ANTIHYPERTENSIVE AND ANTIDIABETIC PEPTIDES DERIVED FROM <i>IN SILICO</i> SIMULATED GASTROINTESTINAL DIGESTION OF QUINOA <i>(Chenopodium quinoa)</i> GLOBULINS AND MOLECULAR DOCKING STUDY

Chirinos, Rosana; Rodriguez-Diaz, Jamerccy; Anticona, Sebastian; Aguilar-Galvez, Ana; Pedreschi, Romina; Campos, David

doi:10.21577/0100-4042.20230126

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Article • Quím. Nova 47 (4) • 2024 • https://doi.org/10.21577/0100-4042.20230126 copiar

ANTIHYPERTENSIVE AND ANTIDIABETIC PEPTIDES DERIVED FROM IN SILICO SIMULATED GASTROINTESTINAL DIGESTION OF QUINOA (Chenopodium quinoa) GLOBULINS AND MOLECULAR DOCKING STUDY

Autoria SCIMAGO INSTITUTIONS RANKINGS

This study evaluated the impact of in silico simulated gastrointestinal digestion (GID) of four quinoa globulins on the potential to release ACE and DPP-IV inhibitor peptides (antihypertensive and antidiabetic properties, respectively), as well as performed a molecular docking study to evaluate the interactions produced in the peptide-enzyme complexes. In silico GID performed on quinoa globulins resulted in the formation of amino acids as well as peptides with two to five residues. The peptides PSF, IPG, CSG, SPR, CSPG and PPN stood out for their high bioactivity scores (> 0.6), for not showing toxicity, as well as presenting potential inhibitory properties to both ACE and DPP-IV enzymes evaluated by ToxinPred, PeptideRanker and BioPep tools, respectively. The molecular docking analysis allowed highlighting that all peptides interacted with the enzymes, finding favorable binding energy values, different number and type of interactions, either at the level of the enzyme active sites or not, characteristics that together would define the potential of the established interaction of the complexes formed. The results, at the level of a first screening, support that GID of quinoa globulins can give rise to peptides with both antihypertensive and antidiabetic properties, requiring further in vitro and in vivo studies.

Protein	Fragments
11S seed storage globulin accession: AAS67037.1	M - A - K - ST - T - T - L - F - L - L - SCS - IA - L - VL - L - N - G - CM - G - Q - G - R - M - R - E - M - Q - G - N - E - CQ - ID - R - L - T - A - L - E - PT - Y - R - IQ - A - E - G - G - L - T - E - VW - D - T - Q - D - Q - Q - F - Q - CSG - VS - V - IR - R - T - IE - PN - G - L - L - L - PSF - T - SG - PE - L - IY - IE - Q - G - N - G - ISG - L - M - IPG - CPE - T - F - E - SM - SQ - E - SW - R - E - G - M - E - R - G - M - R - G - G - R - F - Q - D - Q - H - Q - K - IR - H - L - R - Q - G - H - IF - A - M - PA - G - VA - H - W - A - Y - N - SG - N - E - PL - VA - V - IL - ID - T - SN - H - A - N - Q - L - D - K - D - Y - PK - R - F - Y - L - A - G - K - PQ - Q - E - H - SR - H - H - H - R - G - G - E - SQ - R - G - E - H - G - SD - G - N - VF - SG - L - D - T - K - S - V - VQ - SF - G - VSE - D - IA - E - K - L - Q - A - K - Q - D - E - R - G - N - I - VL - VQ - E - G - L - H - V - IK - PPSSR - SY - D - D - E - R - E - Q - R - H - R - SPR - SN - G - L - E - E - T - ICSA - R - L - SE - N - ID - D - PSK - A - D - VY - SPE - A - G - R - L - T - T - L - N - SF - N - L - P - IL - SN - L - R - L - SA - E - K - G - VL - Y - R - N - A - IM - A - PH - Y - N - L - N - A - H - S - I - IY - G - VR - G - R - G - R - IQ - I - VN - A - Q - G - N - S - VF - D - D - E - L - R - Q - G - Q - L - V - V - VPQ - N - F - A - V - VK - Q - A - G - E - E - G - F - E - W - IA - F - K - T - CE - N - A - L - F - Q - T - L - A - G - R - T - SA - IR - A - M - P - VE - V - ISN - IY - Q - ISR - E - Q - A - Y - R - L - K - F - SR - SE - T - T - L - F - R - PE - N - Q - G - R - Q - R - R - E - M - A - A
11S globulin seed storage protein 2-like accession: XP_021733866.1	M - E - ID - L - SPK - Q - SQ - K - VY - G - G - D - G - G - SY - Y - T - W - SSSD - L - PM - L - A - E - A - K - VG - G - A - K - L - L - L - Q - PH - G - L - A - L - PSY - SD - SA - K - VA - Y - VL - H - G - K - G - R - A - G - I - VM - PE - A - T - K - E - K - V - VPL - R - K - G - D - A - L - A - L - PF - G - V - VT - W - W - F - N - D - G - D - G - E - L - V - VL - F - L - G - D - T - SK - A - H - R - SG - E - F - T - N - F - L - L - T - G - VG - SL - F - H - G - F - ST - E - F - VSR - A - W - D - L - K - E - E - E - VE - K - L - VK - A - Q - K - G - Q - G - I - VK - L - R - E - G - Q - SL - PA - A - SE - E - D - A - K - G - M - VF - N - CE - SA - PL - D - VD - VK - G - G - G - R - V - V - VL - T - D - K - N - L - PL - VG - E - VG - L - G - A - D - L - VR - ID - SA - SM - CSPG - F - SSD - SA - F - Q - VT - Y - V - IR - G - SG - R - VQ - V - VG - ID - G - R - R - VL - E - T - R - VK - A - G - CL - F - I - VPR - F - F - V - VSK - IA - D - G - D - G - M - E - W - F - S - I - IT - T - PQ - P - VF - SH - L - A - G - R - T - S - VW - K - A - L - SPQ - VL - E - A - SF - D - VSPE - M - E - K - L - F - R - SK - R - T - SD - A - IF - F - A - PPN
13S globulin seed storage protein 1-like accession: XP_021752233.1	M - A - F - T - T - T - N - N - N - A - L - L - F - W - VPL - CL - L - VF - L - ISPSL - A - Q - L - PL - L - Q - R - Q - PQ - Q - PR - G - Q - Q - W - Q - H - D - CD - IQ - Q - L - Q - A - A - E - PT - H - R - L - R - A - E - A - G - V - IE - VW - E - SN - SE - Q - F - R - CA - G - VA - A - VR - Y - V - IE - PK - G - L - L - L - PSY - T - N - A - PY - VT - Y - VT - Q - G - R - G - IQ - G - V - I - VPG - CPE - T - F - E - SPR - G - SG - SD - T - T - R - E - G - Q - R - D - Q - H - Q - K - VF - R - VQ - E - G - D - V - IG - SPA - G - V - VQ - W - T - Y - N - D - G - D - A - P - I - VS - VT - L - L - D - L - SN - PN - N - Q - L - D - L - N - F - R - SF - Y - L - A - G - D - PQ - G - G - Q - E - R - R - PK - E - VA - G - K - N - IF - N - G - F - D - D - E - M - L - A - D - A - F - N - VD - T - E - T - IR - SM - K - A - E - N - D - E - R - G - S - I - IR - VE - R - D - L - E - IL - SPE - W - D - D - T - E - E - E - R - T - R - R - L - N - G - L - E - Q - T - L - CSL - IF - K - Q - N - ID - R - PSL - A - D - VF - T - K - H - G - G - R - IN - T - L - N - G - H - K - L - PL - L - Q - Y - L - Q - L - S - VE - R - G - VL - Y - K - N - A - L - M - T - PH - W - N - IN - A - H - S - I - IY - IT - R - G - T - G - W - IQ - VA - R - E - N - G - R - L - VF - D - D - R - VQ - E - G - Q - L - L - V - VPQ - N - F - V - V - VK - K - A - E - Q - E - G - L - K - W - VSF - K - T - N - D - N - A - M - ISPL - A - G - K - L - SA - IR - G - M - PE - E - VL - M - N - SY - D - M - SR - D - E - VR - R - L - K - Y - G - R - E - E - L - SL - F - SPR - T - R - SF
13S globulin seed storage protein 2-like accession: XP_021752668.1	M - SR - VF - L - L - PL - A - L - T - L - L - IL - SPT - SL - A - Q - L - G - F - Q - L - G - Q - SPF - L - PSG - Q - SSPQ - H - SR - L - Q - R - G - Q - Q - A - L - N - D - CQ - IN - Q - L - SA - N - E - PS - IR - IQ - A - E - A - G - IT - E - VW - D - PK - E - Q - Q - E - F - Q - CA - G - VT - V - IR - R - E - IE - PK - G - L - L - L - PH - Y - N - N - A - PS - ISY - V - IR - G - R - G - L - L - G - L - SSL - G - CA - D - T - Y - E - SG - SPE - F - F - SE - E - SR - R - SE - R - F - E - E - SR - R - SE - R - G - SE - E - M - R - D - Q - H - Q - K - VR - R - F - H - K - G - H - V - IG - L - PA - G - VSK - W - VY - N - D - G - E - D - R - L - T - I - VT - L - Y - D - T - N - N - F - Q - N - Q - L - D - D - N - L - R - SF - F - L - A - G - N - PQ - G - R - G - G - D - Q - SG - R - Q - H - E - SSR - R - H - T - R - G - G - Q - E - E - M - G - Q - N - IL - SG - F - D - K - Q - L - L - A - D - A - F - E - VE - SD - T - ISK - IQ - G - E - N - D - D - R - G - A - I - IR - VE - SG - E - L - E - M - L - IPE - W - D - Q - E - E - Q - R - SE - R - H - H - R - G - G - G - SE - R - SE - E - E - E - R - SE - R - H - H - R - G - G - R - G - R - Q - SE - SSR - PH - N - G - IE - Q - T - L - CSA - R - L - S - VN - ID - N - PE - R - A - D - VF - N - PQ - G - G - R - L - T - N - IN - SN - K - L - P - IL - N - Y - L - R - L - SA - E - K - VN - L - Y - K - N - A - IM - T - PN - W - K - IN - A - H - S - I - VY - F - T - K - G - SG - R - VQ - IA - N - H - E - G - E - L - VF - D - D - M - VQ - E - G - Q - L - V - V - VPQ - N - F - V - VL - K - R - A - G - Q - D - G - L - E - W - VA - L - L - T - N - D - N - A - M - SSPL - A - G - R - ISA - IR - G - M - P - IE - V - VM - N - SY - K - L - SR - E - E - A - Q - R - L - K - Y - G - R - Q - E - L - S - VF - SPSK - R - SE - R - R - G - D - E - Y - A - I - V

Protein	Peptides	Predicted bioactivity score^a	Toxicity^b	Possible activity^c	ACE inhibitor sequences previously reported^c	DPP-IV inhibitor sequences previously reported^c
11S seed storage globulin	PSF	0.920	Non	ACE and DPP-IV inhibitor	SF	PS-SF
	IPG	0.696	Non	ACE and DPP-IV inhibitor	IP-PG	IP-PG
	CSG	0.642	Non	ACE inhibitor	SG	-
	SPR	0.617	Non	ACE and DPP-IV inhibitor	PR	SP-PR
11S globulin seed storage protein 2-like	CSPG	0.775	Non	ACE and DPP-IV inhibitor	PG	SP-PG
11S globulin seed storage protein 2-like	PPN	0.728	Non	ACE and DPP-IV inhibitor	PP	PP-PN
13S globulin seed storage protein 1-like	SPR	0.617	Non	ACE and DPP-IV inhibitor	PR	SP-PR
13S globulin seed storage protein 1-like	CSL	0.601	Non	DPP-IV inhibitor	-	SL
13S globulin seed storage protein 2-like	SPF	0.960	Non	DPP-IV inhibitor	-	SP-PF

Peptide	ACE		DPP-IV
Peptide	Binding energy (kcal mol^-1)	Site residues	Binding energy (kcal mol^-1)	Site residues
Lisinopril	–11.81	His387, His383, Ala354, His353, His513, Lys511, Gln281, Tyr523, Glu411, Val380, Ala356, Zn⁺²	-	-
Sitagliptin	-	-	–8.62	Tyr666^&, His740^&, Tyr662^&, Asn710^&, Glu205^&, Glu206^&, Arg358, Arg125, Phe208, Val207, Phe357
PSF	–11.15	Tyr523, His387, Ala354, Glu384, His383*, Arg522, His513, His353, Val380, Val518, Lys368, Asn70, Glu143, Val351, Ser516, Glu411, Phe512, Tyr523, Ser355, Zn⁺²	–8.99	Trp563, Val575, Ala564, Gln527, Lys512, Val558, Phe559, Asn562, Ile529, Thr565, Arg560, Ser577, Lys554, Trp629, Trp627, Gly628, Gly632, Val546, Tyr547, Asp545, Tyr752
IPG	–7.69	His513, Glu384, His353, Tyr520, Ala354*, Phe527, Tyr523, Val380, Phe457, Zn⁺²	–6.43	Glu205^&, Glu206^&, Tyr666^&, Ser209, Arg358, Phe357
SPR	–7.81	Glu411, Glu384, His387, Tyr523, Ala356, His410, Asn70, Glu143, Trp357, Zn⁺²	–6.54	Tyr662^&, Tyr666^&, Glu205^&, Glu206^&, Tyr547, Phe357, Ser552, Asn710, Arg669
CSPG	–10.47	Ala354, His353, His387, Gln281, Glu411, Tyr523, Tyr520, Gln281, Lys511, His383, Gln530, Asp45, Thr282, Val380, Lys454, Val379, Phe527, Ser355, Val518, Phe457, Ser526, Zn⁺²	–7.14	Tyr752, Asp545, Trp627, Trp629, Gly628, Val546, Gly632, Tyr547, Gln527, Arg560, Val558, Lys512, Ile529, Ala564, Trp563, Val575
PPN	–11.03	Glu162, Ala354, Glu384, His383, His513, Tyr520, Lys511, Gln281, Cys370, Asp377, Val380, Gln369, Val380, His353, Tyr523, Glu411, His387, Val518,Phe512, Glu384, Ser355, Lys511, Zn⁺²	–6.79	Tyr631^&, Ser630^&, Tyr662^&, Glu206^&, Arg125^&, Glu205^&, Tyr666^&, Val656, Val711, Tyr547, Asn710, Phe357, Cys551, Gln553, Ser552, Pro550, Gly549, Trp659
SPF	NE	NE	–6.99	Tyr631^&, Arg125^&, Glu205^&, Tyr662^&, Ser630^&, Tyr666^&, Phe357, Ser209

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[1] *e-mail: chiri@lamolina.edu.pe; dcampos@lamolina.edu.pe