Cucurbitane

Cucurbitane
Names
	IUPAC name 19-Nor-5ξ,9β,10α-lanostane
	Systematic IUPAC name (1R,3aS,3bR,5aΞ,9aR,9bS,11aR)-3a,6,6,9b,11a-Pentamethyl-1-[(2R)-6-methylheptan-2-yl]hexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
CAS Number	65441-59-0 (5α/β) ;
3D model (JSmol)	(5α): Interactive image; (5β): Interactive image;
ChEBI	CHEBI:73245 ;
ChemSpider	25936933 (5α) ; 28639243 (5β) ;
PubChem CID	71306377;
UNII	VQU8QE865A ;
CompTox Dashboard (EPA)	DTXSID50745373 ;
	InChI InChI=1S/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24-,25-,26-,28+,29-,30+/m1/s1 Key: ZYZJWAJOTPNVPI-AUAIAXQGSA-N ; (5α): InChI=1/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24-,25-,26-,28+,29-,30+/m1/s1 Key: ZYZJWAJOTPNVPI-AUAIAXQGBW; (5β): InChI=1/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25-,26-,28+,29-,30+/m1/s1 Key: ZYZJWAJOTPNVPI-QJMYWHNVBB; (5β): InChI=1S/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25-,26-,28+,29-,30+/m1/s1 Key: ZYZJWAJOTPNVPI-QJMYWHNVSA-N;
	SMILES (5α): C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2(C)[C@]3([H])CC[C@@]4([H])C(C)(C)CCC[C@@]4([H])[C@]3(C)CC[C@@]21C; (5β): C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2(C)[C@]3([H])CC[C@]4([H])C(C)(C)CCC[C@@]4([H])[C@]3(C)CC[C@@]21C;
Properties
Chemical formula	C30H54
Molar mass	414.762 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Cucurbitane is a class of tetracyclic chemical compounds with formula C
₃₀H
₅₄ (CAS number 65441-59-0). It is a polycyclic hydrocarbon, specifically triterpene. It is also an isomer of lanostane (specifically 19(10→9β)-abeolanostane), from which it differs by the formal shift of a methyl group (carbon number 19) from the 10 to the 9β position in the standard steroid numbering scheme.^[1]^[2]

The name is applied to two stereoisomers, distinguished by the prefixes 5α- and 5β-, which differ by the handedness of the bonds at a particular carbon atom (number 5 in the standard steroid numbering scheme).^[1]

5α-Cucurbitane
5β-Cucurbitane

Derivatives

Natural compounds

Compounds with the basic cucurbitane skeleton are found in many plants, and some are important phytopharmaceuticals.^[3] Natural cucurbitane-related compounds include:

Named

Balsaminapentaol, from Momordica balsamina.^[4]
Balsaminol A, from Momordica balsamina.^[4]
Balsaminol B, from Momordica balsamina.^[4]
Brydioside A from Bryonia dioica^[3]^: 64
Bryoamaride and derivatives from Bryonia dioica^[3]^: 65, 66
Charantin or foetidin, from Momordica charantia^[5] and Momordica foetida^[6]
Charantosides I-VIII, from Momordica charantia.^[7]
Cucurbalsaminol B, from Momordica balsamina.^[4]
Cucurbalsaminol A, from Momordica balsamina.^[4]
Cucurbitacins A-L, O-T^[3]^[8]^[9]^: 3–8
Datiscosides, from Datisca glomerata^[3]^: 16–19
Endecaphyllacins A and B, from roots of Hemsleya endecaphylla^[9]^: 1, 2
Hemslecins A and B, from roots of H. endecaphylla^[9]
Lepidolide, from the mushroom Russula lepida^[10]
Karavilagenin E, from Momordica balsamina.^[4]
Khekadaengosides A, B, D and K, from Trichosanthes tricuspidata^[3]^{: 57, 58, 67, 68}
Kuguacins A-S, from stems and leaves of Momordica charantia^[11]^[12]
Kuguaglycosides A-H, from the root of Momordica charantia^[13]
Mogrosides I-V, from the fruits of Siraitia grosvenorii^[14]
Momordicin I, II and 28, from Momordica charantia^[15]^[16]
Momordicines II and IV, from leaves of Momordica charantia^[17]
Momordicosides A-S, from Momordica charantia fruits^[7]^[18]^[19]
Neokuguaglucoside, from Momordica charantia fruits^[20]
Neomogroside, from the fruit of Siraitia grosvenorii.^[21]
Pentanorcucurbitacins A and B^[22]^: 1, 2
Perseapicroside A, from Persea mexicana^[3]^: 44
Scandenoside R9, from Hemsleya panacis-scandens^[3]^: 45
Spinosides A and B, from Desfontainia spinosa^[3]^: 61, 62

Unnamed

3β,7β,23ξ-trihydroxycucurbita-5,24-dien-19-al, soluble in chloroform, melts at 123−125 °C, from Momordica charantia, Momordica foetida.^[23]^: 1
3β,7β,25-trihydroxycucurbita-5,23-dien-19-al, soluble in chloroform, melts at 188−191 °C, from Momordica charantia, Momordica foetida^[23]^: 2
3β,7β-dihydroxy-25-methoxycucurbita-5,23-dien-19-al, soluble in chloroform, from Momordica charantia, Momordica foetida^[23]^: 3
5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β,19-diol, soluble in chloroform, melts at 182−184 °C, from Momordica foetida^[23]^: 4
5β,19-epoxycucurbita-6,23-dien-3β,19,25-triol, soluble in chloroform, from Momordica foetida^[23]^: 5
5β,19-epoxy-19-methoxycucurbita-6,23-dien-3β,25-diol, soluble in chloroform, melts at 102−104 °C, from Momordica charantia, Momordica foetida^[23]^: 6
5β,19-epoxy-19,25-dimethoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, from Momordica charantia, Momordica foetida^[23]^: 7
5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, melts at 139−141 °C, from Momordica charantia, Momordica foetida^[23]^: 8
19(R)-n-butanoxy-5β,19-epoxycucurbita-6,23-diene-3β,25-diol 3-O-β-glucopyranoside, C
₄₀H
₆₆O
₉, white powder soluble in methanol, from Momordica charantia fruit (8 mg/35 kg)^[18]^: 1
23-O-β-allopyranosylecucurbita-5,24-dien-7α,3β,22(R),23(S)-tetraol 3-O-β-allopyranoside,C
₄₂H
₆₉O
₁₄, white powder soluble in methanol, from Momordica charantia fruit (10 mg/35 kg)^[18]^: 2
23(R),24(S),25-trihydroxycucurbit-5-ene 3-O-{[β-glucopyranosyl(1→6)]-O-β-glucopyranosyl}-25-O-β-glucopyranoside, C
₄₈H
₈₂O
₁₉, white powder soluble in methanol, from Momordica charantia fruit (10 mg/35 kg)^[18]^: 3
2,16-dihydroxy-22,23,24,25,26,27-hexanorcucurbit-5-en-11,20-dione 2-O-β-D-glucopyranoside, soluble in ethanol, from Cucurbita pepo fruits (25 mg/15 kg)^[8]^: 3
16-hydroxy-22,23,24,25,26,27-hexanorcucurbit-5-en-11,20-dione 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside, white powder, soluble in ethanol, from Cucurbita pepo fruits (12 mg/15 kg)^[8]^: 4
7-methoxycucurbita-5,24-diene-3β,23(R)-diol, from Momordica balsamina^[24]
25,26,27-trinorcucurbit-5-ene-3,7,23-trione C
₂₇H
₄₀O
₃, white powder, soluble in methanol, from stems of Momordica charantia (6 mg/18 kg)^[22]^: 3

References

^ ^a ^b "The Nomenclature of Steroids — Revised Tentative Rules". European Journal of Biochemistry. 10: 1–19. 1969. doi:10.1111/j.1432-1033.1969.tb00650.x.
^ Satish Kumar and Raj Kumar (1991), Dictionary of Biochemistry. Anmol Publications, India
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Chen, J. C.; Chiu, M. H.; Nie, R. L.; Cordell, G. A.; Qiu, S. X. (2005). "Cucurbitacins and cucurbitane glycosides: Structures and biological activities". Natural Product Reports. 22 (3): 386–399. doi:10.1039/B418841C. PMID 16010347.
^ ^a ^b ^c ^d ^e ^f Ramalhete, C. T.; Mansoor, T. A.; Mulhovo, S.; Molnár, J.; Ferreira, M. J. U. (2009). "Cucurbitane-Type Triterpenoids from the African PlantMomordica balsamina". Journal of Natural Products. 72 (11): 2009–2013. doi:10.1021/np900457u. hdl:10884/1322. PMID 19795842.
^ Lolitkar, M. M.; Rao, M. R. Rajarama (1962). "Note on a Hypoglycaemic Principle Isolated from the fruits of Momordica charantia". Journal of the University of Bombay. 29: 223–224.
^ Olaniyi, A. A. (1975). "A neutral constituent of Momordica foetida". Lloydia. 38 (4): 361–362. PMID 1186439.
^ ^a ^b Akihisa, T.; Higo, N.; Tokuda, H.; Ukiya, M.; Akazawa, H.; Tochigi, Y.; Kimura, Y.; Suzuki, T.; Nishino, H. (2007). "Cucurbitane-Type Triterpenoids from the Fruits of Momordica charantia and Their Cancer Chemopreventive Effects". Journal of Natural Products. 70 (8): 1233–1239. doi:10.1021/np068075p. PMID 17685651.
^ ^a ^b ^c Wang, Da-Cheng; Pan, Hong-Yu; Deng, Xu-Ming; Xiang, Hua; Gao, Hui-Yuan; Cai, Hui; Wu, Li-Jun (2007). "Cucurbitane and hexanorcucurbitane glycosides from the fruits of Cucurbita pepo cv dayangua". Journal of Asian Natural Products Research. 9 (6): 525–529. doi:10.1080/10286020600782538. PMID 17885839. S2CID 27762659.
^ ^a ^b ^c Chen, J. C.; Zhang, G. H.; Zhang, Z. Q.; Qiu, M. H.; Zheng, Y. T.; Yang, L. M.; Yu, K. B. (2008). "Octanorcucurbitane and Cucurbitane Triterpenoids from the Tubers ofHemsleya endecaphyllawith HIV-1 Inhibitory Activity". Journal of Natural Products. 71 (1): 153–155. doi:10.1021/np0704396. PMID 18088099.
^ Jian-Wen Tan, Ze-Jun Dong, Zhi-Hui Ding and Ji-Kai Liu (2002), "Lepidolide, a Novel Seco-ring-A Cucurbitane Triterpenoid from Russula lepida (Basidiomycetes)". Zeitschrift für Naturforschung Series C, volume 57C issue 11/12, pages 963-965.
^ Chen, J. C.; Liu, W. Q.; Lu, L.; Qiu, M. H.; Zheng, Y. T.; Yang, L. M.; Zhang, X. M.; Zhou, L.; Li, Z. R. (2009). "Kuguacins F–S, cucurbitane triterpenoids from Momordica charantia". Phytochemistry. 70 (1): 133–140. doi:10.1016/j.phytochem.2008.10.011. PMID 19041990.
^ Chen, J. C.; Tian, R. R.; Qiu, M. H.; Lu, L.; Zheng, Y. T.; Zhang, Z. Q. (2008). "Trinorcucurbitane and cucurbitane triterpenoids from the roots of Momordica charantia". Phytochemistry. 69 (4): 1043–1048. doi:10.1016/j.phytochem.2007.10.020. PMID 18045630.
^ Chen, J. C.; Lu, L.; Zhang, X. M.; Zhou, L.; Li, Z. R.; Qiu, M. H. (2008). "Eight New Cucurbitane Glycosides, Kuguaglycosides A – H, from the Root ofMomordica charantia L". Helvetica Chimica Acta. 91 (5): 920. doi:10.1002/hlca.200890097.
^ Takasaki, Midori; Konoshima, Takao; Murata, Yuji; Sugiura, Masaki; Nishino, Hoyoku; Tokuda, Harukuni; Matsumoto, Kazuhiro; Kasai, Ryoji; Yamasaki, Kazuo (2003). "Anticarcinogenic activity of natural sweeteners, cucurbitane glycosides, from Momordica grosvenori". Cancer Letters. 198 (1): 37–42. doi:10.1016/s0304-3835(03)00285-4. PMID 12893428.
^ ^a ^b Begum, Sabira; Ahmed, Mansour; Siddiqui, Bina S.; Khan, Abdullah; Saify, Zafar S.; Arif, Mohammed (1997). "Triterpenes, A Sterol and a Monocyclic Alcohol From Momordica Charantia". Phytochemistry. 44 (7): 1313–1320. doi:10.1016/s0031-9422(96)00615-2.
^ Fatope, Majekodunmi; Takeda, Yoshio; Yamashita, Hiroyasu; Okabe, Hikaru; Yamauchi, Tatsuo (1990). "New cucurbitane trirterpenoids from Momordica charantia". Journal of Natural Products. 53 (6): 1491–1497. doi:10.1021/np50072a014.
^ Daniel Bisrat Mekuria, Takehiro Kashiwagi, Shin-ichi Tebayashi, and Chul-Sa Kim (2006)"Cucurbitane Glucosides from Momordica charantia Leaves as Oviposition Deterrents to the Leafminer, Liriomyza trifolii". Z. Naturforsch., volume 61c, pages 81–86
^ ^a ^b ^c ^d ^e Liu, J. Q.; Chen, J. C.; Wang, C. F.; Qiu, M. H. (2009). "New Cucurbitane Triterpenoids and Steroidal Glycoside from Momordica charantia". Molecules. 14 (12): 4804–4813. doi:10.3390/molecules14124804. PMC 6255097. PMID 20032860.
^ Harinantenaina, L.; Tanaka, M.; Takaoka, S.; Oda, M.; Mogami, O.; Uchida, M.; Asakawa, Y. (2006). "Momordica charantia Constituents and Antidiabetic Screening of the Isolated Major Compounds". Chemical & Pharmaceutical Bulletin. 54 (7): 1017–1021. doi:10.1248/cpb.54.1017. PMID 16819222.
^ Liu, J. Q.; Chen, J. C.; Wang, C. F.; Qiu, M. H. (2010). "One new cucurbitane triterpenoid from the fruits of Momordica charantia". European Journal of Chemistry. 1 (4): 294. doi:10.5155/eurjchem.1.4.294-296.131.
^ Si Jian-yong, Chen Di-hua, Chang Qi and Shen Lian-gang (1996), Isolation and Determination of Cucurbitane-Glycosides from Fresh Fruits of Siraitia Grosvenorii. Archived 2011-10-07 at the Wayback Machine Journal of Integrative Plant Biology, volume 38, issue 6, pages, 489–494
^ ^a ^b Chen, C. R.; Liao, Y. W.; Wang, L.; Kuo, Y. H.; Liu, H. J.; Shih, W. L.; Cheng, H. L.; Chang, C. I. (2010). "Cucurbitane Triterpenoids from Momordica charantia and Their Cytoprotective Activity in tert-Butyl Hydroperoxide-Induced Hepatotoxicity of HepG2 Cells". Chemical & Pharmaceutical Bulletin. 58 (12): 1639–1642. doi:10.1248/cpb.58.1639. PMID 21139270.
^ ^a ^b ^c ^d ^e ^f ^g ^h Mulholland, D. A.; Sewram, V.; Osborne, R.; Pegel, K. H.; Connolly, J. D. (1997). "Cucurbitane triterpenoids from the leaves of Momordica foetida". Phytochemistry. 45 (2): 391. doi:10.1016/S0031-9422(96)00814-X.
^ Spengler, Gabriella; Ramalhete, Cátia; Martins, Marta; Martins, Ana; Serly, Julianna; Viveiros, Miguel; Molnár, Joseph; Duarte, Noélia; Mulhovos, Silva; Maria-; Ferreira, José U.; Amaral, Leonard (2010). "Evaluation of Cucurbitane-type Triterpenoids from Momordica balsamina on P-Glycoprotein (ABCB1) by Flow Cytometry and Real-time Fluorometry". Anticancer Research. 30: 4867–4871.

[iupac69-1] "The Nomenclature of Steroids — Revised Tentative Rules". European Journal of Biochemistry. 10: 1–19. 1969. doi:10.1111/j.1432-1033.1969.tb00650.x.

[kumar-2] Satish Kumar and Raj Kumar (1991), Dictionary of Biochemistry. Anmol Publications, India

[ChenRev-3] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Chen, J. C.; Chiu, M. H.; Nie, R. L.; Cordell, G. A.; Qiu, S. X. (2005). "Cucurbitacins and cucurbitane glycosides: Structures and biological activities". Natural Product Reports. 22 (3): 386–399. doi:10.1039/B418841C. PMID 16010347.

[rama2009-4] ^ ^a ^b ^c ^d ^e ^f Ramalhete, C. T.; Mansoor, T. A.; Mulhovo, S.; Molnár, J.; Ferreira, M. J. U. (2009). "Cucurbitane-Type Triterpenoids from the African PlantMomordica balsamina". Journal of Natural Products. 72 (11): 2009–2013. doi:10.1021/np900457u. hdl:10884/1322. PMID 19795842.

[loli-5] Lolitkar, M. M.; Rao, M. R. Rajarama (1962). "Note on a Hypoglycaemic Principle Isolated from the fruits of Momordica charantia". Journal of the University of Bombay. 29: 223–224.

[olaniyi-6] Olaniyi, A. A. (1975). "A neutral constituent of Momordica foetida". Lloydia. 38 (4): 361–362. PMID 1186439.

[aki2007-7] Akihisa, T.; Higo, N.; Tokuda, H.; Ukiya, M.; Akazawa, H.; Tochigi, Y.; Kimura, Y.; Suzuki, T.; Nishino, H. (2007). "Cucurbitane-Type Triterpenoids from the Fruits of Momordica charantia and Their Cancer Chemopreventive Effects". Journal of Natural Products. 70 (8): 1233–1239. doi:10.1021/np068075p. PMID 17685651.

[DCWang2007-8] Wang, Da-Cheng; Pan, Hong-Yu; Deng, Xu-Ming; Xiang, Hua; Gao, Hui-Yuan; Cai, Hui; Wu, Li-Jun (2007). "Cucurbitane and hexanorcucurbitane glycosides from the fruits of Cucurbita pepo cv dayangua". Journal of Asian Natural Products Research. 9 (6): 525–529. doi:10.1080/10286020600782538. PMID 17885839. S2CID 27762659.

[JCChen2008oc-9] Chen, J. C.; Zhang, G. H.; Zhang, Z. Q.; Qiu, M. H.; Zheng, Y. T.; Yang, L. M.; Yu, K. B. (2008). "Octanorcucurbitane and Cucurbitane Triterpenoids from the Tubers ofHemsleya endecaphyllawith HIV-1 Inhibitory Activity". Journal of Natural Products. 71 (1): 153–155. doi:10.1021/np0704396. PMID 18088099.

[JWTan2002-10] Jian-Wen Tan, Ze-Jun Dong, Zhi-Hui Ding and Ji-Kai Liu (2002), "Lepidolide, a Novel Seco-ring-A Cucurbitane Triterpenoid from Russula lepida (Basidiomycetes)". Zeitschrift für Naturforschung Series C, volume 57C issue 11/12, pages 963-965.

[ChenJC2008c-11] Chen, J. C.; Liu, W. Q.; Lu, L.; Qiu, M. H.; Zheng, Y. T.; Yang, L. M.; Zhang, X. M.; Zhou, L.; Li, Z. R. (2009). "Kuguacins F–S, cucurbitane triterpenoids from Momordica charantia". Phytochemistry. 70 (1): 133–140. doi:10.1016/j.phytochem.2008.10.011. PMID 19041990.

[ChenJC2008a-12] Chen, J. C.; Tian, R. R.; Qiu, M. H.; Lu, L.; Zheng, Y. T.; Zhang, Z. Q. (2008). "Trinorcucurbitane and cucurbitane triterpenoids from the roots of Momordica charantia". Phytochemistry. 69 (4): 1043–1048. doi:10.1016/j.phytochem.2007.10.020. PMID 18045630.

[ChenJC-13] Chen, J. C.; Lu, L.; Zhang, X. M.; Zhou, L.; Li, Z. R.; Qiu, M. H. (2008). "Eight New Cucurbitane Glycosides, Kuguaglycosides A – H, from the Root ofMomordica charantia L". Helvetica Chimica Acta. 91 (5): 920. doi:10.1002/hlca.200890097.

[takasaki-14] Takasaki, Midori; Konoshima, Takao; Murata, Yuji; Sugiura, Masaki; Nishino, Hoyoku; Tokuda, Harukuni; Matsumoto, Kazuhiro; Kasai, Ryoji; Yamasaki, Kazuo (2003). "Anticarcinogenic activity of natural sweeteners, cucurbitane glycosides, from Momordica grosvenori". Cancer Letters. 198 (1): 37–42. doi:10.1016/s0304-3835(03)00285-4. PMID 12893428.

[begum-15] Begum, Sabira; Ahmed, Mansour; Siddiqui, Bina S.; Khan, Abdullah; Saify, Zafar S.; Arif, Mohammed (1997). "Triterpenes, A Sterol and a Monocyclic Alcohol From Momordica Charantia". Phytochemistry. 44 (7): 1313–1320. doi:10.1016/s0031-9422(96)00615-2.

[fatope-16] Fatope, Majekodunmi; Takeda, Yoshio; Yamashita, Hiroyasu; Okabe, Hikaru; Yamauchi, Tatsuo (1990). "New cucurbitane trirterpenoids from Momordica charantia". Journal of Natural Products. 53 (6): 1491–1497. doi:10.1021/np50072a014.

[mekuria-17] Daniel Bisrat Mekuria, Takehiro Kashiwagi, Shin-ichi Tebayashi, and Chul-Sa Kim (2006)"Cucurbitane Glucosides from Momordica charantia Leaves as Oviposition Deterrents to the Leafminer, Liriomyza trifolii". Z. Naturforsch., volume 61c, pages 81–86

[liu2009-18] Liu, J. Q.; Chen, J. C.; Wang, C. F.; Qiu, M. H. (2009). "New Cucurbitane Triterpenoids and Steroidal Glycoside from Momordica charantia". Molecules. 14 (12): 4804–4813. doi:10.3390/molecules14124804. PMC 6255097. PMID 20032860.

[hari2006-19] Harinantenaina, L.; Tanaka, M.; Takaoka, S.; Oda, M.; Mogami, O.; Uchida, M.; Asakawa, Y. (2006). "Momordica charantia Constituents and Antidiabetic Screening of the Isolated Major Compounds". Chemical & Pharmaceutical Bulletin. 54 (7): 1017–1021. doi:10.1248/cpb.54.1017. PMID 16819222.

[JQLiu2010-20] Liu, J. Q.; Chen, J. C.; Wang, C. F.; Qiu, M. H. (2010). "One new cucurbitane triterpenoid from the fruits of Momordica charantia". European Journal of Chemistry. 1 (4): 294. doi:10.5155/eurjchem.1.4.294-296.131.

[21] Si Jian-yong, Chen Di-hua, Chang Qi and Shen Lian-gang (1996), Isolation and Determination of Cucurbitane-Glycosides from Fresh Fruits of Siraitia Grosvenorii. Archived 2011-10-07 at the Wayback Machine Journal of Integrative Plant Biology, volume 38, issue 6, pages, 489–494

[CRChen2010-22] Chen, C. R.; Liao, Y. W.; Wang, L.; Kuo, Y. H.; Liu, H. J.; Shih, W. L.; Cheng, H. L.; Chang, C. I. (2010). "Cucurbitane Triterpenoids from Momordica charantia and Their Cytoprotective Activity in tert-Butyl Hydroperoxide-Induced Hepatotoxicity of HepG2 Cells". Chemical & Pharmaceutical Bulletin. 58 (12): 1639–1642. doi:10.1248/cpb.58.1639. PMID 21139270.

[mulho-23] ^ ^a ^b ^c ^d ^e ^f ^g ^h Mulholland, D. A.; Sewram, V.; Osborne, R.; Pegel, K. H.; Connolly, J. D. (1997). "Cucurbitane triterpenoids from the leaves of Momordica foetida". Phytochemistry. 45 (2): 391. doi:10.1016/S0031-9422(96)00814-X.

[24] Spengler, Gabriella; Ramalhete, Cátia; Martins, Marta; Martins, Ana; Serly, Julianna; Viveiros, Miguel; Molnár, Joseph; Duarte, Noélia; Mulhovos, Silva; Maria-; Ferreira, José U.; Amaral, Leonard (2010). "Evaluation of Cucurbitane-type Triterpenoids from Momordica balsamina on P-Glycoprotein (ABCB1) by Flow Cytometry and Real-time Fluorometry". Anticancer Research. 30: 4867–4871.

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