4(C3C(=CC2C4=O)C5C(C(=O)C6=C(C=C(C=C6O5)O)O)O)O)O	482.40	unknown	via CMAUP database
(1R,3R,6R,7R)-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-8-[(2R,3R)-3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-one	20056308	Click to see COC1=C(C=CC(=C1)C2C3COC4(C3C(=CC2C4=O)C5C(C(=O)C6=C(C=C(C=C6O5)O)O)O)O)O	482.40	unknown	via CMAUP database
(1R,3R,6S,7R)-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-8-(3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl)-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-one	137795484	Click to see COC1=C(C=CC(=C1)C2C3COC4(C3C(=CC2C4=O)C5C(C(=O)C6=C(C=C(C=C6O5)O)O)O)O)O	482.40	unknown	https://doi.org/10.1080/11263508209428058 https://doi.org/10.1177/1534735407301825 https://doi.org/10.1055/S-2006-962330 https://doi.org/10.1055/S-2008-1074893 https://doi.org/10.1016/S0367-326X(00)00134-9 https://doi.org/10.1002/PTR.2650070122 https://doi.org/10.4268/CJCMM20160915 https://doi.org/10.1021/NP070136B https://doi.org/10.1016/S0731-7085(01)00364-8 https://doi.org/10.1055/S-2006-957999 https://doi.org/10.1016/S0731-7085(98)00231-3 https://doi.org/10.1002/CHIN.200338195 https://doi.org/10.1081/JLC-120014271
(1R,3S,6R,7S,10R)-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-8-[(2R,3R)-3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-one	134688545	Click to see COC1=C(C=CC(=C1)C2C3COC4(C3C(=CC2C4=O)C5C(C(=O)C6=C(C=C(C=C6O5)O)O)O)O)O	482.40	unknown	https://doi.org/10.1016/J.LFS.2005.01.011
(2R,3R)-3,5,7-trihydroxy-2-[(1S,3R,7S)-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-4-oxatricyclo[4.3.1.03,7]dec-8-en-8-yl]-2,3-dihydrochromen-4-one	49775709	Click to see COC1=C(C=CC(=C1)C2C3CC4(C(C2CO4)C(=C3)C5C(C(=O)C6=C(C=C(C=C6O5)O)O)O)O)O	468.50	unknown	via CMAUP database
(2R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one	667495	Click to see C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O	272.25	unknown	via CMAUP database
CID 24721272	24721272	Click to see COC1=C(C=CC(=C1)C2C3COC4(C3C(=CC2C4=O)C5C(C(=O)C6=C(C=C(C=C6O5)O)O)O)O)O	482.40	unknown	via CMAUP database
Silidianin	11982272	Click to see COC1=C(C=CC(=C1)C2C3COC4(C3C(=CC2C4=O)C5C(C(=O)C6=C(C=C(C=C6O5)O)O)O)O)O	482.40	unknown	https://doi.org/10.1039/B300099K https://doi.org/10.1016/J.PHYTOL.2012.03.010
Silyamandin	23634490	Click to see COC1=C(C=CC(=C1)C2C3COC(=O)C3C(=CC2C(=O)O)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)O	498.40	unknown	via CMAUP database
Silydianin	12442788	Click to see COC1=C(C=CC(=C1)C2C3COC4(C3C(=CC2C4=O)C5C(C(=O)C6=C(C=C(C=C6O5)O)O)O)O)O	482.40	unknown	https://doi.org/10.1158/0008-5472.CAN-04-4662 https://doi.org/10.1039/B300099K
> Phenylpropanoids and polyketides / Flavonoids / Flavans / Flavanones / Flavanonols
(-)-Taxifolin	712316	Click to see C1=CC(=C(C=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O	304.25	unknown	via CMAUP database
(+)-3,5,7,3',5'-Pentahydroxyflavanone	25073455	Click to see C1=C(C=C(C=C1O)O)C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O	304.25	unknown	https://doi.org/10.1016/J.PHYTOL.2012.03.010
(+/-)-Taxifolin	471	Click to see C1=CC(=C(C=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O	304.25	unknown	https://doi.org/10.1158/0008-5472.CAN-04-4662 https://doi.org/10.1039/B300099K
(2S,3S)-3,4',5,7-Tetrahydroxyflavanone	9838882	Click to see C1=CC(=CC=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O	288.25	unknown	via CMAUP database
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one	662	Click to see C1=CC(=CC=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O	288.25	unknown	https://doi.org/10.1515/ZNB-1981-0426
Aromadendrin	122850	Click to see C1=CC(=CC=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O	288.25	unknown	https://doi.org/10.1515/ZNB-1981-0426
Taxifolin	439533	Click to see C1=CC(=C(C=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O	304.25	unknown	https://doi.org/10.1080/11263508209428058 https://doi.org/10.1158/0008-5472.CAN-04-4662 https://doi.org/10.1055/S-2006-962330 https://doi.org/10.1300/J044V10N01_08 https://doi.org/10.1177/1534735407301825 https://doi.org/10.1016/S0731-7085(98)00231-3 https://doi.org/10.1002/CHIN.200338195 https://doi.org/10.1039/B300099K https://doi.org/10.1007/978-3-540-71095-0_9380
> Phenylpropanoids and polyketides / Flavonoids / Flavones
Apigenin	5280443	Click to see C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O	270.24	unknown	https://doi.org/10.1055/S-2006-962330
Apigenin-7-olate	25200950	Click to see C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)[O-])O	269.23	unknown	via CMAUP database
Kaempferol 3-O-sulfate	44259052	Click to see C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OS(=O)(=O)O)O	366.30	unknown	https://doi.org/10.1055/S-2006-962330
Kaempferol oxoanion	25202062	Click to see C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)[O-])O	285.23	unknown	via CMAUP database
Luteolin	5280445	Click to see C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O	286.24	unknown	https://doi.org/10.1055/S-2006-962330
Quercetin-7-olate	46906036	Click to see C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)[O-])O)O	301.23	unknown	via CMAUP database
> Phenylpropanoids and polyketides / Flavonoids / Flavones / Flavonols
Kaempferol	5280863	Click to see C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O	286.24	unknown	https://doi.org/10.1016/S0031-9422(00)97838-5
Quercetin	5280343	Click to see C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O	302.23	unknown	https://doi.org/10.1055/S-2006-962330 https://doi.org/10.1016/S0040-4039(01)96737-1
> Phenylpropanoids and polyketides / Flavonoids / Flavonoid glycosides / Flavonoid C-glycosides / Flavonoid 8-C-glycosides
Vicenin 2	442664	Click to see C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C(=C3O2)C4C(C(C(C(O4)CO)O)O)O)O)C5C(C(C(C(O5)CO)O)O)O)O)O	594.50	unknown	via CMAUP database
> Phenylpropanoids and polyketides / Flavonoids / Flavonoid glycosides / Flavonoid O-glucuronides
(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[8-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-6-yl]oxyoxane-2-carboxylic acid	163079022	Click to see CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C=C(C=C3O)OC4C(C(C(C(O4)C(=O)O)O)O)O)C5=CC=C(C=C5)O)O)O)O	608.50	unknown	https://doi.org/10.1016/S0031-9422(00)97838-5
3,4,5-Trihydroxy-6-[8-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxychromen-6-yl]oxyoxane-2-carboxylic acid	163079021	Click to see CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C=C(C=C3O)OC4C(C(C(C(O4)C(=O)O)O)O)O)C5=CC=C(C=C5)O)O)O)O	608.50	unknown	https://doi.org/10.1016/S0031-9422(00)97838-5
> Phenylpropanoids and polyketides / Flavonoids / Flavonoid glycosides / Flavonoid O-glucuronides / Flavonoid-7-O-glucuronides
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[8-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid	162902636	Click to see C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O	446.40	unknown	https://doi.org/10.1016/S0031-9422(00)97838-5
[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl] (2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylate	162894173	Click to see CC1C(C(C(C(O1)OC(=O)C2C(C(C(C(O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)O)O)O)O)O)O	592.50	unknown	https://doi.org/10.1016/S0031-9422(00)97838-5
3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl beta-D-galactopyranosiduronic acid	102147829	Click to see CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)C5=CC=C(C=C5)O)O)O)O	608.50	unknown	https://doi.org/10.1016/S0031-9422(00)97838-5
3,4,5-Trihydroxy-6-[8-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid	162902635	Click to see C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O	446.40	unknown	https://doi.org/10.1016/S0031-9422(00)97838-5
Apigenin 7-[rhamnosyl-(1->2)-galacturonide]	14309754	Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)C(=O)O)O)O)O)O)O	592.50	unknown	https://doi.org/10.1016/S0031-9422(00)97838-5
beta-D-Galactopyranosiduronic acid, 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-	101428062	Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)C(=O)O)O)O)O)O)O	592.50	unknown	https://doi.org/10.1016/S0031-9422(00)97838-5
ethyl (2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylate	162938092	Click to see CCOC(=O)C1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=CC3=O)C4=CC=C(C=C4)O)O)O)O)O	474.40	unknown	https://doi.org/10.1016/S0031-9422(00)97838-5
ethyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[8-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylate	162873581	Click to see CCOC(=O)C1C(C(C(C(O1)OC2=C(C3=C(C=C2)C(=O)C=C(O3)C4=CC=C(C=C4)O)O)O)O)O	474.40	unknown	https://doi.org/10.1016/S0031-9422(00)97838-5
Ethyl 3,4,5-trihydroxy-6-[8-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylate	162873580	Click to see CCOC(=O)C1C(C(C(C(O1)OC2=C(C3=C(C=C2)C(=O)C=C(O3)C4=CC=C(C=C4)O)O)O)O)O	474.40	unknown	https://doi.org/10.1016/S0031-9422(00)97838-5
> Phenylpropanoids and polyketides / Flavonoids / Flavonoid glycosides / Flavonoid O-glycosides / Flavonoid-7-O-glycosides
5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one	44257792	Click to see C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O	432.40	unknown	https://doi.org/10.1016/S0031-9422(00)97838-5
Apigenin 7-galactoside	44257799	Click to see C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O	432.40	unknown	https://doi.org/10.1016/S0031-9422(00)97838-5
Apigetrin	5280704	Click to see C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O	432.40	unknown	https://doi.org/10.1055/S-2006-962330 https://doi.org/10.1016/S0031-9422(00)97838-5
kaempferol 7-O-glucoside	10095180	Click to see C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O	448.40	unknown	https://doi.org/10.1055/S-2006-962330
Luteolin 7-O-glucoside	5280637	Click to see C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O	448.40	unknown	https://doi.org/10.1055/S-2006-962330
> Phenylpropanoids and polyketides / Flavonoids / O-methylated flavonoids / 3-O-methylated flavonoids
(2R)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-2,3-dihydrochromen-5-olate	25200448	Click to see COC1=C(C=CC(=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)[O-])O	301.27	unknown	via CMAUP database
4',5-Dihydroxy-3'-methoxyflavon-7-olate(1-)	25203524	Click to see COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O)[O-]	299.25	unknown	via CMAUP database
> Phenylpropanoids and polyketides / Flavonoids / O-methylated flavonoids / 8-O-methylated flavonoids
5-Hydroxy-3',4',7,8-tetramethoxyflavone	9950661	Click to see COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)OC)OC)OC	358.30	unknown	via CMAUP database
5-Hydroxy-7,8,4'-trimethoxyflavone	14353376	Click to see COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)OC)OC	328.30	unknown	via CMAUP database

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Silybum marianum

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