analysis revealed a predominant pea

analysis revealed a predominant peak at m/z 283 that may correspond
to a loss of two C4H8 (56 Da) fragments originating from
the prenyl groups. A loss of a single prenyl group in allylic position
(56 Da) and a subsequent loss of the second prenyl group under
formation of a heterocyclic ring (42 Da) and a fragment at m/z
297 could be also observed. Moreover, collision induced fragmentation
of the [MH] ion yielded a fragment at m/z 326 caused by a
loss of a prenyl radical C5H9 (69 Da). Similar to a-mangostin, the
resulting radical ion is resonance-stabilised. A further fragment at
m/z 271 resulted from the loss of both prenyl groups, one group in
allylic and the other in benzylic (68 Da) position.
The other components of the fingerprint of mangosteen pericarp
and aril segments were present in lower concentrations. Fragmentation
pattern of compound 1 was similar to a-mangostin with
a de-methylated product ion at m/z 310 (15 Da) and a presumptive
subsequent ring closure leading to m/z 267 (58 Da), which
could be corroborated by the MS3 fragmentation experiments.
Based on retention time, molecular weight and fragmentation pattern,
compound 1 was assigned to 1,7-dihydroxy-3-methoxy-2-(3-
methylbut-2-enyl)xanthone.
Compound 3 showed an [MH] ion of m/z 379 and was tentatively
assigned to 8-deoxygartanin. CID of the [MH] ion resulted
in the loss of a C4H7 radical (55 Da), that can be attributed to an
allylic loss of the prenyl group, yielding a prominent fragment at
m/z 324. Unlike fragmentation reactions of other compounds, the
loss of more than one prenyl group (112 Da, 124 Da) could
not be observed. This might be attributed to the structure of 8-
deoxygartanin, with two prenyl groups at the same aromatic ring.
Fragmentation of one prenyl group leads to a loss of aromaticity.
Consequently, formation of stable fragments after further elimination
of the second prenyl group is impossible.
Compound 4 was detected exhibiting an [MH] ion of m/z 379
and tentatively identified as 1,3,7-trihydroxy-2,8-di(3-methylbut-
2-enyl)xanthone. As can be seen in the UV-chromatogram, peak
4 comprises two compounds, while only one single peak could
be detected in the ion chromatogram, indicating the presence of isomeric forms. Since 1,3,7-trihydroxy-2,8-di(3-methylbut-2-
enyl)xanthone is devoid of stereogenic centres, and the UV-spectra
of both peak apexes are identical, this peculiarity needs deeper
investigation. Fragmentation pattern of 1,3,7-trihydroxy-2,8-di(3-
methylbut-2-enyl)xanthon exhibits the same fragments as described
above with the preferred fragmentation of one prenyl
group. The main peak at m/z 379 corresponds to a loss of a prenyl
moiety C5H9 (69 Da).
Peak 5 showed an [MH] ion of m/z 395 that could be assigned
to gartanin. The presence of gartanin in mangosteen pericarp has
previously been described by several authors (Govindachari,
Kalyanaraman, Muthukumaraswamy, & Pai, 1971; Jung et al.,
2006; Mahabusarakam & Wiriyachitra, 1987; Zarena & Sankar,
2009). In agreement with literature findings, gartanin eluted prior
to a-mangostin. For this reason, peak assignment was mainly confirmed
by the elution order and molecular weight. Besides a typical
loss of a C4H7 radical (55 Da) originating from a prenyl group, the
most prominent product ion at m/z 297 (98 Da) resulting from
the loss of a C3H7 radical (43 Da) under formation of a heterocylic
ring could be observed.
Compound 7 exhibiting an [MH] ion at m/z 463 was detected
and tentatively identified as garcinon E. Since the structure of garcinon E exhibits three prenyl groups, the molecule is more lipophilic
than the other xanthones, thus displaying a longer retention.
Moreover, the preferred fragmentation reaction of garcinon E is a
loss of two fragments, each from different prenyl groups. The main
peak at m/z 351 corresponds to a loss of two C4H8 (56 Da) fragments
from the prenyl groups. Furthermore, fragmentation at the
benzylic position and ring closure reactions led to fragments characterised
by a loss of two fragments of prenylic origin (124 Da,
98 Da). Altogether, fragmentation of garcinon E turned out to
be similar to c-mangostin.
Although previous studies of mangosteen pericarp revealed the
occurrence of isomangostin, 9-hydroxycalabaxanthon and ßmangostin
(Mahabusarakam & Wiriyachitra, 1987; Zarena & Sankar,
2009), their unambiguous presence could not be confirmed.
3.1.2. Identification of xanthones from the functional beverage
Analysis of the extract from the functional beverage by LC–MSn
showed good agreement with the xanthone pattern of the pericarp.
a-Mangostin revealed to be the predominant xanthone, followed
by c-mangostin. Other characteristic xanthones were only detected
at low concentrations.
3.2. Quantification of the major xanthones in pericarp, aril segments
and the functional beverage
Only few studies dealt with the quantification of xanthones in
mangosteens and, in most of these studies, the origin and the analysed
fruit part has not precisely been assigned to a specific plant
part. Only one single study by Zarena and Sankar (2009) investigated
the composition of a mangosteen pericarp extract. Since
supercritical carbon dioxide extraction was applied, comparison
with data obtained in the present work is difficult.
Table 2 lists the determined amounts of the identified xanthones
in pericarp, aril segments and the functional beverage as well as the
total xanthone contents. The total xanthone content, as calculated
by summarising individual amounts of all constituents, was
1700.26 ± 40.47 mg/100 g on fresh weight (FW), 106.87 ±
3.15 mg/100 g FWand 18.79 ± 0.49 mg/100 mL, for the mangosteen
pericarp, the aril segments and the functional beverage, respectively.
Despite the large diversity of xanthones that has been found
in the aril segments, xanthone contents are 16 times lower than in
the pericarp. Compared to the fruit parts, the analysed functional
beverage contained even lower concentrations of xanthones, which
is attributable to the low dosage of mangosteen puree (

ผลลัพธ์ (ไทย) 1:

analysis revealed a predominant peak at m/z 283 that may correspondto a loss of two C4H8 (56 Da) fragments originating fromthe prenyl groups. A loss of a single prenyl group in allylic position(56 Da) and a subsequent loss of the second prenyl group underformation of a heterocyclic ring (42 Da) and a fragment at m/z297 could be also observed. Moreover, collision induced fragmentationof the [MH] ion yielded a fragment at m/z 326 caused by aloss of a prenyl radical C5H9 (69 Da). Similar to a-mangostin, theresulting radical ion is resonance-stabilised. A further fragment atm/z 271 resulted from the loss of both prenyl groups, one group inallylic and the other in benzylic (68 Da) position.The other components of the fingerprint of mangosteen pericarpand aril segments were present in lower concentrations. Fragmentationpattern of compound 1 was similar to a-mangostin witha de-methylated product ion at m/z 310 (15 Da) and a presumptivesubsequent ring closure leading to m/z 267 (58 Da), whichcould be corroborated by the MS3 fragmentation experiments.Based on retention time, molecular weight and fragmentation pattern,compound 1 was assigned to 1,7-dihydroxy-3-methoxy-2-(3-methylbut-2-enyl)xanthone.Compound 3 showed an [MH] ion of m/z 379 and was tentativelyassigned to 8-deoxygartanin. CID of the [MH] ion resultedin the loss of a C4H7 radical (55 Da), that can be attributed to anallylic loss of the prenyl group, yielding a prominent fragment at
m/z 324. Unlike fragmentation reactions of other compounds, the
loss of more than one prenyl group (112 Da, 124 Da) could
not be observed. This might be attributed to the structure of 8-
deoxygartanin, with two prenyl groups at the same aromatic ring.
Fragmentation of one prenyl group leads to a loss of aromaticity.
Consequently, formation of stable fragments after further elimination
of the second prenyl group is impossible.
Compound 4 was detected exhibiting an [MH] ion of m/z 379
and tentatively identified as 1,3,7-trihydroxy-2,8-di(3-methylbut-
2-enyl)xanthone. As can be seen in the UV-chromatogram, peak
4 comprises two compounds, while only one single peak could
be detected in the ion chromatogram, indicating the presence of isomeric forms. Since 1,3,7-trihydroxy-2,8-di(3-methylbut-2-
enyl)xanthone is devoid of stereogenic centres, and the UV-spectra
of both peak apexes are identical, this peculiarity needs deeper
investigation. Fragmentation pattern of 1,3,7-trihydroxy-2,8-di(3-
methylbut-2-enyl)xanthon exhibits the same fragments as described
above with the preferred fragmentation of one prenyl
group. The main peak at m/z 379 corresponds to a loss of a prenyl
moiety C5H9 (69 Da).
Peak 5 showed an [MH] ion of m/z 395 that could be assigned
to gartanin. The presence of gartanin in mangosteen pericarp has
previously been described by several authors (Govindachari,
Kalyanaraman, Muthukumaraswamy, & Pai, 1971; Jung et al.,
2006; Mahabusarakam & Wiriyachitra, 1987; Zarena & Sankar,
2009). In agreement with literature findings, gartanin eluted prior
to a-mangostin. For this reason, peak assignment was mainly confirmed
by the elution order and molecular weight. Besides a typical
loss of a C4H7 radical (55 Da) originating from a prenyl group, the
most prominent product ion at m/z 297 (98 Da) resulting from
the loss of a C3H7 radical (43 Da) under formation of a heterocylic
ring could be observed.
Compound 7 exhibiting an [MH] ion at m/z 463 was detected
and tentatively identified as garcinon E. Since the structure of garcinon E exhibits three prenyl groups, the molecule is more lipophilic
than the other xanthones, thus displaying a longer retention.
Moreover, the preferred fragmentation reaction of garcinon E is a
loss of two fragments, each from different prenyl groups. The main
peak at m/z 351 corresponds to a loss of two C4H8 (56 Da) fragments
from the prenyl groups. Furthermore, fragmentation at the
benzylic position and ring closure reactions led to fragments characterised
by a loss of two fragments of prenylic origin (124 Da,
98 Da). Altogether, fragmentation of garcinon E turned out to
be similar to c-mangostin.
Although previous studies of mangosteen pericarp revealed the
occurrence of isomangostin, 9-hydroxycalabaxanthon and ßmangostin
(Mahabusarakam & Wiriyachitra, 1987; Zarena & Sankar,
2009), their unambiguous presence could not be confirmed.
3.1.2. Identification of xanthones from the functional beverage
Analysis of the extract from the functional beverage by LC–MSn
showed good agreement with the xanthone pattern of the pericarp.
a-Mangostin revealed to be the predominant xanthone, followed
by c-mangostin. Other characteristic xanthones were only detected
at low concentrations.
3.2. Quantification of the major xanthones in pericarp, aril segments
and the functional beverage
Only few studies dealt with the quantification of xanthones in
mangosteens and, in most of these studies, the origin and the analysed
fruit part has not precisely been assigned to a specific plant
part. Only one single study by Zarena and Sankar (2009) investigated
the composition of a mangosteen pericarp extract. Since
supercritical carbon dioxide extraction was applied, comparison
with data obtained in the present work is difficult.
Table 2 lists the determined amounts of the identified xanthones
in pericarp, aril segments and the functional beverage as well as the
total xanthone contents. The total xanthone content, as calculated
by summarising individual amounts of all constituents, was
1700.26 ± 40.47 mg/100 g on fresh weight (FW), 106.87 ±
3.15 mg/100 g FWand 18.79 ± 0.49 mg/100 mL, for the mangosteen
pericarp, the aril segments and the functional beverage, respectively.
Despite the large diversity of xanthones that has been found
in the aril segments, xanthone contents are 16 times lower than in
the pericarp. Compared to the fruit parts, the analysed functional
beverage contained even lower concentrations of xanthones, which
is attributable to the low dosage of mangosteen puree (<5%) in the
recipe of the final product. According to the producer’s information,
mangosteen puree is produced from the whole fully ripe fruits after
blanching and milling to obtain a smooth pulp including the juicy
non-lignified red-coloured pericarp. The fruit puree is finally
blended with water and eight further fruit purees and juices,
respectively.
In addition to total xanthone contents in mangosteen pericarp,
aril segments and the functional beverage, xanthone patterns of
the different fruit parts displayed slight differences. While amangostin
represented the major xanthone in both parts of the
fruit and in the functional beverage, the second major xanthone
in mangosteen pericarp was c-mangostin, followed by the minor
components gartanin, 8-deoxygartanin, garcinon E, 1,7-dihydroxy-
3-methoxy-2-(3-methylbut-2-enyl)xanthone and 1,3,7-trihydroxy-
2,8-di(3-methylbut-2-enyl)-xanthone. In contrast, aril
segments from mangosteen showed a deviating concentration
order of the identified minor xanthones. Besides 1,3,7-trihydroxy-
2,8-di(3-methylbut-2-enyl)-xanthone as the second major
xanthone, concentration of minor xanthones decreased in the order
1,7-dihydroxy-3-methoxy-2-(3-methylbut-2-enyl)xanthone,
garcinon E, c-mangostin, gartanin and 8-deoxygartanin. In the
pericarp, all identified xanthones were present at higher amounts
than in the aril segment, except 1,3,7-trihydroxy-2,8-di(3-methylbut-
2-enyl)xanthone. Concentration order of the different xanthones
in the functional beverage turned out to be similar to that
of the pericarp.
To estimate the intake of xanthones with the usual consumption
of one mangosteen fruit and by the ingestion of the functional
beverage, respectively, comparison of major xanthone contents
was conducive. For this purpose, contents of a-mangostin, cmangostin
and 1,3,7-trihydroxy-2,8-di(3-methylbut-2-enyl)xanthone
in arils, pericarp and the beverage were determined. Due
to their very low concentrations minor xanthones have not been
considered.
Quantification of the most prominent xanthones in extracts
from mangosteen aril segments resulted in an a-mangostin content
of 40.59 ± 1.62 mg/100 g FW and a c-mangostin content of
8.25 ± 0.24 mg/100 g FW. Amounts of 1,3,7-trihydroxy-2,8-di(3-
methylbut-2-enyl)xanthone in the aril segments were
25.76 ± 0.68 mg/100 g FW. Compared to the pericarp, the a- and
c-mangostin contents in the aril segments were 37 and 29 times
lower, respectively, whereas the concentration of 1,3,7-trihydroxy-
2,8-di(3-methylbut-2-enyl)xanthone in mangosteen arils
was in the range of the pericarp.
Considering the consumption of the aril segments of one single
Thai mangosteen (30 g), it results in an intake of 12.2 mg, 7.7 mg
and 2.5 mg of a-mangostin, 1,3,7-trihydroxy-2,8-di(3-methylbut-
2-enyl)-xanthone and c-mangostin, respectively. Compared with
the recommended daily dose of the functional beverage (90 mL),
the content of the predominant a-mangostin in the functional
beverage is similar to that of aril segments of one single Thai mangosteen.
Comparable amounts were also determined for 1,3,7-trihydroxy-
2,8-di(3-methylbut-2-enyl)xanthone and c-mangostin.
Consequently, the ingestion of 90 mL of the functional beverage
corresponds to the consumption of carefully peeled edible aril segments
of one single mangosteen. Moreover, 90 mL of the beverage
contain the same amounts of the major xanthones a- and cmangostin
as 0.9 g of pericarp. Accordingly, only minor amounts
of pericarp ingested with the peeled aril segments are needed to
attain an intake in the range of the recommended daily dose of
the beverage. As a consequence of these findings, the bioavailability
of xanthones from fruits and functional drinks should be an issue of further studies to determine the efficacy of xanthones ingested
from different processed food products.

ผลลัพธ์ (ไทย) 3:

การวิเคราะห์ยอดเด่นที่ m / z ที่อาจสอดคล้อง
เพื่อการสูญเสียสอง c4h8 (  56 ดา )
prenyl ชิ้นส่วนที่มาจากกลุ่ม การสูญเสียของกลุ่ม prenyl เดียวในตำแหน่ง allylic
(  56 ดา ) และภายหลังการสูญเสียของกลุ่ม prenyl ที่สองภายใต้
สร้างแหวนเฮเทอโรไซคลิก (  42 ดา ) และส่วนที่ m / z
297 อาจจะยังสังเกตได้ นอกจากนี้ การปะทะเกิดการแตกแยก
ของ [ M ]   H ไอออนจากส่วนที่ m / z แต่เกิดจาก
การสูญหายของ prenyl หัวรุนแรง c5h9 (  69 ดา ) คล้ายกับ a-mangostin ,
) หัวรุนแรงไอออนเป็นเสียงก้อง ก็ดีขึ้น ส่วนเพิ่มเติมที่
M / Z 271 ที่เกิดจากการสูญเสียทั้ง prenyl กลุ่ม กลุ่มหนึ่งใน
allylic และอื่น ๆ ใน benzylic (  68 ดา ) ตำแหน่ง
ส่วนประกอบอื่น ๆของลายนิ้วมือของ
เปลือกมังคุดและกลุ่มเนื้ออยู่ในความเข้มข้นต่ำ รูปแบบการกระจายตัวของสารประกอบ 1 คล้ายกับ

a-mangostin กับ de methylated ผลิตภัณฑ์ไอออนที่ m / z 310 (  15 ดา ) และความเป็นไปได้
ตามมาปิดนำแหวน M / Z ( 267  58 ดา ) ซึ่ง
อาจจะ corroborated โดยการทดลองของ ms3 .
ขึ้นอยู่กับเวลาการเก็บรักษา , น้ำหนัก โมเลกุลและ fragmentation รูปแบบ
สารประกอบ 1 ได้รับมอบหมายให้ 1,7-dihydroxy-3-methoxy-2 - ( 3 -
methylbut-2-enyl ) พบว่าสารประกอบแซนโทน .
3 M  [ H ]  ไอออนของ M / z และก็แน่นอน
มอบหมายให้ 8-deoxygartanin . CID ของ [ M ]   H ไอออนมีผล
ในการสูญเสียของ c4h7 หัวรุนแรง (  55 ดา ) ที่สามารถประกอบเป็น allylic
การสูญเสียของกลุ่ม prenyl ผลผลิตชิ้นเด่นที่
M / Z 324 .ซึ่งแตกต่างจากการปฏิกิริยาของสารประกอบอื่น ๆ ,
การสูญเสียมากกว่าหนึ่ง prenyl GROUP (  112 ดา  124 ดา ) อาจ
ไม่เป็นที่สังเกต นี้อาจจะเกิดจากโครงสร้างของ 8 -
deoxygartanin กับสองกลุ่มที่ prenyl แหวนหอมเดียวกัน
การแตกแยกของกลุ่มหนึ่ง prenyl นำไปสู่การสูญเสียของพระบรมวงศ์เธอ .
ดังนั้นการสร้างชิ้นส่วนที่มั่นคงหลังจาก
ตัดเพิ่มเติมของกลุ่ม prenyl ที่สองเป็นไปไม่ได้
สารประกอบ 4 ที่ตรวจพบแสดงเป็น [ M ]   H ไอออนของ M / Z 379
และไม่แน่นอนที่ระบุว่าเป็น 1,3,7-trihydroxy-2,8-di ( 3-methylbut -
2-enyl ) แซนโทน . ที่สามารถเห็นได้ในแสงยูวี chromatogram ยอด ,
4 ประกอบด้วยสารสอง ขณะเดียวยอดอาจ
ถูกตรวจพบในไอออนโครมาแสดงตนของรูปแบบ isomeric . ตั้งแต่ 1,3,7-trihydroxy-2 ,8-di ( 3-methylbut-2 -
enyl ) xanthone เป็นไร้ศูนย์ stereogenic และ UV Spectra
ทั้งยอดสามารถตรวจเหมือนกัน ลักษณะเฉพาะนี้ต้องสอบสวนลึก

รูปแบบการกระจายตัวของ 1,3,7-trihydroxy-2,8-di ( 3 -
methylbut-2-enyl ) แซนโทน จัดแสดงชิ้นส่วนเดียวกันตามที่อธิบายไว้ข้างต้นกับของที่ต้องการ

prenyl หนึ่งกลุ่มหลักสูงสุดที่ m / z มันสอดคล้องกับการสูญเสียของ prenyl
กึ่งหนึ่ง c5h9 (  69 ดา )
5 M  พีคแสดง [ H ]  ไอออนของ M / Z นั่นอาจจะมอบหมายให้การ์ทานิน
. การปรากฏตัวของการ์ทานินในเปลือกมังคุดมี
ก่อนหน้านี้ถูกอธิบายโดยผู้เขียนหลาย ( govindachari
kalyanaraman muthukumaraswamy & , , , ปาย , 1971 ; จอง et al . ,
2006 ; mahabusarakam & เมนะเศวต , 1987 ; zarena ซังก้า
& , 2009 )