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Sapindus mukorossi Gaertn., also called the washnut, is a tropical tree of the Sapindaceae family. The plant owes its name to its cleaning and washing properties used by the local population as a natural detergent. The most important ingredients of the plant are triterpenoid saponins contained in many parts of the plant, inducing fruits, galls, or roots. The tree also contains other valuable, biologically active compounds that are obtained by extraction methods. Raw or purified extract and isolated saponins are valuable plant products that can be used in the food, pharmaceutical, cosmetic, and chemical industries.
No. | Chemical Name | Abbreviations | Type | Ref. |
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1 | 3β,7β,20(S),22-tetrahydroxydammar-24-ene-3-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside | R1: -Glc2 a-Rha b R2: -CH3 R3: -OH R4: -OH R5: -H |
Dammarane | [41] |
2 | 3β,7β,20(S),22,23-pentahydroxydammar-24-ene-3-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside | R1: -Glc2-Rha R2: -CH3 R3: -OH R4: -OH R5: -OH |
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3 | 3β,7β,20(S),22,25-pentahydroxydammar-23-ene-3-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside | R1: -Glc2-Rha R2: -OH R3: -OH |
Dammarane | [41] |
4 | 25-methoxy-3β,7β,20(S),22-tetrahydroxydammar-23-ene-3-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside | R1: -Glc2-Rha R2: -OH R3: -OCH3 |
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5 | 25-methoxy-3β,7β,20(R)-trihydroxydammar-23-ene-3-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside | R1: -Glc2-Rha R2: -H R3: -OCH3 |
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6 | 21β-methoxy-3β,21(S),23(R)-epoxytirucalla-7,24-diene-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside | R1: -Glc6-Rha R2: β-OCH3 R3: β-H |
Tirucallane | [40] |
7 | 21α-methoxy-3β,21(S),23(R)-epoxytirucalla-7,24-diene-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside | R1: -Glc6-Rha R2: α-OCH3 R3: β-H |
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8 | 21α-methoxy-3β,21(R),23(R)-epoxytirucalla-7,24-diene-3-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside | R1: -Glc2-Rha R2: α-OCH3 R3: β-H |
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9 | 21β-methoxy-3β,21(S),23(R)-epoxytirucalla-7,24-diene-3-O-α-l-dirhamnopyranosyl-(1→2,6)-β-d-glucopyranoside | R1: -Glc2,6-Rha,Rha R2: β-OCH3 R3: β-H |
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10 | 21α-methoxy-3β,21(R),23(R)-epoxytirucalla-7,24-diene-3-O-α-l-dirhamnonopyranosyl-(1→2,6)-β-d-glucopyranoside | R1: -Glc2,6-Rha,Rha R2: α-OCH3 R3: β-H |
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11 | Hederagenin-3-O-(3-O-acetyl-α-l-arabinopyranosyl)-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Ara3 c-OAc R2: -CH2OH R3: -H |
Oleanane | [38] |
12 | Hederagenin-3-O-(4-O-acetyl-α-l-arabinopyranosyl)-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Ara4-OAc R2: -CH2OH R3: -H |
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13 | Hederagenin-3-O-(2,3-O-diacetyl-β-d-xylopyranosyl)-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Xyl2,3 d-OAc,OAc R2: -CH2OH R3: -H |
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14 | Hederagenin-3-O-(2,4-O-diacetyl-β-d-xylopyranosyl)-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Xyl2,4-OAc,OAc R2: -CH2OH R3: -H |
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15 | 3,7,20(S)-trihydroxydammar-24-ene-3-O-α-l-rhamnopyrnosyl-(1→2)-β-d-glucopyranoside | R1: -Glc2-Rha R2: -OH R3: -CH3 R4: -H R5: -H |
Dammarane | [38] |
16 | 3,7,20(R)-trihydroxydammar-24-ene-3-O-α-l-rhamnopyrnosyl-(1→2)-β-d-glucopyranoside | R1: -Glc2-Rha R2: -CH3 R3: -OH R4: -H R5: -H |
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17 | 21α-methoxy- 3β,21(R),23(S)-epoxytirucall-7,24-diene-3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside | R1: -Glc2-Glc R2: α-OCH3 R3: β-H |
Tirucallane | [39] |
18 | 21α-methoxy-3β,21(R),23(S)-epoxytirucall-7,24-diene-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside | R1: -Glc2-Glc6-Rha R2: α-OCH3 R3: β-H |
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19 | Hederagenin-3-O-(3,4-O-di-acetyl-β-d-xylopyranosyl)-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Xyl3,4-OAc,OAc R2: -CH2OH R3: -H |
Oleanane | [38] |
20 | Hederagenin-3-O-(2-O-acetyl-β-d-xylopyranosyl)-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Xyl2-OAc R2: -CH2OH R3: -H |
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21 | Hederagenin-3-O-(3-O-acetyl-β-d-xylopyranosyl)-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Xyl3-OAc R2: -CH2OH R3: -H |
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22 | Hederagenin-3-O-(4-O-acetyl-β-d-xylopyranosyl)-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Xyl4-OAc R2: -CH2OH R3: -H |
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23 | Hederagenin-3-O-α-l-arabinopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Ara R2: -CH2OH R3: -H |
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24 | 21β-methoxy-3β,23α-epoxytirucalla-7,24-diene-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside | R1: -Glc6-Rha R2: β-OCH3 R3: α-H |
Tirucallane | [42] |
25 | 21β-methoxy-3β,23α-epoxytirucalla-7,24-diene-3-O-α-l-dirhamnopyranosyl-(1→2,6)-β-d-glucopyranoside | R1: -Glc2,6-Rha,Rha R2: β-OCH3 R3: α-H |
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26 | 21α-methoxy-3β,23α-epoxytirucalla-7,24-diene-3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucopyranoside | R1: -Glc2,3-Rha,Ara R2: α-OCH3 R3: α-H |
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27 | 21α-methoxy-3β,23α-epoxytirucalla-7,24-diene-3-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside | R1: -Glc2-Rha R2: α-OCH3 R3: α-H |
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28 | 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucopyranosyl-21,23R-epoxyl tirucall-7,24R-diene-3β,21-diol | R1: -Glc2,3-Rha,Ara R2: -OH |
Tirucallane | [44] |
29 | 3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranosyl-21,23R-epoxyl tirucall-7,24R-diene-3β,21-diol | R1: -Glc6-Rha R2: -OH |
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30 | 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucopyranosyl (21,23R)-epoxyl tirucalla-7,24-diene-(21S)-ethoxyl-3β-ol | R1: -Glc2,3-Rha,Ara R2: -OCH2CH3 |
Tirucallane | [45] |
31 | 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucopyranosyl (21,23R)-epoxyl tirucall-7,24-diene-(21S)-methoxyl-3β-ol | R1: -Glc2,3-Rha,Ara R2: -OCH3 |
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32 | 3-O-α-l-arabinopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucopyranosyl-21,23R-epoxyl tirucalla-7,24-diene-21β-ethoxy-3β-ol | R1: -Glc2,3-(Rha3-Ara),Ara R2: -OCH2CH3 |
Tirucallane | [43] |
33 | 3-O-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-[β-l-arabinopyranosyl-(1→3)]-β-d-glucopyranosyl-21,23R-epoxyl tirucalla-7,24-diene-21β-ethoxy-3β-ol | R1: -Glc2,3-(Rha3-Xyl),Ara R2: -OCH2CH3 |
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34 | 3-O-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucopyranosyl-21,23R-epoxyl tirucalla-7,24-diene-21β-methoxy-3β-ol | R1: -Glc2,3-(Rha3-Xyl),Ara R2: -OCH3 |
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35 | 3-O-α-l-arabinopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-[α-l- rhamnopyranosyl-(1→3)]-β-d-glucopyranosyl-21,23R-epoxyl tirucalla-7,24-diene-21β-ethoxy-3β-ol | R1: -Glc2,3-(Rha3-Ara),Rha R2: -OCH2CH3 |
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36 | 3-O-α-l-arabinopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→3)]-β-d-glucopyranosyl-21,23R-epoxyl tirucalla-7,24-diene-21β-methoxy-3β-ol | R1: -Glc2,3-(Rha3-Ara),Rha R2: -OCH3 |
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37 | 3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranosyl-21,23R-epoxyl tirucalla-7,24-diene-21β-ethoxyl-3β-ol | R1: -Glc6-Rha R2: -OCH2CH3 |
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38 | Hederagenin-3-O-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl-28-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl ester | R1: -Ara2-Rha3-Xyl R2: -CH2OH R3: -Glc2-Glc |
Oleanane | [47] |
39 | Hederagenin-3-O-α-l-arabinopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl-28-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl ester | R1: -Ara2-Rha3-Ara R2: -CH2OH R3: -Glc2-Glc |
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40 | Hederagenin-3-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl-28-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl ester | R1: -Ara2-Rha R2: -CH2OH R3: -Glc2-Glc |
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41 | Hederagenin-3-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha R2: -CH2OH R3: -H |
Oleanane | [49] |
42 | Hederagenin-3-O-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Xyl R2: -CH2OH R3: -H |
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43 | Hederagenin-3-O-β-d-glucopyranosyl-(1→4)-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Xyl4-Glc R2: -CH2OH R3: -H |
Oleanane | [50] |
44 | Hederagenin-3-O-β-d-glucopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranosyl-(1→4)-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Xyl4-Glc2,6-Glc,Rha R2: -CH2OH R3: -H |
Oleanane | [51] |
45 | Hederagenin-3-O-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl-28-O-β-d-glucopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranosyl-(1→4)-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosy-(1→2)-α-l-arabinopyranosyl ester | R1: -Ara2-Rha3-Xyl R2: -CH2OH R3: -Ara2-Rha3-Xyl4-Glc2,6-Glc,Rha |
Oleanane | [52] |
46 | Hederagenin-3-O-β-d-glucopyranosyl-(1→3)-β-d-xylopyranosyl-(1→3)- β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Xyl3-Xyl3-Glc R2: -CH2OH R3: -H |
Oleanane | [53] |
47 | Hederagenin-3-O-(3,4-O-diacetyl-α-l-arabinopyranosyl)-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Ara3,4-OAc,OAc R2: -CH2OH R3: -H |
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48 | 3-O-α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranosyl-(1→6)-β-d-glucopyranosyl-(1→3)-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl oleanolic acid | R1: -Ara2-Rha3-Xyl3-Glc6-Xyl2-Rha R2: -CH3 R3: -H |
Oleanane | [46] |
49 | Hederagenin 3-O-(2,4-O-di-acetyl-α-l-arabinopyranosyl)-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Ara2,4-OAc,OAc R2: -CH2OH R3: -H |
Oleanane | [54] |
50 | Hederagenin 3-O-α-l-arabinopyranoside | R1: -Ara R2: -CH2OH R3: -H |
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51 | Hederagenin-3-O-β-d-xylopyranosyl-(2→1)-[3-O-acetyl-α-l-arabinopyranosyl]-28-O-α-l-rhamnopyranosylester | R1: -Xyl2-Ara3-OAc R2: -CH2OH R3: -Rha |
Oleanane | [48] |
52 | Hederagenin 3-O-α-l-rhamnopyranosyl (3→1)-[2,4-O-diacetyl-α-l-arabinopyranosyl]-28-O-β-d-glucopyranosyl-(2→1) [3-O-acetyl-β-d-glucopyranosyl] ester | R1: -Rha3-Ara2,4-OAc,OAc R2: -CH2OH R3: -Glc2-Glc3-OAc |
Oleanane | [55] |
53 | Oleanolic acid 3-O-α-l-arabinofuranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Ara e R2: -CH3 R3: -H |
Oleanane | [22] |
54 | Hederagenin 3-O-5‴-O-acetyl-α-l-arabinofuranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Ara5 e-OAc R2: -CH2OH R3: -H |
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55 | 23-O-acetyl-hederagenin 3-O-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Xyl R2: -CH2OAc R3: -H |
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56 | Gypsogenin 3-O-α-l-arabinopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Ara R2: -CH2O R3: -H |
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57 | Betulinic acid 3-O-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Xyl | Lupane | [22] |
58 | Hederagenin-3-O-β-d-glucopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Glc R2: -CH2OH R2: -H |
Oleanane | [36] |
59 | Hederagenin-3-O-α-l-rhamnopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Rha R2: -CH2OH R3: -H |
Oleanane | [36] |
60 | Hederagenin-3-O-β-d-xylopyranosyl-(1→3)-α-l-arabinopyranoside | R1: -Ara2-Xyl R2: -CH2OH R3: -H |
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61 | Hederagenin-3-O-(4-O-acetyl-β-d-glucopyranosyl)-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Glc4-OAc R2: -CH2OH R3: -H |
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62 | 3-O-β-d-glucopyranosyl-(1→2)-α-l-rhamnopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl oleanolic acid | R1: -Glc2-Rha3-Rha2-Glc R2: -CH3 R3: -H |
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63 | 3-O-β-d-xylopyranosyl-(1→2)-α-l-rhamnopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl oleanolic acid | R1: -Glc2-Rha3-Rha2-Xyl R2: -CH3 R3: -H |
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64 | Oleanolic acid 3-O-(4-O-acetyl-α-l-arabinopyranosyl)-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Ara4-OAc R2: -CH3 R3: -H |
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65 | Gypsogenin 3-O-α-l-rhamnopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Rha R2: -CHO R3: -H |
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66 | Oleanolic acid 3-O-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Xyl R2: -CH3 R3: -H |
Oleanane | [22] |
67 | Oleanolic acid 3-O-α-l-arabinopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside | R1: -Ara2-Rha3-Ara R2: -CH3 R3: -H |