A narrative review of phytochemical profile of Saffron and principal crocetin glycosides
Review Article

A narrative review of phytochemical profile of Saffron and principal crocetin glycosides

Nguyen Huu Tung1^, Nguyen Ngoc Hieu1, Vu Van Tuan1, Yukihiro Shoyama2

1Faculty of Pharmacy, PHENIKAA University, Hanoi, Vietnam; 2Faculty of Pharmaceutical Sciences, Nagasaki International University, Nagasaki, Japan

Contributions: (I) Conception and design: NH Tung, Y Shoyama; (II) Administrative support: Y Shoyama; (III) Provision of study materials or patients: NH Tung, NN Hieu, VV Tuan; (IV) Collection and assembly of data: All authors; (V) Data analysis and interpretation: All authors; (VI) Manuscript writing: All authors; (VII) Final approval of manuscript: All authors.

^ORCID: 0000-0001-6005-9280.

Correspondence to: Nguyen Huu Tung, PhD/Assoc. Prof. Faculty of Pharmacy, PHENIKAA University, Hanoi, Vietnam. Email: tung.nguyenhuu@phenikaa-uni.edu.vn.

Background and Objective: The medicinal plant Crocus sativus L. is widely cultivated to give the dried red stigmas, known as saffron, which is very famous and costly in the world. To date, phytochemical database of saffron contains more than 150 volatile and non-volatile compounds, in which crocetin glycosides or crocin represents as one of three major components (safranal, picrocrocin, and crocin) and defined the saffron quality. The natural product chemistry of the crocin has been extensively studied and reported in the literature. This review aims to summarize and discuss on chemical profile of saffron with focus on the principal composition of the title material, the crocetin glycoside.

Methods: The information in this review has been collected from the electronic scientific database [PubMed and Dictionary of Natural Products (DNP)] and a summary was provided in the form of tables.

Key Content and Findings: In this narrative review, we first outlined the phytochemical profile of saffron, then mainly focused on the crocetin glycosides in the viewpoints of structure, biosynthesis, qualitative and quantitative analyses, biodiversity and chemotaxonomy. The biosynthesis of crocin has been thoroughly proven and found to be related with picrocrocin and safranal. Additionally, the crocin component represents the impact meaning in chemotaxonomy of Crocus genus. The recent advantage of modern hyphenated chromatographic technique suggested new crocetin glycosides.

Conclusions: Saffron is one of the most medicinal materials in the World from its comprehensive health benefit for prevention and treatment of certain diseases. Phytochemistry of saffron and crocin with potential of new analog remains highly attractive and the number of publications has been timely increasing. The crocin has been indexed for standardization and quality of saffron and be potential for phytotherapy and drug development.

Keywords: Crocus sativus; saffron; crocetin; crocetin glycoside; crocin

Received: 11 December 2021; Accepted: 04 July 2022; Published: 30 September 2022.

doi: 10.21037/lcm-21-70


Crocus sativus L. (Iridaceae), well-known native to the eastern Mediterranean-Europe and western Asia region, is a perennial stemless herb that is widely cultivated in many temperate countries including Spain, Greece, Turkey, Iran, India, China, and Japan (1,2) (Figure 1). The massive cultivation of C. sativus is timely developed to produce such the well-known and costly spice “red gold”, called saffron as stigmas of its flower. Since saffron has unique color, aroma, and taste, it is widely used as a spice, coloring and flavoring agent in food and cosmetic products. In addition, it displays a variety of health benefits and has been used in both traditional and modern medicines (3,4).

Figure 1 Field cultivation in Spain (left) and indoor cultivation in Japan (right) of Crocus sativus L.

Phytochemical components of saffron have been extensively reported (5-8), in which safranal, picrocrocin, and crocetin glycosides (crocin) are major components and responsible for typical bitter taste, spicy aroma, and red color, respectively (Figure 2). Crocetin glycosides such as crocins 1–4 are dominated non-volatile components and be marker compounds for quality control and standardization of saffron (5). In addition, the other aspects of natural product chemistry of the crocin such as chemical structure, biosynthesis, and biodiversity have been investigated and reported (6-8). This review then will be focused on the crocetin glycosides as the principal composition of the title material under the viewpoint of natural product chemistry.

Figure 2 The three principal components of saffron.

We present the following article in accordance with the Narrative Review reporting checklist (available at https://lcm.amegroups.com/article/view/10.21037/lcm-21-70/rc).


This narrative review consists of a PubMed search of English publication up to date of January 2022. The keywords used for the search were consecutively: “saffron and crocin OR Crocus and crocin”. This first step released 227 articles. Then, manual screening of the 11 words cited above in Table 1 referring to saffron and crocin were realized for the 227 articles. Sixty articles were ultimately used, as listed in the references.

Table 1

The search strategy summary

Items Specification
Date of search October 2021
Database and other sources searched PubMed
Search term used Search terms: saffron and crocin OR Crocus and crocin
Timeframe Before October 2021
Inclusion criteria Inclusion criteria:
(I) Article languages: English
(II) Article types: all
(III) Articles only relates to saffron or crocetin structure (manual screening of the following words in the abstracts or the whole articles: saffron, Crocus sativus, crocin, crocetin, safranal, picrocrocin, structure, NMR, spectroscopic data, analysis, biosynthesis, pharmacological activity
Selection process NH Tung, NN Hieu, and VV Tuan conducted the selection together

Phytochemical profile of saffron

Principal components

Since first phytochemical report on saffron by Zarghami in 1971 (6), together with development and advancement of chromatography, the phytochemical profile of saffron has been very attractive to Worldwide natural product chemists and being studied in detail and, to date, reveal the occurrence of totally more than 150 volatile and non-volatile compounds (7). In which, there are about 60 constituents have been identified by conventional isolation and structural elucidation. The volatiles consist of more than 40 components that are mainly monoterpenes, their alcohol and ester derivatives, of which, safranal (2,6,6-trimethyl-1,3-cyclohexadiene-1-carboxaldehyde, 60-70% of the volatiles) is the main component. Non-volatile components include crocetin, crocin, picrocrocin and flavonoid. The detailed all the compounds from saffron is listed in the interesting review article by Mykhailenko et al. (8).

Being well documented and notably, crocin is the unique water water-soluble carotenoids found in the title material and the primary component responsible for the red color of saffron. Chemically, crocin is a series of compounds that are glycosyl esters of crocetin are the major components of saffron (9,10). The quantitative study revealed the main crocins including crocin-1, crocin-2, crocin-3 and crocin-4 as shown in Table 2 and Figure 3 (12-15). The detailed outline and insight discussion on their structure, spectroscopic data, distribution, and so on will be addressed mainly in the main following section.

Table 2

Three principal components of saffron

Compounds Chemical name Molecular formula, molecule weight Weight content (%, wt/wt) Reference
Safranal 2,6,6-trimethyl-1,3-cyclohexadiene-1-carboxaldehyde C10H14O, 150 0.24/1.0 (5,7,8)
Picrocrocin 4-(β-D-glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexene-1-carbaldehyde C16H26O7, 330 7.0/16.0 (5,7,8)
Crocin (crocin 1–4) Crocetin esters e.g., crocin 1–4: Crocetin di-(β-D-gentiobiosyl) ester C44H64O24, 976 16.0/30.0; 6.4/18.0 (crocin–4) (5,7,8)
Figure 3 HPLC chromatogram of the saffron sample indoor cultivation in Japan (11). Number to peak identity: 1 (crocin-4), 2 (crocin-3), 3 (crocin-2), and 4 (crocin-1).

Picrocrocin is glycosylated form of safranal and chemically different from crocin but in the viewpoint of biosynthesis, the biosynthesis pathways of three principal components of saffron have been established and relatively from the same precursor of zeaxanthin (16,17). Figure 4 showed the brief biosynthesis pathway with the key intermediate and precursor (18).

Figure 4 The biosynthesis pathway of the main secondary metabolites in Saffron (C. sativus).

The profile of crocin, picrocrocin and safranal contributes to quality control of saffron (19,20) and it has been suggested that the best quality saffron should contain about more than 20% crocin, 5% picrocrocin, and 0.5% safranal (21).

Crocetin and its glycosides

Crocins are crocetin glycosides, in which structure variation depends on the sapogenin backbone of crocetin (C20H24O4; MW: 328.4 g/mol) and, mainly, the terminal sugar chains (glucose, gentibiose, and neapolitanose) (8). Crocetin framework inheriting from zeaxanthin in the proven biosynthesis pathway with a long chain of conjugated carbon-carbon (seven conjugated double bond and two terminal carbonyl function, 4 side-chain methyl groups) is relatively unstable with temperature, oxidants, UV radiation, and pH condition resulting fragmentation of certain double bond of polyene backbone other than variable functional groups. The long-conjugated system of the crocetin backbone makes the crocins appear in red color and can be detected by UV-VIS spectra (characteristic maxima VIS absorbance in the range 400–500 nm), which are helpful in both qualitative and quantitative analyses. In addition, the stereochemistry of crocetin and crocins is only from conformation of double bond and highly oriented in one form, whether cis or trans and, normally, the trans-form is more stable than the cis-form. The cis/trans conformation make influence on their conjugated systems and results in their different UV-VIS spectra at secondary peak beside the characteristic peaks, the cis isomer gives a single peak between 320 and 340 nm and, in case of all-trans isomer, the secondary peak is at ca 256 nm. As shown in Table 3 and Figure 5, since first crocins were isolated in 1975 (30) and then structurally identified in 1982 (24), up to date, there have been 22 compounds including crocetin and crocin derivatives reported from saffron from noteworthy investigation of Speranza in 1984 (31), Tarantilis in 1995 (21), Carmona in 2006 (26), Dufresne in 1999 (11), Shoyama in 2013 (32), and Llorens in 2015 (12), respectively. Among them, four main crocin pigments (crocin-1, crocin-2, crocin-3, and cocin-4), named according to the number of sugar unit in their respective molecules along with minor components of α,β-carotenes, lycopene, zeaxanthin, phytoene, phytofluene, (4R)-4-hydroxy-3,5,5-trimethylcyclohex-2-enone 4-O-β-D-glucopyranoside, (4S)-4-hydroxy-3,5,5-trimethylcyclohex-2-enone 4-O-β-D-glucopyranoside, (4S)-4-(hydroxymethyl)-3,5,5-trimethylcyclohex-2-enone 4-O-β-D-glucopyranoside, and β-D-gentiobiosyl ester of 2-methyl-6-oxohepta-2,4-dienoic acid, respectively (30,33). In our previous study on saffron by dark cultivation in Japan, it is noteworthy that a unique minor crocetin glycoside was isolated and identified as trans-crocetin 1-al 1ʹ-O-β-gentiobiosyl ester based on the extensive chemical and spectroscopic evidence (Figure 6) (33). Table 4 summarizes the NMR data of the typical crocins from the original research (32-35) for forthcoming references. In term of the NMR spectroscopic data, since the structure of crocetin and the crocins are highly symmetric, the NMR signals appears whether in couples or integrated peaks. The 13C NMR spectra display even number of peaks at the range of ẟ 120–150 ppm for olefinic double bonds and, especially, two downfield signals at ẟ 165–190 ppm accounting for two terminal carbonyl carbons. It becomes evident that the relative downfield shift of the carbonyl carbon discriminates the carbonyl functions (ester, carboxylic acid, aldehyde) (32-35).

Table 3

Crocetin and crocin derivatives of saffron

No. Chemical structure Chemical name Molecular formula, molecule weight (amu) Configuration/isomer (cis/trans) References
1 R1 = R2 = H 2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid (Crocetin) C20H24O4, 328 Cis/trans (22,23)
2 R1 = H Crocetin 1-β-D-glucopyranosyl ester (crocin-1) C26H34O9, 490 Cis/trans (21,23)
R2 = Glc
3 R1 = H Crocetin 1-β-D-gentiobiosyl ester (crocin-2) C32H44O14, 652 Cis/trans (21,24)
R2 = Gtb
4 R1 = Glc Crocetin 1-β-D-glucopyranosyl 1ʹ-β-D-gentiobiosyl ester (crocin-3) C38H54O19, 814 Cis/trans (21,25,26)
R2 = Gtb
5 R1 = Gtb Crocetin 1,1ʹ-di-β-D-gentiobiosyl ester (crocin-4) C44H64O24, 976 Cis/trans (21,25,26)
R2 = Gtb
6 R1 = Me Crocetin β-D-glucopyranosylmethyl ester C27H36O9, 504 Trans (27,28)
R2 = Glc
7 R1 = Me Crocetin dimethyl ester C22H28O4, 356 Trans (23,28)
R2 = Me
8 R1 = Gtb(Ac)7 Crocetin di-(2,3,4,8,9,10,12-hepta-O-acetyl-β-D-gentiobiosyl)-ester C72H92O38, 1,424 Trans (24)
R2 = Gtb(Ac)7
9 R1 = Glc(Ac)4 Crocetin di-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) ester C60H80O32, 1,232 Trans (24)
R2 = Glc(Ac)4
10 R1 = Glc(6-1)Glc(6-1)Glc Crocetin-(tri-β-D-glucopyranosyl)-(β-D-gentiobiosyl) ester C50H74O29, 1,138 Cis/trans (26,27)
R2 = Gtb
11 R1 = Glc Crocetin di-(β-D-glucopyranosyl) ester C32H44O14, 652 Cis/trans (21,24,26)
R2 = Glc
12 R1 = Npt Crocetin (β-D-neapolitanosyl)-(β-D-gentiobiosyl) ester C50H74O29, 1,138 Cis/trans (21,26,29)
R2 = Gtb
13 R1 = Npt Crocetin (β-D-neapolitanosyl)-(β-D-glucopyranosyl) ester C44H64O24, 976 Cis/trans (26)
R2 = Glc
Figure 5 The chemical structures of crocetin derivatives.
Figure 6 The structure of trans-crocetin 1-al 1ʹ-O-β-gentiobiosyl ester.

Table 4

C13 NMR data for principle crocins (crocins 1–4) and crocetin 1-al 1ʹ-O-β-gentiobiosyl ester

Position Crocin-1 Crocin-2 Crocin-3 Crocin-4 Crocetin 1-al 1ʹ-O-β-gentiobiosyl ester
Crocetin moiety
   8 166.7 166.6 166.7 166.7 168.6
   9 127.5 127.5 125.8 125.6 126.1
   10 140.3 140.3 140.4 140.4 142.0
   11 124.7 124.6 124.4 124.3 124.3
   12 145.0 145.0 145.1 145.0 146.6
   13 137.4 137.3 137.4 137.4 139.8
   14 136.5 136.4 136.5 136.5 139.3
   15 132.5 132.5 132.5 132.5 135.7
   19 13.0 12.9 13.2 13.1 13.0
   20 13.0 12.9 13.1 13.0 12.8
   8ʹ 169.6 169.5 166.7 166.7 189.6
   9ʹ 125.7 125.6 125.8 125.6 141.9
   10ʹ 138.5 138.5 140.4 140.4 148.7
   11ʹ 124.2 124.2 124.4 124.3 123.4
   12ʹ 143.7 143.7 145.1 145.0 145.8
   13ʹ 137.1 137.1 137.4 137.4 137.7
   14ʹ 135.7 135.7 136.5 136.5 137.1
   15ʹ 132.0 132.0 132.5 132.5 135.3
   19ʹ 13.3 13.2 13.2 13.1 12.7
   20ʹ 13.1 13.0 13.1 13.0 14.5
Sugar moiety
   1ʺ 95.0 95.0 95.1 95.0 96.0
   2ʺ 73.0 72.9 72.9 72.9 75.1
   3ʺ 76.9 76.7 77.4 77.3 77.9
   4ʺ 70.0 69.7 69.7 69.7 71.0
   5ʺ 78.3 78.3 78.3, 77.3 77.2 78.0
   6ʺ 61.0 68.4 68.4, 61.0 68.2 69.5
   1ʹʺ 103.5 103.6 103.5 104.6
   2ʹʺ 73.9 73.9 73.9 74.0
   3ʹʺ 77.2 77.4 77.3 77.9
   4ʹʺ 70.4 70.0 70.4 71.5
   5ʹʺ 77.3 76.8 76.7 78.8
   6ʹʺ 61.4 61.4 61.4 62.7

Quantitatively, standard saffron contain total crocin content not less than 16% but some saffron were reported to be more than 20% crocins with crocin-4 up to 16% (36,37). Furthermore, the chemical fingerprint of individual crocins in saffron have been studied by various colorimetric (38,39) and chromatography techniques (HPTLC, HPLC, UPLC…) (40-44), especially modern hyphenated, GC-MS, FTIR, LC-MS and LC-MS-NMR methods (45-48), so that minor compounds and trace components have been identified. Recently, Aiello and co-workers reported a LC-MALDI MS method for fingerprinting and quantitative analysis of saffron and revealed occurrence of potential and not reported crocetin esters with long sugar chains of four-to-seven sugar units, molecular weight up to 1800 amu in advance (49). These findings are consistent with the biosynthesis pathway of crocin and support variation in biosynthesis as well as potential of new crocin derivative in saffron and Crocus genus.

Under viewpoint of chemotaxonomy, accumulating data shows that crocetin and its glycosides have been occurred in very few medicinal plants including Crocus genus of Iridaceae [C. sativus, C. neapolitanus (50), C. speciosus, C. luteus (51)], Gardenia jasminoides (Rubiaceae) (34,35), Arctium lappa (Asteraceae) (52,53), Mimosa pudica (Leguminosae) (54), Buddleja officinalis (Loganiaceae) (55), Stemona japonica (Stemonaceae) (56), Nyctanthes arbor-tristis (Oleaceae) (57), Jacquinia angustifolia (58), Coleus forskolii (59), and Artocarpus heterophyllus (60), respectively. Of which, the saffron and the fruit of G. jasminoides are most dominated in contents of crocetin and various crocetin glycosides. In the title herb of C. sativus, crocetin and crocetin glycosides are only found in the saffron. So that, crocetin and certain its glycosides contribute impact meaning in chemotaxonomy of Crocus species and others.


Saffron is the well-known traditional medicinal herb and potential application in the modern medicine based on its scientific database, especially the phytochemical profile. This brief review as updating due time and, once again, further supports that crocin is the principal content and defined the saffron quality. In addition, the potential of new crocin have been evidenced by chromatographic fingerprint and need to be more studied.


Funding: None.


Provenance and Peer Review: This article was commissioned by the editorial office, Longhua Chinese Medicine for the series “Multifunctional Saffron”. The article has undergone external peer review.

Reporting Checklist: The authors have completed the Narrative Review reporting checklist. Available at https://lcm.amegroups.com/article/view/10.21037/lcm-21-70/rc

Conflicts of Interest: All authors have completed the ICMJE uniform disclosure form (available at https://lcm.amegroups.com/article/view/10.21037/lcm-21-70/coif). The series “Multifunctional Saffron” was commissioned by the editorial office without any funding or sponsorship. YS served as the unpaid Guest Editor of the series. The authors have no other conflicts of interest to declare.

Ethical Statement: The authors are accountable for all aspects of the work in ensuring that questions related to the accuracy or integrity of any part of the work are appropriately investigated and resolved.

Open Access Statement: This is an Open Access article distributed in accordance with the Creative Commons Attribution-NonCommercial-NoDerivs 4.0 International License (CC BY-NC-ND 4.0), which permits the non-commercial replication and distribution of the article with the strict proviso that no changes or edits are made and the original work is properly cited (including links to both the formal publication through the relevant DOI and the license). See: https://creativecommons.org/licenses/by-nc-nd/4.0/.


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doi: 10.21037/lcm-21-70
Cite this article as: Tung NH, Hieu NN, Tuan VV, Shoyama Y. A narrative review of phytochemical profile of Saffron and principal crocetin glycosides. Longhua Chin Med 2022;5:28.

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